August 14, 2023 10:47AM

The 150 Greatest Hip-Hop Videos of All Time

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

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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

In this crucial document of Chicano rap, Kid Frost and director Andrew Doucette brought the culture of East Los Angeles worldwide. Beyond the fashion and graffiti, “La Raza” showcased L.A.’s vibrant car culture years before Dr. Dre and Snoop Dogg crashed their lowriders into pop radio. Here, hydraulics make automobiles do robotic dances, wiggle from side to side or bounce in ecstatic rhythm. “It’s been something that’s been a part of my heritage and my culture for years and years,” Kid Frost told Fab 5 Freddy on an episode of Yo! MTV Raps. Lowriding is just something that the Chicanos started a long time ago and its time now that the world see where they really got it from.”–C.W.

In a 180-degree turn from the often comedic mood of his videos, Busta largely leans into the sexuality of “What’s It Gonna Be?!” Liquid dreams come to life through watery chrome coverings and liquefied special effects, which ultimately totaled up to an over $2 million budget. Busta (who spends portions of the video as aquatic, non-human figures like sperm and raindrops) wiggles his way through scenes to get closer to Ms. Jackson, who stars as an Afrofuturistic dominatrix. Keeping in line with the video’s titillating theme, Janet admitted to Allure that her iconic purple catsuit and nails were adorned with cock ring appliques. Coupled with her extravagant makeup look, it took her 11 hours to get ready on shoot day.–J.J.

Nick Quested is an award-winning filmmaker behind documentaries like Restrepo and Pussy Riot: A Punk’s Prayer and testified last year to a Congressional committee about footage he shot of Proud Boys meetings prior to the January 6 riots at the U.S. Capitol. But he’s also a former music video director who worked with Trick Daddy on several clips, including “I’m a Thug.” The video presents the Miami rapper as a charming and shamelessly incorrigible bad boy who upsets polite society wherever he goes, from the Black upper-class couple outraged that their video vixen-like daughter is dating him, to the corny white diners at the Biltmore Hotel in Coral Gables who feign disgust at his behavior. Clips like this are designed to tantalize and distill the artist’s persona, and “I’m a Thug” demonstrates Quested’s skill at…uh, showing Trick Daddy peeing in the bushes in broad daylight.–M.R.

DaBaby’s emergence felt like an explosion: he careened into every verse, packing jokes and catchphrases and shit-talk into each bar like he was exhausted that you didn’t know him yet. The video for “Suge” is the same way, starring DaBaby as the titular label honcho and also DaBaby as an unrelated mailman, and he plays both roles with gleeful abandon, chomping cigars and drop-kicking packages and flashing a megawatt “What, me worry?” grin at the camera.–C.P.

Though many of his videos lean on Bart Simpson-esque skits, Eminem shows a much more serious side in this illustration of the dark side of fandom. Stan’s infatuation with Shady metamorphoses from relatively tame (writing letters in hope of a response) to dangerously obsessive (drinking and driving just like Slim Shady in “My Name Is”). Final Destination actor Devon Sawa’s chilling turn as the titular character stands as one of his proudest career moments. “It was like, ‘Eminem? C’mon Dev, I dunno about doing a music video,’” Sawa told Vice in 2018 recalling his agent’s reluctance about the role. “Nobody was really onboard with doing it on my team, and I was the only one who was like, ‘Oh my god, this guy’s really, really good.’ So I did it anyways.” —J.J.

New York rap videos in the early-to-mid-Nineties reveled in grime and grit, and no one laid the tracks for that aesthetic like EPMD. How underground are Erick Sermon and Parrish Smith? “So Wat Cha Sayin’” takes place literally under the ground. “The video was dangerous,” Sermon told Complex. “We were underground in Manhattan, in not really a sewer, but under like a manhole with the pipes.” Director Adam Bernstein — who had placed them in a Brooklyn ice factory for 1988’s “You Gots to Chill” — captured the group in their subterranean lair, making use of shadowplay and showing off the deft turntable work of DJ Scratch.–C.W.

Borrowing the first-person drug/sex/violence orgy concept that Jonas Åkerlund concocted for Prodigy’s “Smack My Bitch Up” video, director Gil Green showcased the anarchic energy of Atlanta’s explosive crunk movement. Along with Lil Jon & the East Side Boyz, the POV video barrels through Atlanta’s famed hotspot Club 112, bumrushes security, spills drinks in V.I.P., hooks up in the restroom and ultimately ends with the same — no spoilers! — reveal of the video’s unlikely troublemaker. “When Lil Jon first stepped on the scene, I got excited for this track,” Green told Miami New Times. “I remember having a meeting with his label and pitching them, and I had to show them that I knew what crunk was. I basically jumped on the desk, throwing papers and acting a fool. Lil Jon was like, ‘Oh, this white boy’s crazy. Let’s do the video.’”–C.W.

When Slick Rick’s third album, Behind Bars, was released in 1994, hip-hop’s most celebrated storyteller was, in fact, behind bars. Unable to shoot a video, Def Jam turned to quirky Eastern European filmmaker Sash Andranikian, who created a three-minute tour de force that’s both beautiful in its hand-drawn animation and excoriating in its satire. With shades of Pink Floyd’s The Wall, Andranikian turned a harsh pencil towards the prison-industrial complex while also showcasing the bleakness inside its facilities.–C.W.

This euphoric celebration of hip-hop itself was filmed in the genre’s 20th year by the hottest film auteur of the early Nineties “Spike Lee was super professional, had multiple setups ready for us, and he even pulled KayGee out of bed to get started because he didn’t want to be late for his Knicks game,” Naughty’s Vin Rock told Vevo. Beyond introducing a timeless chant and arm-wave, “Hip Hop Hooray” showed rap music in full-flower thanks to huge crowds and monster cameos from Run-D.M.C., Queen Latifah, Monie Love, Fab 5 Freddy, Eazy-E and Spike Lee himself, who can be found crowdsurfing in some of the final shots. Though some of it was shot in Naughty By Nature’s Jersey stomping grounds, Lee made sure to bring them to his borough. “Historically, if you weren’t from the five boroughs you weren’t respected as rappers,” Vin Rock said, “but Brooklyn definitely showed us Jersey Boys tons of love.”–C.W.

Months after Hurricane Katrina decimated New Orleans’ Lower Ninth Ward, local music beacon Juvenile reportedly became the first musician allowed to film in its aftermath. Shot with one camera and a police escort, “Get Ya Hustle On”serves as both tribute and reportage, Juvenile rapping a survivalist anthem amid a city destroyed. Picking locations as they went, the darkly poignant images found amid the wreckage include a VHS tape of Armageddon, a limousine parked on top of a pickup truck and a smashed school bus. Director Ben Mor told author Keith Spera in Groove Interrupted: Loss, Renewal and the Music of New Orleans, “It’s a living graveyard; a lot of people died there. It’s Ground Zero, to the tenth power. I’m hoping to be as delicate as possible.”–C.W.

In retrospect, there was no way “U Can’t Touch This” wouldn’t be an early-Nineties smash for Oakland’s MC Hammer; its “Super Freak” sample was deployed too effectively, its catchphrases (the title and Hammer’s exhortation to “Stop! Hammer Time!”) too easy to not repeat on end. But its video helped make it a megahit—the combination of Hammer’s moves, which included the platform-game-evoking side-to-side shuffle known as the Hammer Dance, and his style, which was punctuated by billowing pants that made his every step a resounding statement, towered above MTV’s crowded landscape. Director Rupert Wainwright (who had previously done videos for N.W.A. and Too Short) was looking to take a laidback approach to directing “U Can’t Touch This,” but soon learned that wouldn’t fly around the hard-driving Hammer. “This tour bus turns up and the dancers came out and this, like, sergeant major’s voice started booming,” he recalled years later of the shoot. “I couldn’t believe it. It was the most organized thing you ever saw in your life.”–M.J.

Spike Jonze may be frustratingly unforthcoming in terms of feature films — it’s been a decade since he released Her — but his commercial work shows how efficiently he works in any format. “Till It’s Over,” ostensibly an ad for Apple’s then-new HomePod, follows FKA Twigs as a worker drone who trudges home, asks Siri for an algorithmic recommendation, and is jettisoned by the ensuing Anderson .Paak track into a four-dimensional reverie of color, spatial playfulness, even a dance-off with a doppelganger. The apartment itself plays along, teasing apart its walls and furniture via largely practical means: hydraulics, levers, and shimmering, syncopated lights.–C.P.

Likely inspired by the 3-D Toy Story zoetrope currently on display in Los Angeles’ Academy Musuem, the video for “Cash In, Cash Out” turns Pharrell, 21 Savage and Tyler into animation models. Since the pandemic necessitated CGI instead of claymation, they used London’s video effects team ETC who gave everything fingerprints, imperfections, dust particles and jitter. “Underscoring everything was that we wanted the audience to question whether we went out and built this thing for real,” the video’s ETC, told It’s Nice That. The animation team studied the rappers’ moves and mouths from their live shows, adding one more layer of reality to a video that does kickflips in the uncanny valley. “If you stopped on any frame, we wanted there to be so much detail that people would just go back and watch it again,” ETC’s Jon Purton told One37PM. “Go ahead and test it. Pause any part of thevideo, screengrab it and zoom in to see how immensely detailed every object is.”–C.W.

The conceit of Lauryn Hill’s first solo video without the Fugees succeeds with a simple premise: a split-screen Washington Heights block party separated by 31 years, with retro Lauryn (circa 1967) in a beehive ’do performing on the left and a dreadlocked, neo-soul Lauryn (circa 1998) rocking on the right. The buses, handheld cameras, portable radios and fashion selections all contrast beautifully across the span of the three decades, as the newly liberated Lauryn bridges the eras of doo-wop and hip-hop. That very aesthetic would soon be picked up and run with by the late Amy Winehouse (who often performed a cover of Hill’s song in concert). But this video—co-directed by Monty Whitebloom and Andy Delaney—made visual connections encouraging the idea that hip-hop has more in common with the Motown age than boomers ever admitted.—M.M.L.

This bare bones clip helped turn hip-hop into a pop commodity and launched the career of gravelly storyteller Tone Lōc. Director Tamr Davis did it all with just a Bolex and a budget of under $400: Actress Annabel Schofield, who plays bass guitar in the video, said they were “paid in Margaritas.” The clip, famously, is a tweak on Robert Palmer’s iconic 1987 video “Addicted to Love.” “We were like the cheap club kids that were like ‘Let’s just rip it off. We know really hot girls,” Davis told MTV’s Videohead podcast. The song hit No. 2 and quickly became the biggest selling single since “We Are the World.” “We rolled the first roll, wideshot and Tone Lōc came on and he was just like ‘Bussit.’ He just does the song,” said Davis. “We just looked at each other, we couldn’t believe how much charisma he had. He was all swag. It was amazing.”–C.W.

De La Soul officially bury the Daisy Age with their sardonic dig at the pitfalls of fame on “Ring Ring Ring (Ha Ha Hey).” Mark Romanek perfectly encapsulates the be-careful-what-you-wish-for angst of Trugoy the Dove, Posdnuos, and DJ Maseo in a stripped-down, black-and-white video where the trio try their best to avoid incoming calls and relentless fans looking to score a record deal. De La still manage to have a little fun (the ghoulish masks symbolizing “every Harry, Dick and Tom, with a demo in his palm” are a nice touch). Since the passing of Trugoy in February 2023, the song has taken on new meaning. As Pos noted, “For now on when we perform ‘Ring Ring Ring (Ha Ha Hey),’ we say ‘2-2-2-2-222 we got an angel in heaven who can talk to you.’” —K.M.

Helmed by Oscar-winning director and animation pioneer Zbigniew Rybczyński, the Fat Boys’ “Sex Machine” video splits the difference between The Benny Hill Show and the arthouse. Perhaps the most ambitious clip from the days before rap videos had much of a chance of cracking an MTV playlist, the visionary Polish director turns our hip-hop heroes into flickering human animations thanks to his unique editing. It’s a safe bet that the weiner dog is the same one that appeared in Rybczyński’s groundbreaking “Close (to the Edit)” clip for Art of Noise.–C.W.

There are many Drakes: confessional Drake, spurned Drake, Magic City Drake, and so on. “God’s Plan” captures an extremely rare magnanimous Drake, handing out a million dollars of studio money around Miami. Director Karena Evans finds moments of traditional music-video grandeur amidst otherwise documentarian lensing of the rapper picking up grocery tabs, donating to after-school programs, and handing crisp stacks to working parents. “For something like ‘God’s Plan,’ it was like, let’s capture real people and tell a story about giving back and that came from Drake’s heart,” Evans told MTV News. What sells the whole thing — aside from that miraculously buoyant beat — is the goofball glee Drake brings to the affair, even coaxing a crowd full of people to shout along with the most ridiculous line in his career.–C.P.

A somber study of triumph and tragedy, “A Lot” plays like a Bergman drama in six minutes: A family shares love and laughter when they gather for a wake, but flashbacks reveal the illness, incarceration, trauma and grief they hide under the surface. Director Aisultan Seitov was Inspired by the vintage look of Polish drama Cold War In the final shots, as well as The Godfather. In the final scene, the family patriarch, 21 Savage, sits alone at the banquet. “We had like 15 minutes break and I was thinking what to shoot on this last verse. And I was like, OK let’s make this scene from Godfather II when young Al Pacino is sitting alone in the table with nobody there,” Seitov told Genius. “What’s the last scene of Godfather mean for me personally: The power and the fame leaves you alone. It seems like he sacrificed his family to be on the top, where he is.”–C.W.

Inspired by the works of 20th-century painter LeRoy Neiman and directed by Adam Yauch in his Nathaniel Hörnblowér guise, the video for this dense Paul’s Boutique cut captured the New York hip-hop trio in the abstract. At its core “Shadrach” is a performance clip with blurry footage captured, as the video’s art director Audri Phillips told Beastiemania.com in 2010, by “very bad bank security cameras”; that footage was subsequently broken down and turned into paintings by a team of artists, then turned into animation by the studio Klasky Csupo. The result is a clip that, while evoking a stop-motion animation dreamworld, also distills the kitchen-sink ambitions of the Beastie Boys’ second album.–M.J.

“I love Danny Brown,” actor/director Jonah Hill told 52Insights when asked about his jarring, discomfiting video for a track from Brown’s acclaimed Atrocity Exhibition. “Ain’t It Funny” depicts a sitcom filtered through Brown’s drug-induced psychosis, like a riff on cynical Nineties iconography like Oliver Stone’s Natural Born Killers. Acclaimed director Gus Van Sant plays the “dad” and Joanna Kerns from Eighties sitcom Growing Pains plays the “mom,” while “daughter” Lauren Avery is made up to look like Kelly Bundy from Married with Children. “I made a trade with Gus: he was going to be in my video, and then I was going to be in his film,” said Hill, who later appeared in Van Sant’s Don’t Worry, He Won’t Get Far. Despite the high-wattage cameos, “Ain’t It Funny” looks deliberately washed out and bleak, a disturbing take on Brown’s real-life struggles with addiction. “Don’t ever be afraid to ask for help,” he wrote on Twitter this year as he celebrated 90 days of being sober. “If I can do it, anyone can.”–M.R.

For Tierra Whack’s debut, Whack World, the Philly rapper created 15 separate minute-long songs, each with its own video. Director Thibaut Duverneix told Insider that the resulting 15-minute work “is made for people who have a very short attention span.” Nevertheless, the silly yet sincere sensibility of Whack’s lyrics is mirrored in this avant-garde multiverse of madness. Whether she attempts to rap with a swollen face about the struggles of making it big (“Bug’s Life”), or spits country-tinged bars for her haters while joyously clipping balloon strings (“Fuck Off”), Whack boldly presents the layers of her adventurous, well-rounded artistic identity. While hip-hop often opts to bolster women rappers who adhere to a specific visual aesthetic, “Whack World” argues that the genre still has room for quirky girls to prevail. —J.J.

True-school rap fans know that Biz Markie has made crucial contributions to the artform through his beatboxing, storytelling, freestyling, fashion and Juice Crew membership. But for everyone else, it’s “Just A Friend”‘s indelible images of the hip-hop Clown Prince in a powdered wig singing his tuneless, lovesick plea. “[H]e mentioned he wanted it to look like Mozart so I brought in the powdered wig,” director Lionel C. Martin told Vulture. “Most hip-hop artists would be like, ‘Nah, I’m not doing that.’ Biz was down for anything.” Martin says Biz showed up to shoot the dorm room scenes hours late and told some tale about getting two flat tires. “His friends were there, and he was kinda smiling. What could I do?” said Martin. “That was Biz, and that was who he was. You could never get angry with Biz. I could be frustrated, but he was impossible to be mad at. He was too damn likable.”–C.W.

Swiss Family Robinson meets the strip club, Nicki Minaj’s boldest video updates the funny-freaky vibes of Sir Mix-A-Lot’s “Baby Got Back” for an era where you don’t have to worry about appeasing an MTV censor. Naturally, the steamy, bootylicious video broke the Vevo record for most views in 24 hours. “Some crazy shots didn’t make the cut,” director Colin Tilley told XXL. “It almost would have been too much. It would have been too much for people to handle. Heads would have actually exploded.” Perhaps no one enjoyed “Anaconda” more than Drake, who received a lapdance in the video’s final scenes. “Drake, you know… he’s an actor,” Nicki told MTV News, with an eye roll. “So he did a good job of containing himself. But after the lap dance he was excited like hell. He was like, ‘Yo, do you understand like I’m the man after this video come out?’”–C.W.

An electrifying update of the street-level G-Funk videos of the ’90s, Kendrick Lamar took to his throne in the city of Compton in “King Kunta,” an artful celebration of his neighborhood’s homes, bikes, cars, jewelry, dances, businesses and people. Despite having a widescreen vision — one inspired by Dr. Dre’s 1999 “Still D.R.E.” — “King Kunta” has a uniquely vertical aspect ratio. “It’s a new age man. Instagram and all that, we’re in a new age of aspect ratios and you’ve gotta embrace that,” Director X told Complex. “It’s exciting to me to see people sharing clips of the video on social media and it’s in that aspect ratio.” The highlight of the clip is Kendrick rocking a crowd at the home of the Compton Swap Meet, the fabled location where locals like Eazy-E delivered their under-the-radar, world-changing gangsta rap releases to Wan Joon Kim’s Cycadelic Records.–C.W.

Big Daddy Kane is the essence of O.G. hip-hop charisma in this pioneering Golden Age video, from director Lionel C. Martin. In “Ain’t No Half Steppin,” the Juice Crew kingpin flexes all his smooth-operator cool with his suit, his dance moves, and his high-top fade. “When I look at it now it’s funny,” Big Daddy says in Brian Coleman’s book Check The Technique, “because that was the suit from my [high school] graduation. It was tight, way too small, but I was still tryin’ to do it.” It’s a series of visual metaphors for a rap battle—a poker game, a boxing match—but Kane conquers all foes.. The supporting cast is mosly female. “My man Lionel Martin blessed me with lot of fine women for that video,” Kane said. “It was cool, the whole boxing ring thing. It was pretty unique.”–R.S.

“To get to school every day, I would take a dollar van from Flatbush Ave and Avenue K to the Junction train station at Flatbush & Nostrand Ave,” Talib Kweli wrote in a 2015 Medium piece of his days as a 13-year-old kid making his daily trek through Brooklyn. No doubt the polysyllable lyricist’s nostalgia trip influenced the spirit of Black Star’s around-the-way showcase for their classic 1998 debut single, “Definition.” Kweli and Mos Def ride through their beloved borough in what else? A Brooklyn dollar van. Along the way they pick up passengers, including Dead Prez and Common, call out the maddening violence that took the lives of Tupac and Biggie Smalls, and fight the good fight for hip-hop. —K.M.

This bare-bones clip launched Brooklyn drill with little more than Bobby Shmurda and his crew gleefully grooving in the streets of East Flatbush. Shmurda’s charisma made the infectious tune a success, but it was the deliriously blithe “shmoney dance” that became a viral sensation, appearing in countless Vines in 2014 and TikToks in 2021, performed at Beyoncé concerts, NFL touchdown celebrations and recreated on the Instagram accounts of the hugest pop stars. As Shmurda told Complex in 2014, “[W]e knew it was gonna take off because the first day we put it up, it got like 2,000 views. … Other people from Brooklyn, they stuff be up for like five months and they only have like 5,000 views. Some be up for years.”–C.W.

To be young, gifted and Black living in 1990s Brooklyn meant partying at some point in a brownstone with a mise-en-scène that looked something very much like this 1995 video for the Notorious B.I.G. Director Hype Williams may as well be documenting a celebration coronating Biggie as the new king of New York, given the overwhelming success of his debut Ready to Die. Everyone’s invited, a luminous guest list too extensive to set down in full: the late Heavy D and Aaliyah, Biggie’s one-time wife Faith Evans, Queen Latifah, Spike Lee, Jermaine Dupri, Sean “Puffy” Combs (of course), etc. Evans appeared at Big’s request, replacing one of the models who had been cast in the clip. “Big wanted his real-life woman next to him in that scene,” Evans wrote in her memoir. “And of course, I loved that he was making it clear who the main woman was in his life as well as in the video.”—M.M.L.

For one of hip-hop’s most intimate portraits of self-loathing, Spike Jonze runs ex-Pharcyde sadsack Fatlip through the ringer. He walks through the streets of Los Angeles as a clown, a homeless drunk in a diaper, a commuting used-car salesman and a cyclist terrorized by children. Fatlip and Jonze spent two days winging it in Hollywood and even took a spontaneous trip to Fatlip’s mom. The video’s most emotionally rich moment comes when Fatlip raps a line about drug use next to his mother and then appears to realize what he said. “I didn’t like it. It was too raw,” remembered Fatlip about seeing the video for the first time. “It wasn’t what I expected. It was on videotape, the beginning of the video I get kicked in the nuts, Spike’s talking in the beginning of the video. I dunno, I think I started liking it after I started getting positive feedback from people that saw it.”–C.W.

There’s a reason Busta Rhymes has been nominated for an impressive 16 MTV Video Music Awards during his nearly three-decade solo jaunt. The irrepressible Dungeon Dragon was born for the short music-film medium. None are as infectiously bonkers Hype Williams-stamped joy ride “Gimme Some More.” Here, the director’s trademark fish lens captures Busta as an off-the-wall cartoon come to life: a googly-eyed blue monster chasing a ‘50s sitcom house wife, a pistol-toting nod to Looney Tunes character Yosemite Sam, an exaggerated muscle suit-wearing body builder. It’s Busta Rhymes taking the unserious very seriously. —K.M.

The presence of LL Cool J, Eazy-E, MC Lyte, Too $hort, D-Nice and Biz Markie in the visuals for DigitalUnderground’s first single put hip-hop on notice that the funk-inflected Oakland outfit consideredthemselves a major new addition to the culture, soon to be as vital as anyone making a cameo here.“Doowutchyalike” introduced Humpty Hump (D.U. rapper Shock G “disguised” as a hip-hop lounge lizard, complete with Groucho Marx-like nose and eyeglasses): the jokey, pleasure-driven id that gave the group a distinct visual hook. As Digital Underground’s mastermind, Shock introduced his group by directing their debut video himself—full of underwater swimming pool shots, bikinis, and a festive California house party vibe that summed up the D.U. aesthetic in five minutes flat.—M.M.L.

“I fought that ‘All I Need’ shit. I fought it. I didn’t wanna put it out,” Method Man told podcaster Math Hoffa. “‘Cause it was at a point now where, when we were doing these shows, Wu-Tang together, I would come out and there would be girls screaming. Now for me, I’m grimy, same-clothes-three-days-in-a-row n***a. Who wanna go the sex symbol route at this point?” Luckily for Meth, director Diane Martel kept a gritty edge in this much-adored love letter with Mary J. Blige. Showing off some of the acting chops he would display in Belly and The Wire, Meth enters a family drama and dodges the police when not rapping in front of a gorgeous tableau atop a Harlem rooftop. Director of photography Lance Acord would go on to do cinematography for films like Lost in Translation. Martel would eventually direct discourse-disrupting videos for Robin Thicke and Miley Cyrus, and Meth became a sex symbol regardless.–C.W.

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No director has informed the look of SoundCloud-era hip-hop like Chicago’s Cole Bennett, who turned his Lyrical Lemonade blog into a studio that pumped out quirky, colorful, videos for Lil Pump, Famous Dex, Lil Xan, Smokepurrp and many more. His most acclaimed work is perhaps Juice Wrld’s smash hit “Lucid Dreams,” a trippy, deeply emo horror-noir where Juice bares his emotions while poking his head through a hole in the floor. Although Bennett had been filming and uploading music videos since 2013, “Lucid Dreams” was the first time he had a budget —$5,000 — instead of just his usual “run-and-gun, point-and-shoot-style.” Five years later, the video is close to one billion views. “The video is very all-over-the-place in a sense ’cause it came out of nowhere,” said Bennett. “It was just an idea randomly. … I think it’s funny that it’s the biggest video on the channel today.”–C.W.

White Danish rapper Lucas didn’t make too much of a splash in the States, but the director of his lone hit certainly would. The wildly ambitious one-take clip for “Lucas With the Lid Off” was an early success for French director Michel Gondry, who would unleash his mazelike vision on films like Eternal Sunshine of the Spotless Mind and The Science of Sleep. Inspired by 1920s rent parties and Singin’ in the Rain‘, Gondry, Lucas and about 16 film projectors went through 17 takes of a mind-bending performance — the final take was the only usable one. “When [singers] have to do something physical it’s a relief because they don’t have time to worry about who they are or what they are doing and they can be completely natural,” said Gondry, who filmed the video as Lucas ran around him. “I get the best performances when I do this because they are participating and they see they are achieving something that is not easy.”–C.W.

The first collaboration between hip-hop futurist Missy Elliott and director Dave Meyers—who would go on to direct a slew of Elliott clips, including the similarly mind-bending “Work It” and the feisty “Gossip Folks”—was the result of a movie date turned brainstorming session. “We both flip out over wild visuals and have a similar sense of humor,” Meyers told Fortune in 2019. “We’re different types of people but our harmony was in that, and our collaboration is a result of our differences.” Meyers and Elliott matched the song’s next-generation sonics with a clip that felt beamed in from a post-industrial future, complete with dancers—coached by choreographer Nadine “Hi-Hat” Ruffin—who threw down pugilistic moves while Elliott swung from a crystal-covered chandelier.–M.J.

French director Romain Gavras took M.I.A.’s hectic, up-in-your-grill song and upped the ante, delivering a nine-minute movie about a dystopia where redheads are rounded up and shot. The concept started off as a goof, with the Tamil rapper’s producer Christopher “Rusko” Mercer recalling “how people would beat me up because I was a ginger.” The end result, however, is anything but a joke — it’s graphically violent, remarkably upsetting and a potent allegory about politicizing genocide that inspired a million think pieces and was banned outright by YouTube when it dropped. “I didn’t want to explain myself because if I give my vision it just narrows down the idea to one point of view,” Gavras said. “People are talking by themselves and it’s even better.” —D.F.

Bone Thugs-N-Harmony had initially recorded 1995’s “Crossroad” as a mournful tribute to the Cleveland rap troop’s late member Wallace “Wally” Laird Jr. But by 1996, the group had become overwhelmed by a series of deaths of friends and relatives, including their mentor Eazy-E. The quick-tongued spitters tapped Michael Martin to direct the video for a more uplifting remake of “Crossroad,” the eventual Number One single “The Crossroads.” The clip follows a tall, black Grim Reaper as he leads a procession of the dearly departed to heaven — among them stand-ins for Krayzie Bone’s cousin and brother-in-law, Wish Bones’ Uncle Charles, and the glowing ghost of Eazy-E. But the moment where the angel of death leaves with an infant baby still haunts Krayzie. “It was good for the song,” he said on the Halftime Chat R&B Podcast in 2021. “But knowing what I know now … I probably wouldn’t do a scene like that because I know God doesn’t do things like that.” —K.M.

The primary challenge with directing visuals for Slick Rick, one of hip-hop’s greatest storytellers, is thateveryone already has their own music video for his songs running in their head based on his nth-level lyrical narration. Director Todd Holland takes the literal approach to Rick’s moralistic tale, dramatizing a 17-year-old’s bank heist gone wrong with a Chaplinesque, black-and-white Keystone Kops chase through Soho eventually landing our hero in jail. (The song itself remains so beloved that Nas recorded his own take on its police brutality theme, sampling it on 2019’s Kanye West-produced “Cops Shot the Kid.”) “That was the record label’s idea to go that route,” Rick says of his slightly sanitized video: young ladies do the Steve Martin dance and his whole bedtime story puts a dwarf to sleep. “Maybe they didn’t want to go the route of too gritty.”—M.M.L.

Is there a better encapsulation of peak OutKast than the intro to this video? The duo are discussing video possibilities for a new single. Big Boi wants 30s and Impalas; Andre says the moment calls for “some space futuristic-type thangs”; Big Boi concludes, with no further ado, “Alright then, let’s do both of’em.” Thus: Big Boi rapping in a laser-lit roller disco, Andre rapping at the barbershop dressed for the post-apocalypse. Director Gregory Dark — a porn-industry provocateur who gradually moved to erotic thrillers before taking over millennial MTV — films the affair in lurid hues, letting the player and the poet fly their freak flag in a raucous, street-filling dance party.–C.P.

This clip from the early days of Video Music Box showcases teenage dynamo Roxanne Shanté, whose boasts were some of the boldest of the mid-Eighties. Through some comical vignettes, Shanté recaps her rise to power. In one of the closing chapters of the long-running “Roxanne Wars,” she takes some parting shots at UTFO and the Real Roxanne. “Growing up and being able to see images of myself, especially on Video Music Box, was a blessing ’cause you didn’t see too many kids who looked like me,” Shanté said in the Showtime documentary You’re Watching Video Music Box.–C.W.

In this deeply physical, painfully bleak video, police brutality is portrayed as a battle that crosses day and night, street and home. A white police officer (Shea Whigham) and a Black man (LaKeith Stanfield) wage a fruitless, endless wrestling match that only leaves them both injured and weakened. “It’s provocative, and we all knew this, so we were tasked with making something that expressed the intensity of senseless violence without eclipsing our humanity,” said director AJ Rojas. “I can tell you it was an emotional shoot day. It is tough to re-create moments that are so fresh and prevalent in our world today. It affected all of us in deep ways.” The clip ends as it begins: the war unfinished, it’s participants exhausted. “There is no neat solution at the end because there is no neat solution in the real world,” said the group’s Killer Mike.–C.W.

When you’ve survived being shot nine times to sign a $1 million recording deal with hip-hop behemoths Eminem and Dr. Dre, you are entitled to a bit of myth-making. And so we get the star of “In Da Club,” 50 Cent, literally being rebuilt like Seventies television icon The Six Million Dollar Man. Suddenly he reappears hanging upside down in a gym rapping. But that famous sequence is not the video’s money shot, according to co-director Phillip G. Atwell. “Seeing 50 with Dre and Em having his back is as big a visual statement as it is a musical statement,” he explained to MTV News in 2003, referring to the ending scene in which 50’s mentors appear in lab coats approving of their brilliant creation. “You could see what the commitment was between [them] and what this project was going to be about.” —K.M.

“I Don’t Like” almost single-handedly changed the way rap videos look in the internet age, eschewing almost every music video convention to make something that speaks to the immediacy of social media. Cheap, grainy, shaky, smoky, hyper-local and full of teenage energy, it’s hip-hop with the D.I.Y. attitude and no-budget gloss of hardcore punk, a perfect introduction to Chicago’s homegrown drill phenomenon. Director DGainz gave “I Don’t Like” and early drill scene its cinema verité feel by just showing up, recording and seeing what unfolded. “We were just chilling and [producer Young] Chop put on ‘I Don’t Like’ and everyone started dancing. I just started filming. Everyone was high and drunk — even I was drunk,” director DGainz told BET. “I put it out at like midnight and when I woke up at seven o’clock in the morning it was viral.”–C.W.

This Shawshank-flavored video continued the present-day provocateur’s quest to queer up hip-hop. That meant sporting hot pink prison jumpsuits, proudly displaying love in lockup, and using a prison shower — often seen as a place of violence and violation — as the backdrop for energetic, empowering choreography. Director Christian Breslauer told Vevo that “Industry Baby” also symbolizes Montero’s “unwillingness to conform or be caged in because of his beliefs.” Not only does the clip overturn and reclaim stereotypes of Black men in prison, Lil Nas promotes the importance of unabashed self-acceptance, breaking the chains of the genre’s ingrained machismo. —J.J.

“I wanted to make sure that when she was on that pedestal, she always looked elevated, and I wanted the two white chicks dissing her to look like they were looking up, not down,” Sir Mix-A-Lot recalled of the inspiration behind the memorable “Oh my God, Becky, look at her butt” opening of the 1992 video for his chart-topping “Baby Got Back.” The Seattle rhyme pioneer had originally suggested to director Adam Bernstein that he appear coming out of the controversial music short’s infamous giant ass. That idea was thankfully spiked. Still, the polarizing “Baby Got Back” received backlash for what many critics saw as the sexist objectification of women. MTV censors sidelined it before agreeing to play an edited version after 9 p.m. Mix’s gyrating, shaking ode to the bodacious derriere has since become a campy pop-culture marker, cited by some Black feminists for its rebuke of systematic European beauty standards. —K.M.

“The first video, B.I.G. was gonna direct it. He was gonna play different characters,” director Lance “Un” Rivera told VladTV about “Crush on You,” originally a solo spotlight for Kim’s Junior M.A.F.I.A. cohort Lil Cease. “He had this dance he used to do call the Bum Bitch. And he said ‘I’mma be doing the Bum Bitch tryin’ to lock Cease up’ as the cop from Martin.” However, once Lil Kim hopped on the remix, it became her show: a colorful explosion of matching wigs and outfits in inspired by the 1978 musical The Wiz. The bright, audacious look would promptly become one of the most iconic of the 1990s. “[A]t this point no hip-hop or R&B artist had experimented with bold color. The stages on set turned from blue to green to yellow to red and I saw that her clothes were like that too,” hairstylist Eugene Davis told Vice. “I left Long Island City where we were shooting, went back to New York, bought some wigs put them on her and recut them on her.”–C.W.

As mainstream ambassadors to Houston’s long-percolating hip-hop scene, Mike Jones, Paul Wall and Slim Thug turned the slow-rolling, trunk-rattling sound of Houston rap into a cultural sensation. Director John “Dr. Teeth” Tucker provided the travelogue: candy-painted cars with neon in the trunk, high-circumference rims with protruding “swangas” or rotating spinners, sparkling chains and diamond-encrusted grills, and Swishahouse co-founder Michael “5000” Watts providing the soundtrack on two turntables. “We shot it in Houston, which was the way that I wanted to go. I wanted to show its culture,” Tucker told AllHipHop. “The girl dancing in front of the tables is like the Pied Piper. You also have candy-colored cars swaying in and out on the street. It’s hood, but also artistic at the same time. It all goes together. The amazing thing is that people got it.”–C.W.

In the summer of 1984, Run-D.M.C.’s “Rock Box” became the first hip-hop video to appear on MTV, joining Michael Jackson, Prince, and Tina Turner among the few Black music artists at the time to appear on the largely white video channel. The Steve Khan-filmed promo is as iconic as it gets, opening with Run, D, and Jam Master Jay stepping out of a Cadillac in all their Godfather hat, leather suit, Adidas-rocking glory, as guitarist Eddie Martinez shreds on top of the car’s roof. The group’s label, Prolife Records, even cast a young white kid as an enamored fan to ensure robust airplay. It worked. “If you look at the video, it’s not the park, it’s not the block party,” explained D.M.C. in the 2021 documentary series Hip Hop: Songs That Shook America. “It’s a downtown Manhattan club, it’s punk rock in the video, it’s metal in the video. But the Black hip-hop dudes were the stars!” —K.M.

Hip-hop’s biggest crossover project of the 2010s deserved an equally distinctive music video to commemorate its second single. So, Jay-Z and Kanye West enlisted director Spike Jonze, who in this case took a slightly less auteurish approach to their decadent ode to wealth, fame and badass than was his norm. Filming a $350,000 Maybach getting liberated of its doors and roof, hip-hop’s glimmer twins then took their Thunderdome mobile for a thrill ride spinning doughnuts in Downey Studios, a quartet of giggly models in the backseat. And yet the most indelible image isn’t the fireworks or the Maybach—it’s the brotherly love between two rap superstars at the top of their game, a U.S. flag backdrop serving as a visual symbol of the American dream they managed to acquire despite the odds.—M.M.L.

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