Pop

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. 

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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