Hip Hop didn’t make its first appearance at the Grammys until 1989 when DJ Jazzy Jeff and Will “The Fresh Prince” Smith won an award for “Parents Just Don’t Understand.” The pop-rap duo accepted their awards wearing custom pink Philadelphia jerseys, in an attempt to show the world at large that they were just “around the way guys.”
Contrary to the optics, this was actually a bold fashion move — the Grammy organization was loath to legitimize Hip Hop prior to DJ Jazzy Jeff and the Fresh Prince, and by showing the world that rappers were “just like us,” this duo helped to usher rap into the American mainstream.
Thirty years later, Hip Hop has — thankfully — become much bolder with their fashion choices at the Grammy awards. Let’s take a look at some of the more memorable looks.
LL Cool J
From Hip Hop pioneer to NCIS: Los Angeles star, LL Cool J has become grown and sexy right before our eyes. But though he’s come a long way, this multiple Grammy nominee — and host — never forgets his roots.
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Even in a custom tuxedo with a diamond-encrusted “LL” lapel pin, James Todd Smith still gives the people what they want in a matching custom Kangol-style hat that he made synonymous with the pioneering Hip Hop of New York in the 1980s.
Puff Daddy
There’s nothing subtle or understated about the Hip Hop mogul we know and (sometimes) love as Sean Combs. In 1998, Puff Daddy & the Family’s No Way Out album beat out Biggie’s Life after Death and the Clan’s Wu-Tang Forever album to bring home the Grammy for the Best Rap Album.
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We can’t explain it either, but shortly after the Grammy win, Diddy took to the press room, where he was decidedly not going to pass up the opportunity to show the world all the ice on his neck, his wrist, and his belt, thank you very much.
Missy Elliott
Four-time Grammy winner Missy Elliott has always had a style of her own. But she really flaunted her flirt in 2002 when she showed up on the Grammys red carpet looking slimmed down, smiling and living her best life.
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Donning a soft adidas tracksuit with a custom Kangol-style hat, crisp white sneakers, a matching pearly white smile stuffed with bubble gum, Missy made sure we all knew she could stunt on all dem hoes, no matter what size.
Ja Rule
Long before he would become known for debating the difference between “fraud” and “false advertising,” Ja Rule was accustomed to being a Grammy-nominated rapper. Though he ultimately lost to Outkast (thank God), in 2002, he got tongues wagging’ when he showed up with a barely-dressed Ashanti on the Grammys red carpet.
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To this day, the duo can’t escape the “are they or aren’t they” schtupping speculation, thanks in no small part to this appearance, which certainly can’t make the long-suffering Mrs. Ja Rule a happy woman.
Eve
This picture was taken on last year’s Grammys red carpet, and needless to say, Eve had come a long way from being a so-called “Ruff Ryder.” She grew her hair out, married a “billionaire” and now spends her days (probably) lounging around on a chaise while servants cater to her every whim.
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But even though she’s grown up and glammed out, Eve couldn’t resist showing off her infamous tattoos — and a whole lot more — in this sexy two-piece suit.
The Fugees
The 1996 Grammys was, perhaps, the last time Lauryn Hill showed up to an event on time. And regardless of the troubles the group would face as a collective, right after this multiple Grammy win, we’ll always have the memories of them looking like this, proving that in the right setting, Hip Hop can be the most beautiful thing in the room.
The Carters
JAY-Z and Beyoncé are Hip Hop’s ultimate power couple, and they turned heads at last year’s Grammys with their matching sleek and sexy looks. The fact that they managed to look so bold and powerful while remaining chill was a testament to how much both they — and Hip Hop — grew up. And little Blue Ivy Carter tied their whole look together, too.
Coolio
In 1996, Hip Hop somehow thought Coolio was the answer to all of our prayers. We even went so far as to give him a Grammy for his trouble.
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Now, let us look at this Grammy winner in his denim dashiki and box braids as he poses with Joni Mitchell, so we don’t ever have to speak of this time in history again. Learn from us, children.
50 Cent
2003 was the year White America, as a whole, learned G-Unit was short for Gorilla Unit, and that’s thanks in no small part to this rather, erm, bold fashion statement made on the part of the collective’s capo, 50 Cent.
Lil Wayne
He was an SK8R BOI, he said SEE YOU LATER BOY … you know the rest. You can always count on Lil Wayne to bring more than a little bit of color everywhere he goes,
Big Pun
They didn’t call him “Big Pun” for nothing. When the nearly half-ton rapper appeared on the Grammys red carpet in 1999 with Fat Joe and Cuban Link, photographers from major photo wire services can be heard asking who exactly they were photographing (with someone suggesting the “I’m Not A Player” rapper was actually the house DJ).
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That didn’t stop him from showing up in a larger-than-life chain and custom black suit and looking, frankly, quite good … even for a big guy.
Nelly
Back in 2013, Nelly — who had already won Grammys for songs like “Shake Ya Tailfeather” — had cleaned up his act before stepping onto the red carpet with, of all people, country star Tim McGraw. But ditching the du-rags for the dapper suit proved to be a good move and showed off a more mature side to the “Tipdrill” rapper.
DJ Khaled
Nothing says “adorable” like matching father-and-son red velvet suits. We all couldn’t resist watching Khaled and his son walk down the red carpet looking like this — even if what we would find out about Khaled a few years later would be a total let-down.
Kanye West
It’s getting hard to believe there was a time in history when Kanye West was known as something more than Mr. Kim Kardashian and a sell-out in a MAGA hat, but here, we have the proof. Here he is at the 48th annual Grammy awards in full marching band mode as he performs “Gold Digger” with Jamie Foxx.
Petey Pablo
In 2003, everyone was getting their crunk on, so it made sense to invite — and nominate — North Carolina-born rapper Petey Pablo to the ceremony. Though his Diary of a Sinner ultimately lost to The Eminem Show, his get-up proved Hip Hop still got a lot of love in the streets, no matter how much it had “grown up” at that point.
Beastie Boys
In 1987, the Beastie Boys were one of the few rap collectives that could garner respect from the mainstream, for what are q-white obvious reasons. And while, over time, they would evolve into the beloved legends they are today — who knew that a rapper would get a public park named after them? — they left the Grammy audience in full shock and awe when they appeared onstage to present an award in full B-Boy gear.
A Tribe Called Quest
At the 2017 Grammys, A Tribe Called Quest took to the stage to make a political statement. Donned in matching militant outfits, the collective paid tribute to Phife Dawg, mock-saluted “President Agent Orange” and concluded with raised fists in the air while repeating “resist.”
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Given the parlous state of politics in America today, this is nothing if not a bold statement in and of itself.
Outkast
It’s Outkast. When are they not being bold on the red carpet? Tuh.
Ol’ Dirty Bastard
Long before Kanye interrupted Taylor Swift — and subsequently caused the White Woman Cries Heard ‘Round The World — Wu-Tang’s clown prince Ol’Dirty Bastard was interrupting Shawn Colvin (it was the 90s, you had to be there) at the Grammys.
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Donning a bespoke red suit with a soft white scarf “that costed-ed him a lot of money,” ODB grabbed the microphone and proceeded to deliver the infamous “Wu-Tang is for the children!” speech — to the horror of Shawn Colvin and the delight of hotep-tress Erykah Badu.
Queen Latifah
It took until 1989 for Hip Hop to win a Grammy award 2005 for a Hip Hop star to host the Grammy awards. To this day, John Denver has hosted more Grammy awards ceremonies than rap stars have. While we hope that changes in the near future — Cardi B would probably be hilarious as a Grammy host — we would be remiss if we didn’t give props to the first Hip Hop star to host the awards ceremony.
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And, as a true groundbreaker would, the Queen showed up and showed all the way out with her 1950s retro hairstyle, glorious gold necklace and a red dress so bright you could see it from space. Give it to ’em Queen
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