meta-scriptRelive The Epic GRAMMY Tribute To Hip-Hop's 50th Anniversary With A Playlist Of Every Song Performed | GRAMMY.com
Hip-Hop's 50th Anniversary at 2023 GRAMMYs
GRAMMY Tribute to Hip-Hop's 50th Anniversary

Credit: Getty Images for The Recording Academy

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Relive The Epic GRAMMY Tribute To Hip-Hop's 50th Anniversary With A Playlist Of Every Song Performed

Revisit the historic, celebratory tribute from the 2023 GRAMMYs ceremony with this playlist of every song from the performance, featuring Missy Elliott, Queen Latifah, Salt-N-Pepa, Scarface, Method Man, Ice-T and many more.

GRAMMYs/Mar 31, 2023 - 06:59 pm

Hip-hop icons crowded the 2023 GRAMMYs stage in Los Angeles, uniting for a bombastic and memorable performance in celebration of the genre's 50th anniversary.

Spearheaded by Questlove, who served as musical director, the star-studded performance began with an introduction from LL COOL J and kicked off with the Roots' instrumentation and a narration from Black Thought. Early hip-hop stars Grandmaster Flash and RUN-DMC swiftly lit a fuse that ran through the show, all the way until the 15-minute performance's electrifying end with GloRilla, Future, and LL.

"I’m deeply inspired that I was able to help bring together this incredible and iconic group of artists to the stage on Sunday," LL COOL J said. "This special moment will sit with me for a long time to come.”

The landmark performance never faltered, from Chuck D and Flavor Flav performing "Rebel Without A Pause," to Busta Rhymes' "Look at Me Now," Missy Elliott's "Lose Control" and Lil Wayne's "A Milli." Honoring the genre's spirit and diversity, the tribute underscored both tradition and modernity across three main acts. Rising stars joined forces with living legends, reminding audiences that hip-hop's powerful legacy will continue to live on well past 50 years.

Relive the thrill of Music's Biggest Night with the playlist below, featuring every artist who celebrated hip-hop's spectacular 50th anniversary at the 2023 GRAMMYs ceremony.

How Hip-Hop Took Over The 2023 GRAMMYs, From The Golden Anniversary To 'God Did'

Questlove
Questlove

Photo: Leon Bennett/Getty Images for Netflix

interview

For Questlove, "A GRAMMY Salute To 50 Years Of Hip-Hop" Is Crucial For Rap's Legacy

When Questlove worked on the Hip-Hop 50 revue at the 2023 GRAMMYs, the experience was so stressful that he lost two teeth. But he didn't balk at the opportunity to co-produce a two-hour special; the task was too important.

GRAMMYs/Dec 7, 2023 - 05:45 pm

Today, Public Enemy's 1988 album It Takes a Nation of Millions to Hold Us Back is correctly viewed as a watershed not just for hip-hop, but all of music. But when Questlove's father overheard him playing it, it didn't even sound like music to him.

"He happened to pass my room while 'Night of the Living Baseheads' came on and he had a look of disgust and dismay, like he caught me watching porn," the artist born Ahmir Thompson tells GRAMMY.com. "He literally was like, 'Dude, when you were three, I was playing you Charlie Parker records, and I was playing you real singers and real arrangers, and this is what you call music? All those years I wasted on private school and jazz classes. This is what you like?'

"I couldn't explain to him: 'Dad, you don't understand. Your entire boring-ass record collection downstairs is now being redefined in this very album. Everything you've ever played is in this record,'" he says. "If my dad — who was relatively cool and hip, but just getting older — couldn't understand it, then I know there's a world of people out there that are really just like, whatever."

That nagging reality has powered him ever since — whether he's co-leading three-time GRAMMY winners the Roots, authoring books and liner notes, or directing Oscar-winning films.

And that path led straight to Questlove's role as a executive producer for "A GRAMMY Salute To 50 Years Of Hip-Hop," which will air Sunday, Dec. 10, from 8:30 to 10:30 p.m. ET and 8:00 to 10:00 p.m. PT on the CBS Television Network, and stream live and on demand on Paramount+.

Questlove makes no bones about it: working on that 12-minute Hip-Hop 50 revue at the 2023 GRAMMYs was taxing. So taxing, in fact, that he lost two teeth due to the psychological pressure. But he soldiered on, and the result is an inspiring rush of a two-hour special.

"The thing that really motivated me — Look, man, roll up your sleeves and run through this mud — was like, if there ever was going to be a hip-hop time capsule, a lot of the participants in this show are somewhere between the ages of 20 and 60, and everybody's still kind of in their prime," he says.

"So that way,” Questlove continues, “in 2030, 2040, 2050, when our great, great, great, great grandkids are born and they want to look up someone, this'll probably be one of the top five things they look up. And I wanted to be a part of that."

Read on for a rangey interview with Questlove about his role in "A GRAMMY Salute To 50 Years of Hip-Hop," in all its dimensions.

Explore More Of "A GRAMMY Salute to 50 Years of Hip-Hop"

This interview has been edited for clarity.

What can you tell me about your involvement in "A GRAMMY Salute To 50 Years Of Hip-Hop"?

I could be the guy that complains and complains and complains and complains: Man, I wish somebody would dah, dah, dah. Man, somebody needs to dah, dah, dah. And then the universe the whole time is poking you in the stomach like a dog. You think you're going to be drumming for life — like, that's your job.

So I went through this period where I just hated the lay of the land. And now people are like, "Well, the door is open if you want to come and see if you could change it." And for me, it was just important to.

And at first, I was really skeptical about this because even when I was an artist, my peers all the time would — I say in air quotes jokingly, but it's like, man, I know they're serious — they would just call me a suit. Whenever someone's called a suit in a sitcom or it is like, that's always the bad guy. Or especially for me that's known for all this artistry.

But for me, it's like, I can either just sit on the sidelines and watch this thing slowly kind of go in a direction that I don't want it to go. And often with the history of Black music in America, we're innovating this stuff, but we're really not behind the scenes in power positions to control it or to decide what direction it is. And it's a lot of heartbreaking and hard work.

After the success of the thing that we did in March — that 12-minute revue thing — I'll be honest with you. For 12 minutes that was like going through damn near, and I'm not even using hyperbolic statements by saying, coming out within an inch of my life.

When that moment was literally over and I was on the airplane landing back in New York, two of my teeth fell out. That's the level of stress I was [under]. Imagine landing in JFK and I got to rush to "The Tonight Show," but then it's like, Oh, wait, what's happening? Oh God, no! My teeth are falling out! And going to emergency surgery. My whole takeaway was like: Never again.

So of course when they hit me in July, "Hey, remember that 12 minute thing you did? You want to do the two-hour version of it?" I was like, "Hell no." And of course I hell noed for three weeks and it's like, "All right, I'll do it, but I'll just be a name on it. I ain't doing nothing." And then it went from that to like, "All right, what do you need me to do?"

What I will say is it's a two-hour show in which you got to figure out how to tell [the story of] hip-hop's 50-year totality — its origins, its peak period, its first moments of breaking new ground, the moment it went global around the world. You got to figure out a way to tell this story in two-hour interstitials and be all-inclusive. 

It was just as stressful, even up until four hours ago. I'll just basically say that my teeth didn't fall out, thank God. And it was worth everything, because it's really a beautiful moment.

Sorry for that 12-hour answer, but that's just how my life rolls.

It was a great answer. What was your specific role behind the scenes?

Oh, I'm a producer. Jesse Collins called a group of us in to help facilitate: me, LL [Cool J], Fatima Robinson, Dionne Harmon, Brittany Brazil. There's a group of nine of us who were producers.

So, [part of] my actual division of labor thing was finding people to help facilitate music. This is a genre in which maybe the first six years of the art form, there was no such thing as an instrumental. "Or, "Hey, J.Period, can you recreate 'Check Out My Melody' by Eric B. & Rakim with no vocals in it?"

Finding the right people to do the music, sometimes I'd have to do it myself. And a lot of people in hip-hop have been super burnt. Super burnt. And I mean, that's putting it lightly.

And so you're giving these impassioned, Jerry Maguire, help-me-help-you speeches. The amount of times I was like, "Look, I really want you to reconsider your answer. This is our legacy we're talking about."

I'm using terms that a lot of these people, frankly, are hearing for the first time, Because like I've said in past interviews, hip-hop started as outlaw music. No one thought it was going to be a thing. So there's a whole generation that had to lay out the red carpet, just so that the next generation could benefit from it while we disposed of them.

But then that next generation gets disposed of, and then here comes my generation. And then the next thing, you wake up and it's like, "Oh, we're not relevant anymore," and dah, dah, dah.

And I'm trying to convince people, "Wait, you don't understand. Now we have a seat at the table. Now we get to control. All that we talked about, we need to control our destiny, and this is our culture." And there was a lot of that. And some people [were like], "All right, I'll do it for you." [To which I said,] "No, no, don't do it for me. Do it for the culture."

But then there were also people like, "Man, never again. F— all that." And there was also, "Hey, why wasn't I asked?" and all that stuff.  So in these two hours, you're going to see eight to nine segments in which we try to wisely cover every base.

This is the "Lyricist" section, and this is the "Down South" section. And ["Ladies First"] is all about the ladies. And this is for those that passed away. And this is for the club bangers. And this is for music outside of America. And this is for the left-of-center alternative hip-hop.

Yes, we wanted to include everybody, but this is network television. And at that, you only get eight to 12 minutes at a time. So that's even hard. "Hey, why can't I do my chorus and my verse?" "Look, man, you got 32 seconds." If you've ever seen those "Tom and Jerry" cartoons where they're juggling plates in a kitchen — like 30 at a time — I don't recommend that to anybody.

But we got through it. I want everyone to feel proud of where hip-hop has come, because to be nine years old and to get on punishment for hip-hop — you know what I mean? I come from that generation. You've got to pay a price to live this culture.

And now it's established. So that's why I got involved. So there was a lot I had to do. A lot of calls, a lot of begging, a lot of arrangements, a lot of talking to people about clearing their samples, to call up publishing companies: "Look, it's just a four-second segment. It's just one drum roll. Can you please overlook it just for the sake of it?"

The amount of times I had to give those speeches. So yeah, that's what I had to do.

Jesus.

And that's just me. It's nine of us. So there's lighting directions, and choreography, and wardrobe, and dealing with clearance — like FCC, and, "They can't say that." And, "All right, which one of us is going to try to call Snoop to ask him that sort of thing?"

And the amount of Zooms that we were on at five in the morning in the Maldives or halfway around the world.

There must be some component of this process where you recognize that there could never be a perfect two-hour special. There could never be a perfect 200-hour special. There must be something freeing about realizing that nothing can be comprehensive when you're dealing with a cultural ocean like this.

[At one point], I had to take a hip-hop break. And the first thing that I did a week later, after recuperating, was I went on YouTube and I just watched every award show I remember watching — like prime Soul Train Awards back in '87, '88, '89, the years that Michael Jackson was killing the GRAMMYs.

Award shows were so magical to me, when I was a kid. There was a period just between five to maybe 15 or 16 in which I religiously watched that stuff, and you just take it for granted.

When Herbie Hancock did Rockit back in 1983 with all those mechanical break dancers, I wonder the work and the headaches that it took to make that happen. The drummer from Guns N' Roses [was] missing while they had to do "Patience" at the American Music Awards — and Don Henley, of all people, was just on the sidelines like, "Does anyone know how to drum?"

I was in the audience during the whole Chris Brown-Rihanna controversy of [2009]. I was literally at the GRAMMYs. There were like 40 minutes left, and I watched the producer run up the aisles.

Because the thing was, that was the year they decided, "You know what? This is going to be the first year in which we're going to ask artists to double down on stuff. So we're going to have Rihanna sing three songs, and we're going to have Chris do two songs. We're going to have Justin Timberlake. And then, suddenly, their absence now means that there's five major gaps open.

And they had 40 minutes left before they went to go live and I'm watching the producer make an announcement: "Ladies and gentlemen, something just happened. We can't get into it."

The level of viralness now on Instagram or Twitter is expected, but back then it was like, Oh, I wonder what happened? And they're just running up the aisles to Stevie Wonder, "Yo, can you [mimics rapid-fire, inaudible chatter]?"

And I'm looking at him, pondering: What the hell are they asking him? And then Stevie's getting up and doing it, and then, "Jonas Brothers, can you duh, duh, duh? Boyz II Men. Where's Al Green? Is Al Green here?" So literally, I'm watching them solve a headache in real time. And with 20 minutes left, backstage rehearsing, and we were really none the wiser.

I've seen that a few times. My very first GRAMMYs was when Luciano Pavarotti got sick and someone just randomly asked, "Hey, does anyone out there know the lyrics to 'Ave Maria'?" Aretha Franklin raised her hand, and we were all like, 'Wait, we mean the Italian version, like that 'Ave Maria.'" And she's like, "I do know the version."

We underestimated if Aretha Franklin from Detroit, Michigan knew how to sing something in Italian. And within a half hour she was on that stage and she killed that s—.

So it made me literally recapitulate every award show I ever watched.Now I'm watching with the analytical eye: I wonder what headaches it took to put that together? So, it changed me as a spectator and a participant.

I have a friend who's been a dedicated hip-hop fan his entire life. We were talking about the 50th anniversary of hip-hop. He questioned the entire enterprise, arguing that it's an arbitrary number that doesn't mean much to true rap fans. What does the 50th anniversary of hip-hop mean to you, personally?

Well, to me, it's important. There's an interlude that I put on the Things Fall Apart record. The album starts with an argument from [the 1990 film] Mo' Better Blues in which Denzel Washington and Wesley Snipes' jazz musician characters are arguing about just the disposability of the art form.

And it ends with a quote from Harry Allen saying that the thing about hip-hop is that most people think that it's disposable: Let me get what I can out this thing, and I'll throw them out the window. And on top of that, people don't even see it as art. And that really hit me in the gut, because I see the beauty of it.

This is kind of why I got into the game of: first it was with liner notes, and then with social media doing these mammoth history posts. And then it's like, Alright, well, let me write some books, because I'm afraid that no one's doing this level of critical thinking about this particular thing.

I know that the disdain and the dismissiveness that I got from some of hip-hop's participants does sort of stem from a place of ego being bruised. And it's righteous. It's righteous anger. But I also knew that if I sat on the sidelines, then it's like when I have grandkids and they Google this, and if it was a half-assed job, then that's my fault. And I definitely don't want to be the guy that talks, talks, complains, complains, without being a part of it.

So yeah, for the amount of people that prematurely died before the age of 30, and for the startling volume of people that have recently passed away in the last three years because of health issues, cardiac arrest, strokes, a lot of us are dying… You and I are talking right now, right when Norman Lear has passed away at the age of 101.

I just read that in The New York Times.

Dude, can you imagine "Tupac Shakur Dead at 103"? Can you imagine that for hip-hop?

It's a survival tool, because for a lot of us, that was the way out of poverty. It was vital for me. I couldn't just sit back and not watch one person behind the wheel. I have to be the designated driver. So, that's why it's important to celebrate that number.

And a big part of my convincing them was like when they were going to pass, like, "Nah, dog, I'm cool. I got a gig that night," I was like, "Dude, we're not going to do this for the 51st or the 52nd. And frankly, will we be here?" I will be 92 years old if it makes it to the 75th. You know what I mean?

The only person that got in my face was Latifah like, "Excuse me, I will be here for the 75th and I will be for the 100th. You don't know when I'm leaving." So I was like, "More power to you, Dana. All right, good. Queen Latifah will be here for the 100th."

What I'm gathering from what you're saying is that no matter what, it's important to have an organization of this prestige canonize this cultural force.

Oh, absolutely. And I know that oftentimes we play the game of public appearances for the gaze of the establishment. I don't want to get into that thing either: making performative celebrations just so that the mainstream can celebrate us.

I have to say that when you watch it, it really doesn't come off as compromised. This thing really looks good. That was the one thing that we laughed at in the group chat, like, "Man, we just went through Apocalypse Now, and are we all saying it was worth it?"

There are at least three people in my production thread that were sort of like, "Uh-huh, never again. I will never again subject myself." And one of them is dead serious. One of them started doing something the opposite, like, "Nah, I'm just doing classical music from now on. There's no stress there." But it was worth it. It was worth it to me.

Questlove

*Questlove in 2023. Photo: Jamie McCarthy/Getty Images*

It looks to be a classy, expansive special. I'm excited for it to air.

The best part about it? So if you remember, to me, the star of the 12-minute version that we did at the GRAMMYs in March, was Jay-Z.

It was one of the things where it's like, "Hey, do we even ask Jay-Z?" And that's the one guy we decided ourselves, "Well, let's pass on him because number one, he's already performing with DJ Khaled, so we'll pass on him."

Jay-Z actually wound up being the star of that because he was a fan mouthing it in the audience, which to me was almost like better than us just doing a song with Jay-Z on stage. But the audience is the absolute star.

To see Chuck D smile — I've never seen Chuck D smile. As all these acts are coming out and Chuck D's like, singing [Sly and the Family Stone's] "Everyday People," like Boston fans sing "Sweet Caroline" at Red Sox games. Who knew that Chuck D was so jovial about things? But that's with everyone in the audience watching, supporting each other.

So that to me is also an important thing because as audience members on stage, they're ripping it, but as audience members, they're supporting each other. And that, I think is the most important part, because a lot of my take was like, "Wow, I didn't know that dah, dah, dah was so supportive." Or, "Man, Nelly actually knows every Public Enemy lyric. Who knew?" There are a lot of "Who knew?" moments that will shock people for this show.

I'm so glad you brought that up. That was one of my favorite moments during the Hip-Hop 50 performance at the 2022 GRAMMYs. Jay-Z is a billionaire twice over and a global cultural figure, but we see him in the audience, grinning ear-to-ear like a little boy, doing finger guns in the air.

He's getting his life back. And it's important. Especially now, I'm all about joy. And it's not even just like this particular hip-hop figure celebrating his music.

When Chance the Rapper comes out, again, I'm like, "Wow, [Cee] Knowledge from Digable Planets knows Chance?" And then I was like, "Well, they got kids, so of course I'm sure their kids play around the house." I'm doing all this analytical things like, "Wait, how do they know this song? And this is past their age range."

And that to me is the most telling part of this whole thing, to watch generational people get out of their actual zone and to find out that they're fans of — when GloRilla comes out, to watch [Digable Planets' Ladybug] Mecca mouth the lyrics. I was just like, "Oh, wow, OK."

That kind of puts to bed that stereotype that we only listen to the music in our realm. So, yeah, man — to me, that was the magic part of it all.

10 Albums That Showcase The Deep Connection Between Hip-Hop And Jazz: De La Soul, A Tribe Called Quest, Kendrick Lamar & More

LL Cool J

Credit: Paul Natkin/Getty Images

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20 Iconic Hip-Hop Style Moments: From Run-D.M.C. To Runways

From Dapper Dan's iconic '80s creations to Kendrick Lamar's 2023 runway performance, hip-hop's influence and impact on style and fashion is undeniable. In honor of hip-hop's 50th anniversary, look back at the culture's enduring effect on fashion.

GRAMMYs/Nov 29, 2023 - 03:01 pm

In the world of hip-hop, fashion is more than just clothing. It's a powerful means of self-expression, a cultural statement, and a reflection of the ever-evolving nature of the culture.

Since its origin in 1973, hip-hop has been synonymous with style —  but the epochal music category known for breakbeats and lyrical flex also elevated, impacted, and revolutionized global fashion in a way no other genre ever has.   

Real hip-hop heads know this. Before Cardi B was gracing the Met Gala in Mugler and award show red carpets in custom Schiaparelli, Dapper Dan was disassembling garment bags in his Harlem studio in the 1980s, tailoring legendary looks for rappers that would appear on famous album cover art. Crescendo moments like Kendrick Lamar’s performance at the Louis Vuitton Men’s Spring-Summer 2023 runway show in Paris in June 2022 didn’t happen without a storied trajectory toward the runway.

Big fashion moments in hip-hop have always captured the camera flash, but finding space to tell the bigger story of hip-hop’s connection and influence on fashion has not been without struggle. Journalist and author Sowmya Krishnamurphy said plenty of publishers passed on her anthology on the subject, Fashion Killa: How Hip-Hop Revolutionized High Fashion, and "the idea of hip hop fashion warranting 80,000 words." 

"They didn't think it was big enough or culturally important," Krishnamurphy tells GRAMMY.com, "and of course, when I tell people that usually, the reaction is they're shocked."

Yet, at the 50 year anniversary, sands continue to shift swiftly. Last year exhibitions like the Fashion Institute of Technology’s Fresh, Fly, and Fabulous: Fifty Years of Hip-Hop Style popped up alongside notable publishing releases including journalist Vikki Tobak’s, Ice Cold. A Hip-Hop Jewelry Story. Tabak’s second published release covering hip-hop’s influence on style, following her 2018 title, Contact High: A Visual History of Hip-Hop.

"I wanted to go deeper into the history," Krishnamurphy continues. "The psychology, the sociology, all of these important factors that played a role in the rise of hip-hop and the rise of hip-hop fashion"

What do the next 50 years look like? "I would love to see a hip-hop brand, whether it be from an artist, a designer, creative director, somebody from the hip-hop space, become that next great American heritage brand," said Krishnamurphy.

In order to look forward we have to look back. In celebration of hip-hop’s 50 year legacy, GRAMMY.com examines iconic moments that have defined and inspired generations. From Tupac walking the runways at Versace to Gucci's inception-esque knockoff of Dapper Dan, these moments in hip-hop fashion showcase how artists have used clothing, jewelry, accessories, and personal style to shape the culture and leave an indelible mark on the world.

*The cover art to Eric B and Rakim’s* Paid in Full

Dapper Dan And Logomania: Luxury + High Fashion Streetwear

Dapper Dan, the legendary designer known as "the king of knock-offs," played a pivotal role in transforming luxury fashion into a symbol of empowerment and resistance for hip-hop stars, hustlers, and athletes starting in the 1980s. His Harlem boutique, famously open 24 hours a day, became a hub where high fashion collided with the grit of the streets.

Dapper Dan's customized, tailored outfits, crafted from deconstructed and transformed luxury items, often came with significantly higher price tags compared to ready-to-wear luxury fashion. A friend and favorite of artists like LL Cool J and Notorious B.I.G., Dapper Dan created iconic one-of-a-kind looks seen on artists like Eric B and Rakim’s on the cover of their Paid in Full album.

This fusion, marked by custom pieces emblazoned with designer logos, continues to influence hip-hop high fashion streetwear. His story — which began with endless raids by luxury houses like Fendi, who claimed copyright infringement — would come full circle with brands like Gucci later paying homage to his legacy.

Athleisure Takes Over

Hip-hop's intersection with sportswear gave rise to the "athleisure" trend in the 1980s and '90s, making tracksuits, sweatshirts, and sneakers everyday attire. This transformation was propelled by iconic figures such as Run-D.M.C. and their association with Adidas, as seen in photoshoots and music videos for tracks like "My Adidas."

*LL Cool J. Photo: Paul Natkin/Getty Images*

LL Cool J’s Kangol Hat

The Kangol hat holds a prominent place in hip-hop fashion, often associated with the genre's early days in the '80s and '90s. This popular headwear became a symbol of casual coolness, popularized by hip-hop pioneers like LL Cool J and Run-D.M.C. The simple, round shape and the Kangaroo logo on the front became instantly recognizable, making the Kangol an essential accessory that was synonymous with a laid-back, streetwise style.

*Dr. Dre, comedian T.K. Kirkland, Eazy-E, and Too Short in 1989. Photo: Raymond Boyd/Getty Images*

N.W.A & Sports Team Representation

Hip-hop, and notably N.W.A., played a significant role in popularizing sports team representation in fashion. The Los Angeles Raiders' gear became synonymous with West Coast hip-hop thanks to its association with the group's members Dr. Dre, Eazy-E, and Ice Cube, as well as MC Ren.

 *Slick Rick in 1991. Photo: Al Pereira/Getty Images/Michael Ochs Archives*

Slick Rick’s Rings & Gold Chains

Slick Rick "The Ruler" has made a lasting impact on hip-hop jewelry and fashion with his kingly display of jewelry and wealth. His trendsetting signature look — a fistful of gold rings and a neck heavily layered with an array of opulent chains — exuded a sense of grandeur and self-confidence. Slick Rick's bold and flamboyant approach to jewelry and fashion remains a defining element of hip-hop's sartorial history, well documented in Tobak's Ice Cold.

Tupac Walks The Versace Runway Show

Tupac Shakur's runway appearance at the 1996 Versace runway show was a remarkable and unexpected moment in fashion history. The show was part of Milan Fashion Week, and Versace was known for pushing boundaries and embracing popular culture in their designs. In Fashion Killa, Krishnamurpy documents Shakur's introduction to Gianni Versace and his participation in the 1996 Milan runway show, where he walked arm-in-arm with Kadida Jones.

*TLC. Photo: Tim Roney/Getty Images*

Women Embrace Oversized Styles

Oversized styles during the 1990s were not limited to menswear; many women in hip-hop during this time adopted a "tomboy" aesthetic. This trend was exemplified by artists like Aaliyah’s predilection for crop tops paired with oversized pants and outerwear (and iconic outfits like her well-remembered Tommy Hilfiger look.)

Many other female artists donned oversized, menswear-inspired looks, including TLC and their known love for matching outfits featuring baggy overalls, denim, and peeking boxer shorts and Missy Elliott's famous "trash bag" suit worn in her 1997 music video for "The Rain." Speaking to Elle Magazine two decades after the original video release Elliot told the magazine that it was a powerful symbol that helped mask her shyness, "I loved the idea of feeling like a hip hop Michelin woman."

Diddy Launches Sean John

Sean "Diddy" Combs’ launch of Sean John in 1998 was about more than just clothing. Following the success of other successful sportswear brands by music industry legends like Russell Simmons’ Phat Farm, Sean John further represented a lifestyle and a cultural movement. Inspired by his own fashion sensibilities, Diddy wanted to create elevated clothing that reflected the style and swagger of hip-hop. From tailored suits to sportswear, the brand was known for its bold designs and signature logo, and shared space with other successful brands like Jay-Z’s Rocawear and model Kimora Lee Simmons' brand Baby Phat.

 *Lil' Kim. Photo: Ron Galella/Ron Galella Collection via Getty Images*

Lil’ Kim Steals The Show

Lil' Kim’s daring and iconic styles found a kindred home at Versace with

In 1999, Lil' Kim made waves at the MTV Video Music Awards with her unforgettable appearance in a lavender jumpsuit designed by Donatella Versace. This iconic moment solidified her close relationship with the fashion designer, and their collaboration played a pivotal role in reshaping the landscape of hip-hop fashion, pushing boundaries and embracing bold, daring styles predating other newsworthy moments like J.Lo’s 2000 appearance in "The Dress" at the GRAMMY Awards.

Lil Wayne Popularizes "Bling Bling"

Juvenile & Lil Wayne's "Bling Bling" marked a culturally significant moment. Coined in the late 1990s by Cash Money Records, the term "bling bling" became synonymous with the excessive and flashy display of luxury jewelry. Lil Wayne and the wider Cash Money roster celebrated this opulent aesthetic, solidifying the link between hip-hop music and lavish jewelry. As a result, "bling" became a cornerstone of hip-hop's visual identity.

Jay-Z x Nike Air Force 1

In 2004, Jay-Z's partnership with Nike produced the iconic "Roc-A-Fella" Air Force 1 sneakers, a significant collaboration that helped bridge the worlds of hip-hop and sneaker culture. These limited-edition kicks in white and blue colorways featured the Roc-A-Fella Records logo on the heel and were highly coveted by fans. The collaboration exemplified how hip-hop artists could have a profound impact on sneaker culture and streetwear by putting a unique spin on classic designs. Hova's design lives on in limitless references to fresh white Nike kicks.

Daft Punk and Pharrell Williams. Photo: Mark Davis/WireImage

Pharrell Williams' Hat At The 2014 GRAMMYs

Pharrell Williams made a memorable red carpet appearance at the 2014 GRAMMY Awards in a distinctive and oversized brown hat. Designed by Vivienne Westwood, the hat quickly became the talk of the event and social media. A perfect blend of sartorial daring, Pharrell's hat complemented his red Adidas track jacket while accentuating his unique sense of style. An instant fashion moment, the look sparked innumerable memes and, likely, a renewed interest in headwear.

Kanye’s Rise & Fall At Adidas (2013-2022)

Much more than a "moment," the rise and eventual fall of Kanye’s relationship with Adidas, was as documented in a recent investigation by the New York Times. The story begins in 2013 when West and the German sportswear brand agreed to enter a partnership. The collaboration would sell billions of dollars worth of shoes, known as "Yeezys," until West’s anti-semitic, misogynistic, fat-phobic, and other problematic public comments forced the Adidas brand to break from the partnership amid public outrage.

Supreme Drops x Hip-Hop Greats

Supreme, with its limited drops, bold designs, and collaborations with artists like Nas and Wu-Tang Clan, stands as a modern embodiment of hip-hop's influence on streetwear. The brand's ability to create hype, long lines outside its stores, and exclusive artist partnerships underscores the enduring synergy between hip-hop and street fashion.

*A model walks the runway at the Gucci Cruise 2018 show. Photo: Pietro D'Aprano/Getty Images*

Gucci Pays "homage" to Dapper Dan

When Gucci released a collection in 2017 that seemingly copied Dapper Dan's distinctive style, (particularly one look that seemed to be a direct re-make of a jacket he had created for Olympian Dionne Dixon in the '80s), it triggered outrage and accusations of cultural theft. This incident sparked a conversation about the fashion industry's tendency to co-opt urban and streetwear styles without proper recognition, while also displaying flagrant symbols of racism through designs.

Eventually, spurred by public outrage, the controversy led to a collaboration between Gucci and Dapper Dan, a significant moment in luxury fashion's acknowledgement and celebration of the contributions of Black culture, including streetwear and hip-hop to high fashion. "Had Twitter not spotted the, "Diane Dixon" [jacket] walking down the Gucci runway and then amplified that conversation on social media... I don't think we would have had this incredible comeback," Sowmya Krishnamurphy says.

A$AP Rocky x DIOR

Self-proclaimed "Fashion Killa" A$AP Rocky is a true fashion aficionado. In 2016, the sartorially obsessed musician and rapper became one of the faces of Dior Homme’s fall/winter campaign shot by photographer Willy Vanderperre — an early example of Rocky's many high fashion collaborations with the luxury European brand.

A$AP Rocky's tailored style and impeccable taste for high fashion labels was eloquently enumerated in the track "Fashion Killa" from his 2013 debut album Long. Live. ASAP, which namedrops some 36 luxury fashion brands. The music video for "Fashion Killa" was co-directed by Virgil Abloh featuring a Supreme jersey-clad Fenty founder, Rihanna long before the two became one of music’s most powerful couples. The track became an anthem for hip-hop’s appreciation for high fashion (and serves as the title for Krishnamurphy’s recently published anthology). 

*Cardi B. Photo: Steve Granitz/WireImage*

Cardi B Wears Vintage Mugler At The 2019 GRAMMYs

Cardi B has solidified her "it girl" fashion status in 2018 and 2019 with bold and captivating style choices and designer collaborations that consistently turn heads. Her 2019 GRAMMYs red carpet appearance in exaggerated vintage Mugler gown, and many custom couture Met Gala looks by designers including Jeremy Scott and Thom Browne that showcased her penchant for drama and extravagance.

But Cardi B's fashion influence extends beyond her penchant for custom high-end designer pieces (like her 2021 gold-masked Schiaparelli look, one of nine looks in an evening.) Her unique ability to blend couture glamour with urban chic (she's known for championing emerging designers and streetwear brands) fosters a sense of inclusivity and diversity, and makes her a true trendsetter.

Beyoncé & Jay-Z in Tiffany & Co.’s "About Love" campaign

The power duo graced Tiffany & Co.'s "About Love'' campaign in 2021, showcasing the iconic "Tiffany Yellow Diamond," a 128.54-carat yellow worn by Beyoncé alongside a tuxedo-clad Jay-Z. The campaign sparked controversy in several ways, with some viewers unable to reconcile the use of such a prominent and historically significant diamond, sourced at the hands of slavery, in a campaign that could be seen as commercializing and diluting the diamond's cultural and historical importance. Despite mixed reaction to the campaign, their stunning appearance celebrated love, adorned with Tiffany jewels and reinforced their status as a power couple in both music and fashion.

Kendrick Lamar Performs At Louis Vuitton

When Kendrick Lamar performed live at the Louis Vuitton Men’s spring-summer 2023 runway show in Paris in June 2022 following the passing of Louis Vuitton’s beloved creative director Virgil Abloh, he underscored the inextricable connection between music, fashion and Black American culture.


Lamar sat front row next to Naomi Campbell, adorned with a jeweled crown of thorns made from diamonds and white gold worth over $2 million, while he performed tracks including "Savior," "N95," and "Rich Spirit'' from his last album, Mr. Morale and the Big Steppers before ending with a repeated mantra, "Long live Virgil." A giant children’s toy racetrack erected in the Cour Carrée of the Louvre became a yellow brick road where models marched, clad in designer looks with bold, streetwear-inspired design details, some strapped with oversized wearable stereo systems.

Pharrell Succeeds Virgil Abloh At Louis Vuitton

Pharrell Williams' appointment as the creative director at Louis Vuitton for their men's wear division in 2023 emphasized hip-hop's enduring influence on global fashion. Pharrell succeeded Virgil Abloh, who was the first Black American to hold the position.

Pharrell's path to this prestigious role, marked by his 2004 and 2008 collaborations with Louis Vuitton, as well as the founding of his streetwear label Billionaire Boy’s Club in 2006 alongside Nigo, the founder of BAPE and Kenzo's current artistic director, highlights the growing diversity and acknowledgment of Black talent within high fashion.

Listen To GRAMMY.com's 50th Anniversary Of Hip-Hop Playlist: 50 Songs That Show The Genre's Evolution

André 3000
André 3000

Photo: Marcus Ingram/WireImage

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Everything We Know About André 3000's New Album 'New Blue Sun'

The seven-time GRAMMY winner is back with his debut solo album — his first full album since Outkast's 2006 swan song. One caveat: there are no beats nor bars.

GRAMMYs/Nov 14, 2023 - 08:02 pm

On Nov. 13, the world woke up to the announcement that André 3000 — the seven-time GRAMMY winning and 23-time nominated Outkast star — would release his debut (!) solo album, New Blue Sun, on Nov. 17.

Via an NPR scoop, stunned to learn there are "no bars, no beats, no sub-bass. André doesn't sing on this joint, either." Rather, the instrumental, 87-minute album is the culmination of a years-long preoccupation with various flutes — including contrabass, Mayan, bamboo, and a variety of digital models.

And in their reactions, some of those fans spoke for all of us.

"Andre 3000 has about as much critical goodwill as it's possible to have and he is going to test every fiber of that collective empathy," one journalist and editor opined on X. Another music writer and editor chimed in: "This is the tracklisting. This is going to mess up so many peoples' Spotify algorithms."

And Roy Wood Jr., a correspondent on "The Daily Show," summed it up: That boy trained wit Pai Mei & got a Hattori Hanzo Flute. He ready."

With New Blue Sun on the immediate horizon, here's everything we know about it.

It's Built On Improvisation

As NPR points out, New Blue Sun materialized in part due to André's relocation from Atlanta — where Outkast famously hails from — to Los Angeles. There, he ran into the potent percussionist and experimental jazzer, Carlos Niño.

After André and his flute began dropping by Niño's house for basement jam sessions, he was introduced to a whole new world of collaborators, including keyboardist (and Alice Coltrane disciple) Surya Botofasina and guitarist/multi-instrumentalist Nate Mercereau.

"We're listening to each other, we're responding to each other, we're supporting each other at certain times… it's kind of mirroring real life," the artist told NPR. "It's a full living, breathing album because it's fully alive. We didn't sketch it out."

The Titles Are Absolutely Gonzo

Check them out for yourself:

  1. I swear, I Really Wanted To Make A "Rap" Album But This Is Literally The Way The Wind Blew Me This Time 

  2. The Slang Word P(*)ssy Rolls Off The Tongue With Far Better Ease Than The Proper Word Vagina . Do You Agree? 

  3. That Night In Hawaii When I Turned Into A Panther And Started Making These Low Register Purring Tones That I Couldn't Control ... Sh¥t Was Wild 

  4. BuyPoloDisorder's Daughter Wears A 3000™ Button Down Embroidered 

  5. Ninety Three 'Til Infinity And Beyoncé 

  6. Ghandi, Dalai Lama, Your Lord & Savior J.C. / Bundy, Jeffrey Dahmer, And John Wayne Gacy 

  7. Ants To You, Gods To Who ? 

  8. Dreams Once Buried Beneath The Dungeon Floor Slowly Sprout Into Undying Gardens

Have Gandhi, Jeffrey Dahmer, and the Dalai Lama ever appeared in the same song title? We think not.

The Album Title Represents Rebirth

André described New Blue Sun's title in heavily sci-fi, yet personal terms.

"The next world or the next beings will be under a bluer, cooler burning sun. It will burn cooler, but it will be large," he explained to NPR. "So when you look up at the sky in these times, there'll be this larger globe of bluish, still bright but bluish because it's cooler. It's kind of like this whole album and this whole direction is a new world for me."

It Represents A Culmination Of His Interest In Jazz

In said interview, André 3000 shouts out jazz/pop crossovers, like Dave Brubeck's "Take Five" and Chuck Mangione's "Feels So Good," as galvanizing.

"As a rapper, I associated jazz music with old people and elevator music," he admitted. "I remember that playing on the radio as a kid and humming the melodies. So I'm getting affected by these instrumental cats. And once I started really getting into it, I'm like, hold up: Jazz was the rap of that time."

From there, he absorbed John Coltrane, Eric Dolphy, Yusef Lateef… the rest is history.

"That Night In Hawaii…" Is About An Ayahuasca Trip

Yes, he really did turn into a panther… or felt like it.

"We did it like a three-night kind of phase. The first night was inviting and beautiful and the most powerful love and connection with all things I've ever felt in my life," he said — and the second was a different story.

"My stomach was hurting, my mouth contorted like a panther and I actually turned into a panther," he related. "And I was doing like GRRRRRRRRRRRRRRRRRRRRRRRRRRRRRRR — like, that kind of thing."

If you find yourself purring for this strange, lovely offering, check it out this Friday, and read the full NPR interview — and keep checking GRAMMY.com for more info about New Blue Sun!

10 Reasons Why Outkast's 'Speakerboxxx/The Love Below' Is One Of Rap's Most Influential Double Albums

Wu-Tang Clan in 1994 group shot
(From left) Ol' DIrty Bastard, GZA, U-God, Method Man, Raekwon, Masta Killa and Inspectah Deck of Wu-Tang Clan

Photo: Al Pereira/Michael Ochs Archives/Getty Images

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Nothing To F With: How 'Enter The Wu-Tang' Established One Of The Greatest Rap Groups Of All Time

In 1993, Staten Island's Wu-Tang Clan laid the ground for hardcore hip-hop acts to follow. Their weapon of choice: 'Enter The Wu-Tang (36 Chambers)' — a debut LP with an outsized impact on hip-hop and the trajectory of its members.

GRAMMYs/Nov 9, 2023 - 02:21 pm

In the early 1990s, hip-hop was on the verge of being its broadest. 

Hip-hop had grown far beyond its origins in the Bronx, as acts like Public Enemy, A Tribe Called Quest, and De La Soul drew listeners outside New York’s five boroughs. Elsewhere, a legion of MCs from L.A., the Bay, and the South were cementing their legacies. 

Amidst the plethora of sonic riches of hip-hop's golden age, Staten Island’s Wu-Tang Clan stands out. Comprised of lyrical spartans GZA, Method Man, Raekwon, Masta Killah, Ghostface Killah, Inspectah Deck, later Cappadonna, U-God, master producer RZA, and the late, charismatic force Ol’ Dirty Bastard, the group laid the ground for hardcore hip-hop acts to follow. 

Their weapon of choice: 1993’s Enter The Wu-Tang (36 Chambers) — which celebrates 30 years on Nov. 9. Enter The Wu-Tang sparked a new brand of hardcore, gritty street rap that transported listeners with its dark sonic landscape. 

Filled with martial arts and comic book references, loogie-spitting posse cuts, and mystifying street tales, Enter The Wu-Tang drew audiences to the borough of "Shaolin." The album's darkly-brewed beats and mixes had an amateurish charm, but all nine tracks were laced with RZA’s early musical wizardry and ear for ominous, hard-hitting instrumentals. 

For every musical or budgetary limitation, Enter The Wu-Tang boasted some of the best lyrical assaults the genre has ever heard. Now-classic songs like "Da Mystery of Chessboxin’" and "Protect Ya Neck" and conjured visions of the Shaolin streets, and added to New York’s stronghold on the genre. 

Unlike the more socially conscious and jazz-influenced sounds of New York rap at the time, the influential album was marked with soundbites from kung-fu flicks and sped up soul samples with an eerie, grudgeful echoe. Among the gallery of inspiring cuts, "C.R.E.A.M. (Cash Rules Everything Around Me)" features a sample of the Charmels’ 1967 song "As Long As I’ve Got You." 

Despite the group’s size, every member had a stand out moment on the project. And most, with the exception of Masta Killa, have several. Method Man goes full nuclear on his self-titled track, Raekwon and Ghostface show early flashes of their collaborative magic on "Can It All Be So Simple," and the infectious charm of Ol' Dirty Bastard runs wild on "Protect Ya Neck." 

The album was off-kilter in design, but Wu-Tang carved a path for hard-edged acts to follow. The album even inspired New York instrumental soul group El Michels Affair, which released their own version of the album, Enter The 37th Chamber, in 2007 in echo of the legendary beats sampled on Wu-Tang's the classic project. 

Since its release, Enter The Wu-Tang has sold more than 3 million records and landed on countless all-time best album rankings. As of June 2023, the album is at the No. 27 spot on Rolling Stone’s 500 Greatest Of All Time list. For its relatively short length, Wu-Tang Clan's debut has had an outsized impact on hip-hop — both in terms of influence and the trajectory of its members. 

With Enter The Wu-Tang and their subsequent releases, Wu-Tang cornered the rap market in the 1990s. Before Wu-Tang, there were no other notable rap acts from Staten Island. While Brooklyn, Queens, Manhattan and the Bronx held most of the industry’s grip, Wu-Tang helped blaze the path for acts outside of those regions to flourish. 

While groups like Public Enemy, A Tribe Called Quest, N.W.A. and Run-D.M.C. are certainly influential, the star power within Wu-Tang is unique. Between the group’s debut and follow-up album Wu-Tang Forever — which was nominated for Best Rap Album at the 1998 GRAMMYs — GZA, Method Man, Raekwon, Ghostface Killah, Ol' Dirty Bastard, and others released critically acclaimed solo albums.

Method Man even received a Best Rap Performance by a Duo or Group GRAMMY for Tical’s "I'll Be There For You/You're All I Need To Get By" at the 1995 GRAMMYs. Outside the accolades, Raekwon’s Only Built For Cuban Links and Ghostface’s Ironman lit up the New York streets in 1995, and GZA’s Liquid Swords remains one of the more acclaimed outings from the group’s more withdrawn characters.

While some were more commercially successful than others, they all added to the group's influence and arguably proved its distinction for best rap group of all time. 

Read more: RZA’s Constant Elevation: From Wu-Tang to 'Kill Bill,' The Rapper/Producer Discusses His Creative Process And History Ahead Of Bobby Digital Reprise

Method and New Jersey legend Redman brought their comedic chops to the big screen in How High. The pairing was like a hip-hop Cheech and Chong, and the film went on to become a cult weed movie classic. Like Meth, RZA and other members appeared in TV shows and films for decades. 

In 1995, Wu-Tang Clan established the apparel brand Wu Wear, one of the first artist-inspired lines in music history. It opened the doors for hip-hop culture in retail, and inspired a global interest in Wu-Tang's simple, raw style. The group and the apparel line helped usher in the militant street style of the era, complete with baggy jeans, oversized t-shirts, Timberland boots, durags, gold fronts, sports jerseys, and puff jackets. 

As the group grew in popularity, the members joined forces with business partner Oliver "Power" Grant and opened four Wu Wear stores across the country, including one on Victory Boulevard in Staten Island. The line was carried by retail giants such as Macy’s and renamed Wu-Tang Brand in 2008, and Grant discontinued the Wu-Wear line. But after RZA joined hands with Live Nation Merchandise, the brand was relaunched in 2017. 

The cult interest in Wu-Tang's image continued. In 1999, Powers developed a video game centered on the group, called Wu-Tang: Shaolin Style. The 3D fighting game for PlayStation featured characters based on the group members’ stage personas and mirrored the martial arts themes in their music. They also provided voiceover work and music contributions to the four-player game. 

Other artists followed Wu-Tang's blueprint in the decades since the group debuted. Acts like Mobb Deep, Nas, the Notorious B.I.G. and others adopted the hardcore rap style mastered by Wu-Tang — but none harnessed the same manpower or presence as the group over the decades. But the 2010s saw the re-emergence of rap supergroups. 

In Harlem, the Diplomats and ASAP Mob captured the same collaborative and entrepreneurial spirit of Wu-Tang, but with a more varied musical approach. Out West, the Tyler, The Creator-led Odd Future surpassed the 11-member group in scale, but their work and impact haven’t matched that of the Staten Island collective. 

The closest to mirror Wu-Tang was Pro Era, which adopted the classic, boom-bap sound of the '90s. The mega group also pursued an assortment of branding and entertainment ventures, and one of the group’s founders, Joey Bada$$, even played Inspectah Deck in the Hulu biographical series "Wu-Tang: An American Saga." The group’s presence also inspired future Staten Island products like Killarmy, G4 Boyz, and Cleotrapa.

Given the group’s accolades and cultural impact in the decades since their debut, it’s true: "Wu-Tang Clan ain’t nothing to f— with." Its members have redefined longevity in rap by continuing to have a hand on the pulse of popular culture, both in music, film, TV, and entertainment. Few other groups have matched their successes, and as the collective continues to etch its path, there’s no telling how many more barriers they will break. 

A Guide To New York Hip-Hop: Unpacking The Sound Of Rap's Birthplace From The Bronx To Staten Island