Greatest Pop Stars of 21st Century

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. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20, No. 19, No. 18, No. 17, No. 16, No. 15, No. 14, No. 13 and No. 12 stars, and now we remember the century in Usher — a complete-package superstar who’s evolved with the times and amassed one of the century’s most formidable pop and R&B catalogs.

Not many artists can say they’ve made the successful transition from teen sensation to adult superstar. It’s an exclusive club whose membership brings to mind all-time greats like Stevie Wonder, Michael Jackson, Beyoncé, Taylor Swift… and then there’s Usher, baby: the singing, dancing triple-threat in the Braves hat and the U chain. 

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This year, Usher has basically been running on one long career-spanning victory lap, celebrating his 30th anniversary in music and the 20th anniversary of his diamond-certified 2004 classic Confessions, and performing at the Apple Music Super Bowl LVIII Halftime Show in February to the tune of 123 million viewers — the most-watched halftime show ever. And that’s not to say that he’s been stuck in the past either: This February also saw the release of his ninth studio album Coming Home (debuting at No. 2 on the Billboard 200), while in August, he also launched his Past Present Future arena world tour. And all this follows on the heels of Usher’s talk-of-the town My Way – The Vegas Residency that packed both The Colosseum at Caesars Palace in 2021 and the larger Dolby Live at Park MGM a year later – an act he took across the pond with the eight-date Rendez-Vous Á Paris, documented in a concert film released this September. Bottom line: the eight-time Grammy Award winner, who turns 46 on Oct. 14, is riding the wave of one of the most impressive, legacy-cementing comebacks of the last decade.  

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It’s a multigenerational R&B/pop legacy built on nine Billboard Hot 100 No. 1 singles and 18 top 10 singles plus four Billboard 200 No. 1 albums. The latter streak began with the singer-songwriter’s epic 2004 album Confessions, whose nine weeks at the top led to it being crowned the Year-End Billboard 200’s No. 1 album – the same year that his era-defining “Yeah!” team-up with Lil Jon and Ludacris ended up No. 1 on the Year-End Hot 100. But more significant than the history-making chart stats, sales certifications and industry accolades that Usher has racked up along the way is his innate artistry — a crucial key to his staying power.  

There’s his sensual, supple tenor, which easily shape-shifts from crooning balladeer to party jam belter and hits the entire emotional spectrum in between. Equally as arresting are the intricate choreography and smooth footwork that are the hallmarks of his energetic and engaging stage presence. Who else could make rollerskating and singing simultaneously look so cool and easy? Then there’s the music itself: Yes, R&B and pop played the central roles in his career evolution, but the inquisitive music lover has never shied away from experimenting with other genres — dabbling in everything from hip-hop and crunk to EDM and trap, crafting engaging melodies, ear-worm lyrics and hooks you can’t help but sing along with. He’s also been unafraid to reach out to the next generation, linking up over the last several years with younger artists like Chris Brown (“New Flame”), Summer Walker (“Come Thru”), Ella Mai (“Don’t Waste My Time”), H.E.R. (“Risk It All”) and Justin Bieber (the remix to Bieber’s Hot 100-topping hit “Peaches”) — all of whom no doubt also count Usher as a key influence on their own artistry.  

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Usher Raymond IV was just 15 years old himself when LaFace/Arista Records began setting the stage for the precocious newcomer with the 1994 release of his self-titled debut album. Mixing R&B, hip-hop and new jack swing, the album — preceded by puberty claiming Usher’s vocal range at one point — bowed at No. 167 on the Billboard 200. Despite that low entry point, the project still proved to be a buzz-builder, presaging Usher’s first major breakthrough as a singer-songwriter on the cusp of the new millennium: 1997’s My Way.   

At a time when the ‘70s-influenced neo-soul movement — embodied by D’Angelo, Erykah Badu and Maxwell — was making its mainstream ascendance, Usher’s refreshing brand of contemporary R&B was striking a chord with fans by way of its youthful, vibrant take on love, sexuality and burgeoning adulthood. The now-7x-platinum RIAA-certified project spun off three top-two Hot 100 smashes: “You Make Me Wanna…,” “Nice & Slow” (his first No. 1) and “My Way.” 

A year after the millennium’s arrival, Usher catapulted into the upper level of the Billboard 200 with the No. 4 first-week debut of 8701. Initially titled All About U, his third album was delayed from its original 2000 release date thanks to leaks of several tracks, including under-performing first single “Pop Ya Collar.” Collaborating with a bevy of hitmakers — Antonio “L.A.” Reid, Kenneth “Babyface” Edmonds, Jimmy Jam & Terry Lewis, The Neptunes, Jermaine Dupri and Bryan-Michael Cox — the revamped and retitled album (reportedly a reference to the year Usher first performed publicly, 1987, and the album’s Aug. 7, 2001 release date) found Usher delivering a spirited and emotive next-gen take on love and relationships primarily inspired by R&B/soul giants such as Wonder, Jackson, Marvin Gaye and Donny Hathaway.  

Two of the album’s U-titled tracks, “U Remind Me” (the new album’s official first single) and “U Got It Bad” nabbed the top spot on the Hot 100. A third, “U Don’t Have to Call,” reached No. 3. Since certified 5x platinum, 8701 gave Usher his first Grammy for best male R&B vocal performance (“U Remind Me”) plus a second win in that category the following year (“U Don’t Have to Call”). An added plus: fans finally got the chance to experience firsthand the versatile tenor’s falsetto and other vocal riffs plus his agile dance moves when the showman-in-the-making embarked on his first concert outing, 2002’s 44-city 8701 Evolution Tour. 

If 8701 was Usher’s coming-of-age bow, 2004’s Confessions was the coronation of his status as one of the marquee pop artists of the 2000s. Bowing at No. 1 on the Billboard 200 with first-week sales of 1.1 million, the now diamond-certified, career-defining project found the 25-year-old crooner reuniting with Dupri and Cox and Jam & Lewis, sharing deeper experiential musings about love and relationships alongside banging party jams. Chief among the offerings on the dance, pop, hip-hop and crunk-infused album were three Hot 100 No. 1s: the club-ready “Yeah!” with Lil Jon and Ludacris, the yearning “Burn” and the guilt-wracked “Confessions Part II.” Added as a bonus cut to the album’s deluxe edition, the nostalgic love duet “My Boo” with Alicia Keys became Usher’s fourth No. 1 of the calendar year, with fifth single “Caught Up” becoming the set’s final top 10 hit. Confessions later won the Grammy for best contemporary R&B album. Prior to the end of 2004, Usher added yet another top five hit to his arsenal when he and Ludacris reteamed with Lil Jon on the latter’s single “Lovers and Friends.” 

Confessions’ epic success sparked a string of three more Billboard 200 No. 1 albums for Usher, reminiscent of idol Michael Jackson’s No. 1 run beginning with 1982’s Thriller in 1982. Usher’s own run kicked off four years after Confessions with 2008’s Here I Stand. By then a husband and father, Usher ongoing maturation musically and personally was reflected in its six single releases. Those included the synth-layered, Polow da Don-produced lead single “Love in This Club” featuring Young Jeezy (another Hot 100-topper, and the set’s biggest hit) and the Grammy-nominated ballad/title track. Here I Stand was another success, but industry observers noted as well that the album’s double-platinum success paled in comparison to Confessions’ more ee-popping achievements.  

Here I Stand was followed by fellow No. 1 albums Raymond v. Raymond in 2010 and Looking 4 Myself in 2012. The former project, certified 3x platinum and released in the wake of the artist’s divorce from Tameka Foster, included the Hot 100 No. 1 dance-pop single “OMG,” produced by and featuring will.i.am, as well as the R&B hits “Hey Daddy (Daddy’s Home)” and “There Goes My Baby.” Also of note was the song “Papers”: Recorded before the singer filed for divorce, the song was a insightful and vulnerable nod to the personal struggles he was dealing with at the time. The song reached No. 1 on Billboard’s Hot R&B/Hip-Hop Songs chart and peaked at No. 31 on the Hot 100. 

Usher deepened his experimentation into electronic music, with forays into Euro-pop and dubstep, on Looking 4 Myself. His first project for RCA Records boasted the respective top 10 and top 20 hits “Scream” and Grammy winner for best R&B performance “Climax,” co-produced by Diplo. The latter track, an electronic-punctuated slow jam about a tenuous relationship, brought Usher some of his strongest critical acclaim. However, the album – lauded for its alt-R&B vibes in what Usher described as “revolutionary pop” — was his lowest-selling No. 1 entry. At that same time, mainstream R&B was in the midst of shifting away from the pop star hybrid model that Usher symbolized, and moving towards more underground-leaning emerging stars like The Weeknd, Frank Ocean and Miguel. 

The ebb and flow that can accompany any veteran hitmaker’s career trajectory continued for Usher into the mid- to late 2010s. Prior to the 2016 release of his eighth studio album Hard II Love, he released three singles in 2014 — the Grammy-nominated, platinum-certified R&B hit “Good Kisser,” “She Came to Give It to You” featuring Nicki Minaj (a top 20 Rhythmic Airplay hit and the electro/R&B percolator “I Don’t Mind” featuring Juicy J (No. 11 on the Hot 100; No. 1 Hot R&B/Hip-Hop Songs). All three were intended for Hard II Love, but only appeared on the album’s Japanese edition. 

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Leaning back in a more R&B direction, the artist collaborated with songwriter-producers such as Raphael Saadiq, Pop & Oak, The-Dream and Metro Boomin for the resulting Hard II Love. Debuting at No. 5 on the Billboard 200, the album gained the dubious distinction of becoming Usher’s first album to not bow at No. 1 on the Billboard 200 in 12 years, and failed to generate a Hot 100 hit bigger than the No. 32-peaking Young Thug collab “No Limit” (though the song topped R&B/Hip-Hop Airplay, while later single “Missin U” went top 10 on Adult R&B Airplay). Meanwhile, his last North America tour had been 2014’s UR Experience. 

Five years after Hard II Love — with no new full-length releases, aside from his 2018 mini-album A alongside producer Zaytoven — Usher and his team placed their bets on another venture: launching his first Las Vegas residency. The July 2021 gamble paid off in more ways than one: The sold-out My Way tenure wasn’t only an affirmation of Usher’s estimable career, it also doubled as a creative rebirth and introduction to a new generation of fans. Next came the Super Bowl and the ongoing world tour. In between, Usher’s ninth studio album Coming Home arrived — the first release on his indie label Mega, co-founded with L.A. Reid and in association with Larry Jackson’s gamma. Featuring the No. 25 Hot 100 hit “Good Good” and “Risk It All,” the project bowed at No. 2 on the Billboard 200 to become his highest-charting effort in over a decade. 

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Growing up musically and personally in the public eye isn’t an easy feat. But Usher has proven his staying power with aplomb — and an indefatigable outlook. As he told Billboard in August 2021 with his always-disarming smile, “People are critical. But you continue to do it for the love. You do it for the people to connect with what you’re trying to articulate. That pressure is there every time. That’s why I try to give myself as much of a shot as I possibly can by giving fans variety. You’re going to like something.” 

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back next Tuesday as we start to unveil our top 10 artists!

On this week’s (Sept. 6) episode of the Greatest Pop Stars of the 21st Century podcast, we take a look at a pair of rap savants: mixtape phenom turned Queen of Rap Nicki Minaj, and polarizing superstar turned reliable veteran hitmaker Eminem. Explore See latest videos, charts and news See latest videos, charts and news First, host […]

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. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20, No. 19, No. 18, No. 17, No. 16, No. 15, No. 14 and No. 13 stars, and now we remember the century in Eminem — a singular force in early 21st century pop culture whose impact continues to reverberate today.

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At the peak of the TRL era in popular music — a turn-of-the-century period dominated by bubbly teen-pop stars and punctuated by furious nu-metal rockers — the biggest artist of all was actually a late-20-something rapper from Detroit. Eminem, who seemingly went from underground battle-rapper to omnipresent superstar by the end of his first week on MTV, reached commercial heights and levels of popular exposure as a solo artist that only the defining the stars of pop’s ’80s golden age (and certainly no prior MC) could previously claim.

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It couldn’t last, and it didn’t — with Em’s run as a culture-defining superstar flaming out sooner than anyone likely would’ve predicted. Eminem himself has lasted, however, remaining a commercial fixture and a high-level rapper since retooling at the turn of the 2010s, rarely quite as central to pop culture as he was during his all-consuming first few years of the century, but always a factor on the charts and in the conversation.

By the year 2000, Eminem was already close to a household name, thanks to his breakthrough major-label debut The Slim Shady LP and its lead single “My Name Is.” The wisecracking, s–t-stirring and mercilessly catchy mission statement explicitly introduced him to America as every parent’s worst nightmare — with Em ending the first verse by claiming that God (or, in the song’s radio edit, his iconic producer, label head and mentor Dr. Dre) “sent me to piss the world off.” That breakout hit only reached No. 36 on the Billboard Hot 100, but it made him an immediate MTV sensation with its cartoonishly comedic music video, featuring the artist portraying pop culture figures ranging from shock-rocker Marilyn Manson to impeached president Bill Clinton (and all eight stars of The Shady Bunch).

Eminem

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Eminem

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Ironically, it was Eminem’s extremely anti-pop energy in his early days that made him the perfect pop star for the moment. The early ’90s had been largely been defined by Seattle-based grunge and L.A.-based G-funk, but by the late ’90s, those genres had largely run their course in the mainstream, and their sonic and thematic heaviness was largely replaced by upbeat, kid-friendly, occasionally brilliant megapop that nonetheless left a lot of still-pissed-off young folks desperate for a darker, more skeptical alternative. Out of that hunger came the rise of rap-rockers like Korn and Limp Bizkit, as well as the inner-turmoil-driven hip-hop of DMX — all of whom would be present at Woodstock ’99, a bad-vibes festival of such historic proportions that the negative energy ultimately manifested in literal flames that engulfed much of the fest. The world was clearly ready for a rapper like Eminem, a (peroxide) blond-haired, blue-eyed, angry young white man who combined the youth-galvanizing outsider appeal of the nu-metalers with the intensely personal rhymes of DMX, also with a healthy dose of South Park creators Trey Parker and Matt Stone’s bratty humor and cultural commentary mixed in.

That potent blend would reap immediate blockbuster returns with the release of Eminem’s first album of the new century, 2000’s The Marshall Mathers LP. Led by “The Real Slim Shady,” which doubled down on the “My Name Is” formula with even funnier and ruder results (and reached No. 4 on the Hot 100), the album sold an unthinkable 1.78 million copies in its first week — then second to only the 2.4 million moved by *NSYNC’s No Strings Attached months earlier, and to this day the highest-selling single week for a rapper in the Soundscan era. The album also drew mostly rave reviews from critics, impressed with Eminem’s verbal dexterity, storytelling chops and ability to take on a wide breadth of topics and perspectives in his music, and even earned a Grammy nomination for album of the year and a win for best rap album, first of Em’s 15 career Ws at the awards. The praise for Eminem was hardly universal, however: His R-rated language and subject matter and tendency towards extreme violence in his lyrics — especially towards women, including his real-life then-wife Kim — made him public enemy No. 1 among American parents, and arrests for separate altercations in back-to-back days that June raised public concerns that he was dangerous even beyond his rhymes.

While questions about the album’s more misogynistic content were absolutely fair to ask, the criticism over its violent content took on a somewhat unfair tenor due to it coming during a particularly sensitive cultural moment over the subject, following the tragic 1999 massacre of a dozen students at Columbine high school at the hands of two of their classmates. In the aftermath, much of the public blame for the shooting was placed at the feet of shock rockers Marilyn Manson (who the shooters were reportedly fans of, though the idea of them being cult-level devotees has since been debunked) for supposedly inspiring the catastrophe — an artist-blaming panic that Eminem also felt the brunt of in 2000, as Lynne Cheney (wife of soon-to-be-VP Dick Cheney) brought up the album’s lyrics on the senate floor, calling it “astonishing to me that a man whose work is so filled with hate would be so honored by his peers.” (Eminem mentioned Manson on the album’s “The Way I Am,” positing that those pointing fingers should take accountability themselves: “They blame it on Marilyn… Where were the parents at?”)

Equally pervasive in the public discourse at the time was discussion about Eminem’s use of anti-gay slurs on Marshall Mathers — occasionally in such explicitly malevolent contexts as the “Criminal” lyric “Hate f–s?/ The answer’s yes” — and his efforts to explain himself at the time (“[The f– word] has nothing to do with sexual preference. I meant something more like a–holes or d–kheads,” he said in response to GLAAD’s criticism of him) mostly landed flat. The backlash over the album’s homophobic content did lead to one of the most iconic moments of that cycle, when he teamed up with the openly gay pop and rock legend Elton John for a performance of its third ingle “Stan” — whose chilling account from the perspective of an obsessed fan was so unforgettable that its title ended up becoming common parlance to refer to all overly invested pop fans — at the 2001 Grammys, which ended in an embrace between the two artists. (Though some remained unmoved by the gesture of allyship, the pair have remained good friends in the decades since, with Sir Elton even revealing that the rapper got him and his husband diamond-encrusted sex toys for a wedding gift in 2017.)

While criticism of some of the album’s more inflammatory content ranged from the thoughtful to the histrionic, all of it served the purpose of making Eminem not just the biggest star, but the most unavoidable topic of conversation in early 2000s pop culture. His famous performance of “The Real Slim Shady” at the 2000 MTV Video Music Awards — in which an army of white-teed, peroxide-blond Eminem clones stormed New York’s Radio City Music Hall — resonated not only because Em had already inspired so many followers, but because he was so unavoidable at the time it felt like there may as well have been hundreds of him running around simultaneously. And it wasn’t just on his own songs: Eminem also stole the show as a featured guest and hype man on Dr. Dre’s back-to-the-old-me 2000 hit “Forgot About Dre,” and as the lone guest on Jay-Z’s universally acclaimed 2001 masterpiece The Blueprint for the late-album highlight “Renegade” (which he also co-produced with Luis Resto, a burgeoning skill of Em’s he’d make greater use of as the decade went on). He also released Devil’s Night with his old Detroit rap crew D12, now signed to Em’s Interscope imprint Shady Records, which topped the Billboard 200 and generated a top 20 Hot 100 hit in “Purple Hills” (or “Purple Pills” on the non-radio edit).

As central to pop music and pop culture as Eminem was throughout the first two years of the 2000s, it simply shouldn’t have been possible for him to get any bigger. And yet, 2002 marked another leap forward for the superstar: In May, he released The Eminem Show, which followed Marshall Mathers back to the top of the Billboard 200, with over 1.3 million sold in its first full week of release. The album spawned his third straight classic culture-slapping lead single in the pulsing fake-superhero theme “Without Me,” followed by perhaps his most vicious diss track yet — tellingly, about his own mother Debbie Nelson, who’d previously sued him for defamation of character over lyrics in “My Name Is” that alleged heavy drug use on her part — in “Cleaning Out My Closet,” with both singles reaching the Hot 100’s top five. Like its two predecessors, The Eminem Show drew rave reviews, with critics particularly praising Em’s self-awareness and incisiveness on songs like the stomping “White America,” where he aptly proclaims, “Let’s do the math/ If I was Black, I would’ve done half.”

But the main event of his 2002 was still to come. In November, the Curtis Hanson-directed drama 8 Mile was released, starring Eminem (in his first major film role) as the Detroit trailer park resident, factory worker and aspiring battle MC Jimmy “B-Rabbit” Smith. Em was clearly playing a loosely fictionalized version of himself, but the steely intensity of his star turn was well received critically, and his captivating performances in some of the movie’s battle scenes gave him the electricity of a young Sylvester Stallone. Most crucially, his character came with theme music that was even better than Rocky Balboa’s: “Lose Yourself,” the seize-the-day jock jam that essentially tells Rabbit’s story (and seems to play in his head throughout the movie), became Eminem’s most ubiquitous hit; while previous singles of his were more impactful on MTV than on radio, there was no chance the latter could be able to resist a pop song this accessible and enormous. It topped the Hot 100 shortly after the movie’s release — his first No. 1 on the chart — and stayed there for 12 consecutive weeks, easily his biggest hit to date, and maybe the first Eminem song you didn’t even really even have to be an Eminem fan to love.

This was Eminem’s peak — and one of the highest of any pop artist, in either this century or the last. But in many ways, it was also the end of his run on top. In 2003, The Eminem Show continued to spin off medium-sized hits (the gleefully chauvinistic “Superman,” No. 15; the Aerosmith-sampling “Sing for the Moment,” No. 14) while Eminem mostly focused on production work for the likes of Jay-Z, his Shady signee Obie Trice and even the late 2Pac. For perhaps the first time in four years, Eminem was not the culture’s most ubiquitous rapper, though he still got to take partial credit for the guy who was: 50 Cent, who he signed to Shady the year before. Eminem appeared on two tracks and co-produced five total on his new protégé’s blockbuster debut LP Get Rich or Die Tryin’, released that February, with Get Rich going on to be the year’s best-selling album, a huge secondhand win for Em.

But by the time he was ready to resume recording his own next solo project, Eminem seemed a little lost. After D12 scored its first top 10 hit with D12 World lead single “My Band” — a light-hearted look at Eminem’s outsized role as the group’s frontman, with Em playing the clueless lead singer role to perfection — he returned in September in “Just Lose It,” the lead single from his own upcoming Encore. The song peaked at No. 6 on the Hot 100, but confounded fans and critics alike with its outdated Michael Jackson and Pee Wee Herman references, sexually confused chorus (“Yeah, boy, shake that ass/ Oops, I mean girl/ Girl, girl girl”), recycled hooks from “Without Me” and “Superman,” and relatively limp beat. After three straight game-changing lead singles, “Just Lose It” was an extremely puzzling release — and Encore was full of similarly wheel-spinning tracks for Em, where even he seemed unsure of what he was trying to do. (It did contain a few more-focused highlights, including the Martika-sampling “Like Toy Soldiers,” which recapped all the beef Em had gotten embroiled in on both his and his crew’s behalf over the past couple years, and the George W. Bush-protesting “Mosh,” which made him perhaps the only U.S. pop star bold enough to literally say “f–k Bush” in the midst of GWB’s 2004 re-election campaign.)

Encore still debuted at No. 1, with a sky-high first-week total of 710,000 copies sold (in just three days of release, with the album’s release date being moved up to counteract online leaks). But Eminem himself seemed dissatisfied with the project — he’d eventually dismiss it outright as a miss — and once its promo cycle was over, he ended up mostly disappearing from the public eye for a few years. He scored another two top 10 hits with the foreboding “When I’m Gone” and Akon-featuring “Shake That,” both from his Billboard 200-topping greatest hits collection Curtain Call, but that set’s title pointed (again) to the idea that he was toying with the idea of bowing out of music altogether. Eminem had rapped about drug use his entire career, but during the recording of Encore his pill usage (as he would later recount) had spiraled into full-blown dependency. That addiction and associated depression would get worse in 2006, after Eminem’s D12 bandmate and best friend since childhood DeShaun “Proof” Holton was shot to death in a tragic club incident.

Following a nearly fatal overdose in 2007, Eminem went sober in 2008 — and began work with Dr. Dre on his comeback album, Relapse. Released in 2009, and led by his third Hot 100-topper in the Dre and 50 team-up “Crack a Bottle,” the album had all the hallmarks of an athlete returning from injury and still getting back in game shape — the entire set carried a serial killer theme that he didn’t quite seem ready to totally commit to, and the singles were relatively weak, with Em trying out some new vocal tics and inflections that he’d later express regret over (and his rhymes still a little rusty). The comeback effort topped the Billboard 200 and sold over 600,000 copies in its first week, and contains a couple moving moments of true introspection in “Deja Vu” and “Beautiful” — but today, it represents (along with Encore) a low period in Eminem’s career, for both his fans and for himself. On Em’s his next album, he even basically asked his listeners to allow him a do-over, rapping on “Talkin II Myself,” “Them last two albums didn’t count/ Encore I was on drugs, Relapse I was flushing ’em out.”

Luckily for Eminem, he would get that do-over attempt with that next album, 2010’s Recovery, and he’d make the most of it. Now fully clean, he was hungry and refocused in a way that he hadn’t been since The Eminem Show — and the results were immediate, as the set’s lead single, the anthemic perseverance ballad “Not Afraid,” debuted atop the Hot 100, his first No. 1 since “Lose Yourself” in 2002. Recovery followed in June, and though the set divided critics with its more somber tone and greyscale production — Dre only co-produced one track, the late-album cut “So Afraid,” with more contemporary collaborators like Boi-1da and Just Blaze handling the brunt of duties — the commercial response was massive, as it debuted at No. 1 with 741,000 copies sold and ultimately ended 2010 as the Year-End Billboard 200 No. 1 album. The set also scored a second Hot 100-topper with the seven-week No. 1 “Love the Way You Lie,” an amour fou team-up with fellow megastar Rihanna that became something of a linchpin hit for the second phase of Eminem’s star career.

Though Eminem seemed to be starting a new chapter with Recovery, his next album would take him back to the beginning of the century: The Marshall Mathers LP 2. Leading off with the “Stan” sequel “Bad Guy,” the set featured Eminem sounding like he was having fun for the first time in a long time — getting loose over classic rock on songs like the fame-bemoaning “So Far” (Joe Walsh’s “Life’s Been Good”) and the block-rocking lead single “Berzerk” (Billy Squier’s “The Stroke”), and breaking Guinness records with his lightning-quick spitting on the viral “Rap God.” (That song also revisited the Marshall Mathers era by courting accusations of homophobic content — criticism Eminem has continued to cultivate in moments throughout his career — which he responded to by reasserting that his words were not meant to be interpreted literally: “I think people know my personal stance on things and the personas that I create in my music.”) MMLP2 was another huge success for Eminem, selling 792,000 copies in its first week, earning his best reviews in a decade and spawning his fifth Hot 100 No. 1 with a second smash Rihanna collab, “The Monster,” further confirming the early 2010s as something of a second renaissance for Eminem.

Eminem

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Eminem

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Eminem’s next album would come in 2017 with Revival, led by a long pre-release rollout that included his much-hyped first team-up with Beyoncé, “Walk on Water.” Both the album and the single underwhelmed expectations; Revival debuted atop the Billboard 200 — every new Eminem album this century has — but with mixed reviews and only about a third of MMLP2‘s first-week numbers, while the ponderous “Walk on Water” debuted and peaked at No. 14 on the Hot 100. He seemed to sense that he had done the album few favors with the extended walk-up to it, so he came back the next year with the surprise release Kamikaze, spawning a top 10 hit in the Joyner Lucas-featuring “Lucky You” — one of the first real examples of Em extending his arm to the next generation of rappers — and getting a better reception from fans and critics for its more inspired, focused rhyming. (As of Kamikaze, Eminem’s approach to music has clearly prioritized demonstrating his still being a top-tier MC above all hitmaking concerns — with him even saying, “If I had a choice between being the best rapper or making the best albums, I’d rather be the best rapper” — which makes perfect sense for an artist born from the battle rap circuit.)

The most social media attention Eminem got in the back half of the 2010s was actually for a pair of non-album cultural moments. At the 2017 BET Hip-Hop Awards, he again entered the political protest realm by using his cypher performance to decry then-president Donald Trump with an a cappella performance titled “The Storm,” even calling out some of his own fans in the process: “And any fan of mine who’s a supporter of his/ I’m drawing in the sand a line, you’re either for or against.” (Em would later rap that the move “practically cut my motherf–kin’ fanbase in half,” but continued to stand by his anti-Trump stance.) Then, in 2018, he engaged in his first celebrity beef in some years with then-rapper Machine Gun Kelly, who he had issues with dating back to a 2012 comment MGK made about Em’s daughter Hailie, and who he called out again on Kamikaze‘s “Not Alike.” This time, Kelly responded with a full dis track: “Rap Devil,” which drew enough media and streaming attention to also become his biggest unaccompanied Hot 100 hit, reaching No. 13. Eminem responded with the vicious “Killshot,” which outperformed “Rap Devil” by reaching No. 3, and largely ended the on-record back-and-forth.

In the 2020s, Eminem has continued to perform well commercially, with loyal, reliable fan support that ensures that he’s not as vulnerable to the changing tides of popular music as most other veteran rappers (or artists of any genre) are. His 2020 album Music to Be Murdered By marked his 10th No. 1 album and spawned a top five hit with the posthumous Juice WRLD teamup “Godzilla,” while this year’s The Death of Slim Shady (Coup de Grace) revisited Eminem’s most classic era and many of its most memorable characters for a (supposedly) final time. The “Without Me”-echoing, Steve Miller Band-sampling lead single “Houdini” has been Em’s biggest hit since “The Monster,” debuting at No. 2 on the Hot 100 and receiving a VMAs-opening performance in September that saw him recreating the Slim Shady Army from his epochal “Real Slim Shady” performance at the century’s beginning, a nice full-circle moment for the rapper and his longtime supporters.

It can be a little tough to size up Eminem’s legacy in pop stardom — which, aside from some unfortunate gaps in the 2000s, has essentially spanned the entire 21st century so far — because whatever Eminem has accomplished in the years since is always going to be held up against those first three years where he was on top of the world in nearly every conceivable way, and it’s inevitably going to pale in comparison. While Em has put up impressive stats and released a lot of good music in the years since, the greatness of his early run still ensures that any retelling of his story, or nearly any ranking of his best albums, songs or moments, is going to be impossibly weighted towards that initial era. The numbers Eminem put up in those years were jaw-dropping, but his impact also went far beyond them; like Taylor Swift’s more recent run of dominance during her Eras Tour, you probably had to live through it to totally understand just how all-consuming it was.

But while Eminem may have never been quite able to match the impact of his own early-2000s run in his later career, neither has any other rapper. And even if younger listeners may have trouble comprehending Eminem as one of the truly great and dominant pop stars of the 21st century, they can see it in the unmistakable importance he’s had on some of their own favorite artists in the next generation. That rangers from vividly introspective rappers like Juice WRLD and Mac Miller to line-crossing provocateurs like the early-days Odd Future crew to verbal technicians like Kendrick Lamar and Logic to singing pop stars like Ed Sheeran and The Weeknd — all of whom bear Eminem’s imprint, and all of whom have specifically cited him as an inspiration. They don’t all look (or sound) exactly like him, but the prophecy from the 2000 VMAs still essentially came true: an army of Slim Shady acolytes really did take over the world in the 21st century.

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back on Tuesday when our No. 11 artist is revealed!

On this week’s (Sept. 6) episode of the Greatest Pop Stars of the 21st Century podcast, we take a look at a pair of Tennessee natives: Fictional pop superstar turned IRL pop superstar Miley Cyrus (No. 15) and *NSYNC spotlight-stealer-turned-solo game-changer Justin Timberlake (No. 14). Explore See latest videos, charts and news See latest videos, charts and […]

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. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20, No. 19, No. 18, No. 17, No. 16 and No. 15 stars, and now we remember the century in Justin Timberlake — a true triple-threat whose insane winning streak to start this century seemed for a while like it might last indefinitely.

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Justin Timberlake came into the 21st century as pop’s golden child. From his scene-stealing time as the baby bro of *NSYNC at the turn of the century, to his one-two-three punch of a solo start with the hit-making Justified in 2002, gliding into the cutting-edge FutureSex/LoveSounds in 2006, and rounding out a decade-plus of pop supremacy with the glossy two-part 20/20 Experience in 2013, it began to seem like no amount of time off from music (or even a globally televised Super Bowl catastrophe) could kill his vibe. And while that golden touch has lost a bit of its sheen in the past few years – as Timberlake’s commercially dominant streak tapered to an end – his chokehold on pop culture for those 15 years can’t be overstated.

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But Timberlake’s transition from one-fifth of a blockbuster boy band to solo superstardom was never guaranteed. For every Michael Jackson, there are dozens of… well, we won’t name names, but for most boy banders, the group is the beginning and end of their success story. Timberlake was able to be the exception to the pop rule by choosing the exact right time to strike out on his own, and he had the most epic launch pad possible in the turn-of-the-millennium juggernaut that was *NSYNC.

Justin Timberlake

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Before we arrive at the year 2000, let’s quickly rewind to 12-year-old Timberlake landing a spot on Disney Channel’s All-New Mickey Mouse Club in 1993, where he met kindred pop spirit JC Chasez (and Britney Spears too, but we’ll get to her later). That was of course well before both were selected by Lou Pearlman as two of the five members of a new boy band, designed to recapture the late ’80s/early ’90s fan frenzy around New Kids on the Block, and backed by earworm productions from Swedish pop maestros, including the soon-to-be-legendary Max Martin. While *NSYNC made a huge impression with their 1997 self-titled debut album – spinning off four Billboard Hot 100-charting hits – their arrival was preceded by Pearlman’s other group, Backstreet Boys, and it felt a bit like the junior group was playing catch-up to their pop peers.

That perception was obliterated when *NSYNC’s new millennium kicked off with the January 2000 release of their first top five Hot 100 hit “Bye Bye Bye,” leading up to March’s No Strings Attached – which marked not just their biggest album debut yet, but the biggest album debut of all time, selling an unprecedented 2.4 million copies in its first week (setting a record that held for 15 years, until Adele’s 25); topping the Billboard 200 for eight weeks; and producing the group’s lone Hot 100 No. 1 in “It’s Gonna Be Me.”

One giant album led to another, with *NSYNC returning the next year with 2001’s Celebrity, their second Billboard 200 No. 1, which saw Timberlake’s introduction as the group’s true star. While Timberlake and Chasez had shared lead vocals on every song to that point, there was a solo showcase on Celebrity that painted the picture of what was to come: “Gone” found JT – who traded his famous ramen-noodle curls for a bad-boy buzzcut – singing every verse (showing off his vocal range, from a gravelly baritone to a floating falsetto) and starring front and center in the black-and-white music video, backed by his groupmates for lush harmonies on the chorus. Another sign of Timberlake’s future: Celebrity’s breakout hit “Girlfriend,” *NSYNC’s first foray into hip-hop-flavored pop and a Hot 100 top five hit, included a guest verse from Nelly and production by The Neptunes, foreshadowing the core sound JT would pursue on his solo debut.

Justin Timberlake

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And we can’t paint a picture of just how massive a star Timberlake was at this point without talking about the power couple that catapulted his public profile into another stratosphere. Timberlake started dating Spears, his fellow Mickey Mouse Club alum, in 1999, and their combined pop powers launched a thousand teen-magazine covers (and led to an iconically bizarre dual-denim fever dream of a red-carpet appearance at the 2001 American Music Awards).

The beginning of the end for *NSYNC arrived in April 2002, when the Celebrity Tour, the group’s fourth and (so far) final trek, wrapped up and was followed by an indefinite hiatus. Also in the spring of 2002: Timberlake broke up with Spears – meaning his public identity as both a boy bander and Britney’s boyfriend were behind him as he headed into the summer 2002 creation of his debut solo album, Justified. For the 13-track set, he reunited with The Neptunes on seven cuts and connected with hip-hop heavyweight Timbaland for the first time on four songs. Just four months after pressing pause on *NSYNC, JT’s debut solo single, the Neptunes-produced “Like I Love You,” arrived in September 2002, followed by the Nov. 5 release of the full album. 

“Like I Love You” peaked just outside the Hot 100 top 10, and Justified debuted and peaked at No. 2 on the Billboard 200 – but the heat around Timberlake’s budding solo stardom had just started boiling. The Timbaland-produced “Cry Me a River” came next, climbing all the way to No. 3 on the Hot 100 by memorably mining the Britney breakup, fueling cheating rumors and deploying a Spears doppelganger in its eyebrow-raising music video. JT scored two more top 40 Hot 100 hits with a final pair of singles from the album: the MJ-indebted “Rock Your Body” (No. 5) and the Pharrell-intro’d “Señorita” (No. 27). Aside from his chart success, Timberlake also managed something on his debut album that *NSYNC never accomplished, picking up his first two career Grammys at the 2004 ceremony: best pop vocal album for Justified and best male pop vocal performance for “Cry Me a River,” from five nominations.

After Justified, Timberlake was hot enough to get the call to appear onstage with headliner Janet Jackson at the 2004 Super Bowl halftime show. What should have been a victory lap for the newly minted solo star turned into a world-famous nightmare when Timberlake accidentally exposed Jackson’s breast in front of 140 million TV viewers (just as he sang the “Rock Your Body” lyric “better have you naked by the end of this song”), later coining the infamous phrase “wardrobe malfunction” in his apology. But while Jackson’s career famously suffered in the aftermath, JT was largely left strikingly unaffected.

After back-to-back releases from *NSYNC followed quickly by his solo debut, fans had to wait a grueling four years for Timberlake’s next album. Led by “SexyBack” — his most experimental single yet, with a harsh but intoxicating electro-funk sound — FutureSex/LoveSounds debuted atop the Billboard 200 in September 2006 and signaled his arrival as a fully formed adult pop star. He leaned into his Timbaland partnership on the project, scoring his first three solo Hot 100 No. 1s with the album’s first three singles: “SexyBack”; the percussive T.I.-featuring ballad “My Love” and the two-part “What Goes Around…Comes Around,” basically a karmic sequel to “Cry Me a River.” He picked up another four Grammys across the ‘07 and ‘08 ceremonies for the project, cementing his spot as both a critical and commercial heavyweight. He also sprinkled his pop magic onto other artists’ singles in his downtime, returning the favor to Timbaland with the Hot 100-topping “Give It to Me” (also alongside Nelly Furtado) and gracing a trio of top five hits in Madonna’s “4 Minutes,” T.I.’s “Dead and Gone” and 50 Cent’s “Ayo Technology.”

By this point, Timberlake had introduced a new layer to his many talents by hosting Saturday Night Live during both of his solo album cycles (he’d eventually join the Five-Timers Club in 2013) and introducing his recurring sketch “The Barry Gibb Talk Show” with Jimmy Fallon during his debut 2003 hosting gig. But the real gift came in December 2006, when Timberlake co-starred in The Lonely Island digital short “D–k in a Box,” which went on to win an Emmy for outstanding original music and lyrics the next year and virtually invented the idea of a viral hit on YouTube, the video-sharing site that had debuted only a year prior.

That SNL success seemed to feed into Timberlake’s next move, as he took a nearly seven-year break from music to pour himself into an acting career, with varying degrees of success (there was Oscar-favorite The Social Network and charming Mila Kunis rom-com Friends With Benefits, but there was also The Love Guru). At this point, it was unclear whether Timberlake would ever return to his recording career, but it was a testament to the level of stardom he’d reached that his fans never stopped anticipating his musical return, no matter how long he stayed on the sidelines.

He eventually found his way back to music, taking on a natty Rat Pack-inspired persona in a tuxedo and slick new hairstyle as he rolled out the smooth Jay-Z-featuring “Suit & Tie” (No. 3 peak on the Hot 100) in January 2013 and the eight-minute ode to wife Jessica Biel “Mirrors” (No. 2) in February ahead of the March release of The 20/20 Experience. The breathless excitement for Timberlake’s crooning comeback was made clear when 20/20 sold 968,000 copies in its first week – the largest solo week ever for JT – and finished as the year-end No. 1 Billboard 200 album for 2013. While the project was generally embraced by fans and critics alike, there were a few misgivings this time – including some hand-wringing over the songs’ excessive runtimes – compared to the flawless approval rating of its FutureSex/LoveSounds predecessor. 

Justin Timberlake

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The long-awaited album wasn’t the only music JT had up his tux sleeve that year: Timberlake surprised fans by announcing an imminent Part 2 coming for The 20/20 Experience – and it arrived just months later, scoring him a pair of Billboard 200 chart-toppers in 2013. The project was preceded by what might be considered Timberlake’s first musical misstep: Lead single “Take Back the Night” shared a name with a sexual-assault awareness group, but its suggestive lyrics instead told the story of a carefree, sexy night. JT apologized (“neither my song nor its lyrics have any association with the organization”) and shed light on the group’s efforts (“something we all should rally around”), but the song never really rose above the controversy, topping out at No. 29 on the Hot 100. There were two success stories from 2 of 2, however: The dreamy ballad “Not a Bad Thing” climbed all the way to the Hot 100’s top 10 eight months after the album’s release, and the twangy “Drink You Away” became JT’s first song to reach Billboard’s Country Airplay chart, following a lauded team-up with Chris Stapleton at the 2015 CMA Awards.

After sticking to his electro-pop sound on top 10 lead single “Filthy,” Timberlake found another country moment on his February 2018 album Man of the Woods when he re-teamed with Stapleton for the strummy standout cut “Say Something” and scored another Hot 100 top 10. Days after the release of his fifth studio album – which debuted atop the Billboard 200, but with a much smaller first week than 20/20 — Timberlake returned to the Super Bowl stage, 14 years after the Janet incident, for a much less incendiary showing and headlining for the first time. 

As JT made a memorable meme out of #SelfieKid in the Minneapolis crowd and paid tribute to hometown hero Prince at Super Bowl LII, some fans questioned why Timberlake was invited back to the Super Bowl when Jackson never was, and the pop star directly addressed that criticism years later in a 2021 Instagram statement. His comments were prompted by the February 2021 release of the documentary Framing Britney Spears, which put his post-breakup behavior in a new light and led to renewed criticism over the double-standard at play following the Super Bowl controversy, and Timberlake’s failure to properly support Jackson over the blowback she’d faced at the time, which he’d since expressed regret over. “I specifically want to apologize to Britney Spears and Janet Jackson both individually because I care for and respect these women and I know I failed,” he wrote in part.

While he had amassed his fair share of detractors by this point, Timberlake had also broken through to a new, much younger generation of fans by combining his Hollywood aspirations with his musical prowess and voicing Branch in the pop-music-obsessed Trolls animated movie series, scoring his fifth Hot 100 No. 1 along the way with the bouncy, Oscar-nominated 2016 soundtrack single “Can’t Stop the Feeling!” Timberlake brought things full-circle in 2023 for Trolls Band Together, when he reunited his *NSYNC bandmates in the movie and for their first new song in 21 years, the whistling confection “Better Place.” 

And that wasn’t all he had in store for fans who had been with him from the beginning: For his sixth studio album Everything I Thought It Was (led by top 20 single “Selfish”), the pop quintet got together yet again for “Paradise,” which they live-debuted just before the album’s March 15 release, and which seemed to speak directly to the fans who had been begging the boy band to reunite for decades (sample lyric: “I’ve been waiting forever/ Right here for this moment”). 

Justin Timberlake

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Aside from the *NSYNC reunion, JT’s latest album mostly underwhelmed, debuting at No. 4 on the Billboard 200 and failing to produce any lasting hits. That lackluster performance was further compounded when Timberlake’s summer DWI arrest in The Hamptons amid the Forget Tomorrow World Tour became an online punchline, thanks to his police-reported prediction of “This is going to ruin the tour… the world tour.” But it didn’t: In fact, the recently extended trek is on track to land in the top 10 of Billboard’s year-end tours list. And the hunger for a potential *NSYNC reunion tour is still raging as well: “Bye Bye Bye” even recharted on the Hot 100 this year – 24 years after its initial Hot 100 debut – off its use on the Deadpool & Wolverine soundtrack. 

It seems fitting that Timberlake would find himself approaching the quarter-century mark by (however briefly) returning to the turn-of-the-century group responsible for much of what he’s created so far in his career. After all, while he’s surely picked up fans along the way who weren’t around for his *NSYNC heyday – whether they were too old to be invested in a boy band or too young to understand (or not even alive for it, for that matter) – the bond formed from watching someone at age 12 on Disney Channel to following along on their boy-band journey to seeing their ascension to the top of the pop pyramid is impossible to replicate. There’s an unconditional love that comes from those day 1 fans that has unquestionably fueled JT’s nearly three decades in pop, through its highs and lows. In the end, ain’t nobody love him like we love him.

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back on Tuesday when our No. 13 artist is revealed!

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. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20, No. 19, No. 18, No. 17 and No. 16 stars, and now we remember the century in Miley Cyrus — who at age 31 has already lived through several artistic lifetimes, generating numerous pop classics and countless unforgettable moments in the process.

For many artists, it’s their hit songs, pop culture-defining albums or chart successes that are easiest to pinpoint as landmarks for the most pivotal stages of their careers. But for Miley Cyrus, it’s hair. 

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Though she certainly has plenty of all the above accomplishments, the 31-year-old generational talent’s phases of life have always been irrevocably intertwined with what’s going on atop her head — from the blonde wig that made her famous in the mid 2000s to the bleached pixie cut that introduced the world to a very different Miley in 2012. It goes beyond the public’s obsession with beauty standards, which a thin, blue-eyed Cyrus would embody for the first several years of her career before rejecting that mold altogether; the singer’s hair has had a way of symbolizing where she’s at personally and artistically over the years.   

And where she’s been, in both regards, has been all over the map. From eager Disney Channel prodigy to unruly pop outlaw, freewheeling genre experimenter and mature modern hitmaker, Cyrus’ knack for earnest reinvention has sustained her through all the peaks and valleys of her career. With no shortage of chart hits and even more iconic culture-shocking moments, she’s endured as one of the century’s most significant pop stars – because no matter what style she’s trying out, at the end of the day, she’s always still just being Miley. 

Born Destiny Hope Cyrus on Nov. 23, 1992, in the Nashville metropolitan area of Tennessee, the most recognizable head of hair in the young star’s childhood wasn’t her own, but father Billy Ray’s signature mullet. Miley, who legally adopted her childhood nickname in 2008, grew up in a constellation of other stars before she would become one herself, with her dad becoming a country sensation in the ’90s for the massive crossover hit “Achy Breaky Heart” and her godmother being none other than Dolly Parton.

Seeing Billy Ray act on his early-’00s medical drama Doc inspired Miley to want to be a performer, too, leading her to audition for Disney Channel’s Hannah Montana at just 12 years old. After first reading for the part of sidekick Lily, the preteen was instead asked to try for the sitcom’s main character instead: Miley Ray Stewart, a Malibu teen who could transform at any moment to global pop sensation Hannah Montana, with a wig that somehow carried the same camouflaging powers as Clark Kent’s glasses. Billy Ray was cast as her character’s dad, their natural chemistry translating beautifully on screen.  

It’s hard to describe just how magnetic Cyrus was on that show. Here was a girl who could deliver a cheesy catch phrase — usually “Sweet niblets!” or  “Yeeee doggies!” — like a seasoned comedic actor, unafraid of appearing unattractive or goofy in service of a good bit with an innate power and resonance in her voice that was almost unnatural for her age. 

Miley Cyrus

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Miley Cyrus

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And you’d better believe that Disney capitalized on her raw talent. During Hannah Montana’s run from 2006 to 2011, the children’s network churned out four seasons of TV, five soundtrack albums, a feature film, a tour and a concert movie — not to mention countless clothing lines, lunch boxes, backpacks, accessories, makeup, blankets, throw pillows and Happy Meal toys plastered with Miley and Hannah’s shared face.  

All the while, Cyrus was essentially holding down two music careers at once, signing with Walt Disney Records for all things Hannah and then with Hollywood Records for her own work as Miley. Her first two albums, Hannah Montana and Hannah Montana 2/Meet Miley Cyrus both debuted at No. 1 on the Billboard 200. On the Best of Both Worlds Tour, she performed one half as herself and the other as her alter ego (the trek grossed more than $54 million, according to Billboard Boxscore). She scored numerous chart hits under Hannah — “Best of Both Worlds,” “Nobody’s Perfect” and 18 more tracks made the Billboard Hot 100 during the show’s run – which gave way to additional hits as Miley. Both “See You Again” and the Nick Jonas breakup anthem “7 Things” reached the Hot 100 top 10 and gave her credibility outside of the Disneyverse, leading pop fans to start taking her seriously outside of her lane as a kids’ TV star.   

As Miley and Hannah became increasingly inextricably linked, however, it got harder for the public to detangle Miley Cyrus from Hannah Montana, or even from Miley Stewart. Activities like posing bare-shouldered on the cover of Vanity Fair in 2008 or hitting a salvia bong the week of her 18th birthday in 2010 weren’t the mere antics of a maturing teenage girl, they were affronts to a squeaky-clean, million-dollar brand dependent on the adoration of little kids and the approval of their parents. This left Cyrus with few options for mapping out her career post-Hannah: risk spending the rest of her life living in her own character’s shadow or control the narrative by inelegantly demolishing that character and forcing the world to watch. We all know which route she chose – but first, attempts at a more seamless transition were made.  

In 2009, the same year Hot 100 No. 4 hit ballad “The Climb” and barn-raising dance tune “Hoedown Throwdown” came out for Hannah Montana: The Movie’s soundtrack, Cyrus dropped the 7-track EP The Time of Our Lives, featuring what is still one of her most beloved and easily recognizable hits: “Party in the U.S.A.” The Dr. Luke-produced quasi-patriotic banger immediately became Cyrus’ biggest home run so far, exploding on pop radio and reaching No. 2 on the Hot 100 thanks to its charming lyrics and infectious main hook. (Seriously, how does one not sing along to that “Yeah-ee-ah-ee-ah-ee-ah” in the chorus?) The track also offered a glimpse at what her post-Disney pop music career might’ve looked like for the next decade if she’d wanted it: polished, widely palatable and performed by the same Miley Hannah Montana fans knew and loved, just with a more mature sound and maybe slightly shorter shorts

But then, she got on stage at that year’s Teen Choice Awards and innocently performed the track on top of a prop ice cream cart, holding onto a silver bar so as not to fall off while dancers pushed her around. Except, the masses didn’t see it that way: The showcase sparked global gasps and pearl-clutching over what scandalized audiences interpreted as a risqué pole dance. One famous tabloid headline asked if Miley was “turning into Britney.” Instead of coming to her defense, her network quickly released a statement: “Disney Channel won’t be commenting on that performance, although parents can rest assured that all content presented on the Disney Channel is age-appropriate for our audience – kids 6-14 – and consistent with what our brand values are.” (This is why we can’t have nice things.) .  

After that, Miley came back with 2010’s Can’t Be Tamed, an album meant to showcase her edgier side and her last with Hollywood Records. Its title track was the effort’s biggest hit, peaking at No. 8 on the Hot 100 that summer – assisted by a music video showing the star in a leggy feather leotard, writhing sensuously in a bird cage – but public interest in the rest of the album petered out quickly, and Cyrus would disavow it as her “last pop record” soon afterward. In January 2011, Hannah Montana’s final season finished airing, and its soundtrack became the show’s first to not break the top 10 on the albums chart. Miley took a break from music to focus on acting, filming the Nicholas Sparks tear-jerker The Last Song (during which she met future ex-husband and frequent muse, Liam Hemsworth), detective comedy So Undercover and teen romance LOL over the course of two years. 

But let’s get back to hair. Cyrus’ signature brunette waves were aesthetically quintessential to the Miley-Hannah package. That’s why it was so shocking when the star shaved the sides of her head in August 2012 and bleached the scruff that remained on top. Miley Stewart – and certainly Hannah Montana – were long gone. Cyrus tweeted, “Never felt more me in my whole life.” 

The makeover was the first domino in a pop culture-disrupting series of events and a full metamorphosis for Cyrus, who still wouldn’t reach legal drinking age until November 2013. In March of that year, she posted a video of her twerking to J. Dash and Flo Rida’s “WOP” in a unicorn onesie. In June, she dropped “We Can’t Stop,” a Mike Will Made-It production originally penned for Rihanna. The hedonistic, anti-polite-society earworm and its music video were both massive year-defining hits, with the track reaching No. 2 on the Hot 100 and the Diane Martel-directed visual deliberately showing Cyrus in the most extreme anti-Hannah light possible: shaking her ass at a grimy house party, making out with a doll in a swimming pool full of nearly naked friends, wagging her tongue Gene Simmons-style and repeatedly flashing her grill to the camera.  

In August, she caused nothing short of nationwide panic by grinding on Robin Thicke and miming sex on a foam finger at the VMAs, earning bemused looks from Rihanna and One Direction in the audience that were nothing compared to the horrified outcries from parents and think piece writers everywhere the next day. It sparked months – years, even – of discourse surrounding Cyrus’ body, the children she’d supposedly scarred and whether she was mentally “disturbed,” as MSNBC anchor Mika Brzezinski put it at the time. Her “stripper pole” incident in 2009 now seemed like child’s play.  

In September, she swung butt-naked on a demolition ball and made out with a sledgehammer in the since-disgraced Terry Richardson-directed “Wrecking Ball” music video, leading the late Sinead O’Connor to urge Cyrus to stop “pimping” herself in an open letter. In October, she unblinkingly said that Hannah Montana “was murdered” while hosting Saturday Night Live. 

Miley Cyrus

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You could say Cyrus was overcompensating. You could say she was being raunchy just for the sake of being raunchy. You could definitely say that she was appropriating and caricaturing Black culture, a critique that would plague her career for years to come.  

But you can’t say that it wasn’t working: “Wrecking Ball” became her first No. 1 hit on the Hot 100, topping the chart for three weeks, and album Bangerz debuted atop the Billboard 200 with assists from Nelly, Future, French Montana, Ludacris and Cyrus’ oft-claimed predecessor, Britney Spears. The corresponding world tour grossed a reported $63 million in 2014, according to Billboard Boxscore. Love it or hate it, the era remains one of the most commercially successful and iconic of her career, so much so that Billboard’s staff named her the Greatest Pop Star of 2013. 

“I know what I’m doing,” she told Rolling Stone at the time. “I know I’m shocking you.” 

From there, Cyrus embraced her role as provocateur, raving about her love of smoking weed and taking molly and appearing on late night shows with heart-shaped pasties covering her nipples. She also discovered new passions outside of music and acting. Fueled by the attention she so easily captured with her and Thicke’s NSFW performance, Cyrus began her Happy Hippie Foundation in 2014 — “If the world is going to focus on me and what I am doing, then what I am doing should be impactful and it should be great,” she told Wonderland — dedicated to helping homeless and LGBTQ+ youth. The next year, she returned to the VMAs as host, which had some hiccups (“Miley, what’s good?”) but seemed like something she truly enjoyed doing; seven years later, she’d host Miley’s New Year’s Eve Party with her famous godmother for NBC.  

During the 2015 ceremony, she would also announce her psychedelic LP Miley Cyrus & Her Dead Petz, having severed ties with Dr. Luke amid his legal battle with Kesha. Seemingly rebuking the spotlight she’d earned with Bangerz, Cyrus dropped the album for free on SoundCloud before making it available commercially with new label RCA Records much later. The record was panned by critics and ineligible for chart consideration, but ended up being a wise move even disregarding its retroactive love from fans down the line; with Dead Petz, Cyrus effectively cleaned her slate to do whatever she wanted next without the pressure of matching Bangerz’s commercial success. 

Miley Cyrus

Jason Merritt/Getty Images

In 2016, she came out as pansexual, a major moment of visibility for the LGBTQ community considering her conservative Disney Channel roots. “My first relationship in my life was with a chick,” she told Variety. “I grew up in a very religious Southern family … Once I understood my gender more, which was unassigned, then I understood my sexuality more. I was like, ‘Oh — that’s why I don’t feel straight and I don’t feel gay. It’s because I’m not.’” 

Either satisfied that she’d made her point or having simply outgrown her rebellious phase, Cyrus calmed down a bit in the mid-to-late 2010s. But she would spend her next few albums trying to reckon with her past behavior, starting with 2017’s Younger Now, a lighter album partly inspired by her newfound domestic bliss with Hemsworth, whom she married the following year. On the title track, she made a point of explaining that she’d moved on from grinding on Teddy bears and straddling giant hot dogs —  “No one stays the same … what goes up must come down” — and in the serene beachside music video for lead single “Malibu,” she appeared with her bleached hair symbolically growing out to reveal her natural brown roots. The project peaked at No. 5 on the Billboard 200, a new low for Cyrus, and barely eked out a top 10 hit with “Malibu.”  

After scrapping a planned three-EP rollout after its first installment, She Is Coming – the highlight of which was “Slide Away,” an ode to her pending split from Hemsworth — Cyrus again wrestled with her past on Plastic Hearts. “They told me I should cover [my body], so I went the other way,” she sang on “Golden G String.” “I was trying to own my power, still I’m trying to work it out.” It was during this era that Cyrus embraced rock music – marked, of course, by her edgy blonde mullet – a style that was arguably a better fit for her than pop ever had been, artistically speaking. Though not her most commercially successful album, she proved herself in other ways, holding her own in the booth next to the LP’s special guests Billy Idol, Joan Jett and Stevie Nicks and earning viral moments for her exquisite Blondie and Cranberries covers. 

Over these years, she also set a new precedent for herself when it came to touring: With the Bangerz trek marking her most recent proper solo headlining tour to date, Miley opted not to tour at all for Younger Now and performed only a limited run of festival dates for Plastic Hearts, preferring instead to give fans live numbers through her years-long Backyard Sessions series. For someone whose life was so heavily regimented by other people when she was young, there’s no doubt that shirking the traditional touring model was an especially meaningful boundary for her to set on her own behalf in adulthood.  

In 2023, years after it seemed Cyrus might never again score a smash as huge as “Wrecking Ball,” she circled back to a more straightforward pop sound on Endless Summer Vacation (via new label Columbia Records) and found runaway success with lead single “Flowers.” The Bruno Mars-echoing, Hemsworth-teasing track spent eight weeks at No. 1 on the Hot 100 and earned Cyrus best pop solo performance — her first-ever Grammy — at the 2024 awards, as well as record of the year. On final single “Used to Be Young,” she once again addressed her past: “I know I used to be crazy, I know I used to be fun/ You say I used to be wild, I say I used to be young.” 

Cyrus has already lived multiple lives in her nearly-two-decade career — from tween idol to pop rabble-rouser to rock star and everything else in between – but now, the label that suits Miley best at age 31 is simply seasoned professional. Her versatile talents are sought out by many in the industry, from Beyoncé on Cowboy Carter duet “II Most Wanted” to acclaimed indie studio A24 on a recent cover of Talking Heads’ “Psycho Killer.” And the little girls she raised as Hannah Montana make up the next generation of stars, from Sabrina Carpenter — who at 10 years old won a fan contest to meet Miley — to Chappell Roan, whose fandom of the Disney Channel show inspired her own sparkly alter ego.  

In 2024, Cyrus seems especially at peace, with both her past and who she is now. And after years of the world struggling to catch up to her, it seems the culture – far less uptight than it was when she entered it, thanks in part to her so loudly disavowing the standards of sensibility we used to force on female artists – is finally giving the singer credit for leaving such a lasting impression. 

In an emotional full-circle moment, Cyrus got the rare chance to bask in that recognition at the Disney Legends Ceremony in August. Tearfully facing the crowd with her hair mostly brunette for the first stretch since 2013 – aside from a few streaks of blonde highlight, perhaps showing that all her past selves will always be with her in some capacity – she said that “a little bit of everything has changed” since she first donned her famous wig in 2005. 

“But at the same time, nothing has changed at all,” Cyrus continued. “I stand here still proud to have been Hannah Montana. Because she made Miley in so many ways.” 

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back on Thursday when our No. 14 artist is revealed!