Greatest Pop Stars of 21st Century

With the first quarter of the 21st century coming to a close, Billboard has spent the last few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. You can see the stars who have made our list so far here — and now, we examine the century in Rihanna, who pushed her way into the center of pop music and pop culture for a game-changing decade of absolutely dazzling dominance, then headed back to the sidelines. (Hear more discussion of Rihanna and explanation of her list ranking on our Greatest Pop Stars podcast, with her episode debuting Wednesday, Nov. 20.)

In 2007, Rihanna told Paper that she wanted to be “the Black Madonna.” Nearly 20 years have passed since, and the billionaire pop icon has taken the 20th century’s greatest female pop star template and fashioned into a blueprint of her own. Rihanna’s version – the Rihprint, if you will – combines a unmistakable vocal tone, a rarely faulty ear for hits, an eye for fearless, futuristic fashion and a complete rejection of the role model archetype in favor of a gleeful embrace of sexual liberation. It’s now arguably the most prized and clamored-after playbook for burgeoning 21st century pop singers. 

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Born Robyn Rihanna Fenty in Bridgetown, the capital of the picturesque island country of Barbados, Rihanna’s musical odyssey boasts a familiar beginning: she and two childhood friends started a girl group. Without a name or any original material, the trio scored an audition with Evan Rogers, a veteran producer with credits dating back to 1984’s landmark Beat Street soundtrack, who remarked to Entertatinment Weekly, “[Rihanna] carried herself like a star even when she was 13. But the killer was when she opened her mouth to sing [Destiny’s Child’s cover of ‘Emotion’]. She was a little rough around the edges, but she had this edge to her voice.”  

Rihanna

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Those two things – her effortlessly natural allure and her distinct vocal tone that infuses her Bajan accent with trademark throaty rasp – proved to be the most important building blocks for her impending domination. That initial audition impressed Rogers so much that he spent the next year helping Rihanna sharpen her craft in Stamford, Conn. during her breaks from school. In 2004, she signed to Roger’s and Carl Sturken’s Syndicated Rhythm Productions, allowing her four-track demo tape – which included an early cut of “Pon De Replay” from her then-unreleased debut studio album – to begin circulating. 

Upon hearing “Pon De Replay” for the first time, Jay-Z, Def Jam’s president and CEO at the time, felt that track was too big to be a new artist’s first single. But after hearing her sing the song live during an audition in NYC, he was convinced and honored L.A Reid’s request to make sure Rihanna didn’t leave the building without signing a deal with Def Jam. In a 2005 appearance on The Tyra Banks Show, Rihanna recalled Jay-Z saying, “There are two ways to leave here. I go through the door with the deal signed or through this window, and we’re on the 29th floor.” That day, Jay-Z locked down a six-album deal with Rihanna that would go on to completely revolutionize the pace of modern pop music production and the expectations fans have with how often their favorite artist’s release music.  

With “Replay,” Rihanna introduced herself in 2005 as the girl next door with an island twist. Her sweet, flirtatious vocal tone and casual exchanges with the DJ kept her in lockstep with top 40’s proclivity for the dancefloor, but she did all of it over a handclap-laden, dancehall-lite beat that recalled Skatta’s “Coolie Dance” riddim, which owned pop radio the year prior. A no-brainer pick for her debut album’s lead single, “Pon De Replay” reached No. 2 on the Billboard Hot 100; Music of the Sun, its parent album, would debut No. 10 on the Billboard 200 and spawn the follow-up single “If It’s Lovin’ That You Want” (No. 36), announcing Rihanna as one of pop’s most promising newcomers, but not doing enough to fully convince the world that she’d be in it for the long haul. Though “Pon De Replay” was a verifiable success, Teairra Mari was still the “Princess of the Roc” at the time, and more of a priority for Def Jam. 

Exactly six months after the release of “If It’s Lovin’,” Rihanna obliterated the one-hit wonder allegations and unleashed “SOS” as the lead single for her sophomore effort, 2006’s A Girl Like Me. “SOS” became her first Hot 100 No. 1, clearing a path for the set’s future top 10 hits “Unfaithful” (No. 6) and “Break It Off” (No. 9, with Sean Paul). While A Girl Like Me, which reached No. 5 on the Billboard 200, didn’t mark the stark change in image and sound that we’d later come to expect from a new Rihanna album release – after all, she was still cementing her spot in the pop ecosystem – it did help transform her into a pop girl who could spin hits out of dance-pop and R&B as easily as she could with more Caribbean-adjacent styles.   

If A Girl Like Me established Rihanna as bonafide pop princess, then 2007’s Good Girl Gone Bad solidified her as a capital-P, capital-S Pop Star. Every great pop star has an album or series of albums that demarcates exactly when they’ve transformed into a new animal. For Rihanna, Good Girl Gone Bad was that album– an aptly titled pop&B record that transposed the spunky, rebellious energy of her new shaggy, jet-black bob into a sleek collection of tentpole pop singles that housed some of the stickiest hooks of the late ‘00s. Led by the utterly enormous “Umbrella” — the 2007 Jay-Z collaboration (their first of many!) that topped the Hot 100 and earned her her first Grammy — Good Girl Gone Bad soundtracked the birth of Rihanna as a truly singular pop singer. Its eye-grabbing accompanying music video – who can forget that umbrella choreography?! — also helped establish Rihanna’s penchant for aesthetically rich visuals and won her first Moonperson for video of the year the MTV Video Music Awards. 

As would be the case with many of her singles, “Umbrella” embarked on quite the journey — including stints in Britney Spears’ and Mary J. Blige’s camps – before landing in Rihanna’s hands. “When she recorded the ‘ellas’ [in the hook], you knew it was about to be the jump-off,” “Umbrella” songwriter and producer Christopher “Tricky” Stewart told MTV News in 2008. “[You knew] your life was about change if you had anything to do with that record.” With her Bajan lilt evolving into a de facto Riri idiosyncrasy, Rihanna’s delivery single-handedly turned the last two syllables of the word “Umbrella” into one of the most unforgettable refrains in pop history. She made the song her own in a way that even those other legends probably wouldn’t have been able to. With “Umbrella,” Rihanna became the strongest producer of rap/sung collaborations since Mariah Carey effectively pioneered them with 1995’s Ol’ Dirty Bastard-assisted “Fantasy” remix; to date, five of Rihanna’s nine Grammy wins are for best rap/sung performance. 

In addition to “Umbrella,” Good Girl Gone Bad birthed hits in “Shut Up and Drive” (No. 15) and the No. 3-peaking, MJ-sampling “Don’t Stop the Music.” Rih also visited the top 10 with “Hate That I Love You” (No. 7), a duet with Ne-Yo, another pop&B Def Jam labelmate seeing success under Jay-Z’s guidance. In 2008, Rihanna revamped Good Girl Gone Bad with a deluxe edition that tacked on the Grammy-nominated Maroon 5 collaboration “If I Never See Your Face Again” (No. 51), a Halloween anthem in “Disturbia” (No. 1, two weeks) and “Take A Bow,” her first Hot 100-topping ballad. After barely scraping more than one hit off her sophomore LP, Rihanna had morphed into a pop music behemoth by her third album. To close out the year, she joined forces with T.I. for “Live Your Life,” which spent six weeks atop the Hot 100. Outside of the music, the Good Girl Gone Bad era also helped position Rihanna as the fashion icon and sex symbol she remains today; her edgy bob (she finally deaded those pesky Beyoncé comparisons) and seductive stage show shredded the girlish image of her first two albums and properly cast her as an adult pop star. 

Rihanna

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The night of the 51st Grammy Awards (Feb. 8, 2009) – where she earned three nods for the deluxe edition of Good Girl Gone Bad – was supposed to be a victory lap moment for Rihanna. But the pop superstar ended up canceling her scheduled performance. Initial reports claimed her then-boyfriend Chris Brown – one of the few teen-pop stars on Rih’s level at the time — had physically assaulted her. By March 5, Brown was charged with assault and making criminal threats. 

It’s hard to overstate just how deeply this incident rocked the world. Here were two of music’s biggest and brightest young stars – essentially America’s pop&B sweethearts — at the center of harrowing public example of intimate partner violence (IPV) – a haunting echo of the experiences Rihanna described of growing up witnessing her father physically abusing her mother. Just weeks after closing out an incredibly dominant year in music, Rihanna was cast by some fans and members of the media as the villain and endlessly harassed by those who felt Brown did nothing wrong. Two weeks after the incident, TMZ published an unauthorized photo of a battered and bruised Rihanna that appeared to have been leaked from the Los Angeles police department, effectively changing the public’s relationship to celebrity survivors of IPV forever.  

Those photos circulated cable news stations and gossip blogs alike, with any and everyone clamoring for access to jeer at Rihanna while she was at her lowest. This phenomenon even spurred the proposal of “Rihanna’s Law” — which, if enacted, would have discouraged law enforcement employees from releasing photos or information that exploits victims. By June, Brown pleaded guilty to felony assault, and he received five years of probation and an order to stay 50 yards away from Rihanna barring public events. Brown and Rihanna would reconcile both romantically and musically a few years down the line, but their reunions would always be met with some degree of discomfort, disapproval and confusion. 

By August, Rihanna would return to music alongside Kanye West and Jay-Z with “Run This Town” (No. 2), which won a pair of Grammys and served as her first post-assault release. Meanwhile, the events and subsequent chaos of the 2009 Grammys loomed large over Rihanna’s next release, Rated R, her fourth studio album. Led by the somber “Russian Roulette,” Rihanna processed the emotional trauma of the preceding months and the demise of her and Brown’s relationship through rock-infused ruminations on love, lust, loss, violence, longing and how all of those different energies intersect. Her commanding tone took on a more militant vibe that was reflected in music videos like the clip for her Jeezy-assisted “Hard,” while her fashion became even more punk-influenced, exacerbating the album’s overall grayscale bleakness.  

Both “Russian Roulette” (No. 9) and “Hard” (No. 8) reached the Hot 100’s top 10, but Rated R’s sole No. 1 hit, “Rude Boy,” found Rihanna returning to the dancehall influences that she first captured America’s attention with. Perhaps one of her most important Hot 100 chart-toppers, “Rude Boy” marked the moment Rihanna committed to a truly unapologetic embrace of her sexuality – a daring, provocative and admirable choice in an era where most expected her to dial down her forwardness following Brown’s assault. Rihanna’s decision to double down on owning and flaunting her sexuality in spite of the patriarchy’s attempts to silence and conceal her became paramount to her brand going forward. The more she stood firm in her expression of her sexuality, the more loved, hated and influential she became. But she outwardly rejected the “role model” label – and would continue to throughout her career – making her pop’s favorite rebel and one of celebrity’s greatest challengers. 

Before Taylor Swift (Folklore and Evermore) and Ariana Grande (Sweetener and thank u, next) were putting out “sister albums” in quick succession, Rihanna was doing it with Rated R and Loud. Released just three and half months after the final Rated R single (“Te Amo”), Loud traded Riri’s heavy eyeliner and highlight-streaked bowl cuts for fire-engine red curls and a bold red lip. Musically, buoyant dance-pop and explosive love-centric choruses took the place of Rated R’s penchant for foreboding rock ‘n’ roll. Returning to the commercial glory of Good Girl Gone Bad, Loud launched three Hot 100 chart-toppers: “Only Girl (In The World),” “What’s My Name” (with Drake) and “S&M,” with Britney Spears’ much-hyped remix appearance pushing the song over the top. (Fascinatingly, “Only Girl” remains the only solo Rihanna song to ever win a Grammy, for best dance recording.)  

Across Loud — which earned four Grammy nominations, including album of the year – Rihanna added much-needed levity and verve to the artistic strides she made on Rated R. She dialed up her embrace of her sexuality to 100 – live performances of “S&M” sparked concern for producers at both the 2011 Brits and Billboard Music Awards – while beloved cuts like “Man Down” continued Rated R’s exploration of vengeance and loving things that may not always be good for you. In addition to its bevy of hits, Loud also spawned a tour of the same name that saw Rihanna performing at London’s iconic O2 arena for a whopping 10 dates. As pop entered the 2010s, that Rihanna reign had indeed not let up. Such was the magic of Rihanna’s yearly album releases, she offset her near-constant presence with radically different sounds and looks, making her a chameleon, always a step or two ahead of where pop music was at a given time. 

To bridge Rated R and Loud, Rihanna linked up with Eminem for “Love the Way You Lie,” a haunting rap ballad that topped the Hot 100 for seven weeks during the summer of 2010 and earned five Grammy nominations. Inspired by her own experiences in an abusive relationship, Skylar Grey penned the track’s chorus for Alex da Kid’s demo before Eminem heard it and specifically asked Rihanna to hop on it. Both Rihanna and Eminem have had public stints in abusive relationships – albeit on different sides of the equation – so their real-life experiences infused the song’s exploration of the IPV cycle with stunning gravitas. (She made another cameo on another similarly themed hit later in the year, with her appearance on Kanye West’s spellbinding and brutal “All of the Lights.”) At once a grueling emotional undertaking and an expertly constructed pop song, “Love the Way You Lie” marked the beginning of a union that would spawn three more collaborations – including 2013’s Grammy-winning Hot 100 chart-topper “The Monster” — and a joint six-date stadium trek in 2014. 

By the time Rihanna dropped Talk That Talk in 2011, top 40 was comfortably in the throes of its love affair with EDM-driven dance-pop. Having already visited similar styles dating back to “SOS,” Rihanna easily and unsurprisingly adapted to Eurodance dominance of the times with “We Found Love,” the era-defining lead single for Talk That Talk. The rousing dance track simultaneously doubled as a thesis for Rihanna’s entire musical career – what’s a Rihanna song without searching for a love in places that should be devoid of it? — and helped further introduce Calvin Harris, who was about to break out with “Feels So Close.”  

With an acclaimed Grammy and VMA-winning music video (she’s the first woman to win video of the year at the MTV Video Music Awards twice), millions of copies sold worldwide and 10 weeks atop the Hot 100, “We Found Love” is arguably the defining song of Rihanna’s career. Just as her commanding voice developed a militant edge for Rated R, Rihanna morphed her voice into something closer to the anthem-belting house divas of the ‘90s with a robust, joyful timbre. When she slips into her falsetto each time she sings the word “hopeless,” effortlessly capturing the whimsy of the Harris’ blaring synths, that’s the stuff pop greatness is made of. “We Found Love” was so massive and so undeniably great that everyone wanted to be part of its lore; both Leona Lewis and Nicole Scherzinger claimed to have had the song before Rihanna, a testament to Riri’s evolution from perusing other pop stars’ scraps to being the biggest get in the world for a pop songwriter. 

Talk That Talk reached No. 3 on the Billboard 200 and spawned five additional singles: “Where Have You Been” (No. 5), “You Da One” (No. 14), “Talk That Talk” (No. 31, with Jay-Z), “Birthday Cake” (No. 24, with Chris Brown) and “Cockiness,” which did not reach the Hot 100 but did earn a remix with A$AP Rocky, the future father of Rih’s two sons who also performed a notably frisky, booty-grabbing rendition of the track with Rih at the 2012 VMAs. While some critics derided the album’s overt preoccupation with sexual themes, Talk That Talk reiterated Rihanna’s position as a hit machine who was unafraid to court controversy. 

Rihanna

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After years of seamlessly shifting in and out of seemingly disparate styles and looks, 2011 and 2012 were the years when it seemed like Rihanna was finally getting recognized for her gifts as a master aesthetic curator in real-time. In simpler terms, everyone wanted to be like Rihanna, and the explosion of the Instagram era put that collective yearning for her specific cool on full display.  

Between her Twitter (now X) clapback era, the Isis chest tattoo, pitch-perfect street style, her black pixie cut and her affinity for blunts and free nipples, Rihanna’s cavalier, mess-with-me-if-you-dare attitude dictated an entire generation’s curation of their own personalities and styles. You couldn’t scroll Instagram without coming across several accounts that were trying to recreate some part of Rihanna’s aesthetic. Whether she was sparring with Ciara or dismissing Kendall Jenner, Rihanna was pop’s favorite mean girl during this time, Regina George be damned. (2012 was also the year of Rih’s acting debut – Peter Berg’s critical and commercial stinker Battleship; a more successful foray into live-action film would come in 2018 with Gary Ross’ $300 million-grossing Ocean’s 8.) 

Less than a month after “Cockiness” closed the Talk That Talk era, Rihanna launched the Sia-penned “Diamonds” as the lead single for Unapologetic, her seventh studio album. Though “Diamonds” slowed down the tempos of her previous records, the soaring ballad wasn’t entirely representative of its parent album’s high-octane combination of trap, reggae, R&B and dance-pop. The rest of the album’s singles – including “Stay” (No. 3, with Mikky Ekko) and “Pour It Up” (No. 19), “Right Now” (No. 50, with David Guetta) and “What Now” (No. 25) — all reached the Hot 100.  

Both her first album to top the Billboard 200 and win a Grammy (best urban contemporary album), Unapologetic is – in quite a few ways – an unofficial sequel to Good Girl Gone Bad. Not only did Rihanna spend the set feeding her cross-genre inclinations, but she also infused her songwriting and themes with the high drama of celebrity; anxiety-wracked tracks like “Get It Over With” complemented more jaw-dropping moments like “Nobody’s Business,” an unsubtle Brown duet that explicitly winks, nods and scoffs at the expected, horrified reactions to the two ex-lovers’ reunion. Aided by a nifty mixture of hip-hop/R&B samples and an all-star roster of songwriters and producers, Unapologetic, for many, remains Riri’s magnum opus. 

Before Rihanna got to 2016’s Anti – the other album most frequently considered her masterpiece – she spent some time completing side quests and getting a little weird. She commenced 2014 with “Can’t Remember to Forget You” — an underrated Shakira duet – and a planned break from music. After spending summer 2014 on tour with Eminem, Rihanna wouldn’t return with new music until the very beginning of the next year. At the top of 2015, she recruited West and Paul McCartney for “FourFiveSeconds,” a folksy acoustic pop ditty that peaked at No. 4 on the Hot 100 and signaled a massive shift from digitized soundscapes of Unapologetic. Rambunctious trap banger “Bitch Better Have My Money” arrived in March, reaching No. 15 on the Hot 100, with a cinematic, Mads Mikkelsen-starring music video that played into the theory that song was (at least partially) inspired by the former accountants Riri sued in 2012. Finally, the American Dream-exalting “American Oxygen” (No. 78) arrived in April with an accompanying patriotic music video; the dubstep ballad would unwittingly herald President-Elect Donald Trump’s arrival in the U.S. political arena two months later. 

Despite each of the three singles earning critical acclaim, none of them ended up attached to a larger project, and details on what would eventually be known as Anti remained muddied. In fact, the only musical project Rihanna released in 2015 was Home, a tepidly received companion soundtrack to the children’s animated film she starred in that year. While she cooled off on the music side, this is when Rihanna truly started to make strides in the fashion world beyond her capacity as a pop star; she was appointed creative director of Puma in 2014 and expanded her fragrance line to men’s scents that same year. By this point, Rihanna was a MET Gala regular, but her 2015 appearance in Chinese designer Guo Pei’s dramatic yellow gown cemented her as the undisputed queen of the fashion event. Easily the most-memed MET Gala fashion moment of all time, Rihanna’s regal pose and eye-popping train once again reminded us of her ability to dominate the news cycle with a single garment – just as she did with her sheer, Swarovski crystal-encrusted gown at the 2014 CFDA Awards, where she was honored with the Fashion Icon award. 

In late 2015, Roc Nation successfully orchestrated a deal with Samsung to sponsor the rollout and tour for Rihanna’s forthcoming album. The album in question, of course, was Anti. That deal gave way to “AntiDiary” — a series of digital and in-person activations that brought fans inside the world of the album. Ultimately, the “AntiDiary” endeavor fell flat, with its accompanying visuals uninterestingly reflecting on past Rihanna eras in anticipation for the one on the way. Plagued by a start-stop creative process, the looming shadows of Samsung and Tidal, West dropping out as executive producer and an eleventh-hour leak, Anti finally arrived on Jan. 28, 2016. The Hot 100-topping, Drake-assisted “Work” preceded the album by a day, and the full set was accidentally uploaded prematurely to TIDAL, through which one million copies of the album were available for free download via Samsung. Due to its messy release, Anti earned a meager No. 27 debut before peaking at No. 1 on the Billboard 200 after its first full week of release.  

Despite the extremely messy rollout, the album ended up being a resounding success. Nominated for six Grammys, Anti harnessed the emotional turmoil and faith-based crises of Rihanna’s post-Unapologetic years into a liberating journey through soul, hip-hop, folk, trap, dancehall and more. Though the Prince-evoking “Kiss It Better” topped out at No. 62, two more Anti singles joined “Work” in the Hot 100’s top 10: the doo-wop-infused “Love on the Brain” (No. 5) and “Needed Me” (No. 7), a continuation of the murderous path she first ventured on with “Man Down” that doubles as the longest-running Hot 100 entry of her career (45 weeks).  

With Anti, Rihanna reached levels of artistic triumph that she had never previously seen. From the Dido-nodding “Never Ending” to a beloved cover of Tame Impala’s “New Person, Same Old Mistakes,” Anti fearlessly flaunted the full breadth of Rihanna’s musical influences and interests. For the first time since Rated R – maybe ever – people were lauding a Rihanna album as a musical and artistic statement, not just an impressive hodgepodge of hit singles. Despite its rocky start and the Grammys’ cold shoulder, Anti remains on the Billboard 200 today, now the longest-running album by a Black woman in the chart’s history (445 weeks and counting). 

While the business side of things may have been hectic, 2015-16 housed some of Rihanna’s best and most defining performances. In addition to her routinely lauded career-spanning medleys at the 2016 MTV Video Music Awards – where she was honored with the Michael Jackson Video Vanguard Award and hilariously curved a kiss from Drake on national television – Rih also shut down the 2016 Brits with SZA and Drizzy, made a green fur coat and an onstage helicopter nothing short of iconic with her 2015 iHeartRadio Music Awards performance and brought the 2016 BBMAs crowd to tears with an impassioned rendition of “Love on the Brain.” Rihanna’s stage show has never been the single most vital part of her artistry, but she certainly found her pocket in this era – probably because the songs finally sounded the most like what Rihanna wants to make versus how other cooks think her music should sound. That level of artistic maturation after already debuting with such a keen eye and ear is what made – and continues to make – Rihanna such an outstanding and alluring pop star.  

Outisde of her own music, Rihanna spent the rest of 2016 and 2017 pumping out collaborations. In retrospect, she was probably giving the world as much music as she could before she shifted her focus to her growing business empire – but at the time, it just felt like Rih was meeting the public’s bottomless demand for more of her, as 2016 spawned more Rih-assisted hits for West (“Famous”), Harris (“This Is What You Came For”) and Drake (“Too Good”), while the following year found her linking up with N.E.R.D. (“Lemon”), Future (“Selfish”), Kendrick Lamar (“Loyalty”) and DJ Khaled and Bryson Tiller (“Wild Thoughts”). 

With the launch of Fenty Beauty in 2017, Rihanna effectively quiet-quit pop stardom – kind of. The makeup brand continues to be a resounding success, cementing Rihanna as a pioneer in beauty industry inclusivity and a powerhouse brand across mediums and disciplines. She has since launched skincare (Fenty Skin) and healthcare (Fenty Hair) offshoots for the brand. In 2018, she debuted Savage x Fenty, a lingerie brand whose annual fashion show quickly became a worthy competitor to the iconic Victoria’s Secret fashion show. By 2019, she launched the now-closed Fenty fashion brand under luxury goods company LVMH, which made her both the first woman to create an original brand for LVMH and the first woman of color to lead an LVMH brand. Of course, these business strides came years after she teamed up with Puma for products like the “Creeper” sneaker, which allowed fans an avenue to literally buy Rihanna’s swag for themselves. 

Rihanna

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The last five years or so of Rihanna’s career have seen more personal developments than musical ones. Currently in domestic bliss with longtime beau A$AP Rocky and their two sons, RZA, 2, and Riot, 1, Riri has popped back into music for two major moments since the turn of the decade. In 2022, she contributed two original songs to the Black Panther: Wakanda Forever soundtrack: “Born Again” and “Lift Me Up,” a moving tribute to the late Chadwick Boseman that peaked at No. 2 on the Hot 100 and earned Academy Award and Grammy nominations. The following year, she reversed her Colin Kaepernick-inspired NFL boycott and headlined the 2023 Super Bowl Halftime Show. She played hits from across her career, cheekily promoted Fenty Beauty, and revealed a then-unannounced pregnancy in one fell swoop, earning two Emmys and the most-watched halftime show in history (121.017 million viewers). 

With 14 Hot 100 No. 1 hits (the most chart-toppers of any artist this century), two Billboard 200 No. 1 albums, nine Grammys, an endlessly imitated voice and a single name that can make virtually any door open from music to cosmetics to fashion, becoming the “Black Madonna” is comfortably in Rihanna’s rearview mirror. She’s something arguably even more awe-inspiring: a Black Caribbean immigrant woman whose talent, grit and inimitable charisma made her one of the important and successful pop singers in history. She’s Rihanna – there are tens of hundreds of pop stars out there eager to put a modifier in front of her name and fashion her blueprint into something of their own. 

Read more about the Greatest Pop Stars of the 21st Century here — find our accompanying podcast deep dives and ranking explanations here — and be sure to check back next Tuesday (Nov. 26) as we reveal our No. 2, before unveiling our No. 1 Greatest Pop Star on Dec. 3!

THE LIST SO FAR:

Honorable Mentions

25. Katy Perry24. Ed Sheeran23. Bad Bunny22. One Direction21. Lil Wayne20. Bruno Mars19. BTS18. The Weeknd17. Shakira16. Jay-Z15. Miley Cyrus14. Justin Timberlake13. Nicki Minaj12. Eminem11. Usher10. Adele9. Ariana Grande8. Justin Bieber7. Kanye West6. Britney Spears5. Lady Gaga4. Drake3. Rihanna

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. You can see the stars who have made our list so far here — and now, we examine the century in Lady Gaga, a game-changing phenomenon whose peerless opening run continues to loom large in contemporary pop music. (Hear more discussion of Gaga and explanation of her list ranking on our Greatest Pop Stars podcast, with the new episode debuting Nov. 6.)

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When considering the entirety of pop star greatness across the first 25 years of this century, there might not be a more iconic sound than these five nonsensical syllables: “Rahhh, rahhh, ah-ah-ahhh!”

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Behold “Bad Romance,” pop perfection incarnate. There’s that earworm refrain, followed by formidably declarative verses, a powder keg of a chorus and a high-concept bridge. There’s the collection of raved-out synths, and the voice that met their harshness with beauty and command. There’s the music video — still perhaps the greatest of the 21st century so far — full of bathhouse coffins, exploding beds, disorienting contact lenses and bewitching dance moves. There were the TV performances, which ranged from piano-medley stately to nude-bodysuit, alien-mask outrageous. It all elevated contemporary pop — clock the French phrases before the final chorus, or the body horror and feminist fury of its video — without looking down on it, or veering too far away from its most immediate pleasures.

Every millimeter of Lady Gaga’s 2009 single, and how it was presented to the world, stood out as special — burned into the memory of any pop fan paying the slightest bit of attention 15 years ago, and largely remaining so today. “Bad Romance” was not Gaga’s first hit, her biggest hit, and it’s not her most-streamed song today. Yet a moment like “Bad Romance” – one that capped a year of increasingly massive moments, in one of the most unforgettable breakout runs in pop music history – is the reason why Lady Gaga is so indispensable to the modern pop landscape, an audacious superstar who can stun, thrill, bewilder and satisfy in the span of one radio-ready single.

Such is the power of Stefani Joanne Angelina Germanotta, who has spent her career holding up fragile ideas of modern pop stardom and vigorously shaking them like a snow globe. Lady Gaga started off as an overnight sensation, then maintained that superstardom as pop’s center of gravity for the next few years -– before an inevitable comedown period, a fascinating reinvention (or three), and a return to music’s forefront that sees Gaga remaining one of its top hitmakers and headliners today.

Once her hits multiplied, she switched up her electro-pop aesthetic, diving into classic rock, country and the great American songbook; she has made philanthropy and LGBTQ+ rights a core part of her professional identity; and she is the only person on the planet who has been nominated for a best actress Oscar and headlined a Super Bowl halftime show. She has kept us on our toes for 15 years, reinventing what a modern pop star can achieve, while also delivering banger after banger.

Lady Gaga

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Lady Gaga

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That run began with “Just Dance,” which catapulted the native of New York’s Upper West Side — a musical prodigy and theater kid who landed a role as an extra on The Sopranos a few years before attending NYU — onto top 40 radio with her first single as a solo artist. Adopting her moniker from the Queen song “Radio Ga Ga” after dropping out of college, she kicked around the industry for a few years, playing NYC club gigs and writing for other artists — but ‘00s pop and R&B hitmaker Akon took a shine to Lady Gaga, signed her to his KonLive imprint through Interscope, and co-wrote “Just Dance” with Gaga and a rising producer named RedOne.

Before turbo-pop took off at the beginning of the 2010s by enmeshing top 40 with EDM music, Gaga’s glammed-up synth-pop anthem captured the feeling of being bleary-eyed at the club but dancing to your favorite song anyway. “Just Dance” (which featured another Akon protege, Colby O’Donis) was a bright, ultra-catchy entry point for Gaga, spending three weeks atop the Billboard Hot 100 in early 2009 and introducing her as a striking new star, a lightning bolt painted on her cheek in its music video. The song — which almost ended up with The Pussycat Dolls or Gwen Stefani before Gaga claimed it as her own — may have downplayed her audacious personality for sake of accessibility, but “Just Dance” was a spiked-toe boot in the door.

With “Poker Face,” the follow-up single that followed it to the Hot 100’s summit a few months later, Gaga kicked that door wide open. The song was another club-ready electro-pop jam, but contained far more Gaga fingerprints, from the murmured “Muh-muh-muh-MA!” refrain, to the steely cool of the verses, to the big-voiced chorus, to the “I’m bluffin’ with my muffin!” winks. Its music video began with a cracked disco ball fashioned into a mask covering Gaga’s eyes, stepping out of a pool in slow motion as lightning crackles in the sky behind her; it’s a superhero’s entrance, and it helped establish Gaga as a striking visual artist, worthy of peak-MTV greatness and ready to dominate in the YouTube era.

Those two smashes kicked off one of the finest imperial eras in modern pop stardom: The Fame, Lady Gaga’s 2008 debut album, became a juggernaut through 2009, as follow-up singles like “LoveGame” and “Paparazzi” streaked into the top 10. The hits showcased different sides of Gaga’s aesthetic: while the “LoveGame” music video placed her sexuality front and center as Gaga kissed men and women, “Paparazzi” received an extended visual fantasia, commenting on the trappings of fame while exacting vengeance on a murderous lover, played by Alexander Skarsgård. 

As they started to take off on the charts, Gaga went on a run of jaw-dropping primetime performances: most memorably at the 2009 VMAs, where fake blood dripped down Gaga’s torso as she belted out “Paparazzi,” eliciting gasps from the audience. At the start of the 2010 Grammys, where The Fame was nominated for album of the year, Gaga played “Poker Face” as a heart-wrenching ballad, before surprise guest Elton John came out to perform his classic “Your Song” and her own ballad “Speechless.” Just like that, the most audacious pop performer of his generation had seemingly blessed the new torchbearer.

Every new Gaga single from The Fame hit with force, every new music video created an eye-popping ecosystem, every awards performance became must-see TV – and the artist in the eye of the hurricane started to look like a generational talent. Then, Lady Gaga decided to do the best thing she could at the end of The Fame era: she extended it. The Fame Monster, an eight-song project bundled with the rest of its predecessor that was released in time for the 2009 holidays, sent her even higher into pop’s stratosphere – first with “Bad Romance,” then the breathless Beyoncé team-up “Telephone” and finally the Europop opus “Alejandro,” which all hit the top 10 and added to her cultural ubiquity. The “Telephone” music video – a nine-minute, revenge-fueled Tarantino riff co-starring Gaga and Bey – was the type of pop culture event that was seldom seen in a post-TRL pop landscape.

The Fame Monster may have existed as a precursor to the modern deluxe edition of an album, but those singles proved so vital that it followed The Fame to an album of the year Grammy nom the following year. Meanwhile, the project also set up Gaga’s first arena headlining shows as part of the Monster Ball tour, which kicked off one week after the release of The Fame Monster and emerged from the ashes of a failed co-headlining tour with Kanye West. No matter: Gaga got to dazzle in front of her ever-growing fan base, the Little Monsters, and after opening the tour with theater dates, the Monster Ball eventually grew big enough to produce an HBO special filmed at New York’s Madison Square Garden.

The fact that Lady Gaga kept making headlines as her first proper era started to wind down — at the 2010 VMAs, for instance, she won Video of the Year while rocking the immediately iconic “meat dress” — heightened expectations for her follow-up to an unfathomable level. Gaga’s rise was meteoric; how could she possibly top it, now working with a much bigger budget and impossible clout? 

Born This Way, released in 2011, brandished its flashier pedigree in spots, with E Street Band sax-man Clarence Clemons and Queen guitarist Brian May listed among the liner notes. But the album’s mix of empowering dance-pop and bombastic arena rock was unquestionably Gaga’s brainchild — no one else made the decision to place her head at the front of a motorcycle on the album cover. The title track’s whirring percussion and synth throb was overshadowed by its message of self-acceptance, explicitly aimed at the LGBTQ+ community (“Don’t be a drag, just be a queen,” goes the most quotable line), and i tmade history as the 1,000th song to top the Hot 100 when it debuted at No. 1 in February 2011 — becoming the first chart-topper to include the word “transgender” in its lyrics.

The rest of the Born This Way era was a bit bumpier than the all-killer-no-filler Gaga run that preceded it: though it was an immediate smash, the title track never escaped accusations that it sounded too similar to Madonna’s “Express Yourself,” with both artists asked about the melodic callback throughout 2011 and sharing different POVs on what was and was not re-created. And the singles that followed “Born This Way” — the thumping RedOne reunion “Judas”; the lungs-deflating rock anthem “The Edge of Glory”; the country-tinged, Mutt Lange-helmed “Yoü and I,” which introduced Jo Calderone, Gaga’s male alter ego-as-performance art — were all top 10 Hot 100 hits, but not quite with the radio-rupturing magnitude of her Fame singles. Yet at this point, Gaga was too big to fail: Born This Way bowed with 1.1 million copies sold in its first week, which easily remains the best mark of her career — although Amazon offering the full album as a 99-cent download during its release week ultimately placed something of an asterisk next to those seven figures in the view of some onlookers.

If cracks in the foundation of Gaga’s superstardom started to show over the course of the Born This Way campaign, its 2013 follow-up Artpop was a full-blown sinkhole. Dreamed up as a multimedia compound of fine art and modern pop, Artpop was rolled out with “the world’s first flying dress,” named the Volantis; new works by renowned artists like Jeff Koons (who created a statue of Gaga for the album cover), Marina Abramović and Robert Wilson, among others; and an app that let fans create their own pieces of artwork while chatting about the new album. Oh yeah, the album: It was a re-imagining of Gaga’s synth-pop beginnings – with lead single “Applause” serving as an EDM-adjacent commentary on performing on the world’s grandest stages – but also included forays into hip-hop (“Jewels n’ Drugs,” with T.I., Too Short and Twista), glam rock (“Venus”) and industrial (“Swine”).

Artpop remains a fascinating mishmash of styles and messages, and “Applause” became another top 10 hit, but the album underperformed relative to Gaga’s track record, was derided as a flop, and generally confused a public that was hungry for more groundbreaking songs and videos. A decade later, even the album’s cult following still can’t figure out what the heck the flying dress had to do with anything.  Worst of all, second single “Do What U Want” co-starred R. Kelly as Gaga’s duet partner — released years prior to the R&B star’s conviction on sex trafficking and racketeering charges, but around the time that allegations had begun to resurface. Upon Kelly’s 2019 arrest, Gaga removed “Do What U Want” from streaming services, a moral stain wiped away from a misfire.

Following Artpop, Lady Gaga needed a reset — and she turned to an unexpected source. Tony Bennett was 88 years old when Cheek to Cheek, an album of jazz-standard duets with Gaga, was released in September 2014, an industry legend who sounded as warm and charming in the studio as ever; meanwhile, Gaga could showcase the potent vocals that had distinguished her as a theater student but had been masked by artifice on Artpop. 

Cheek to Cheek was a surprise hit, bringing Gershwin and Porter songs to the top of the Billboard 200 decades after their deaths; Gaga’s mojo had been slightly regained, but more importantly, her creative partnership and personal friendship with Bennett blossomed. When they re-teamed for another set, Love for Sale, in 2021, the pair earned an album of the year Grammy nomination, Bennett’s final such nod before his 2023 passing at the age of 96.

Lady Gaga

Kevin Mazur/Getty Images for Live Nation

The reinvention that Cheek to Cheek represented coincided with Gaga taking some time away from album-campaign mode and delving into other interests. She dabbled in Hollywood projects like Sin City: A Dame to Kill For and American Horror Story, and became an ambassador for a Versace campaign. At the 2015 Academy Awards, Gaga earned a standing ovation for belting out a medley from The Sound of Music — and at the following year’s Oscars, she was a nominee for best original song, for the harrowing “Til It Happens to You” from the campus rape documentary The Hunting Ground. As more time elapsed from Artpop, Gaga reminded the world that she was a captivating visual performer and gifted vocalist; the comeback narrative was ripe for the taking.

Joanne, Gaga’s 2016 album, was named after her late aunt, and featured Gaga looking up into a cowboy hat on its cover. As such, the full-length was more personal than Artpop and boasted a country undercurrent, with nods toward classic rock and Americana akin to Born This Way. Gaga had moved into a different phase of her career as a hitmaker by this point — “Perfect Illusion,” the album’s sneakily excellent dance-rock lead single co-produced by Tame Impala’s Kevin Parker, received a splashy rollout, but peaked only at No. 15 on the Hot 100, and its parent album debuted at No. 1 on the Billboard 200 but drew mixed reviews. Yet Gaga’s return to the spotlight was in part presented as a legacy artist with a bulletproof back catalog, thanks in part to something that took place four months after Joanne: the Super Bowl.

Although Gaga’s halftime performance on Feb. 5, 2017 was not the politically barbed showcase that some expected following the election of Donald Trump a few months prior, her show was both visually dazzling (beginning with a dive from the rooftop of Houston’s NRG Stadium) and culturally impactful (performing “Born This Way” on the biggest stage in the world was a raised fist in support of the LGBTQ+ community). And the Super Bowl halftime show also partially redeemed the commercial legacy of Joanne: “Million Reasons,” the album’s piano-led power ballad, was given a prime slot in the set list, and belatedly reached No. 4 on the Hot 100.

The success of “Million Reasons” unwittingly served as the blueprint for an even bigger hit the following year. After spending the rest of 2017 touring the world behind Joanne (including a headlining slot at Coachella, swooping in to replace a pregnant Beyoncé atop the bill), Gaga devoted 2018 to her first Hollywood starring role, in Bradley Cooper’s remake of A Star is Born. After spot acting roles in the 2010s, Gaga was given ample room to emote and bewitch as Ally, a struggling singer-songwriter who begins a wind-swept romance with Cooper’s country-rock A-lister, Jackson Maine.

A Star is Born became a box office smash and meme-spawning pop culture phenomenon that earned Gaga an Oscar nomination for best actress, cementing the pop superstar as a Hollywood headliner. Yet for longtime fans of her music, the film’s original soundtrack was the true payoff from the project, with plenty of heartfelt torch songs and eye-watering balladry across a track list that Gaga helmed with producers like Dave Cobb and Lukas Nelson, and artists like Mark Ronson and Jason Isbell. Most importantly, the film and soundtrack contained a centerpiece song that lived up to its placement.

“Shallow,” a duet between Gaga and Cooper posited in Star as the song that solidifies their characters’ bond forever, harnessed Gaga’s pop power for a country-rock sing-along, recalling the sweep of “Million Reasons” and heightening the drama tenfold. “Shallow” transcended A Star is Born to become a pop hit in its own right — and after Gaga and Cooper performed the duet at the Academy Awards, where “Shallow” won the best original song trophy, the song zoomed to the top of the Hot 100, the general population embracing a special moment at the awards ceremony. Years after dazzling in primetime by covering herself in fake blood, Gaga had graced the Oscars stage with utmost elegance, capable of evolving her talents and becoming a stately pop spokeswoman.

At this point, Gaga was squarely in her thirties and with nothing left to prove as a commercial star — yet it had simply been too long since she had unleashed any radio-ready bangers. Chromatica, her 2020 album that represented a return to unabashedly hooky electro-pop, was released at the height of the COVID-19 pandemic lockdown, and acted as a balm for pop fans during a difficult moment in the world.

Although Chromatica recalled elements of The Fame and The Fame Monster sonically and lyrically, with lead single “Stupid Love” built around ecstatic electronic squeals and “Sour Candy” (featuring K-pop girl group BLACKPINK) bursting with sexually charged double entendres, the album featured a more mature perspective as it explored themes of healing, overcoming trauma and embracing positivity. “Rain on Me,” Gaga’s house-inspired duet with Ariana Grande, turned into an unexpected rallying cry in quarantine — “I’d rather be dry, but at least I’m alive/ Rain on me,” goes the chorus — and the song debuted atop the Hot 100, later winning a Grammy for best pop duo/group performance.

More than a decade after her breakthrough, Gaga had successfully returned to the sound where she began, and offered a piece of personal evolution for mass consumption. When lockdown ended, and Little Monsters got to watch Gaga perform “Rain on Me” in stadiums on her Chromatica Ball tour, the moment felt hard-earned, and euphoric.

Lady Gaga

Kevin Mazur/WireImage

If the history of Lady Gaga’s career is any indication, she is never going to stop entertaining, even as that entertainment takes different forms and plays out in different media. Just in the past few months, she co-starred in Joker: Folie à Deux, an R-rated musical where she got to play Harley Quinn; released Harlequin, a surprise “companion album” to the film full of jazz-standard covers; scored a soft-rock smash alongside Bruno Mars with “Die With a Smile,” currently the No. 2 song in the country; and dropped “Disease,” a darkly lit synth-pop single that will lead into a 2025 album. 

There are viewers and listeners in the center of the Venn diagram that those projects form, but Gaga has also demonstrated an ability to cater to different audiences by allowing her creativity to roam free. She’s been chasing her muse for 15 years, and whatever she comes up with next, you can bet that she’s going to pour her entire artistic soul into that endeavor, and that a lot of people will wrap their arms around it.

That’s why Lady Gaga has resonated with an entire generation of pop fans, from the longtime Little Monsters to the casual fans who can hum along to more of her hits than they realize, to the new stars like Chappell Roan who are internalizing Gaga’s performance art while existing at pop’s current vanguard. As a breath of fresh air on late 2000s radio, a button-pushing provocateur trying on different sounds, or a leading lady gracing the most prestigious stages or a daring performer commanding audiences of thousands, Lady Gaga has always been authentically herself, and will continue to be that forever – whether making social statements, presenting grand artistic projects, or simply proclaiming, “Rahhh, rahhh, ah-ah-ahhh!”

Read more about the Greatest Pop Stars of the 21st Century here — find our accompanying podcast deep dives and ranking explanations here — and be sure to check back every Tuesday this November as we unveil the rest of our top five, leading up to our No. 1 Greatest Pop Star being revealed on Dec. 3!

THE LIST SO FAR:

Honorable Mentions

25. Katy Perry24. Ed Sheeran23. Bad Bunny22. One Direction21. Lil Wayne20. Bruno Mars19. BTS18. The Weeknd17. Shakira16. Jay-Z15. Miley Cyrus14. Justin Timberlake13. Nicki Minaj12. Eminem11. Usher10. Adele9. Ariana Grande8. Justin Bieber7. Kanye West6. Britney Spears5. Lady Gaga

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. You can see the stars who have made our list so far here — and now, we examine the century in Britney Spears, a pop force whose dominance over Millennial culture earned her the title as Princess of Pop for her signature vocal tone, hit catalog and show-stopping performances. (Hear more discussion of Britney Spears and explanation of her list ranking on our Greatest Pop Stars podcast tomorrow (Oct. 30).)

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Few came, saw, and conquered global superstardom quite like Britney Spears. At the turn of the millennium, the teen queen captured the hearts of millions with her pop hits — and, unknowingly, set a business model that would carry for decades to come. But even when record labels tried to replicate the magic, they fell short, because it was largely Spears incorporating her creativity and personality into her career that made the Mississippi-born talent such a unique force. As the calendar changed centuries, no one held a tighter grip on pop’s new golden age than Britney, who became an icon with a reliable talent for creating zeitgeist-y moments — years before social media even existed. 

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While Spears’ celebrity and artistry recalled pop juggernauts Madonna and Janet Jackson, she was more reserved in relation to the limelight and never fully leaned into her fierce cultural impact. While some of her predecessors purposely aimed to bust down societal doors, Spears just wanted to excel as a pop star. She led with Southern charm and understated humility, and that juxtaposition added something special to her star power as it ascended (and sometimes tumbled) through the 2000s and into the 2010s, remaining squarely in the public consciousness to this day.

Britney Spears

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Britney Spears

Jon Reynoso/WireImage

Ironically, there was once a time when Spears’ endurance was up for debate, with comparisons to flash-in-the-pan pop stars of yesteryear. But really, we should’ve known from her first single that she was here to stay. The release of her debut single “…Baby One More Time” in late 1998 marked a cultural reset, jump-starting a reign that enthralled fans, initially shocked parents and forced the industry to follow her lead. With Swedish producer Max Martin at the helm, the song reached No. 1 on the Billboard Hot 100 — due, of course, in no small part to the accompanying high school-set music video (which, to the singer’s credit, was all her idea, coming after she rejected a video treatment that was much more convoluted). 

At just 16, it was a long time coming for Spears, whose experience and professionalism spanned pageants, gymnastics and a stint on Disney’s All-New Mickey Mouse Club. For the rest of us, it felt instantaneous, with her accompanying album of the same name dropping months later. Coming on the heels of debuts by the Backstreet Boys and *NSYNC, the LP brought the burgeoning TRL era of pop music to new heights and became the best-selling debut by a female teenage artist, moving over 14 million copies in the United States. With her growing arsenal of polished pop hits, dance-heavy music videos and girl-next-door persona, Spears set the stage for an even bigger splash at the beginning of the 21st century. (Britney’s ‘90s accomplishments were not factored into the Billboard staff’s calculations when determining her ranking on this solely 21st century-based list.) 

Spears’ 2000 sophomore LP Oops!…I Did It Again reunited the star with Max Martin, while bringing in veteran hitmakers Rodney Jerkins and Diane Warren for the “more mature” new effort — an arguable assessment, but the 17-year-old knew how to strike a chord with her fans: After all, she was already on a first-name basis with them. In April 2000, she returned with the ultimate friend zone anthem in the set’s title track, decked out in a cherry red catsuit for the now-iconic music video. Its parent album stormed the Billboard 200 upon its release a month later, selling a staggering 1.319 million copies in its first week — at the time garnering the largest first-week sales ever for an album by a female artist.

If critics dismissed her artistry due to her flashy showmanship and sex appeal, it was that very stage prowess that set her apart. Later that year, she hit the 2000 MTV Video Music Awards to perform a medley of “Oops” and a cover of The Rolling Stones’ “(I Can’t Get No) Satisfaction.” In three minutes, she managed a whole career pivot, tearing off a black suit to reveal a little sparkly ensemble — giving new meaning to being “not that innocent.” The media further vilified her for the performance, but it also set high expectations for what women (and Britney herself) could do in pop music. It was also one of the few windows in her career where she tried to strike a balance between live singing and the athleticism of her choreography as future performances would be mostly lip-synced, with Britney focusing on the physicality of her dancing.

With so much access to celebrity nowadays, it’s hard to fully understand the phenomenon that was Britney Spears at her commercial peak, but she was everywhere — dominating award shows, gracing magazine covers, starring in TV commercials, available for purchase as a Barbie doll and, of course, on the tip of everyone’s tongue. She was the pop princess for a new generation, at once sex-positive but demure, and arm-in-denim-arm with *NSYNC’s Justin Timberlake, the pair making for Y2K music’s ultimate power couple. While she supported her fellow women in pop and minded her business, the teen queen had some people angry, and others excessively inquisitive, a misogyny-laced treatment that would only get its proper reckoning years down the line. From intrusive questions about her virginity to men twice her age discounting her work, she remained mostly posed and polite until her next studio offering: 2001’s Britney.

Spears upped the ante for her third album, stepping to the plate as a young woman who unapologetically owned her sexuality. With a backbone provided by hip-hop superproducers The Neptunes, the set’s slinky lead single, “I’m a Slave 4 U,” served as a radical sonic shift for the star. She was still months away from her 20s, but the transition from teen sensation to adult superstar was met with criticism. Yet the song became another vehicle for her to shine on stage — and at the 2001 VMAs, she draped herself in a seven-foot python and churned out her most unforgettable performance to date. While she played up the role of sex kitten, the accompanying project, which continued her No. 1 streak on the Billboard 200, also captured her exploration of womanhood (“Not a Girl, Not Yet a Woman”), yearned for the normalcy of an average life (“Overprotected”) and channeled her inner Janet Jackson (“Boys”). 

Those follow-up singles failed to make the same impact as her former releases, possibly due to a rumored radio suppression, reportedly demoting the songs from high rotation. But by then, Spears had something else to focus on: her foray into Hollywood with her debut feature film, Crossroads. The coming-of-age story boasted a noteworthy ensemble, including Zoe Saldaña, Taryn Manning and Kim Cattrall, with Shonda Rhimes debuting her first screenplay — but despite Spears’ affable charm translating well to the silver screen, the movie didn’t hit the mark with critics. Simultaneously, her culture-dominating romance with Timberlake came to an end after three years, with the heartthrob reportedly ending the relationship via text message. With their split, the tabloids took sides, as rumors of infidelity spread concerning Spears and their joint choreographer Wade Robson, and Timberlake fueled the flames while launching his own solo career – particularly with his second solo single, the No. 3 Hot 100 smash “Cry Me a River,” which included a Britney lookalike in its video. 

It was clear that Spears needed some time away from the limelight, but before the end of 2002, she called off her planned six-month hiatus and started work on her most liberating album to that point, In the Zone. That set was also preceded by a new wave of headlines, courtesy of another steamy VMA performance – this time finding her lip locking with her idol, Madonna. The lightning-in-a-bottle moment prompted international headlines and downright hysteria: It was actually pretty tame by today’s standards, but those few seconds, complemented by cameras panning to a stone-faced Timberlake, rocked the world. In what could be perceived as the passing of the torch, Spears also recruited Madge for the frisky “Me Against the Music,” the album’s lead single, which was highly-anticipated and well received by fans, but failed to end her commercial dry spell, peaking at No. 35 on the Hot 100. 

Released a month after “Music,” Zone dabbled in hip-hop (“Outrageous”), pulsating euro-pop (“Breathe on Me”) and delicate slow songs (“Everytime,” soon to become her signature ballad). Most importantly, tucked six tracks deep on the album was “Toxic,” a theatrical dance-pop track with producers Bloodshy & Avant, led by a thick guitar line and Bollywood strings sample. Spears reportedly fought with her label to release the track as the album’s second single in early 2004 — and in the end, her vision paid off. The hit reached No. 9 on the Hot 100 and won best dance recording at the 2004 Grammys, marking her first (and to date only) win. It remains perhaps the most critically acclaimed three minutes and eighteen seconds of Britney’s career, and was ranked earlier this year as the Billboard staff’s No. 1 song of 2004. The companion video saw secret agent Spears dress as a stewardess, slither around in nothing but diamonds and poison her boyfriend, quickly becoming one of her most beloved visuals. 

At a time when it wasn’t cool to like Britney, “Toxic” shifted that narrative. Even though the world still regarded her and pop idol counterparts as record label puppets, she was nothing close to it — calling the shots on single releases and collaborators, and pushing back on the head honcho executives several times during this campaign. She ran with that agency and never looked back. Behind closed doors, though, things were starting to unravel. An impromptu visit to Las Vegas to marry her childhood friend Jason Allen Alexander caused concern. The union was annulled 55 hours afterward. Then, the overworked star suffered a leg injury while filming the video for “Outrageous” during a rare break in between dates of her “Onyx Hotel World Tour,” forcing her to cancel the rest of the trek and altering her performance ability forever.

Britney Spears

Jason Merritt/FilmMagic

The next few years for Spears were, well, chaotic, to say the least. Her romance with backup dancer-turned-husband Kevin Federline (and their subsequent reality show together) was heating up and the star shifted her perspective. The gloves were off and she was going to do as she pleased, both personally and professionally. Though she never earned the public’s stamp of approval for the relationship, Miss American Dream found ways of owning her decisions and clapping back with her music. A cover of Bobby Brown’s 1988 hit, “My Prerogative,” fronted her first compilation: 2004’s Greatest Hits: My Prerogative, while the eerie “Mona Lisa” foreshadowed her looming troubles. With only hours left until 2005, she dropped by Los Angeles’ KIIS-FM unexpectedly to preview the track, revealing it to be part of a project titled The Original Doll. 

For the next few years, career priorities would take a backseat as she and Federline welcomed two children, Sean Preston and Jayden James — but the unrelenting attention of the paparazzi increased and the star became the go-to cover girl for tabloid culture. Juggling motherhood, laying the groundwork for her next album and an eventual divorce from K-Fed put her at the eye of the gossip media storm, helping fuel the rise of outlets like Perez Hilton, TMZ and X17. Embarrassing and intrusive coverage of her led to headlines labeling her an unfit parent, while flashbulb moments like her shaving her head or attacking a paparazzo’s car with an umbrella turned her into a source for national mockery — but in the middle of the madness, Spears frequented nightclubs for inspiration, while recording what was to become her next album, 2007’s Blackout. For the first time in her career, there was no one to reel her in and she took agency, serving as executive producer of the project and exploring new sonic directions and collaborators. 

The result? Her magnum opus — demanding the attention of her peers, including Beyoncé and Rihanna, and the rest of the public eye. To this day, Blackout is still celebrated as an influential record for its edgy electro-pop sound and confidently sexual lyrics, and the album was even added to the Rock and Roll Hall of Fame’s musical library and archive in 2012. Brash, experimental and self-aware in its almost-menacing approach, the set was fronted by the Danja-produced “Gimme More,” where the star asserted her celebrity with a seismic three-word intro: “It’s Britney, bitch.” The song reached No. 3 on the Hot 100 — a massive win, considering it followed a lethargic comeback performance of the track on the VMA stage that year that saw her body-shamed and ridiculed. 

Despite the universally panned performance and continued public derision of Spears’ personal life in the media, Blackout still sold 290,000 copies in its first week and bowed at No. 2 on the Billboard 200. Even with sizable hits on her hands like the media clapback “Piece of Me” (a top 15 Hot 100 hit, and also her first VMA win for video of the year the next September), her personal life was imploding. She lost physical custody of her sons, while separately, parents Jamie and Lynn Spears (and soon-to-be business manager Lou Taylor) orchestrated a conservatorship over her personhood and estate after putting the singer on a 5150 involuntary psychiatric hold under California state law. The temporary-turned-permanent arrangement declared Britney was incapable of managing her financial affairs and making basic life decisions, but her workload over the following years would prove otherwise.

With all autonomy lost, Spears was pushed to work almost immediately, and everyone turned a blind eye to her restricted freedom as she hit the gym with fresh blonde extensions. She appeared on CBS’ How I Met Your Mother, helping the series log its highest ratings ever, and began recording yet another album, Circus. The 2008 project and its promo cycle was marketed as her return to form, a comeback project to redeem her from the turbulence of recent years — and released on her birthday, no less. It produced the lead single, “Womanizer,” which brought her back to the top of the Hot 100 for the first time since “…Baby One More Time.” She was smiling, in-shape and seemingly happy — and the success continued with follow-up singles: the dance-ready title track (a No. 3 hit) and the cheeky “If U Seek Amy” (No. 19). 

The subsequent Circus Starring Britney Spears Tour made its way around the world, but much like an actual circus, the star of the show was being mistreated. A growing disconnect between Spears and her craft became evident in music and performances, showing up more prominently throughout her following releases. Her next album, Femme Fatale, which dropped in 2011, embraced the EDM trend of the early 2010s. While the hits kept on coming (“Hold it Against Me,” No. 1; “Till the World Ends,” with a much-hyped remix featuring Nicki Minaj and Ke$ha, No. 3; and “I Wanna Go,” No. 7), the charm and charisma was starting to lose its spark in her performances and the impact of the conservatorship had taken its toll. Her appearance on Rihanna’s “S&M” remix and “Scream & Shout,” alongside will.i.am, extended her streak of hits, but she was about to run another victory lap and change the face of Las Vegas entertainment forever — whether she liked it or not. 

After years of releasing albums and counterpart tours, Spears’ next move revitalized both her career and the Las Vegas entertainment scene. Once a refuge for singers looking to relive their glory days, Sin City was given a facelift when her 2013 residency landed and she became the first contemporary act of her time to hit the strip. Aptly titled Britney: Piece of Me, the 90-minute show featured more than two dozen hits, incorporating classics and fan favorites, with the bells and whistles of her typical pop production. The show debuted weeks before the release of Britney Jean, a makeshift album marketed as her most personal project to-date, yet only produced a medium-sized hit with the campy “Work Bitch” and drew middling reviews. 

While still a contrast from the performer she once was, the residency saw Spears slowly come into her own again, running for four years and grossing $137.7 million. And for a fleeting moment, Britney Spears was Britney Spears again – with her million-dollar smile, dancing to a medley of hits at the 2016 Billboard Music Awards, where she also became the third recipient of the BBMA Millennium Award honor. Towards the latter part of the Vegas residency, the singer dropped 2016’s Glory, her last studio album to date, and it sounded like the spark was back: The collection was led by Weeknd-esque “Make Me,” featuring G-Eazy, and followed by a remix of “Slumber Party” with then-newcomer Tinashe. Those singles didn’t become the enduring hits of her ’00s albums, but Glory received strong reviews and served as an invaluable experience for the star, who later described it as “the one thing … that [she] really put her heart into” during her decade-plus conservatorship. 

Once the residency wrapped, Spears was seemingly gaining her autonomy back, but a reported dance rehearsal dispute with her father led to the cancellation of a follow-up Vegas residency, Britney: Domination. One red flag led to another and eventually a whistleblower alleged that she had been forced into a mental health facility against her will  — and the Free Britney movement was born. Court documents and (most fascinatingly) her Instagram account suddenly became sources to fans for possible clues and hints about her true feelings, turning the conspiracy theory into a full blown pop culture movement, garnering support from other pop icons like Miley Cyrus and Cher. In 2021, the Framing Britney Spears documentary brought more attention, while fan-orchestrated protests outside of court and a brighter spotlight on conservatorship abuse eventually helped Spears secure the right to choose her own legal representation and dismantle the arrangement. Since then, Spears has also told her story on her own terms in her memoir, The Woman in Me, in 2023. The bombshell tell-all sold 1.1 million copies and became a New York Times best-seller within a week of its release. A film adaptation of the book directed by Jon M. Chu is currently in the works at Universal Pictures.

Britney Spears

Frank Micelotta/ImageDirect

The future of Spears’ pop superstardom since ending the 13-year conservatorship remains in question. Since giving up her childhood to an industry that overlooked her creative vision and discounted her achievements, she’s focused on a different chapter of life. Today, she lives a life free from the shackles of her family and the guardianship, and is relearning just how to be an independent adult. For that, she stands as a survivor and perhaps a reluctant hero to many – one whose hits, performances and aesthetic have had an incalculable influence on the last 25 years of pop culture. 

Her 2022 Elton John teamup “Hold Me Closer” is her lone hit since the Glory cycle, yet her impact is still alive and well in 2024, even shaping a fresh new batch of stars. Just take a look at this year’s VMAs ceremonies, where countless new-gen pop stars, including Sabrina Carpenter, Tate McCrae and Megan Thee Stallion, incorporated allusions to classic Britney in their appearances and performances. It’s that multigenerational legacy that’s helped Spears become one of the few acts to span top 10 hits across four decades, further cementing her legacy as one of pop’s greatest. Now that she’s achieved her independence and control over her career, whether she’ll make a full return to pop music remains unclear — we only know that if and when she does, the entire pop world will be rapt in attention to watch Britney Spears do it again.

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back Tuesday as we kick off the top five with our No. 5 artist!

THE LIST SO FAR:

Honorable Mentions

25. Katy Perry24. Ed Sheeran23. Bad Bunny22. One Direction21. Lil Wayne20. Bruno Mars19. BTS18. The Weeknd17. Shakira16. Jay-Z15. Miley Cyrus14. Justin Timberlake13. Nicki Minaj12. Eminem11. Usher10. Adele9. Ariana Grande8. Justin Bieber7. Kanye West6. Britney Spears

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. You can see the stars who have made our list so far here, and now we remember the century in Kanye West — whose career has featured near-unparalleled runs of artistic brilliance and pop cultural centrality, but whose legacy has grown more complicated by the year over the last decade.

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It’s funny now to think of a time when confusion over Kanye West’s first name was a common issue. Like NBA star Dwyane Wade (who, like West, also went pro in 2003-04), a lot of people who hadn’t seen or heard his name before – an Ethiopian-French name meaning “only one” – mentally jumbled the placement of the “y,” leading to a lot of first-time misspellings and mispronunciations when bracing it for the first time. The Netflix documentary jeen-yuhs includes an early-’00s scene of an unknowing receptionist referring to Kanye as “Cayenne,” and West himself even bemoaned the then-still-common cognition error in his 2005 hit “Diamonds From Sierra Leone”: “Now all I need is y’all to pronounce my name/ It’s Kanye, but some of my plaques, they still say ‘Kayne.’” 

Flash forward to two decades later, and it’s damn near impossible to imagine a single person on the planet who doesn’t know Kanye’s name. For a solid 20 years now, the monocultural figure has been in headlines on a weekly basis – sometimes daily, sometimes hourly – for just about every reason an artist can be. He’s been attached to stories about every kind of commercial and critical achievement: chart-topping singles and albums, best-of year-end and decade-end list placements, award wins and losses – even ones that weren’t his own. He’s also been at the center of celebrity weddings, billion-dollar business dealings, friendships and feuds with plenty of the other most famous people of the 21st century; one sitting U.S. president publicly thanked him for his “very cool” service, another called him a jackass. 

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And he’s also dominated the news for things no one should ever want to be known for – for ignorant comments and for allegations of terrible behavior, and for ensuing backlash that pushed him to the fringes of an industry he once lorded over from the absolute center. But even in 2024 – and even after he legally changed his name to the less scrambleable “Ye” – you can still never go too long without hearing the name Kanye. That’s how inextricable Mr. West was to American life in the first two decades of this century, that’s how brilliant his music and artistry were for the great majority of that period, that’s how blinding his sheer star power was throughout, and that’s how unshakeable he ultimately still remains in the culture today. 

Dave Hogan/Getty Images

Frank Micelotta/Fox/Getty Images

But before Kanye was the Kanye that the whole world would know, he began the 21st century as a Chi-town college dropout still trying to make his name as a producer. In the late ‘90s, he’d gotten beats on albums by hitmakers like Jermaine Dupri, Foxy Brown and Goodie Mob, but in 2000 that he would land the placement that would jumpstart the next phase of his career: “This Can’t Be Life,” from Jay-Z’s The Dynasty: Roc La Familia. The beat exemplified Kanye’s signature early-career production style: a classic soul sample, pitched up to the heavens, laid over the knocking snare from Dr. Dre’s “Xxplosive.” The song wasn’t a single, but it was a highlight from Jay’s third straight No. 1 album, getting him in the good graces of the rapper (and his Roc-a-Fella label) who was about to become the most powerful in hip-hop.

That takeover kicked off in earnest on 2001’s The Blueprint, Jay-Z’s career-defining masterpiece, on which Kanye placed five beats (including, appropriately, Jay’s beef track “Takeover”). The most important song on the set for the producer was “Izzo (H.O.V.A.),” a Jackson 5-lifting pop-rap singalong which gave the rapper his first Hot 100 top 10 hit as a lead artist, and gave the producer his first Hot 100 hit, period. From there, the floodgates opened for Kanye, and by the end of 2002, he’d scored Hot 100 hits with Scarface, Trina and Talib Kweli – as well as second Jay smash “03 Bonnie & Clyde,” this time with a newly solo Beyoncé riding shotgun – making him a rising star in a golden age of superproducers. 

But Kanye wasn’t satisfied with superproducerdom, since he’d long harbored aspirations of being an MC as well. While by 2002, hip-hop producers grabbing the mic had become relatively common – Kanye’s production heroes Dr. Dre and Q-Tip had both found stardom doing so in the ‘90s, while Pharrell’s falsetto was becoming as ubiquitous in 2000s top 40 as his beats – Kanye found difficulty convincing labels to take him seriously as a rapper, partly because his middle-class image and rhymes largely conflicted with the street rap ruling radio at the time. Eventually, Roc-a-Fella signed him — in large part to keep his beatmaking talents in-house — but even they weren’t totally convinced yet.

His debut single would quickly validate their decision. While Kanye had been garnering notice with mixtapes like Get Well Soon and I’m Good, as well as for additional hit beats for Alicia Keys (“You Don’t Know My Name”) and Ludacris (“Stand Up,” his first Hot 100 No. 1 as a producer), “Through the Wire” was the song that brought Kanye to national renown. Inspired by a near-fatal 2002 car accident – he rapped the song (over a chipmunked sample from Chaka Khan’s ‘80s R&B hit “Through the Fire”) while his jaw was still wired shut, hence the title – “Wire” introduced Kanye as a clever, compelling and culturally omnivorous underdog, winning listeners over with both its triumphant message and its well-placed references to everything from Vanilla Sky to Making the Band. Helped by an MTV-conquering living-collage music video, the song reached No. 15 on the Hot 100, establishing Kanye’s two-way bonafides and building massive buzz for his debut album. 

The College Dropout, released in Feb. 2004, lived up to the hype. Drawing rapturous reviews and debuting at No. 2 on the Billboard 200 with 441,000 in first-week sales, the album spawned three more huge hits in “All Falls Down,” “Jesus Walks” and “Slow Jamz” (his first Hot 100 No. 1 as a recording artist, though the song was originally featured on fellow Chicago rapper Twista’s Kamikaze album with Kanye as a featured artist). The album made Kanye a cultural phenomenon and media darling, as his pink polos, popped collars and unique combination of arrogance and insecurity (“We all self-conscious, I’m just the first to admit it,” he boasted on “Falls”) made him an irresistible presence, and his oft-uplifting storytelling drew stark contrast with the crime tales and caddishness of the previous year’s breakout rapper, 50 Cent. (50 would later theorize that his own ubiquity directly led to Kanye’s subsequent success.) 

In particular, “Jesus Walks” took Kanye into the center of public discourse for his grappling with his faith in a way that was extremely rare (and risky) for pop music at the time. The song only reached No. 11 on the Hot 100, lower than “Falls” and “Jamz,” but made its way to a lot of new fans outside of mainstream hip-hop, and drew the most critical acclaim of any of Dropout’s singles. “Jesus” nominated for two awards at the 2005 Grammys, where Ye’s attendance was a source of much discussion in the lead-up – since he’d previously crashed the stage at the 2004 American Music Awards to protest country hitmaker Gretchen Wilson beating him for best new artist. The awards outburst – certainly not the last of its kind for Ye – drew some backlash and ratcheted up Grammy night tension, which turned out to be for naught when he won best rap album for Dropout. “Everybody wanted to know what I would do if I didn’t win,” Kanye offered in his still-oft-referenced acceptance speech. “I guess we’ll never know.”

As successful as Kanye’s debut was, his sophomore album would prove it was just the beginning. Late Registration debuted at No. 1 in Aug. 2005 with nearly two times the first-week number of Dropout, and its second single – the Jamie Foxx-featuring “Gold Digger,” a comedic and absurdly catchy tribute to (and warning about) get-rich-quick female social climbers – became Kanye’s first No. 1 as a lead artist, and an immediate pop classic. The album’s expanded sonic palette, aided by co-producer (and regular Fiona Apple collaborator) Jon Brion, proved Ye was no one-trick wonder as a beatsmith, while songs like “Hey Mama” and “Heard ‘Em Say” plumbed new depths of personal and political subject matter lyrically. The latter side of Ye would also come into full focus that year on a televised benefit for those hit hardest by Hurricane Katrina, where his frustration over the then-President’s slow response in providing aid to the less-well-off victims of the incident boiled over into his second unforgettable quote of 2005: “George Bush doesn’t care about Black people.” 

Kanye would spend much of 2006 touring – taking a brief pause for another stage-crashing incident at the ‘06 MTV EMAs, where he greeted news of his “Touch the Sky” losing best video to Justice vs. Simien’s “We Are Your Friends” with a loud “Oh, HELL no!” – and drawing inspiration for his next studio album, 2007’s “stadium status”-aspiring Graduation. Though the set was scheduled a week after rival 50 Cent’s Curtis album was due, Kanye later moved it up to the same day, starting a much-hyped sales battle that 50 would raise the stakes of by swearing he’d retire if he lost. Graduation ultimately soared past Curtis, selling 957,000 (still Kanye’s best first-week number) to Curtis’ 691,000, confirming Ye – who by then had also embraced electronic influences (particularly via Daft Punk-sampling lead single “Stronger,” another Hot 100 No. 1) and high fashion – as hip-hop’s present and future. Once again earning rave reviews, Graduation made Kanye 3-for-3, and very arguably the biggest artist in the world. (50 declined to retire as promised, but his career was never the same again.)

While Kanye was on top of the word artistically and commercially, he was about to hit a personal low. In late 2007, his mother Donda passed, and the next year, he broke off his engagement with long-time girlfriend Alexis Phifer – with both events inspiring the decidedly downbeat tone of his next album, 2008’s 808s and Heartbreak. Though Kanye had rarely sung on his records before, 808s mostly featured his Auto-Tuned warbling – with rapping kept to a minimum – of heart-on-sleeve lyrics over icy, synth-driven beats that felt a world away from the chipmunk soul he’d made his name on. The album became his third straight No. 1 and spawned a pair of top five Hot 100 hits in “Love Lockdown” and “Heartless,” but for the first time in his career, critics and fans were mixed on the new set. Time would largely prove Ye simply ahead of the curve, however, as the combination of chilly nu-wave sonics and hip-hop/R&B hybridized vocals (largely inspired by Kid Cudi, a signee to Ye’s GOOD Music imprint) ended up being profoundly influential on leading 2010s hitmakers like Travis Scott, Childish Gambino and Drake. 

Though 808s wasn’t the unqualified success of Kanye’s first three albums, he was still one of pop music’s leading artists at the time of the 2009 MTV Video Music Awards. That night would quickly prove infamous for Ye, as the megastar – seen with a bottle of Hennessy on the red carpet – would grab the mic during Taylor Swift’s best female video acceptance speech to claim that the award should have gone to fellow nominee Beyoncé instead. Though Ye’s stage-crashing antics were well-known by that point, none of them had ever occurred on this widely watched an event, or with co-stars as well known as Swift or Beyoncé – or during the social media era, as the then-rising app Twitter gave everyone watching the opportunity to express their disbelief and/or disapproval in unison. Kanye had received blowback for plenty of moments in his career to this point, but never backlash on this level; the public response was so immediate and so loud that he pulled out of his planned Fame Kills tour alongside Lady Gaga and essentially went into hiding in Hawaii for the rest of the year. 

The experience ended up leading to Kanye’s next album, 2010’s My Beautiful Dark Twisted Fantasy. Recorded in a free-flowing Hawaii studio setup with a rotating cast of high-profile collaborators, Fantasy featured Ye really leaning into playing the anti-hero (if not the outright villain) for the first time on cinematic hits like “Power,” “Monster” and “All of the Lights,” with newly growling, grimy, ‘70s rock-influenced production. He did still make room for contrition, however, particularly on the spellbinding album centerpiece “Runaway,” which he unveiled with an instantly iconic performance at – where else? – the 2010 VMAs. The album debuted at No. 1 with nearly 500,000 in first-week sales, and drew Ye’s most ecstatic reviews yet: Leading critical voice Pitchfork, which a decade earlier had been an indie rock-rooted publication that might not have even reviewed a rap blockbuster like Fantasy, gave the set its first 10.0 score for a new album since 2002 – a sign not only of Ye’s now-unanimous acclaim, but of how he’d helped shift the entire critical discourse over the course of his career. 

For the next couple years, Ye was unquestionably back, and as entrenched in the mainstream as ever. In 2011, he teamed up with longtime collaborator, label head and big brother Jay-Z for the gaudy Watch the Throne, a purposeful exercise in hip-hop opulence and excess that nonetheless contained several classic moments: “N—as in Paris,” in particular, with its imminently quotable lyrics and earthquaking dubstep drop, proved a culture-moving moment, particularly when the duo started playing it double-digit times in a row on tour. The next year, his Cruel Summer quasi-compilation collected songs from then-rising GOOD Music artists like Big Sean, Teyana Taylor and newly solo Clipse rapper Pusha T – but the best and biggest songs were all headlined by Kanye, including the hit singles “Mercy” and “Clique.” Meanwhile, Ye had started to date reality TV superstar and budding entrepreneur Kim Kardashian, increasing his Q rating and pushing him to new corners of pop culture, as he also began premiering his “DW by Kanye West” lines of women’s clothing during Paris Fashion Week.

By summer 2013, it had been nearly three years since the last new Kanye solo album – the longest layover of his career to that point – and rumors of a dark and difficult set had long buzzed around hip-hop blogs and fan communities, many of which by this point (particularly the Kanye to The forum) were tracking Kanye’s happenings with singular diligence and worship. The rumors were true: after a ninth-inning edit job by legendary “reducer” Rick Rubin, Yeezus debuted as Ye’s most-abrasive and least-commercial set, equally influenced by 2010s Chicago drill rap and 1980s Chicago acid house, with largely aggressive, hedonistic lyrics that seemed to occasionally border on outright nihilism. Yeezus made Fantasy sound like “Through the Wire,” and not all listeners were down with the darkness – but the set generally drew song reviews and fan response, and became his sixth straight album to debut at No. 1. 

Beginning with Yeezus, though, West’s output generally trended away from playing the pop crossover game. Just a couple years earlier, he had picked up his fourth Hot 100 No. 1 by appearing on the single version of top 40 megastar Katy Perry’s “E.T.”; such pop appearances would quickly be unthinkable for the post-Yeezus Kanye, who began reserving his guest appearances almost exclusively for fellow rappers and occasional R&B stars. Music videos also became rarer, as did award show performances and media interviews – and Yeezus notably contained no pre-release singles, though “Bound 2” eventually became a No. 12 hit following the release of its Kim Kardashian-co-starring, easily parodied music video. 

In fact, West’s primary engagement with pop music and pop culture in the mid-’10s came through his continued back-and-forth with Swift – who, a half-decade after their initial VMAs conflict, was still linked to West in ways neither of them could really shake, with the latter apologizing for the incident but then later seemingly retracting his apology. At the 2015 VMAs, the two appeared to bury the hatchet, as Swift introduced West as the recipient of the Michael Jackson Video Vanguard Award, with her speech even making joking reference to the ‘09 incident. But in early 2016, Kanye released “Famous,” which included the lyric “I feel like me and Taylor might still have sex/ Why?/ I made that b–ch famous,” seemingly resetting the dormant beef in an instant. Swift appeared to respond to the song when accepting the album of the year Grammy just days later, warning the young women watching of “the people along the way who try to… take credit for your accomplishments and your fame.” (A video for the song, released months later, would further the acrimony by picturing a nude wax sculpture of Swift, along with similar sculptures of Ye and many other celebrities, sleeping together in a giant bed.) 

“Famous” appeared on The Life of Pablo, Kanye’s first album since Yeezus, released in Feb. 2016 after several false starts and renamings. The album was less difficult than its predecessor, but far messier – particularly because West was still tinkering with the album by the time it was released as an exclusive on the new streaming service Tidal, of which he was a co-owner. Months into the album’s release, he was still reworking songs and fiddling with the tracklist – which, depending on who you asked, either made a profound statement on the permanent malleability of the album format in the streaming era or simply displayed Kanye’s increasing lack of artistic self-assuredness. Regardless, the set was mostly received well, giving Ye yet another No. 1 and spawning fan favorites like the two-part “Father Stretch My Hands,” the Kendrick Lamar teamup “No More Parties in LA” and the gospel-influenced, Chance the Rapper-spotlighting opener “Ultralight Beam.” 

More notable than the actual music on Pablo might have been the event that premiered it: a live listening party at New York’s Madison Square Garden, the largest scale such an event had been conceived on to that point. In truth it was far larger than even a simple arena gig, because thanks to livestreaming, it also became a communal event on social media, with secondhand excitement over the quasi-live show extended to the album itself. The Pablo era was further helped by the successful and acclaimed Saint Pablo Tour that followed, and the soon-omnipresent merch from it that – along with his increasingly successful Adidas partnership – officially turned Kanye into a lifestyle brand. Perhaps best of all for Ye, Snapchat video released online by Kim Kardashian – then his wife, as the couple were married in 2014 – seemed to show Swift giving him her pre-release approval for the controversial “Famous” lyric, which flipped public sentiment back against the pop megastar and towards Kanye. He was just a couple months away from ending 2016 on a high note to rival any in his career to that point. 

It was not to be that simple. West’s year was shaken first by wife Kardashian’s robbery at gunpoint in Paris that October, forcing him to cancel multiple Pablo dates. Then, after Donald Trump was elected president in November, Kanye expressed onstage that he didn’t vote in the election, but would have supported Trump if he had – kicking off a run of erratic on-stage behavior that also included his ranting about Beyoncé’s alleged politicking at the 2016 VMAs and how Jay-Z never called him after Kardashian’s robbery. He eventually pulled the plug on the rest of the tour, and was hospitalized that Thanksgiving for temporary psychosis – after which he had a controversial summit at Trump Tower with the then-president to discuss “multicultural issues,” much to the horror of many of his peers, including longtime collaborator John Legend. It was a brutal end to a once-triumphant year. 

The rest of the decade was a rocky period for Kanye. He released two more albums, 2018’s introspective, seven-track Ye – part of a five-album “Wymoning Sessions” series all produced by Kanye, which also included his Kids See Ghosts teamup with longtime collaborator Kid Cudi – and 2019’s gospel-themed Jesus Is King, and again topped the Billboard 200 with both. But both sets drew mixed reviews, and as became increasingly the case with Kanye post-Pablo, got more attention for their bumpy releases and listening party premiere events than for most of the music actually contained therein. Meanwhile, he made further public appearances in support of then-President Trump, began to speak out against abortion and the Black Lives Matter movement, and most infamously, said to TMZ about Black slavery that “when you hear about slavery for 400 years … for 400 years? That sounds like a choice” – comments that earned swift, massive backlash from both fans and the media. (Later that year, he apologized for “how that slave comment made people feel.”) Even the Taylor Swift feud flipped back on Kanye, as 2020 saw the leak of a longer version of the infamous “Famous” approval conversation between the two stars, seemingly adding more context and validity to Swift’s claims that she never gave full approval to the “b–ch” lyric. 

SGranitz/WireImage

Still, no matter how severe the fallout from any of his controversies, at the turn of the 2020s Kanye still clearly held the public’s interest whenever he released an album, or debuted a new shoe line, or held a high-profile concert – or engaged in a high-profile beef, as he did with 2010s rap kingpin Drake in the lead-up to his 2021 album Donda. After Ye held what was essentially a promotional residency at Atlanta’s Mercedes-Benz Stadium, literally living in the stadium between promotional events as he attempted to finalize the set, the 27-track collection was belatedly released in June, and again entered at No. 1, with 309,000 units moved, the highest mark of the year to that point. The occasionally inspired but wildly overstuffed album had its supporters, and earned an album of the year Grammy nomination – but as Drake’s Certified Lover Boy album was released the next week to an even bigger first-week bow, and then the two rappers made up months later for the Free Larry Hoover concert, it was hard not to feel like the entire era was more sound than fury.

The next year would bring about new lows for Kanye, as Oct. 22 kicked off with him wearing an inflammatory “WHITE LIVES MATTER” t-shirt at a Yeezy SZN Paris fashion show, then making a post to Instagram calling Black Lives Matter “a scam.” Later in the month, West had his accounts locked on both Instagram and Twitter for comments perceived as anti-semitic, particularly a tweet that threatened to go “death con 3 on JEWISH PEOPLE.” The rapper’s rhetoric continued, and eventually his business partners began to sever ties with him – including his CAA agency, his UMG parent label, and even his Adidas shoe partners, about whom Kanye had recently boasted, “I can say anti-semitic things and Adidas can’t drop me.” (In Dec. 2023, Kanye would apologize for his comments in an Instagram statement: “I sincerely apologize to the Jewish community for any unintended outburst caused by my words or actions.”)

And yet, even with seemingly all of his industry backing lost, Kanye remains majorly impactful in present day. His Instagram apology was followed in early 2024 with the independent release of his Ty Dolla $ign teamup Vultures 1 – again, after plenty of false starts, delays and listening-event hype, and again, with a No. 1 debut on the Billboard 200. This time, the set was also able to do something no Kanye album had done since before Yeezus: spawn a major, long-lasting Hot 100 hit, with the soccer-chanting, No. 1-peaking “Carnival,” also featuring Playboi Carti and Rich the Kid. The song carried some of the red-eyed, goblin-mode spark of Ye’s best early-2010s work – though in calling back to some of those songs rather explicitly (including a mid-song sample of Fantasy’s “Hell of a Life”), it missed both the ingenuity and the shock of the new that made them so special. 

When you tell the story of Kanye West’s career, you realize how few of the larger narratives about 21st century popular music could be related without him. The mixtape hip-hop era of the early 2000s, rap’s mainstream takeover in the mid-’00s and the blog era in the late deacde, the EDM breakthrough and pop star megaboom of the turn of the 2010s, the complete reinvention of music consumption throughout the social media and streaming ages of the ‘10s, the event-ification of pop music in the late ‘10s, and the outsized role of identity politics and post-#MeToo questions of cancelation (or at least accountability) within the industry that have hung over all of entertainment for the past eight years… Nearly every important sonic, cultural or technological trend in the last 25 years of popular music has been touched by Kanye, and none of these chapters of pop history could be written without extensive mention of him. Sometimes on the first page. Sometimes in the first sentence.

Dan Tuffs/Getty Images

It’s impossible to deny Kanye’s impact, or his greatness. But it’s equally impossible to deny the impact that his hurtful comments and bad behavior (allegations of which have continued in 2024) have had on his overall legacy. He’s hardly the only one: Rock, rap and even pop history are all full of critical figures whose problematic conduct threatens to overshadow or at least taint their seismic contributions to the genre. How much it impacts our own personal enjoyment or listening habits when it comes to their music – either going forward or looking back – is something every fan must figure out for themselves. But clearly, even with Kanye’s recent chart comeback, he’s been ostracized from too many corners of pop music and pop culture to ever be as central to either as he was at his near-decade-and-a-half peak – and now, for many, even memories from that peak have been regrettably shaded to the point where they will never quite feel the same again. 

Still, it’s a testament to just how singular that peak run was, and how impactful it was on popular music and culture – in countless ways we can still feel the reverberations of today, and others we might not properly understand for decades yet to come  – that so many still bother with Kanye at all. Perhaps no other artist since Prince has better matched the Purple One’s combination of mold-breaking creativity with record-breaking commercial success, of studio perfectionism and prolificity with spellbinding performance abilities and iconic visuals, of cultural innovation and technological wizardry with personal artistry and deep soulfulness. And like Prince, he can change his name to whatever he wants, but the world will still never, ever forget the name Kanye. 

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back Tuesday as we reveal our No. 6 artist!

THE LIST SO FAR:

Honorable Mentions

25. Katy Perry24. Ed Sheeran23. Bad Bunny22. One Direction21. Lil Wayne20. Bruno Mars19. BTS18. The Weeknd17. Shakira16. Jay-Z15. Miley Cyrus14. Justin Timberlake13. Nicki Minaj12. Eminem11. Usher10. Adele9. Ariana Grande8. Justin Bieber