It’s refreshing to discover new artists in this day and age. The Internet has essentially blurred the lines between what constitutes as underground these days, and depending on who you’re talking to, one can make the case that the world wide web has replaced the underground scene in hip-hop completely with social platforms like TikTok being critical to new music discovery.

Enter Laila!, the teenage Brooklyn phenom with rap royalty coursing through her veins. The daughter of Yasiin Bey (formally knowns as Mos Def), her songs “Like That” and “Not My Problem” went viral before the masses really knew what she looked like. It wasn’t until she performed the songs on YouTube shows On the Radar and From the Block, that we really got a chance to put a face to the music we kept hearing on social media. She sings, raps, writes, and produces everything herself and her stage presences isn’t half bad either.

Last month, Laila! performed her first headlining show at Baby’s All Right in Brooklyn, a place that’s earning the reputation as the first venue to catch your favorite up-and-coming artist. The place was packed to the brim and featured a diverse crowd of all races, ages, and creeds coupled with an infectious energy in the air as we all waited for her to hit the stage. She ran through the hits, but also performed some cuts from her earlier work featured on her In Ctrl! EP that fans in the crowd seemed to know the words to. There was also a part of the show where she reminded me of her father.

In the middle of her set, Laila! brought out the keyboard and started jamming out and singing. Yasiin did something similar in back in 2010 during his Martin Luther King Day Weekend performance at the Highline Ballroom. During the middle of his performance, Bey hopped on the drums and started jamming out, too. I don’t know, it just felt like a surreal, full circle moment. “That’s sweet,” she said when I brought it up during our talk. “I get anxious, but I like being on stage. I like showing people that I’m versatile.” And versatile she is, all you have to do is check out her debut album Gap Year! if you haven’t already.

We talked about a wide range of topics including her freestyling with her father and Jay Electronica in Puerto Rico when she was just a kid. Hopefully, that footage will be released from the vaults one of these days. Maybe for the documentary.

Check out our chat with Laila!, October’s Rookie of the Month, below.

I went to your show at Baby’s All Right in Brooklyn, so I want to lead off with that. Tell me about that experience, because you seemed nervous at first, but you did pretty good for it being your first headlining show.

Yeah, I was definitely really nervous. I always get really nervous before I got on stage. I don’t know what it is, I just get super anxious. But then when I saw everyone’s energy and how excited they were to be there, it was just really beautiful. It was special for me, so I kind of was able to calm down and give them a good show.

I was impressed because people knew the words to songs that were relatively new.

That was the most insane part to me. Just to hear them, not even just singing the most popular songs, but the other ones too. It was just insane. It was very big for me. It was also my first time ever in front of my own audience, people that really came specifically to see me. It was really special. I was able to take pictures with some of them and sign stuff. And it was just really sweet. It was the sweetest thing ever.

I’m assuming you had a lot of family and friends there too because it was a packed house, and you could tell some people were family.

I had some people from my high school, my tías [my aunts] were there. Like, just everybody. But then there were kids with their parents and it was the cutest thing ever. It felt very supportive.

You mentioned your “tías” and you had a voicemail of your grandmother Mami Nelly on your album telling you how proud she is of you. Are you Dominican or Puerto Rican? The Caribbean delegation is looking to claim you.

Yeah, she has a thick accent. I’m Dominican and African-American. My mom is Dominican and my dad is from here. My accent comes out sometimes [Laughs.]

Your sister Sani DJ’d your show and she killed it. Is that the same sister that was freestyling about you not wanting to go to school on your album?

Yeah, it was so funny because me and my sister put the whole show together. We rehearsed for like two weeks and put everything together, and we literally did not even think about doing the freestyle song live. We didn’t even think about that. Looking back, we should’ve done it, but we were so focused on making sure everything was right. Definitely a learning experience, but it was also very fun doing the show with her.

I liked her set. She was playing U.K. garage and jungle, some Jersey Club, and mainly dance music. I know you mentioned Brent Faiyaz, Frank Ocean, Solange and SZA — these are people that you listen to a lot — but what are some other genres or artists that you also listen to and draw inspiration from?

I really like jungle music, too. My sister Sani introduced me more to like jungle music because she’s a DJ. She has such a broad taste in music. I feel like she’s kind of helped me in that aspect where she’ll play really good club tracks from forever ago, or a lot of old mixes. The thing that’s really cool about it is you can find a mix and sometimes it’s just specific to that period of time or that specific DJ, so you can’t find that same version of the song anywhere else, which is kind of cool about garage music or jungle music.

You could hear a song that you like and then hear a part of it that you’ve never heard before, and it’s only specific to that remix. I listen to jungle, I listen to a lot of Budgie. He does sample flips. He’s mad cool, and I found him on SoundCloud, but he does like stuff like that. I also listen to a lot of older ICYTWAT beats when I’m trying to get into a hype mood.

His song “Shirt” is one of the greatest songs ever. I still play some ICYTWAT’s Soundcloud remixes and mixes.

I listening to his older stuff, those are my favorite albums from him, like Fubu vs. Twat any ICYTWAT Radio.

He’ll have some ill flips too, like he’ll remake songs and s–t like that.

I love listening to all kinds of flips. Also, I just be playing my SoundCloud, it just be playing shit. Like once you play a song, it’ll keep recommending really good stuff.

Do you have any flips or remixes that you have in the stash?

I certainly do, and I used to post them on TikTok. So like, some of the real OG people that follow me, they’d be like, “Where’s this flip? Where’s the Aaliyah flip? You need to post this.” And I’m like, “Yo, the fact that they remember that is so insane because they’ve been around for a minute.” I have so many that I want to put out.

You were working the crowd and it was crazy when you started playing the keyboard. Is the piano the only instrument that you know how to play?

I would say officially, yes. When I was younger, I used to be in band like in elementary school and stuff like that. And the first instrument that I learned was the trumpet. My mom was a teacher, so they had a steel pan band. So I would like, go there and play steel pan sometimes. But then, yeah, I think piano was like the first instrument that I learned that really stuck with me. I feel like it’s the basis for everything that I produce, or everything that I make. But I’m not classically trained, and I really want to learn, so hopefully that’s something I build on in my future.

When you were on the keys and Juan was on the guitar, that was my favorite part of the whole show.

I think that was probably one of my favorite parts as well, because it was just so special. And when I was putting together the show, and thinking about what I wanted, I was like, I have to have Juan come and do “Talent Show.” We made this song together, and it’s so special to me. And to hear people singing along was even more insane for me.

The show felt like a New York show before the pandemic. There used to be shows with that energy all the time in the city. It was interesting to experience. You and Cash Cobain have NYC on lock right now. The city is behind you guys.

Yeah, I love that. That’s so sweet. That’s all I ever wanted to do. Whenever I talked to my team about doing a show, ,all I wanted was it for just to feel like good vibes, comfortable, just very familial so everyone could enjoy themselves in a good environment. That’s all I’ve ever wanted. So I’m glad that it felt that way.

So, you taught yourself how to play the piano and the keyboard. What do you use when you make beats? Any programs or drum pads?

More often than not, I’m actually just using the keys on the keyboard because it’s easy and it’s simple for me, but then a lot of times I also just use my MIDI keyboard that I could just put into my computer, and then I’ll just play like that. And yeah, it has beat pads on it too, which is cool, because you can do fun little stuff there. If I wanna play the drums, and maybe don’t wanna use the keyboard, I can use that.

Do use a program like Fruity Loops or something?

I use GarageBand, it’s very helpful. There’s so much good stuff on there that I feel people tend to overlook.

You know when you’re young and growing up, you don’t always know what your parents do for a living. Were you always musically inclined, like even before you knew what your father did for a living?

Yeah, it was just always a part of me. My mom has videos of me just singing and doing all this stuff, and I was like, a little, little kid. I wasn’t at the age where I knew what my dad did. The moment I could form words, I think I was singing and dancing and doing all that stuff. I don’t know a life without music, or making music.

When did it really click for you, though, where you wanted to take music seriously? Angela Yee mentioned in an interview with that you were in Puerto Rico freestyling with your father and Jay Electronica, when you were really young — which, I wish there was audio or a video of this. I wanna hear this freestyle.

I feel like my mom probably has a video [laughs]. I think it wasn’t until my sophomore year of high school. I always wanted to make music and have that be my career. That was always my plan. I was like, ‘I’m gonna get out of school and then I’m gonna start making music and, you know, whatever.’ But I was always so shy and so nervous about it, and I just didn’t really know what I was doing. So, at certain point I had to stop being so afraid and follow my passion do what it is that I feel like I love to do the most. I put out my first song, and that’s kind of where it all began.

So this was when you’re 16, right? When you made “Like That.” Do you feel like you’ve gotten better since then already?

I think I’ve definitely gotten a lot better. I don’t know how to explain it, but once you make something, you’ve sat with the feelings, you felt the way that you felt, you’ve written the lyrics, and then once you release it and it’s out there, it’s kind of like, OK, I don’t necessarily have those same feelings or I’m not the same person. It’s almost like a release. You know what I mean? I don’t know. So I feel like, when I look back at “Like That,” it was a period of time in my life, but now I’m moving on, and I’m growing up, and with everything that I make, it feels like I’m growing up a little bit more.

So yeah, I think that the stuff that I’m making now versus “Like That,” I think it it shows my growth in that sense, even just as a person, maybe not so much like sonically, maybe it doesn’t sound a million times different, but as a person, I feel different.

I definitely get what you’re saying. You blew up so fast and I’m curious about how old some of the songs are on Gap Year!

Yeah, that’s actually such a good question, because Gap Year! is basically just a compilation of the stuff that I made from the time I was, like, 16 until now. So a lot of the songs on there are actually older. “If You’re Listening,” I recorded that when I was 16. “We’re So Over,” too. But then I made “Want To” around four months before we dropped the album. I made the beat for “Are You Down?” maybe when I just turned 16. That was one of the first beats that I made where I was like, “Yo, I’m kind of good. Maybe I’m nice at this like, maybe I could really make beats.” I made the “Like That” beat when I was 15, and didn’t record on it until about a year later. It was a blend of the journey that I’ve taken with music and learning how to make beats.

You mentioned feeling anxious when you go on stage. Do you feel any pressure right now?

Yeah, sometimes. I feel like I always feel pressure, though. I’ve always felt pressure even before I had put out a song, even before people followed me, or anything like that. I always felt pressure because… I don’t know, sometimes pressure can be bad, but sometimes it also can feel like I wanna get this done, I wanna execute an idea I have, or whatever. And when I say pressure, it’s not like pressure from my family or pressure from external people, because I always have so much love and support around me, which I’m so grateful and thankful for. Everybody’s always just trying to make sure I’m good or whatever, just whatever I need. They’re always there for me. I’m just really grateful about that. But I think the pressure kind of comes from within. I want to make sure I’m doing everything to the fullest capability. I’m just always trying to be better than I was before.

This is a complicated question, but how would you describe your sound?

I think I really would describe my sound as fresh and fly and cool, but also nostalgic, I pull from so many things that I love. I have such a love for R&B and writing. I always think so melodically. And a lot of that comes from my biggest inspirations, and I kind of take the bits and pieces that I can.

I feel like an important thing about music and even human life, is that we learn through imitating. We see something we like, and we try to become that. For me as a producer, it’s been really interesting being able to take like, ‘Okay, I like this progression, or I like the way that this bassline sounds, or I like the way that the snare hits here on this song. And you take those little bits and pieces and almost transform that into something that’s completely different by studying things that I really like, whether it’s The Neptunes or an Aaliyah song or whatever, or a Darkchild beat. I’ll sit there and I’ll listen to things that really make that specific song click for me. Nostalgic, but fresh is how I would describe my music.

Yeah, it’s like an amalgamation of all these things. It’s like retro and futuristic at the same time.

Thank you. That’s what I’m going for.

Your On the Radar performance made me look into you more — and and then obviously when people figured out who your father was, everyone’s minds were blown.

Yeah, it was very funny how it kind of just built up and people started. None of this has been planned. The only thing that was planned was to do something cool like On the Radar. The whole objective was to get my face out there. I wanted people to get a sense of who I am or what I do.

As it was going viral, were you like, “Yo, I have to put my name on this somehow?”

I just wanted people to be able to connect the song with who I am, like, as an artist, because I feel like, I don’t know, nowadays, it’s so easy for the artists to get lost in the shuffle when something gets really popular. So, I just kind of wanted to do something. And I did the From the Block, which was really cool. That was just an awesome experience. Doing that like at the playground was mad fun. But yeah, I wanted to do stuff that people could be like, “OK, this is her, this is her face. This is what she’s doing.” It was such a cool moment for me, aand I did not anticipate how crazy it was gonna go at all. And then even the whole thing with my dad, I couldn’t have anticipated that would happen. That was the Internet.

So, you wanted to be a rapper first, right?

Yes. When I was a little kid, I used to always love singing songs and always write songs. But I really used to freestyle. I had a whole thing, I had a little swag. I was probably, like, nine or or 10, but I used to write all these raps, and I used to go to school, and I used to show all my friends. It was my thing.

And I remember I had this one teacher, and I was like, “I guess we were talking about our future?” This was in middle school, so I must have been like, 11 or 12, and they were like, “What do you want your career to be?” And I was like, “I’m going to be a rapper.” And the teacher was like, “Sure.” That always stuck with me — because what do you mean, “Sure?” Like, you really don’t think that I could do this? From that day on, I was like, “You know what? This is exactly why I’m going to do whatever the f–k I want to do.” And I was like, 11, but I was like, “No” — because what do you mean, “Sure?” Like, I know, I know I could do this.

Did you have a rap name?

I never had a rap name. I was just writing raps. Like, I wasn’t rap name. Even now, sometimes I’m like, damn, should I have come up with an artist name or something cool, but I just couldn’t think of one. I literally just couldn’t think of one. That’s why I put the exclamation point, because there was too many other Lailas and I just couldn’t think of anything else.

Now that the the album is out, are you going to produce for other artists? I know one of your dreams is to produce for artists that you like. Send some beat packs out.

Absolutely. That’s what I’m working towards now. I really want to be able to work with other artists that I admire, but I really love working with artists in person, like I like to show, like, I don’t know. I like to see how people feel about what they’re listening to. I prefer to show people what I’ve been working on when I’m with them. Let’s actually connect. And feel the music together.

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.

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. 

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. 

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. 

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.

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 Perry
24. Ed Sheeran
23. Bad Bunny
22. One Direction
21. Lil Wayne
20. Bruno Mars
19. BTS
18. The Weeknd
17. Shakira
16. Jay-Z
15. Miley Cyrus
14. Justin Timberlake
13. Nicki Minaj
12. Eminem
11. Usher
10. Adele
9. Ariana Grande
8. Justin Bieber

Rihanna is a Billie Eilish fan!

In an interview with an 11-year-old journalist at her recent launch event for her new Fenty x Puma collection this week, RiRi was asked who her dream musical collaborator would be. “If I could only do a song with Billie Eilish. She’s so good,” she shared.

New music has been a longtime desire for RiRi fans. The “Love on the Brain” singer hasn’t released an album since Anti dropped in 2016 , and spent two weeks at No. 1 on the Billboard 200 chart. The project also featured three Billboard Hot 100 top 10 hits, including the No. 1 “Work,” featuring Drake. In July 2017, she hit No. 2 with Bryson Tiller on DJ Khaled’s “Wild Thoughts.”

Most recently, just before she headlined the 2023 Super Bowl halftime show, Rihanna dropped “Lift Me Up,” featured on the soundtrack of the Marvel sequel Black Panther: Wakanda Forever.

Rihanna also revealed that she’s starting over with her elusive ninth studio album, and the beauty mogul’s “prepared” to get back in the studio with her newfound perspective. “Yeah, I’m starting over,” RiRi declared to Entertainment Tonight. “But I don’t want to neglect the songs that I have, so I actually want to go back and listen to stuff with new ears, with my new perspective and then see what applies and what I’m still in love with.”

Watch her full interview at the Fenty x Puma launch event below.

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BTS fans can travel through Jung Kook’s Golden moments in a pop-up exhibition opening in Los Angeles next month. Jung Kook Exhibition ‘Golden: The Moments’ offers an immersive, deep dive into Golden, the K-Pop star’s debut solo album.

Golden: The Moments launches at Ace Mission Studios in Los Angeles on Nov. 1. According to the description, the exhibition takes fans on a visual and audible journey sharing the story behind Jung Kook’s solo debut and “capturing key moments that shaped his musical world.”  

Tickets for Golden: The Moments are priced at $26.86 for general admission, plus an additional $2 for parking and another $2.58 in fees. Tickets are selling fast, but a select number of passes are available for opening weekend, in addition to Nov. 6-10 and Nov. 13-17. The exhibit lasts for 60-90 minutes and opens from 11:40 a.m. until 6:40 p.m.

Golden: The Moments opened in Seoul, South Korea in late August. The traveling exhibit, which features Samsung Frame speakers with photos of Jung Kook, lands in Los Angeles ahead of the first anniversary of Golden, released on Nov. 3, 2023.  

The BTS Army can learn more about Golden in Jung Kook: I Am Still – Party Edition, an updated edition of his documentary releasing in select theaters on Oct. 11.

Jung Kook’s solo effort, featuring the Latto-assisted, hit single “Seven,” debuted at No. 1 on Billboard’s Top Album Charts and peaked at No. 2 on the Billboard 200.

Although Jung Kook, Jin, Jimin, V, Suga, RM and J-Hope, have been focused on their respective solo projects and completing mandatory military service, the Bangtan Boys will be back together soon. BTS is scheduled to reunite in 2025.