Home Music Music Lists

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.


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


Onyx, ‘Slam’

“We wanted to bring slam dancing to rap,” Onyx’s Fredro Starr says in Brian Coleman’s Check the Technique. “Believe it or not, Nirvana was a big influence on us. Red Hot Chili Peppers too.” Hey ho, let’s go: “Slam” is one big mosh pit of grimy Queens hip-hop and hardcore punk, with a room full of crowd-surfing, body-slamming, slap-happy hooligans. The director: Parris Mayhew, from the NYC hardcore band Cro-Mags. “Slam” made these baldhead rappers massive on MTV and broke their classic debut, Bacdafucup. The whole project was influenced by some serious psychedelic chemicals. “While we were recording the album, n***as was on LSD the whole time, straight up,” Fredro said. “We was dropping papers, taking meth tabs, during that whole album. That’s just the creative side of making music. We were like Jimi Hendrix.” —R.S.


LL Cool J, ‘Around the Way Girl’

In a little gem of fake reality TV, LL Cool J takes his candid camcorder to the streets of New York to film “regular girls” — “I don’t want Ivana,” he says at the clip’s start “I want Tawana.” One of those girls was Leslie “Big Lez” Segar, who would go on to be a storied choreographer and host of Rap City. “[Y]ou don’t expect LL to be someone who’d dance. Not to say he doesn’t have rhythm, but he’s too cool for school! This is ‘Gimme my radio! I’m thugalicious, on the block, Hollis, Queens! I don’t dance. I may bop side to side in my Timberlands,’” Segar told Rock the Bells. “[S]ometimes you have to pull teeth with artists to get them to dance. But he was open, and he was ready and very participatory in regards to whatever the choreography was.” —C.W.


Neneh Cherry, ‘Buddy X’

A straightforward battle of the sexes scene, this Neneh Cherry music video — directed by French fashion photographer Jean-Baptiste Mondino — might not ordinarily qualify as a hip-hop video at all, if not for the evolution of the genre pushed forward by MC’ing vocalists like Drake, Juice WRLD, Travis Scott, etc. As an early hybrid of the rapping chanteuse, Cherry leads a posse of female feminists speak-singing into a broom handle and taking a cheating man (reportedly rocker Lenny Kravitz) to task about his infidelity in front of a crew of misogynistic men. But her closing salvo takes it: She removes her panties and tosses them to the guys as a drop-the-mic gesture that effectively ends the argument, the song, and the video. —M.M.L.


Azealia Banks feat. Lazy Jay, ‘212’

A simple brick backdrop, goofy dance moves, and Banks — clad in a Mickey Mouse sweater and braided pigtails — spouting obscenities through a gleaming grin. It was a simple image that created a viral moment that felt equal parts endearing and intimidating. Though the black-and-white clip was filmed in Montreal, quick clips of a bodega and Yung Rapunzel’s charming, no-nonsense lyrics brought undeniable NYC energy to this Vincent Tsang-directed video. Canadian musician Lunice, who appears in “212” alongside electronic producer Jacques Greene, told Billboard, “The shoot was a perfect moment of spontaneous creativity. The kind you can’t rehearse or re-formulate.” —J.J.


Missy Elliott, ‘She’s a Bitch’

“What she goes through to create these images, people will never know,” said makeup artist Billy B. while making Missy Elliott’s $2 million blockbuster “She’s a Bitch.” “The prosthetics and the airbrush, makeup, and then two hours of gluing on rhinestones. She’s a trouper.” For Elliott’s first video after returning from the success of 1997’s Supa Dupa Fly, Hype Williams, the director of the most colorful videos of the ’90s, took a sharp turn into an Tron noir world of blacks, grays, and silvers — fewer hues, but no less dazzling. Here Missy emerges from the water with a bedazzled look that’s part bondage, part punk, part Matrix, and all visionary. “Back then every1 thought I was a lil off because I rocked a bald head,” Missy Elliott posted to Twitter, “but me & Hype & [Timbaland] was just decades ahead.” —C.W.


Kendrick Lamar, ‘The Heart Part 5’

“The Heart Part 1,” from 2010, is all grainy digital footage, convenience stores, and van rides. By “The Heart Part 5,” Kendrick Lamar is wielding state-of-the-art technology to transform into figures old (O.J. Simpson) and new (Jussie Smollett), still spitting minutes-straight bars but now speaking with sweeping conviction for a nation of millions. Lamar and longtime collaborator Dave Free created the clip’s series of deep fakes with the help of Deep Voodoo, a studio launched by South Park creators Trey Parker and Matt Stone. Like other “Heart” tracks, “Part 5” hypes an album but sits outside it; where Mr. Morale & The Big Steppers is gnarled and conflicted, “Heart” is sanguine, resolved. This tone even carries into the video’s heart-stopping final moments, when Lamar assumes the form of his late friend Nipsey Hussle. ” “I look at everything as a social experiment,” Free told The New York Times. —C.P.


3rd Bass, ‘The Gas Face’

Here is a surrealist peak behind the curtain of the record industry during hip-hop’s initial commercial boom. The snarky but poignant call-out of shady record executives (embodied by a perfectly cast Gilbert Gottfried), racist stereotypes in media, and commodification of rap culture was among the first of its kind. MC Serch and Prime Minister Pete Nice were unlikely guardians of hip-hop purity, but cameos from respected names in rap including Public Enemy’s Flavor Flav, EPMD, Run-D.M.C.’s D.M.C. and Jam Master Jay, and Def Jam head Russell Simmons provided necessary credibility. Through the lens of rap history, the video is now best remembered primarily for two things: a scene where MC Hammer is stomped out in effigy, and the introduction to the world of Zev Love X, then of rap group KMD, who years later became better known as the elusive underground legend MF Doom. —N.C.


Q-Tip, ‘Breathe and Stop’

Quite possibly the original bohemian B-boy, Q-Tip set a standard for anti-bling hip-hop with a quartet of A Tribe Called Quest albums from 1990 to 1998. So much so that his first glitzy singles as a solo act—“Vivrant Thing” and “Breathe and Stop”—felt like a jarring commercial grab with Hype Williams-directed clips full of sexy models and beaucoup gluteus maximus jiggling under a fish-eye lens. With decades of hindsight, Q-Tip planting a flag for his relevance in the jiggy era by speaking the lingua franca might have been his smartest move. The bandana holding his Afro in place seems way more Hendrix than 2Pac, as he ambles about in a long leather poncho owning his rep as a hip-hop sex symbol. Eye candy Leila Arcieri (Miss San Francisco 1997) practically launched King magazine and the video vixen era with her appearance here as well.—M.M.L.


Fugees, ‘Ready or Not’

Filmed over three 16-hour days at the height of the group’s multi-platinum popularity, “Ready or Not” is widely considered the first rap video to cost over a million dollars, and its production forecasted the eye-popping visual excesses of Y2K hip-hop. In the clip, Pras Michel, Lauryn Hill, and Wyclef Jean are rebels on a “quest for justice,” and dodge military helicopters on ski boats and motorbikes. They also hide out from the Illuminati while rapping in a submarine, courtesy of Universal Studios’ backlot. Veteran music video director Marcus Nispel, who eventually graduated to directing genre flicks like the 2003 remake of The Texas Chainsaw Massacre, films the trio in shadowy lighting reminiscent of an adventure film. When faced with criticism from fans upset with the big-budget theatrics of “Ready or Not,” Michel responded, “I don’t believe in laws or rules.”–M.R.


Cardi B, ‘Money’

The Jora Frantzis-directed visual acknowledges Cardi’s stripper past, and through clips of the rapper breastfeeding, provides glimpses of her maternal present. Pepper in nipple flashes, money guns, and sexy bank tellers, and you have an iconic take on the power of female sexuality in all forms. The video is bolstered by eye-popping fashion choices, like Cardi appearing in a Cleopatra-inspired outfit made entirely of watches — a look Rihanna famously dubbed “the most ghetto shit.” Even though she’s draped in designer looks these days, the Bronx-bred MC has never forgotten her roots, and “Money” doesn’t shy away from highlighting what gives her — and all women — the right to flex. —J.J. 


Jay-Z, ‘Moonlight’

Let’s pretend for a moment that Friends wasn’t a whitewashed remix of the African-American sitcom Living Single to begin with. For the first five minutes of this clip, directed by Master of None co-creator Alan Yang, an extremely A-list cast (Issa Rae, Tiffany Haddish, Tessa Thompson, Lakeith Stanfield, Lil Rel Howery, Jerrod Carmichael) shoot the third season Friends episode “The One Where No One’s Ready” beat for beat on the series’ original set. (An opening montage set to Whodini’s “Friends” looks fabulous.) A disillusioned Carmichael eventually wanders off set as Jay-Z’s lyrical critique of hip-hop’s superficiality and creativity begins in the background. Things end poignantly with Carmichael pondering a full moon as the video references the titular inspiration of the Oscar-winning indie drama, Moonlight. Like a lot of the song’s source album, 4:44, “Moonlight” leaves plenty to ponder.—M.M.L.


El-P, ‘Deep Space 9mm’

El-P’s solo debut Fantastic Damage is a deeply cinematic affair, its boom-bap blasted to shit by shifty cyberpunk unease and its narrator a snarling wise-ass who keeps falling face-first into trouble. Brian Beletic’s video for “Deep Space 9mm” follows El-P through a grainy post-9/11 NYC in which violence lurks around every corner, quite literally: cabbies, bar patrons, nuns, even boy scouts pull shimmering red revolvers on the emcee. El-P wrote the record before 9/11, but none of it was intended as prescient: “It’s meant to tap into something that I think lurks underneath it all, all the time,” he told NPR.–C.P.


Ludacris, ‘Get Back’

“[One of my] pet peeves in life is going into the restroom and a fan following me in there and trying to have a conversation with me,” Ludacris told Esquire. “Art imitates real life.” Equipped with huge Popeye-esque arms in the Spike Jonze-directed video for “Get Back,” Ludacris strangles and punches an aspiring entrepreneur with bad urinal etiquette — the unlucky beating recipient is played by none other than Fatlip from the Pharcyde. Ludacris was rap’s king of comedy in the years between Biz Markie and 2 Chainz and was he was at his larger-than-life best in “Get Back,” doing Hulk smashes on walls and mailboxes. “And those big arms, it was all about ludicrous in every definition of the word, beyond crazy, ridiculous, wild,” he said. Unfortunately, Ludacris did not get to keep the prop arms, but he’s been known to pull out the bulging bicep look in his live shows.–C.W.


B.G. feat. Big Tymers & Hot Boyz, ‘Bling, Bling’

The opulent, ostentatious flexing of the Cash Money empire defined an era and their expensive taste in “Bling Bling” updated the Oxford English Dictionary. The video exuded peak flamboyance at every turn: a stretch Range Rover, watches on both hands, diamond grills, boats, cars, helicopters, steel briefcases, candelabras and an ice bucket filled with cash. “People from New York, people from L.A. were always asking me, ‘These guys really got that amount of money? Are those houses theirs? Are those cars theirs? Is that all theirs?’ Universal A&R Dino Delvaille told The Fader. “And I was honest with them. I’d say, ‘Yes, that really is theirs.’”–C.W.


DMX, ‘Ruff Ryders’ Anthem’

“We went out, we shot four days,” “Ruff Ryders’ Anthem” director J. Jesses Smith told This Is 50, “and DMX was actually, visually born at that point.” DMX’s hit “Get At Me Dog” had shown a stylized visions of the gruff MC rocking a crowd, but “Ruff Ryders’ Anthem” solidified DMX in the national imagination: shirtless, bandana’d, rapping out in the streets with the incredibly large Ruff Ryders posse. Scads of dirtbikes popping wheelies and four-wheelers leaping up stairs added a tangible sense of danger to the clip, giving a hardcore rapper a different type of outlaw cool — when DMX passed in 2021, tributes poured in saying how he influenced a generation of sport bike enthusiasts. The original video was supposed to have white Harley Davidson riders, but instead the crew ended up shooting the aftermath of “the Wink Parade” where hundreds of bikers show their stuff. “It was a celebration,” Queens rider Craz-1 told GQ. “Police couldn’t do nothing about it. There was too many of us.”–C.W.


Megan Thee Stallion, ‘Thot Shit’

Inspired by the moral panic stemming from her 2020 hit “WAP,” Houston’s foremost “Hot Girl Coach” and her mob of “super regressive whores” reclaimed this song’s titular phrase by grinding on garbage trucks and clappin’ on counters, delivering a declarative message to coochie-pop critics who refuse to mind their own business. The horror film-influenced clip culminates in Megan Thee Surgeon and her naughty nurses cosmetically replacing a conservative senator’s mouth with a vulva; the audacious move was added by director Aube Perrie in the eleventh hour to symbolize “the very absolute object of all [detractors’] anxiety.” —J.J.


Odd Future, ‘Oldie’

“It was all very surreal. I didn’t even know what was goin’ on,” Odd Future’s Earl Sweatshirt told The Ringer. “I remember we was at the XXL cover shoot and then literally at some point, n*****s was just like, ‘Yo, we don’t want to do this. We just ’bout to shoot this video.’” By 2012, the Odd Future collective had already mastered the disruptive art of attention-grabbing videos. An XXL cover shoot in a Chelsea studio quickly turned to chaos — as things were wont to do around Odd Future in 2012. Someone put their 10-minute posse cut “Oldie” on the speaker and suddenly the afternoon was no longer in the hands of the magazine or photographer Terry Richardson. Seasoned chaos-capturer Lance Bangs of Jackass fame caught the group as they spontaneously made a music video on the fly, everyone dancing, mugging, moshing and serving as each other’s hypemen.–C.W.


Migos, ‘T-Shirt’

When you hear Migos’ “T-Shirt,” and the trio’s rise from “doing dirt” in a white T-shirt to selling out concerts, the last image you’d conjure is the group stunting in the mountains and cabins of Lake Tahoe, surrounded by impossibly buxom video models. The frisson is what makes Quavo and Oladapo “DAPS” Fagbenie’s clip so memorable. “I wanted to put a picture to it. I wanted to put, like, a movie to it,” Quavo told Billboard in 2017. The trio dress like Inuit hunters, a metaphor for their prior careers as street pharmacists. “It’s basically an alternative trap universe,” DAPS wrote on Twitter. “We tried to build a real igloo but the snow wasn’t dense enough.”–M.R.


Puff Daddy feat. Mase, ‘Can’t Nobody Hold Me Down’

This high-budget, high-gloss, high-fashion victory lap for record mogul Puff Daddy essentially kickstarted the Jiggy Era. It was Puff’s debut single as a performer, and he wasn’t going to be demure about it, driving a Rolls Royce through the desert, getting pawed by faceless women and dancing in a room that looks like an illuminated Gravitron. With new recruit Ma$e in tow, “Can’t Nobody Hold Me Down” was the first of the five Puff-produced songs that would hold the top of the charts for 25 weeks of 1997. “We got in the first video and [Puffy] started dancing and everybody was just standing there thinking, what are we doing?” Ma$e told MTV News. “I was like, Man, I can’t let this dude show me out. I know how to dance. That’s how it all started. So then we started dancing in the videos and before I knew it, we were falling out the sky and flying.”–C.W.


Coolio feat. L.V., ‘Gangsta’s Paradise’

A dramatic song that got an equally dramatic video, Coolio breaks it down, face-to-face with Dangerous Minds star Michelle Pfeiffer. “Michelle was kind of nervous, because I don’t think that, up to that point, she’d ever been around that many black people in her life,” Coolio told Rolling Stone with a laugh. “And, you know, my boys were‘hood!” Helmed by future Training Day director Antoine Fuqua, the clip for “Gangsta’s Paradise” is saturated in shadows and smoke, a vivid cautionary tale that focuses on the storytelling itself. The evocative, high-rotation clip helped launch “Gangsta’s Paradise” into topping Billboard’s year-end charts for 1995 — the first rap song to ever stake that claim. “I wasn’t completely happy with Antoine Fuqua’s concept at first, because I wanted some low-riders and some shit in it; I was trying to take it ‘hood,” Coolio said. “But he had a better vision, thank God, than I did. I couldn’t completely see his vision, but I trusted him.”–C.W.


N.W.A., ‘Express Yourself’

“Directing rap videos at the time was definitely like the lowest of the low in terms of a white video director. Everyone wanted big budgets with Poison and Metallica and all of that stuff,” said Rupert Wainwright in the ESPN 30 for 30 documentary “Straight Outta L.A.” “About the time that N.W.A. hit, there was this sea change.” Wainwright’s clip for “Express Yourself” reflects that moment when N.W.A captured the imaginations of America’s white bros: Tone-Loc (of “Wild Thing” fame) lip-synchs along to the chorus, and Dre sits in a parade, waving to his fans. But it’s not just a celebratory moment. Perhaps inspired by Public Enemy’s “Black Steel in the Hour of Chaos,” the video also shows the historical links between slavery, the Christian church, and Black men unjustly incarcerated in prisons. It’s all too much for Dre, who finds himself in an electric chair at the clip’s end, even though he “don’t smoke weed or sess.”–M.R.


The Notorious B.I.G. feat. 112, ‘Sky’s the Limit’

It looks like a classic music video from Brooklyn’s finest circa the late-Nineties with Biggie rocking an impeccable pinstripe suit, Puffy mugging for the camera, ladies dancing by the pool during the day and the rappers clinking drinks at the V.I.P. table at the club by night. There’s just one thing: Everybody from B.I.G. and the Bad Boy Entertainment stable of artists around to the paparazzi are roughly 10-12 years old. Spike Jonze had pitched Sean “Puffy” Combs on doing this posthumous video for the late hip-hop icon as a riff onBugsy Malone,the 1976 movie that cast kids as Thirties gangster-flick archetypes. It added an innocence to Biggy’s legacy; Combs said it broughtback memories of their days as young men, dreaming of success. “Those kids moved like us, they acted like us — that’s exactly how we rolled up to the club!” he noted on the commentary track for a DVD collection of Jonze’s videos. “You could almost feel Biggie’s spirit [there]…it was surreal and scary. I thought it was genius.”—D.F.


Jay-Z, ‘Picasso Baby’

Borrowing the concept from Marina Abramović’s landmark The Artist Is Present performance at the Museum of Modern Art, Jay-Z, “the new Jean-Michel,’ performed “Picasso Baby,” for six hours at New York’s Pace Gallery, allowing attendees to become part of the show. The five-minute video that emerged from the event shows celebrities and art figures amused, awed, ecstatic or confident enough to trip up Jay entirely. Spectators take the stage. Artists like George Condo, Kehinde Wiley, original uptown/downtown bridge-builder Fab 5 Freddy and Abramović herself make appearances. Judd Apatow does a bit. Jim Jarmusch remains cool as ever. “The whole thing ended up being a document of completely unfeigned joy,” director Mark Romanek told Vulture. “There’s smiles and laughter, and people were strangely moved by it, actually. It’s got an extremely humanistic vibe for something that you could describe as from an elitist New York art world.”–C.W.


Vince Staples, ‘Fun!’

Using Google Earth to survey the fictional neighborhood of Norfy, California, “Fun!” makes potent statements about inequality, the surveillance state, police brutality, poverty tourism and white voyeurism. Zooming in to witness a memorial, a fight and an arrest, it makes a harsh point about outsiders peeking into the Black neighborhoods that artists like Vince rap about. Locals flip off the camera, shield their faces or throw rocks. “I think there’s certain aspects of culture that are always there, whether it be people outside the culture visiting from a perspective or a standpoint of safety and not having to deal with the realness of being part of that culture. I feel like that’s always there,” Calmatic said. “But it changes with technology as far as how they do that. In 2019, whether it be YouTube or social media or Google Earth, you can actually, from the comfort of your bedroom, see what life is like on the other side.”–C.W.


Afrika Bambaataa & Soulsonic Force, ‘Planet Rock’

The 808 electro-pulse of “Planet Rock” famously launched hip-hop and dance music out of its disco phase — and its video provided a colorful glimpse of the future. Though Bam and the Force’s “wildstyle” fashion — walking sticks, beads, headdresses, geometrically sharp sunglasses — implied the Afrofuturistic visions of George Clinton and Sun Ra, the “Planet Rock” video was also bound to Earth, showing off hip-hop’s D.I.Y. roots in gymnasium parties and park gatherings where the Rock Steady Crew showed off their gravity-defying breakdance moves. It seems highly unlikely that MTV played this at all, but the record still managed to sell thousands of copies. “‘Planet Rock’ and the other uptown street records are not just for inner city kids, but have a much wider appeal than many give them credit for,” Tommy Boy Records founder Tom Silverman told Billboard in 1982. “Luckily, this is the kind of music that doesn’t need radio, but through clubs and street play can succeed.”–C.W.


Salt-N-Pepa feat. En Vogue, ‘Whatta Man’

This hit song viewed hip-hop romance through the female gaze and its video flipped pop music masculinity on it’s head: Here, strong men are the cheesecake. “I came of age in my still [photography] work in the mid and late Eighties, a period of gender-bending, the beginning of the breakdown of traditional gender roles,” director Matthew Rolston told MTV’s Video Head podcast. The video doesn’t use just any bandana’d hunk to snuggle with Salt: That’s none other than Tupac Shakur. The record label requested his face be obscured due to his ongoing legal troubles. “Me and Tupac had a little chemistry, but I knew not to mess with that. I wouldn’t have been able to handle that guy!” Salt told Rolling Stone. “When we won a Grammy, he sent us, to our hotel room, a cake shaped like a gun. I think it was a Glock. And we didn’t know if he was threatening us or congratulating us. … This has to be his way of congratulating us. And it was. But that was such a Tupac thing to do.”–C.W.


Busta Rhymes, ‘Woo-Hah!! Got You All in Check’

When the dragon-sized presence of Busta Rhymes’ and the color-saturated visions of Hype Williams joined forces in 1996, it caused an absolute tectonic shift for hip-hop, not only launching a madcap motormouth solo star, but establishing Williams’ next 25 years as the genre’s premier visual auteur. Williams had been directing stylish rap videos for half a decade, but “Woo-Hah!!” was the first to embrace what would be come to be as his signature style: fisheye lenses, banks of lights, unlikely post-production effects and insane color schemes. The style — carried on by Williams along with his protégés and imitators — would help define the larger-than-life look of hip-hop’s jiggy era. “I set out to kind of change things and make rap music videos just as big as rock and alternative music videos,” Williams said in 1998. “If I’ve been able to help do that then I succeeded in what I was trying to do.”–C.W.


Kanye West feat. Lupe Fiasco, ‘Touch the Sky’

Financed by the rapper himself after he was unhappy with Def Jam’s version, the Evel Knievel-inspired clip for “Touch the Sky” has a Seventies aesthetic that perfectly compliments the song’s Curtis Mayfield sample. Filmed at Grand Canyon West, the million-dollar movie co-stars Pamela Anderson, Nia Long, and Tracee Ellis Ross. (It nearly featured Fall Out Boy as a group of reporters, but the band bowed out due to scheduling conflicts.) Not only was the visual a way for West to flaunt his grandiose ideas, it also served as a tongue-in-cheek way to poke fun at his ginormous ego and recent controversies (which now seem quaint considering what was to come). In one hilarious scene, a TV sportscaster asks “Kanyevil” about his comments toward President Nixon, mirroring West’s pointed real-life words about George W. Bush after Hurricane Katrina. —J.J.


Lil Pump, ‘Gucci Gang’

With over one billion YouTube views, “Gucci Gang” gave SoundCloud rap what may be its most iconic image: Miami’s Lil Pump, with a neon shock of pink hair and reflective silver jacket, stalking the hallways of a high school alongside a live tiger. “That was real,” director Ben Griffin told Pigeons & Planes. “[The animal trainers] were like, ‘If he comes a day before the shoot and practices with the animal — and the animal likes him — you can do the shot. But if the animal gets antsy around him, you’ll have to do a composite shot.’ So he went and did the training, and the animal was fine with him… It wasn’t CG or green screen or anything.” The images were instantly indelible enough to help carry a Saturday Night Live parody with Pete Davidson: The show’s director of photography even hit up Griffin to find out what lenses he used.–C.W.


Arrested Development, ‘Tennessee’

The vision of Atlanta’s Arrested Development — part rural South, part righteous Afrocentrism, part alternative-era bohemia — made them one of the most critically adored rap groups of the early-Nineties. Macedonian director Milcho Manchevski helped introduce their look in their debut video, a community gathering shot softly and starkly. Inspired by Depression-era photography and the austere shots of Diane Arbus, Henri Cartier Bresson and Robert Frank, the video cut a warm path across flashier MTV fare. “It took me a long time to convince [the label] that we should shoot the video in black-and-white,” said Manchevski. “But once the video came out, it was extremely successful, it became a Buzz Clip on MTV, it went around the world, and the band exploded.”–C.W.


Missy Elliott feat. Timbaland & Da Brat, ‘Sock It 2 Me’

Missy blasts off into outer space, where she’s still the weirdest and coolest thing on any planet. After Miss E blew up in the summer of ’97 with “The Rain (Supa Dupa Fly),” she could have toned it down for her next video. But she got even crazier with “Sock It 2 Me,” a Hype sci-fi trip where she dons her superhero astronaut suit, red wig, and silver eye shadow, to battle alien robots on another planet. Her trusty sidekick? Lil Kim. Things look bad for our heroes until Da Brat rides to the rescue on her space motorbike, chanting like she’s on a playground: “I’m the B-R-A-T, her be Missy/We some bad bitches who be fucking it up!” Timbaland flosses in his Albert Einstein fit. It’s a utopian celebration of late-Nineties Southern hip-hop feminism, a moment when the whole world was wired to every move Missy made. Like Da Brat declares, “It’s ’97! This the motherfucking Bitch Era!” Long live the Bitch Era.–R.S.


Snoop Dogg feat. Pharrell Williams, ‘Drop It Like It’s Hot’

Really, it’s all about that beat: Maybe the apex of the Neptunes’ early-oughts era, a mad-scientist concoction of tongue clicks, pneumatic drum hits, and white noise that Snoop laces as carefully as possible. Veteran music director Paul Hunter films the video as if he’s documenting history’s victors, capturing striking monochromatic imagery from low angles and cutting only when it complements the beat. “I was influenced by Richard Avedon and the way he captures celebrities,” Hunter recalled. “And we wanted a Sixties, Frank Sinatra feel to it — we wanted to really show that lifestyle, that class.” While Snoop unleashes a pharmaceutical-grade C-walk at the video’s outset, it’s that simple park-it-like-it’s-hot move that has been enshrined in GIF immortality, as simple and inimitable as the track itself.–C.P.


Drake, ‘Best I Ever Had’

There are at least three great jokes in Kanye West’s video for Drake’s debut single, which was shot at Bishop Ford Central Catholic High School in the Windsor Terrace neighborhood of Brooklyn. The first is pretending that its ebullient hook is a coach talking to his team. (Drake plays the coach, riling his squad before a big game.) The second joke is: What if that team were composed entirely of babes? (Kanye, as director, seems to particularly relish this component.) The last and best joke is: What if they played a really good team? (They get absolutely wiped, 14 to 91.) It’s all ridiculous, as confectionary as the track itself — a reminder of both artists in less dour days.Drake summed up the casual vibe: “I was in New York, Ye was in New York. We just decided, why not go to Brooklyn and shoot a video.”–C.P.