Illuminated by the pale white light of a New York City subway platform, Aaliyah stares into the frame on the cover of her album, One in a Million. Her eyes hidden behind a pair of silver-frame sunglasses. Her slim figure cloaked in a black jumpsuit. Her pout brushed in a shade of brick-red lipstick. Her countenance unfalteringly confident as she faced her new era.

In the two years between the release of her multiplatinum debut album Age Ain't Nothing But a Number in 1994 and her follow-up, One in a Million, on August 27, 1996, Aaliyah had established herself as a budding musical talent. But in the fallout of her marriage scandal with R. Kelly and subsequent professional split from the signer, who wrote and produced the majority of Age Ain't Nothing but a Number, Aaliyah and her team faced the taxing task of finding a new team of producers equipped to push her sound forward.

Aaliyah recorded One in a Million while finishing her studies at Detroit High School for the Fine and Performing Arts, from which she graduated in 1997. She had also ended her contract with Jive Records, and then signed a joint deal with Atlantic Records and her uncle Barry Hankerson's Blackground Records. She was 16 when she began recording the album, having turned 17 when it dropped, a pivotal time in her personal life journey. She perfectly captured the transition in her iconic One in a Million era.

"I faced the adversity, I could've broken down, I could've gone and hid in the closet and said, 'I'm not going to do this anymore.' But I love singing, and I wasn't going to let that mess stop me," Aaliyah said in a 1996 interview with  writer Michael Gonzalez, per a retrospective on her career for Wax Poetics. "I got a lot of support from my fans and that inspired me to put that behind me, be a stronger person, and put my all into making One in a Million."

THE SOUND

Many artists Aaliyah's age may have been the product of the creative strategizing of their label—with managers, A&R teams, and other members of their crew choosing their producers, lyrics and overall sound with little to no input from the artists.

But Aaliyah challenged this expectation and misconception by taking creative control of One in a Million, making the sound on the project all her own. She led each member of her production and writing team to craft a One in a Million era with a variety of production styles.

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"She definitely had an executive producer's ear. She had a great sense of what was right for herself, and you have to give her a lot of credit for steering those sessions to a place that obviously created meaningful hit records," Craig Kallman, CEO of Atlantic Records, told Vibe.com.

"She obviously made One in a Million, an album that was very, very much ahead of the curve and didn't sound like anything that had come before it," he added.

To aid in uncovering Aaliyah's new, "ahead of the curve" sound, Craig King and Vincent Herbert became the earliest producers to lay the musical groundwork of One in a Million, which Aaliyah first started recording in 1995.

"We caught [Aaliyah] at her probably second-most vulnerable stage in her career. We caught her at her sophomore jinx and when people were like, 'This will never work without R. Kelly because he put this signature sound on you,'" King told GRAMMY.com about working on One in a Million. "She was really trying to redefine all of that narrative, and we weren't interested in replicating what he was doing. We wanted to bring our own sound into the game, too."

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Recording out of the famed Vanguard Studios in Aaliyah's hometown of Detroit, Michigan, King and Herbert produced a total of eight tracks for the project over three months, though only four made the final cut for the album. The album's production team also included contributors Jermaine Dupri, Darryl Simmons, Missy Elliott, Timbaland, and others, as well as writers Diane Warren, Monica Bell, Japhe Tejeda, and more.

With a team of production and songwriting heavy hitters in Aaliyah's corner, One in a Million began to take shape. The album would become a whole embodiment of Aaliyah's sound, building the R&B-rooted stylings that made her debut album a success into genre-blending productions while also giving listeners a fuller look into sonic complexity of the singer as an artist.

The Timbaland-produced lead single "If Your Girl Only Knew" bumps along, with its beat pulling from pop and funk inspirations, as Aaliyah calls out a flirtatious guy who's in a relationship. "4 Page Letter" and the album's title track slink along with multilayered productions packed with hi-hats, clicks, triple-beats, strings, and stacked harmonies, all the while reimagining the essential production elements of a love ballad. "Got's to Give It Up" and "Choosey Lover" put a modern spin on '70s throwback jams, while "A Girl Like You" samples "Summer Madness" by Kool & the Gang.

"I love all kinds of music, and I want to be known as the kind of singer that can do all of that. So, that's why I wanted the different varieties on the album to showcase that—showcase each part of my personality," Aaliyah said in an interview with the Associated Press during her press run for the project. "Definitely I love the soul, the hip-hop, the R&B. I love it all. But I do want people to see me as the type of artist that can sing any kind of music."

Along with their lyrical content and innovative productions, the album's tracks, like the paired-down, Warren-written "The One I Gave My Heart To" and the Herber- and King-produced "Never Givin' Up," also highlighted Aaliyah's vocal abilities, expanding the strength of her falsetto and upper register while allowing her the full space to showcase other elements of her vocal range and stylings.

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"I remember being in the studio when she was singing ['The One I Gave My Heart To'] and hitting those notes and it was just beautiful," Warren told Vibe.com. "It just showed another side to her. The octave goes up in the end and some of that was what I'd written into the song, but she took it somewhere else. She not only rose to it, she went beyond it. She nailed that song and it was amazing what she did. It's still one of my favorite records."

Speaking on "Never Givin' Up," King said he was completely enamored with her interpretation of the track when they recorded it.

"The vocal arrangement. Every single time we layered a vocal, she was just so on point," King said. "She just superseded all my expectations. I was very, very impressed with her style there."

"This album, it shows the growth of the past two years. I'm 17 now. So, I've grown in a lot of ways. And this album, I think it shows a lot of my vocal range," Aaliyah told the AP while speaking on developing her sound for the project.  "I took a lot of risks on this album. I tried different things. And that's the main change from the two albums."

Aaliyah's shift in her sound resulted in some standout commercial wins. There were a staggering six singles released from One in a Million: "If Your Girl Only Knew," "One in a Million," "Got to Give It Up," "4 Page Letter," "Hot Like Fire," and "The One I Gave My Heart To." The latter eventually peaked at No. 9 on the Billboard Hot 100 chart, making it the highest-charting single from the album. The remaining tracks saw varying degrees of success in both the U.S. and internationally — with "If Your Girl Only Knew" topping the Hot R&B/Hip-Hop Songs and "One in a Million" topping the R&B/Hip-Hop Airplay.

THE LOOK

While her fashion remained a key piece of her overall creative narrative as an artist throughout her career, Aaliyah's style transcended in the One in a Million era. She elevated her aesthetic with the assistance of her stylist and costume designer Derek Lee. As his first project with her, Lee styled Aaliyah's "One In A Million" music video after the two had a chance encounter in Santa Monica, California, just days before shooting the video in Los Angeles.

"[Aaliyah's] look was already established in a certain sense, but I wanted to start a progression. Prior to One In A Million, [her look] was definitely younger, her look was her age. Now, when we get to One in a Million, it's still her age, but it shows a little bit more of a maturity as well," Lee told GRAMMY.com.

Much like her album cover shoot, which featured moody shades of black, concrete gray, merlot, and the grey-green paint of the subway platform, Aaliyah's One in a Million era was often framed around a dark styling narrative that reflected her favorite colors and fabrics, including her affection for leather pieces.

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"It was easy to make black stuff look cool and hard and sexy at the same time. One of her favorite colors was black. She liked it. She felt comfortable in it. It was easy to feel,"  Lee said. "One thing with Aaliyah is that her biggest accessory was her swag. She sold confidence, and the color black just enhanced it."

Aaliyah opted for minimal outfit combos consisting of one to three pieces that were fuseless and easy and in no way distracted from her presence on stage or on camera: See her oversized leather-coat-and-pants combo she wore during an appearance on "Live With Regis and Kathie Lee," her looks on the her "One in a Million" and "4 Page Letter" music video, and the metallic boiler suit Lee hand-painted and airbrushed for her performance on "The Tonight Show with Jay Leno."

"She was so sweet and just regular, when you're sitting there with her and kicking it with her. But soon as she gets on stage, she's this persona, which is her, honestly. She turns up that swag so much that you don't really want anything to distract from it because it shined so bright," Lee said of Aaliyah's looks, which regularly played with proportions by pairing oversized pants with mid-drift-baring T-shirts, bra tops and crop tops. "That was always on purpose. Even though she was dressed cool, it wasn't so over­ the ­top where you weren't still paying attention to what she was doing."

Much like she held creative control over the album's sound, Aaliyah exercised full agency over her One in a Million style narrative. She refused to buckle to any perceived pressure regarding the sexed-up styling arcs often employed by labels, stylists and other industry entities looking to rebrand a late-teen music artist approaching young adulthood. She instead chose to let her style reflect her authentic self, offering an example for her younger listeners that even in their own lives, they didn't have to rush to meet any standard or expectation that misaligned with what they wanted to portray.

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"When she was ready for something, she was ready for something and was sure. If she wasn't mentally ready for something, then we wouldn't do it. Because she never wanted to look like she was dressed by somebody. I never want anyone I dress to look like they're dressed by anybody," Lee said. "She trusted me when she saw that I understood that. It was almost an unspoken agreement between me, her and her mom.

"I was always protective of her and never wanted her to sexualize herself in a certain way and dress in a certain way until she was ready … She never did anything before the time. She never forced it."

THE LEGACY

For 17-year-old Aaliyah, One in a Million became a career-defining project that silenced any lingering questions regarding her industry viability and influence. It also allowed her to grow as an artistic leader as she voiced her expectations for the project to her roster of contributors, working with them to ideate and execute the album's musical and visual concepts.

"[Aaliyah] never really chased after anybody else's style or chased what was going on at the moment," Lee said. "She knew her lane, wanted people around her that understood that lane, and wanted those people to accentuate her in that lane and leave the rest up to her … Her leadership was consistent. She was someone that had conviction and had a vision. I thank God for that because it made my job a lot easier knowing someone's vision, instead of having to guess what their vision was."

"I hope [listeners] appreciate the songbird that she is, the writer that she is, the singer that she is, and the vocal choices that she's made in this project," album producer King added. "I hope people really embrace and lean into her vocal abilities on this record. It really has set a precedent for a lot of singers in the game."

Released in the U.S. 25 years ago to the day, One in a Million continues its legacy in 2021. This month (Aug. 20), the album was released on streaming services after being largely absent on the digital market for over a decade, allowing music fans worldwide easier access to the album that has served as an inspiration for countless artists in the decades since its release. The rerelease comes days before the 20th anniversary of Aaliyah's death and the 25th anniversary of One in a Million.

But beyond its commercial impact and influence on pop culture, One in a Million, and its true wonder, will forever rest in what the album represented for Aaliyah personally as she stepped into her late teens and flexed her creative voice with reposeful fervor and unwavering certainty.

One in a Million marked Aaliyah's new beginning. And 25 years later, the project remains a symbol of her self-awareness and artistic sureness as she plotted the next steps in her journey from breakout star to an established music industry force who's confident in her sound, her self-image, and the creative story she wanted to tell.

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On "Dear Life," R&B singer Genia pens a farewell letter to her lover — while simultaneously reflecting on how the intense saga crumbled her.

"I can't take anymore/ Put my pride aside, thought you could save me," she cries in the first verse. "These days, I don't know what I need/ You destroy me from the inside out/ If I go off the deep end/ You'll be sure not to bring me back."

In this episode of Press Play, watch Genia deliver a stripped-down performance of the vulnerable track alongside her guitarist.

The California native released "Dear Life" on Nov. 10, via Def Jam Recordings. She has also dropped three more singles — "Like That," "Know!," and "Let Me Wander" — leading up to her sophomore mixtape, 4 AM In The Ville, on April 19. 4 AM is a sequel to her debut, 4 PM In The Ville; both projects are inspired by Genia's experience of growing up in Victorville, California.

""[The songs] explore the different stages of grief in a relationship," she revealed in an interview with Urban Magazine. "The second tape is really me touching on falling in love, betrayal, anger, and rape."

Watch the video above to hear Genia's acoustic performance of "Dear Life," and check back to GRAMMY.com for more new episodes of Press Play.

10 Ways TLC Shaped The Future Of R&B

Coco Jones is feeling more inspired than ever following a year of exciting surprises and breakthroughs. In 2023, the 25-year-old budding star celebrated her first Billboard Hot 100 entry thanks to her platinum-selling "ICU" single, embarked on her first headlining tour, and earned her first GRAMMY nominations.

"Being a GRAMMY-nominated artist changes everything. It's such a different creative mindset when the world says, 'You're good, we like what you do,'" Jones tells GRAMMY.com. "It's like a gold star. It makes you want to work harder, it makes you wanna continue to impress, and it makes you impressed with yourself, too."

Jones is nominated across five categories at the 2024 GRAMMYs: Her 2022 EP What I Didn't Tell You is up for Best R&B Album and its "ICU" will compete for Best R&B Performance and Best R&B Song. Her feature on Babyface's "Simple" has received a nod for Best Traditional R&B Performance. Jones is also up for the coveted golden gramophone for Best New Artist.

In recent years, her vocal prowess has received praise from SZA, Janet Jackson, and Beyoncé, but anyone who's even remotely familiar with Jones' story knows that her newfound success is anything but overnight. Jones first found success at age 14, when she starred in the 2012 Disney movie musical Let It Shine. The Tennessee native faced colorism early on, which she addressed in a 2020 YouTube video that went viral.

"I always wanted that representation that my dreams were possible growing up," she shares. "I definitely was not based in reality of what the entertainment industry is. It's tough and it's challenging and sometimes it isn't fair and that is not what I was prepared for as a kid."

During the pandemic, Jones secured a spot in "Bel-Air" (Peacock's reimagining of "The Fresh Prince of Bel-Air") as the spoiled yet beloved Hilary Banks, but she never let go of her love of  music. Following her 2014 departure from Hollywood Records, Jones released music independently, including the ominous "Hollyweird" and "Depressed"; when Def Jam approached her in the summer of 2021, she was ready for her close-up.

Fast forward to present, and Jones is gearing up for one of the most pivotal nights of her blossoming career. But perhaps the most precious thing she's collected along the way is self-assurance. "I'm learning that I have to believe in my creative choices and that I shouldn't second guess what I feel because it does well," she says with a laugh.

Of her recent success, Jones says the back-to-back accolades shocked her, but like a true artist, she's already thinking ahead and manifesting an exciting first for 2024: "I want my debut album to hit No. 1 on the Billboard 200 chart."

Ahead of the 2024 GRAMMYs, Jones discusses the power of representation for dark-skinned Black women, why her mother is her biggest inspiration, and how joining forces with Babyface created momentum in her career.

This interview has been condensed and edited for clarity.

After finding out that you received five GRAMMY nominations, you posted an Instagram video showing you and your mother reveling in the excitement of it all. Tell me more about that moment and your mother's role in this journey.

I'm one of four children and my mom owned multiple businesses, but she made us all feel loved and supported while also being a boss. Watching her navigate the entertainment industry — which she had no prior experience with — was very inspiring. She took every challenge head-on and still managed to make time with all of her kids. 

She's always been a visionary, so I think for her, it's like, This is exactly what we worked for. The end goal is to be award-winning, to be show-stopping, to be classic, to be timeless. That's what she saw for me even when I was a little girl on stage singing Aretha Franklin.

There were times when it was hard for me to see what she saw in me, especially when you're dealing with the rejection that is the music industry. But she always knows the right thing to say to keep me going and to keep my faith. So, when it wasn't like how it is now, she was the entire team. She did anything she could to help me progress.

You retweeted a meet-and-greet with a fan, who donned your merch from 2018, which seemed to take you by surprise. It seems like your 2023 breakthrough was a win for not just yourself, but for those early supporters as well.

I would definitely say it's a win for my fans and my supporters, but also for young Black women who look like me and have big dreams and just want to see what they are dreaming about is possible. I know that I inspire so many young Black women — they tell me almost every day that seeing me win helps them believe in themselves winning.

My goal is to continue to break those barriers down for young Black women so that it's not such a surprise when we succeed.

In a 2022 interview, you said you wanted to experience the highs of being an entertainer and being on stage "even if it meant a lot of lows." Many creatives feel that way. Do you have any advice for struggling artists who feel like no one's paying attention?

You can make it this thing where you feel like you're running out of time, or you can make it feel like you're adjusting to time. Time is whatever you decide it is.

There were so many obstacles I didn't understand, but hindsight is 20/20. I needed the lessons that I learned, I needed the self-reliance, I needed the optimism and the faith. So, I think it was all very growing but still tough not knowing what was going to happen, not knowing if I was going to have that life-changing job, that life-changing song. 

I'm just grateful to God for protecting me through all the confusion and for not giving up. I had enough support around me and enough doors to open even though they felt far and few between to keep me sustained and pursuing this dream, even though I was pursuing it without any guarantees.

What I Didn't Tell You isn't the first EP you released, but it's the one that made you a first-time GRAMMY nominee. What was different this time around?

I was very supported; when Def Jam approached me, they seemed so understanding of my vision that I couldn't help but feel like we were already a team. They helped me put the pieces together. Before this, I was just on my own or it was me and my mom, so I felt more supported with this EP release. My label understands me and what I want to be, and there's no pushback against who I am and what I can naturally do. It's all about enhancing. 

As part of R&B's new class, what do you want to bring to the genre?

More uptempo! I want to be able to sing my heart out but make a bop that you wanna dance to. I love how Whitney Houston would do that with some of her songs like "I'm Your Baby Tonight" and "How Will I Know."

Your breakthrough single, "ICU," is up for Best R&B Song, but what lesser-known song off What I Didn't Tell You (Deluxe) would you nominate in the same category if you could?

"Fallin'" because it's a sensual song, and I feel like it sits in a really cool, pretty place in my voice. It also tells a good story of the chaos that my life is while also starting to fall for somebody.

In 2022, you joined forces with R&B legend Babyface for his collaborative Girls Night Out project. Your "Simple" duet with him is nominated for Best Traditional R&B Performance. Do you think collaborating with Babyface acted as a precursor for the incredible year you had?

When I learned Babyface wanted me on his album, I was beside myself. He was really one of the first legends to give me that stamp of approval. I definitely think the recognition I got from him was like a turning point in what was next for my life. The world started to notice around that time. 

When I interviewed Babyface soon after the release of Girls Night Out, he talked about doing his homework to better understand the differences in today's R&B. That was surprising to hear, because he's clearly an expert at writing hit songs but not above learning from others. What did you learn from his mentorship?

I just learned that you can be a legend and you can still be open to ideas, open to new talents, and open to suggestions. Just stay open to what’s new, who's new, and why they're doing well, and that's what will keep you legendary. 

I'm a big fan of studying music, so I will continue to be a student. Creating music and studying music are two different things to me. I study it and then I feel creative, so I think it's about separating them because sometimes if you're creating while studying, you just end up repeating exactly what somebody's doing and that doesn't feel authentic. It's more about getting inspired and then creating.

My love for music and being a creative is what keeps me going because it's not always fun, it's not always easy. Sometimes it's about business, sometimes it's about pushing past your exhaustion. I don't think I would do that, not for this long, if I didn't love the payoff of being a creative. 

How will you celebrate if you win a GRAMMY?

I haven't thought about how I'm gonna celebrate. I think my favorite type of celebrations are intimate. They're with people who are in the mud with me — my family, my team. I would probably just want to have a great dinner and think about how far we've come and what's next.

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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

Updated Friday Oct. 13, 2023 to include info about Kendrick Lamar's most recent GRAMMY wins, as of the 2023 GRAMMYs.

A GRAMMY veteran these days, Kendrick Lamar has won 17 GRAMMYs and has received 47 GRAMMY nominations overall. A sizable chunk of his trophies came from the 58th annual GRAMMY Awards in 2016, when he walked away with five — including his first-ever win in the Best Rap Album category.

This installment of GRAMMY Rewind turns back the clock to 2016, revisiting Lamar's acceptance speech upon winning Best Rap Album for To Pimp A Butterfly. Though Lamar was alone on stage, he made it clear that he wouldn't be at the top of his game without the help of a broad support system. 

"First off, all glory to God, that's for sure," he said, kicking off a speech that went on to thank his parents, who he described as his "those who gave me the responsibility of knowing, of accepting the good with the bad."

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He also extended his love and gratitude to his fiancée, Whitney Alford, and shouted out his Top Dawg Entertainment labelmates. Lamar specifically praised Top Dawg's CEO, Anthony Tiffith, for finding and developing raw talent that might not otherwise get the chance to pursue their musical dreams.

"We'd never forget that: Taking these kids out of the projects, out of Compton, and putting them right here on this stage, to be the best that they can be," Lamar — a Compton native himself — continued, leading into an impassioned conclusion spotlighting some of the cornerstone rap albums that came before To Pimp a Butterfly.

"Hip-hop. Ice Cube. This is for hip-hop," he said. "This is for Snoop Dogg, Doggystyle. This is for Illmatic, this is for Nas. We will live forever. Believe that."

To Pimp a Butterfly singles "Alright" and "These Walls" earned Lamar three more GRAMMYs that night, the former winning Best Rap Performance and Best Rap Song and the latter taking Best Rap/Sung Collaboration (the song features Bilal, Anna Wise and Thundercat). He also won Best Music Video for the remix of Taylor Swift's "Bad Blood." 

Lamar has since won Best Rap Album two more times, taking home the golden gramophone in 2018 for his blockbuster LP DAMN., and in 2023 for his bold fifth album, Mr. Morale & the Big Steppers.

Watch Lamar's full acceptance speech above, and check back at GRAMMY.com every Friday for more GRAMMY Rewind episodes. 

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