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The 150 Greatest Hip-Hop Videos of All Time

From Run-D.M.C. to Doja Cat, from Missy to Busta, and beyond

Cardi B and Megan Thee Stallion

Cardi B and Megan Thee Stallion's "WAP" has already topped the Hot 100 charts.

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HIP-HOP WAS BORN IN the Bronx in the summer of 1973. To celebrate the music’s 50th anniversary, “Rolling Stone” will be publishing a series of features, historical pieces, op-eds, and lists throughout this year.

From the moment Run-D.M.C., clad in all-black leather and fedoras, emerged from the Cadillac in the “Rock Box” clip, the music video was turning hip-hop artists into icons. Then and now, rap videos serve as ambassadors to sound, fashion, art, and emotion, transforming localized subcultures into vital elements of Planet Rock. The world could now visit Grandmaster Flash’s New York, Dr. Dre’s Compton, Juvenile’s New Orleans, Mike Jones’ Houston, and Chief Keef’s Chicago. Kids from every corner of the globe could learn to scratch or do the Humpty Dance.

The rap clips of the early Eighties, like those of Roxanne Shanté, were triumphs of creating a big impression with practically zero budget, mostly shown on Ralph McDaniels’ pioneering New York public television show, Video Music Box. Soon the undeniable force of artists like Run-D.M.C., the Beastie Boys, LL Cool J, and DJ Jazzy Jeff and the Fresh Prince would knock down the segregated walls of MTV airplay. A pilot for a show called Yo! MTV Raps would do bonkers ratings numbers for the channel in 1988, and soon suburban living rooms across America could be bum-rushed by the righteous anger of Public Enemy, Boogie Down Productions, and Ice Cube. The pay-to-play jukebox channel the Box would show the videos they wouldn’t touch. BET’s Rap City took the message to other parts of our cable network.

By the Nineties, hip-hop was America’s pop music, and filmmakers like Hype Williams, Paul Hunter, Spike Jonze, Sanji, and Diane Martel began tweaking and rethinking the visual language of the genre, bending it prismatically toward their visions. Directors like the Hughes Brothers, Michel Gondry, Antoine Fuqua, F. Gary Gray, and Brett Ratner caught early breaks from rap videos. Artists like Busta Rhymes, Missy Elliott, Lil Kim, and Puff Daddy were almost inseparable from their larger-than-life video personae.

As the video age gave way to the YouTube era, blockbuster stars like Kanye West, Jay-Z, and Drake did their best to keep grand (and expensive) artistic statements alive in a period where budgets were shrinking exponentially. However, the democratic nature of the internet meant that anyone with access to a camera could find a way to ensnare millions and millions of eyeballs, whether that means the shock of Odd Future, the hyper-local intimacy of Chief Keef and Bobby Shmurda, the arthouse fury of Kendrick Lamar and Childish Gambino, or the deeply charismatic presence of Ice Spice and GloRilla.

Our list of the 150 greatest hip-hop videos was compiled by the editors of Rolling Stoneand a panel of music critics. It’s a celebration of hip-hop’s incredible history of making a big impact on small screens.

From Rolling Stone US

25

Missy Elliott, ‘Work It’

By the time Missy Elliott hooked up with Dave Meyers for their fifth video, the future Rock & Roll Hall of Famer had already redefined the medium. After a run of clips that rivaled peak Michael Jackson, she might’ve been forgiven for mailing one in. Instead, she turned it up to 11 with an unforgettable barrage of visual vignettes that never gave viewers the chance to catch a breath. There’s Ms. Misdemeanor rocking the turntables while inexplicably being swarmed by real bumblebees, a Prince impersonator in heat, Elliott backed by a crew of dancers getting down in a dystopian children’s playground, and a defiant slave literally slapping the white off his master’s face. In other words, it’s Missy being Missy. —K.M.   

24

Geto Boys, ‘Mind Playing Tricks on Me’

Full of nighttime darkness and multiple dissolves, this Richard Hunt-directed clip takes viewers through literal interpretations of each of the Geto Boys losing himself to paranoid flights of fancy. As an (albeit exaggerated) early exploration of mental health in hip-hop, visuals illustrating vignettes from Scarface, Bushwick Bill and Willie D straight up was the way to go, given each MC’s lyrical mastery. With art imitating life, the late Bushwick Bill ends the video on a hospital gurney after a mental episode punching the concrete of the Houston streets. As Geto Boys’ fans were already well aware, Bill rode a similar wheeled stretcher on the album cover to 1991’s We Can’t Be Stopped—evidence of a real-life suicidal episode involving a self-inflicted gunshot to his right eye.—M.M.L.

23

Cardi B feat. Megan Thee Stallion, ‘WAP’

The music video for one of 2020’s most undeniable hits breathes subversive life into the iconic sample that pulses through the song — the titular refrain from DJ Frank Ski’s 1992 Baltimore club banger “Whores in This House.” The highly digitized and meticulously elaborate funhouse that the “WAP” video is set in is filled with scantily clad and enthusiastically erotic women; when they’re not channeling wild animals, Cardi B and Megan Thee Stallion lead troupes of sultry dancers and stumble upon the young sex symbols Kylie Jenner, Normani, Rosalia, Sukihana and Rubi Rose behind foreboding doors. But with its colors and kookiness, the video summons an element of play that seems in contrast to the song’s sense of domination. As director Colin Tilley worked to bring a vision Cardi articulated to life, he realized the power of making a clip that would have, “a little bit more innocence than the song.” The result feels far less like a bid to strike back at any conservative backlash against Wet Ass Pussy in all its glory and more like an ode to the levity, joy, and imagination of sexuality that was always the song’s beating heart. —M.C.

22

Run-DMC, feat. Aerosmith, ‘Walk This Way’

In one of MTV’s earliest heavy-rotation hip-hop vids, heavy symbolism turned into self-fulfilling prophecy. In the first half, a literal wall between rock and rap is broken when Aerosmith’s Steven Tyler breaks through to Run-D.M.C.’s practice space. For the second, Run-D.M.C. crashes Aerosmith’s show in their laceless Adidas, teaching rock ‘n’ roll a few moves. The video would be a watershed moment in getting black artists on white-dominated MTV. The crew had to overcome no shortage of racism to even film it. “I advertised on the radio that Aerosmith would be playing so we could get a crowd, and the black radio station they made the announcement too,” director Jon Small told the Golden Age of Music Video. But when we got there at 10 o’clock, there must have been 5,000 black people there. There were no white people. That’s when I said ‘Shit, I can’t do this with no white people — it’s supposed to be an Aerosmith concert!’ Now I’m outside walking around with my assistant director and we could see all these rockers sitting in different cars. There were hundreds of them — they were just too scared to get out of their cars.”–C.W.

21

Drake, ‘Hotline Bling’

Working in the same medium as the luminous, radiant “light and space” installations of American modern artist James Turrell, Julien “Director X” Lutz and Drake turned a deeply minimalist art movement into a national conversation. With some financial assistance from Apple, Lutz got access to the type of big sets and big budgets that were more commonplace in the music videos made 15 years prior. However, it was the singular dancing of Drake that turned “Hotline Bling” into countless gifs and reaction memes. “That’s really him. That’s who he is. It’s not so much me bringing it out. I guess he can just express it with me in a different way,” Lutz told Rolling Stone. The viral impact hit a unique peak when Donald Trump did his own version of “Hotline Bling” on Saturday Night Live a year before he was elected president. –C.W.

20

De La Soul, ‘Me Myself and I’

Back in 1989, no one in hip-hop had put themselves on blast with the type of self-deprecation evident in Long Island rap trio De La Soul’s “Me Myself and I” video. Directed by Charles Stone III (known for Drumline by 2002), the visuals introduced Pos, Dave, and DJ Maseo in a classroom surrounded by students resembling LL Cool J: gold chains, Kangols, hard-rock visages. On the receiving end of disdainful scowls, pelted by balls of looseleaf, De La made their argument for individuality wearing leather medallions and, in Pos’ case, spectacles with a daisy-patterned button-down. The message: De La looked and sounded different, and that was OK. “I’m a big ‘Twilight Zone’ fan,” Posdnuos recalled in a recent interview, “so when it was time to figure out how to include [De La producer] Prince Paul in the video, we went with him being a hip-hop Rod Serling to set up the story.” —M.M.L.

19

Grandmaster Flash and the Furious Five, ‘The Message’

Alvin Hartley shot the groundbreaking clip for Grandmaster Flash & the Furious Five’s seminal, genre-defining single during a one-day shoot in Harlem for $8000. “Not enough black videos are being shot and those that are use the same old stereotyped black imagery,” he told Billboard’s Nelson George in 1983. For “The Message,” he sets the group in a concrete tableau that looks misty and stark when bathed in afternoon light, and they stand out with their flashy leather outfits and casual B-boy poses. Sadly, Duke Bootee, the Sugarhill Records producer/songwriter who made the song with Melle Mel, is absent; Rahiem and Mel rap Duke’s parts instead. After Mel concludes his legendary verse about the “stick-up kid” whose life goes awry, a cop car pulls up and arrests the Furious Five for no apparent reason. It’s just another day in the jungle. “In a city like New York, there is all the visual variety you need for any song,” said Hartley.–M.R.

18

Dr. Dre feat. Snoop Doggy Dogg, ‘Nuthin’ But a ‘G’ Thang’

This video’s indelible images of California Love — a daytime BBQ, a nighttime house party, lowriders in full sproing — helped recenter California as hip-hop’s new focal point, and cemented gangsta rap as America’s new feel-good pop music. “I think [the video was a success] because we went out to capture as opposed to stage,” art director Dwight Patillo told Ego Trip. “And even though things were staged, we just tried to keep it as loose as possible and get the little nuances that just popped up and happened. Nobody knew that Warren G was gonna be doing what he was doing in the video at that time. The little kid [in the video] actually just got into the moment and was grooving to the music all on his own. No one directed him to do that.”–C.W.

17

Childish Gambino, ‘This Is America’

Donald Glover’s hip-hop alter ego struts, shuffles, and shimmies his way through a tableau of dancing kids, angry cops, and scenes of both social unrest and unfettered Black joy. References to everything from viral dance videos to the 2015 shooting in a Charleston church, minstrelsy to Michael Jackson’s “Black or White” car dance, collide into each other; given the way director Hiro Murai fills each frame with lots of moving parts and background business, it’s a clip that rewards dozens of viewings. The gut-punch impact remains, however, no matter how many times you see it. “The violence is harrowing,” Murai said “[but] there’s a part of it that also feels cartoony. There’s “Looney Tunes” logic in there somewhere.” —D.F.

16

Juvenile, ‘Ha’

The video for Juvenile’s “Ha” was an immediate standout when it debuted in 1998, from its sun-scarred tableau of weathered yet proud Black children to close-ups of Juvenile’s gold-pearled teeth as he punctuates each stanza with the word “ha.” It remains the moment when the world awakened to the world-class rapper — and his label, Cash Money Records. “It was the first video shot in the Magnolia Projects,” Juvenile told Vice in 2016. “Marc and them set up camp in the projects for three days. The neighborhood stood by me a hundred percent — all the drug dealers shut down. That ain’t easy to do, gettin’ people to put aside gettin’ their money so they could do something for me.” Meanwhile, Klasfeld conjured a reality that was light years removed from the fish-eyed fantasies typical of rap videos at the end of the Nineties. It felt rooted in the everyday struggle that lies at the heart of hip-hop culture.–M.R.

15

Ice Cube, ‘It Was a Good Day’

Directed by childhood friend F. Gary Gray, “It Was a Good Day” presents Ice Cube as a working-class hero eager to enjoy the fruits of life, resulting in his best-known and most accessible hit. Save for a handful of scenes where Cube raps along in a darkened studio, the clip literally illustrates his story rap. There’s “mama” cooking Cube’s breakfast “with no hog,” and Shorty of Da Lench Mob sadly shaking his head as Cube scores a rare “Lil Joe” in a game of craps. As a stark contrast to Cube’s fiery, controversial Black power image, “Good Day” feels dreamy and destined to turn sour …a premonition that comes true at the end of the video, when Cube gets home after a rendezvous with Kim and finds himself surrounded by cops as the phrase “to be continued” flashes across the screen. The moment set the stage for his follow-up video, “Check Yo Self (Remix).”–M.R.

14

The Pharcyde, ‘Drop’

In a physical feat used to disorienting effect, the Pharcyde perform the lead single from 1995’s Labcabincalifornia in reverse. Following the lead of future Being John Malkovich director Spike Jonze, the group defies gravity, gets clothes slurped onto their bodies and unpaint a mural, all mirroring a woozy beat from a young J. Dilla. “We had to practice talking backwards and walking and just the whole thing. It’s really difficult,” explained the Pharcyde’s Tre Hardson. A linguist was recruited to turn backward lyrics into phonetic nonsense for the group to memorize “Everything was just practice. A lot of practice,” said Hardson. “We had to take a flight to New York and we had to take our lyrics with us — our reverse lyrics — and the tape with us and study it.”–C.W.

13

Herbie Hancock, ‘Rockit’

The first musician to connect hip-hop with jazz as if they organically deserved to share the same space was pianist Herbie Hancock on “Rockit,” the Grammy-winning centerpiece of his 35th album, Future Shock. On “Rockit,” Hancock embraced GrandMixer DXT’s turntablism and the latest Fairlight synthesizers to explore a postmodern jazz with his Afrofuturist eyes and ears toward the 21st century. Its video — directed by the former English rock duo Godley & Creme — looked as bold as the song sounded, with robotic movable sculptures (courtesy of British artist Jim Whiting) flailing away on beat and the jazzman himself only visible as a projection on a television receiver. Hancock’s handful of MTV Video Music Awards (five in total) the following year scored an uncontested win for hip-hop. —M.M.L.

12

DJ Jazzy Jeff & the Fresh Prince, ‘Parents Just Don’t Understand’

Part Style Wars, part Benny Hill, part Pee-Wee’s Playhouse, this colorful clip was the first time anyone shot the Fresh Prince, a.k.a. the teenage alterego of Will Smith. A star was born, and so was rap’s pop crossover potential. “I had the idea of doing a human cartoon, because the song was so funny,” director Scott Kalvert told the authors of I Want My MTV. “People were hesitant, though. They said ‘They’re rappers. You’ve gotta put them on the street.’” Jive Records’ Ann Carli saw sparks flying when she and Kalvert watched the video transfers from the one-day shoot. “Up until that point, Will to me had been this loud-mouthed, gangly kid who always had a pimple on the side of his face. He always wore ball caps, he wasn’t even bothered with grooming his hair. Basically, he was a kid,” Carli told author Brian Coleman. “But we were looking at the footage as it was synced up with the lyrics of the song, and we both turned to each other and said, ‘This kid is going to be a star’.”–C.W.

11

Public Enemy, ‘Night of the Living Baseheads’

The video for this anti-drug screed came with more chaos than the shrapnel bomb sampling techniques of Public Enemy’s Bomb Squad production team. For nearly six minutes, this post-modern collage vacillates between news anchors, in-jokes, MC Lyte as an investigative reporter and Chuck D rapping in front of the ballroom where Malcolm X was assassinated. “We have two turntables to work with in hip-hop,” said Chuck D in P.E.’s official biography, “why can’t you do it from a film perspective? If you come from hip-hop, going in and out of a song is not unusual.” Director Lionel C. Martin, long serving as “Vid Kid” on New York’s pioneering Video Music Box, wasn’t familiar with Public Enemy at the time. “They had some crazy ideas,” he recalled in I Want My MTV. “Hank Shocklee said, ‘Could we stop the music and insert a commercial?” The group’s loose cannon, Flavor Flav served as ersatz casting director, recruiting some real crack addicts to play the titular baseheads.–C.W.

10

Kanye West feat. Pusha T, ‘Runaway’

Director Kanye West presents a culture clash of epic proportions on this visual gem from My Beautiful Dark Twisted Fantasy, a troupe of 27 Czech and Slovak ballerinas entertaining a highbrow(n) dinner party made up of African Americans and one sexy interstellar alien (model Selita Ebanks). Sporting gold grills and a white tuxedo jacket, he taps the upright piano’s E key like a spoon on a crystal glass, and dancers come running in black tutus. What follows (as Ye rouses sympathy for assholes and douchebags) is a company of white European dancers performing their purportedly elite art form for an audience of black-tie Black sophisticates, subversively turning the tables on hip-hop as a mainly Black performance art for its largely white fan base. How’s that for highbrow? —M.M.L.

9

The Notorious B.I.G., ‘Hypnotize’

Hip-hop video as Hollywood blockbuster: yacht parties, black helicopters, speedboats, motorcycles, a backwards car chase, Puff Daddy literally throwing money, and the Notorious B.I.G. remaining as smooth as ever. “I just remember Diddy going, ‘Man, you better be on top of your game. ‘Cause I’ve got all kinds of people wanting to shoot this video, there’s Michael Bay … blah, blah, blah, blah,’” director Paul Hunter told Spin. “The whole thing was that we wanted to show this buddy comedy and really bring out the friendship and the personalities of Biggie and Puff together. They were like a dynamic duo, and it was really just saying if you get on the ride with Biggie that you’re gonna find yourself in a really unexpected place.” Tragically, Biggie never got to see the final product. —C.W.

8

Jay-Z, ’99 Problems’

“I wanna shoot the ghetto like a photographer would shoot it,” Jay-Z remembered telling “99 Problems” director Mark Romanek. “I wanna shoot it as art.” Filming hours upon hours of footage, Romanek captured Brooklyn’s Marcy Projects in an evocative black-and-white “street reportage” style. “I never felt like I was making a rap video, I felt like I was making a rock video that had rapping in it,” Romanek said on his Director’s Label DVD. “We did really deep location searching all through the fringes and the deep pockets of Brooklyn. And I was just looking for stuff that felt raw and rock & roll and transgressive, but was still connected to Black culture.” For “99 Problems” this meant streetball, step dancing, motorcycle stunting, dog fighting, mattress flipping, a street brawl, jailhouse dehumanization, and a coda where Jay-Z gets shot and killed, kick-starting a battle with MTV over what they could and could not air on the channel. “It’s Brooklyn, New York, it’s real life,” said Jay. “It’s harsh realities, and then there’s beauty there.” —C.W.

7

LL Cool J, ‘Going Back to Cali’

Directed by the late Ric Minello, LL Cool J’s contribution to the Less Than Zero soundtrack is suffused in the kind of grainy black-and-white artistry that marked MTV clips during the Eighties and reached an apotheosis in Madonna’s “Justify My Love” and sundry Dennis Leary bumpers. Resplendent in a Kangol and turtleneck that he easily fills out with his muscles, Ladies Love Cool James strikes a cool, haughty flow and homeboy demeanor. Visually, the song is a marked upgrade for hip-hop videos during that era, and Minello fills the screen with faded glamour and po-faced wit — from LL posing at the Griffith Observatory to go-go girls shimmying on telephone booths — so that even an L.A. partisan can’t help but enjoy the clip. It’s also a sly putdown of West Coast style from a Queens native — months later, West Coast rap pioneer Ice-T would return fire on “I’m Your Pusher.” Ironic, then, that both LL and Rick Rubin would later decamp to L.A. for Hollywood glory, making the chorus “I’m going back to Cali … man, I don’t think so” sound like a harmless in-joke. —M.R.

6

Kendrick Lamar, ‘Alright’

Super timely given 2015’s nascent Black Lives Matter movement, “Alright” deserved some high-concept visuals considering its position as a newly minted anthem, and Kendrick Lamar (courtesy of director Colin Tilley) didn’t disappoint. Filmed in stark black and white, the clip contains images of law enforcement officers at various points: carrying Kendrick and his Black Hippy crew aloft in a car like ancient emperors; blowing Kendrick out of the sky with a finger gun. But the video mostly centers on Black joy, as youth dance with abandon in front of stacked boomboxes, and later point in wonder at Kendrick ambling through the sky in Timberlands like an urban warrior from Crouching Tiger, Hidden Dragon. Embodying the whole message of the song, Kendrick ends the video with a smile after he seems to succumb to police brutality — letting viewers know that in the end, he’s alright, and we will be too. As director Colin Tilley put it, the clip is about how “one man can basically spread positivity through all of the madness that’s going on and how everything is gonna be alright.” —M.M.L.

5

Outkast, ‘B.O.B.’

“B.O.B. (Bombs Over Baghdad)” remains Outkast’s peak glorious freakout, a 155 beats-per-minute joyride that never lets up. So it was appropriate that the boundless Atlanta duo of Andre 3000 and Big Boi tapped visionary director Dave Meyers to helm the video for the revolutionary first single from their masterpiece Stankonia. In Outkast’s euphoric, Technicolor world, the grass is purple, a tour bus transforms into a dimensionally transcendental nightclub on wheels, and pimped-out Cadillacs travel at the speed of light. “I had it shipped to India for individual painting of each frame in the early days of accessible online effects,” Meyers recalled. “So it was quite special at the time.” Yet there’s a grounded message that permeates the trippy euphoria of “B.O.B.” This is an unapologetic Black gathering where project kids, corner boys, booty shakers, church folk, dance crews, and freaks unite for an Afrofuturistic throw down for the ages. —K.M. 

4

Beastie Boys, ‘Sabotage’

This loving, hilarious tribute to cop shows like Baretta and Starsky and Hutch was the creative pinnacle of Nineties artists cheekily paying homage to Seventies culture. “The wardrobe fitting was where it all began as far as creating the characters,” said director Spike Jonze on his Directors Label DVD. “Mike D would start putting on clothes with a salt-and-pepper wig, and he was suddenly the boss, yelling at everyone. I always wished we would’ve recorded dialogue ’cause the stuff those guys were saying was so funny, especially when the chief would start chewing out the rookie for pissing on his shoe or something.” In making the action-packed clip, the team ended up destroying two rented cameras — one by wrapping a Ziploc bag around the lens for an underwater shot, the other in a car-chase mishap. “The camera was mounted up on the hood,” said Beastie Boys’ Adam Yauch. “Somehow we went really fast, like down a curb or up a curb, and I just remember seeing the [magazine] go flying off the camera and then the spool actually come out and the film was unrolling, like rolling up an alleyway.” —C.W.

3

Busta Rhymes, ‘Put Your Hands Where My Eyes Can See’

“When we were mixing the record, the TV in the studio is on, but no sound is coming out,” Busta Rhymes told XXL. “We mixing the song and Coming to America came on … no audio. The record sounded like some African shit, and the movie was some African shit. I bugged out when I looked at that shit. I said, ‘Nigga, I’m going to call Hype.’” Hype Williams was on his way to becoming the most iconic, game-changing music video director in hip-hop history, and “Put Your Hands Where My Eyes Could See” was just one more notch in his slam-dunk 1997. Loosely inspired by Coming to America, the video explodes past that video’s margins into black-light insanity, feather-flailing dance sequences, an elephant chase and the always-electric Busta. ”I wasn’t seeing what I wanted to see in videos,” Williams told The New York Times. “There was no color, no originality. Record companies assumed that the people who bought rap records didn’t need to see quality, so nobody was putting in the effort or the money.” For a while, his fish-eye perspectives and skyrocketing budgets became rap’s most wanted look. Sylvia Rhone of Elektra told Complex, “My colleagues at other companies used to blame me for raising the price of videos ’cause now all their artists wanted the same kind of videos.” —C.W.

2

Public Enemy, ‘Fight the Power’

One of the most inflammatory protest anthems of all time gets its own Brooklyn rally — making for some of rap’s most indelible images. Director Spike Lee had used the “Fight the Power” song as the electric leitmotif of 1989’s Do the Right Thing. Though Public Enemy didn’t get paid for its use, this blockbuster video, according to producer Hank Shocklee, was “a really good thank-you that Spike did for us.” Shot on the same block where director Spike Lee filmed Do the Right Thing, the clip played like a hip-hop update of 1963’s March on Washington. They put a call out for people to appear in a Public Enemy video, and they came out in droves. “It was like a rose really sprouted in Brooklyn,” Chuck D told Rolling Stone. “It was seriously a Black movement of just being able to stand up and demand that the systems and the powers that be don’t roll you over. And this was a threat to America, and it was a threat to the record companies at the time. That video was really powerful.” —C.W.

1

Missy Elliott, ‘The Rain (Supa Dupa Fly)’

Missy Elliott started her career working behind the scenes as a songwriter for other artists, but the individuality and ingenuity she unveiled in the first of her many Hype Williams linkups allowed the Virginia rapper to become a front-facing, overnight sensation in her own right. The cartoon-like visual introduces what would become hallmarks of Missy’s creative identity: out-of-this-world concepts, women supporting women, and en vogue yet future-forward fashion choices. Per Essence, when Williams asked her for ideas for the video for “The Rain (Supa Dupa Fly),” she answered simply, “Do everything in the song.” The results flipped the script and brought a new type of bravado to hip-hop.The track’s onomatopoeic “vroooooom” is illustrated with an effortlessly cool joyride in a 1994 Hummer H1. Elliott’s friends serve as her video vixens, with rapper Yo-Yo and SWV singer Coko dancing in the fish-eye lens as Misdemeanor references them. The video’s iconic patent-leather blow-up suit put up a proud middle finger to industry standards, worn in spite of her omission from Raven-Symoné’s 1993 music video for “That’s What Little Girls Are Made Of.” “I said ‘I’m-a show them … I’m-a stay my size and have a big record,’” she said during her 2011 Behind the Music episode. It has since become one of hip-hop’s most renowned sartorial staples. Missy’s official step into the spotlight with “The Rain (Supa Dupa Fly)” kicked off a decades-long career of expectations-defying genius, proving that being true to yourself will always be in style. —J.J.