The 150 Greatest Hip-Hop Videos of All Time

“[M]y aesthetic for videos now are more everything at once, just more chaotic, organized chaos,” A$AP Rocky told Complex. “I think it is a nice way to display my ADHD.” On “Shittin’ Me,” the Harlem rapper’s psychedelic visuals took a turn toward the trenchant. The concept is like an LSD-fried version of Weekend at Bernie’s: a rapper’s death fails to stop the activities of his crew, his label or the fame machine. Though released in an era where rappers end up with a constant stream of posthumous releases and collaborations, Rocky waved off accusations that the video was critical toward the industry. “I think it’s just art. Art is subjective, take what you will from it,” he told Hypebeast. “It’s supposed to strike emotion, and that’s all I wanted to do.” —C.W.

Gang Starr took four years to release their fifth LP, Moment of Truth, and rapper Guru spent that time growing displeased with the state of hip-hop. “You Know My Steez” roars out of the gate — it’s the LP’s first track and first single — with a hard-knock beat that goads Baldhead Slick to deliver a stern state of the union (“The wackness is spreading like a plague,” he intones). The video, by Terry Heller, merges Guru’s damning vision of late-Nineties hip-hop with George Lucas’ fascist bunker dystopia THX-1138, complete with S&M-chic centurions and bleached-white torturescapes. Guru breaks free, of course — DJ Premier’s beat on the track could knock down any wall. —C.P. 

Maybe all you need for a great video is one set, one car under one streetlight, one verse stretching on for three effortless minutes by one 17-year-old with outsized charisma, and a singular flow. Kodak Black’s premiere video is a case study in minimalism, the camera’s autofocus flinching beneath the head-on gaze of the rapper. Director BonesVision switches to night vision, sometimes doubling the image against itself, but the effect is almost documentarian. There’s some styrofoam or something on the ground behind Kodak, if you can take your eyes off him. —K.M.

Few cultural artifacts capture flip-phone-era virality as well as the video for Soulja Boy’s infinitely memeable “Crank That (Soulja Boy),” which follows the adventures of Atlanta record mogul Mr. ColliPark as he tries to find the source of a dance craze that’s captivated the kids both in his office and in blurry clips he watches on his phone. Soulja Boy is, of course, at home in front of his webcam, keeping tabs on his instant messages and the hit count at souljaboytellem.com — and the clip’s story ends happily, with Mr. ColliPark giving the kid a record contract and a celebratory amulet, and Soulja Boy leading a gym full of devotees in the dance he dreamed up. —M.J.   

“It ain’t really a lot of people that represent females from the hood and ratchet females,” Memphis crunk star GloRilla told BET.com. “We was just in the video having fun, doing what we normally do, and people like the authenticity — the realness to it.” “F.N.F. (Let’s Go)” was a TikTok smash that had the energy of a TikTok video, GloRilla and her all-female squad dancing, doing doughnuts in a parking lot, and dancing at a red light. The simple clip launched her from the video-sharing app to the Grammy stage within months. To keep the energy of their collaboration, Hitkidd pushed GloRilla to shoot the video the same day as a recording session. “I got to the studio by 12:00 and we got done at 1:00,” GloRilla told Billboard. “He was like, ‘We’re gonna shoot the video at 4:00 today. Go get all your friends.’” —C.W. 

“Fun-loving” isn’t a term often used for the serious-as-cancer Public Enemy, but there’s no other way to describe this satire of the way American medical care underserves the Black community. Flavor Flav lies in a funeral casket, enjoying life after death; his mom collapses from a heart attack, only to have an ambulance worker dribble bits of sandwich on her face; and some random guy falls onto a snowy street, convulsing after suffering a broken neck, while his homeboy calls for an ambulance that never arrives. Somehow, the whole thing is hilarious, thanks to Rupert Wainwright’s sitcom visuals — which earned him a 1991 Soul Train Music Awards nomination — as well as Flav’s flamboyant, indescribable “Flavor Dance.” Lookout for cameos from a pre-fame Samuel L. Jackson, Jam Master Jay of Run-D.M.C., and DJ Hurricane from the Beastie Boys and highly underrated Def Jam parody act The Afros. —M.R.

In a clip made to look like one continuous take — it was actually 13 shots craftily edited together — Xzibit raps with unflappable ease as his neighborhood roils with chaos around him: a swerving police car chases a suspect, a pickup truck explodes, someone with sticky fingers crashes through a pawn shop window. “Nobody wanted to shoot that video,” Xzibit told the Breakfast Club. “‘Cause I came up with the concept. And everybody was like, ‘Oh, it can’t be done, it’s too expensive.’” Still Xzibit estimated that they managed to do it for less than $100,000. Beyond explosive action sequences, the clip also features a cameo from human pyrotechnic Flavor Flav. Said Xzibit, “Flavor Flav wasn’t even on the schedule; he [was] just driving by, saw us, and hopped out and got in the video.” —C.W.

Like her Video Vanguard inspirations Beyoncé Knowles, Missy Elliott, and Nicki Minaj, Doja Cat is dedicated to adventurous fashion choices, chameleonic looks, and arresting visuals. Perhaps her most audacious video is the cyberpunk-meets-hyperpop clip “Need to Know,” a brutalist retro-future nightlife party conceived by Doja and her creative team. On Planet Her — inspired by Blade Runner‘s Los Angeles and The Fifth Element‘s New York— a blue-skinned alien Doja goes out for a night on the town with her squad (which includes Grimes and actress Ryan Destiny). Though filmed in the digital age, Doja and directors Miles Cable and AJ Favicchio opted for big sets on a soundstage and laborious makeup. “They had, like, a 20-person prosthetics team,” Favicchio told Nylon. “It was a huge undertaking to get that done. I think their call time was obviously hours and hours before ours.” —C.W.

“Outkast wanted me to film ‘Bombs Over Baghdad,’ but ‘Ms. Jackson’ really stood out to me,” director F. Gary Gray told GQ. “You never know if it’s going to work — animals bobbing their heads to the music and the guys fixing an old, broken-down house? But people really got it.” Gray matched one of Outkast’s most earnest songs with a color-saturated, bittersweet video where the duo tends to weather damage on a broken home. Soon, “Ms. Jackson” would become the group’s first Number One single. Remembered the group’s André 3000 to BlackFilm.com, “I was doing the close-up scenes, and he was looking at the playback monitor and he said, ‘I think you’re going to have a great career in film if you ever go in that direction.’” André would go on to his first starring role in Gray’s Be Cool, launching a career that would see the rapper working with action directors like John Singleton and Guy Richie as well as arthouse heroes like Claire Denis, Noah Baumbach, and Kelly Reichardt. —C.W.

Directed by Peter McCarthy, who helmed the 1994 slacker gem Floundering and co-produced indie films like Repo Man, the video for “Love’s Gonna Get’Cha” triumphantly illustrates BDP’s tragic fable. KRS-One plays both the song’s narrator — his JA-colored cap symbolizes knowledge of self — and the protagonist, a Black teen who sees crack dealing as a way out for his impoverished family. Several members of the BDP crew make cameos, including his brother Kenny Parker, the late Ms. Melodie, Heather B, and Harmony. They’re all cast in shadows illuminated by a single spotlight, like characters striding into a stage play. The way McCarthy shows dollar bills and Uzi machine guns circling in the air like dreams and nightmares gives “Love’s Gonna Get’cha” a poetic quality and enhances BDP’s classic story rap. —M.R.

This kinetic video by experimental filmmaker Zbigniew Rybczyński turns Grandmaster Flash and his rebooted mid-Eighties crew (which includes Furious Five alum Kid Creole and Rahiem) into a human game of Perfection, sproinging the group into the air over and over again, matching the beat with rhythmic editing. Complementing another one of the group’s post-“Message” message raps about contemporary chaos and disorder, the band raps as Rybczyński’s bespoke machine launches them alongside boomboxes, speakers, and trash. Two years later, the director would collect the MTV Video Vanguard Award. —C.W.

“Everything you see in this video was completely authentic. There wasn’t any treatment, any budget, any planning,” director Cole Bennett told Genius. “We just went with the flow, and we were seeing how things went.” A mix of the spontaneous and the chaotic, “Catch Me Outside” captures the off-the-cuff wildness of the SoundCloud rap era, with Florida rapper Ski Mask the Slump God bringing a one-man party to the middle of Times Square. Filmed during Bennett’s first trip to New York City, Ski Mask interacts with tourists and dances with a Statue of Liberty street performer (Bennett says Ski put $20 in his tip jar). “With every shot in this video, you didn’t know what to expect. Someone could look at you crazy, or someone could hop in the video and start dancing with Ski,” said Bennett. “So with every shot we took, it was fun because we didn’t really know what was going to happen.” —C.W.

“Get at Me Dog” was how DMX began 1998, a year in which he would make good on his long-simmering hype by releasing two Number One albums and starring in Hype Williams’ hallucinatory Belly. The track’s video, by J. Jesses Smith, does its best to capture an uncontainable talent. DMX rapped as physically as he sounds on record, lunging back and forth toward the audience with every line, falling into a boxer’s shuffle only long enough to catch his breath. His off-hand punctuates each syllable, lifting the crowd at legendary NYC nightspot Tunnel along with each pumped fist. “I knew that ‘Get at Me Dog’ was a hit at the Tunnel, and I knew what that meant,” DMX recalled in 2012. “They told me, ‘When this shit comes on at the Tunnel, motherfuckers go crazy.’ But I’d never been — until I performed there, when we shot the video.” —C.P.

“Triumph” was a victory lap: Four years after releasing their debut, the Staten Island nonet had held together, releasing a string of instant-classic solo records and keeping egos in check for a double LP. How else, then, to declare triumph but with “Triumph”? Six minutes, no hooks, just verse after perfect verse. Shit-hot (and since-disgraced) director Brett Ratner stages this moment with a video of almost psychedelically bad green-screen effects and endless highlights: GZA becoming a star child, Masta Killa giving sight to the blind, RZA showing up in a bee costume. “Triumph” enshrines the unrepeatable apex of the Wu. —C.P. 

The clip for newbie Bronx rapper Ice Spice’s “Munch (Feelin’ U),” directed by George Buford in the home borough of hip-hop, offers a perfect example of how to grab the brass ring of rap success in 2023. The song’s 1:44 length makes it perfect for repeat streaming. And Ice virtually guaranteed the video’s virality by releasing it through Worldstar, the popular platform occasionally known for less savory, more pugilistic content. Ice Spice commands the camera by cheekily adjusting her bandeau boob tube and shaking her fanny in high-cut jean shorts in front of the Paya Deli bodega. Simple, suggestive, effective. —M.M.L.

“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.

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.

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.

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.

“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.

“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.

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.

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.

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.

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. 

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’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.

“[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.

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.

“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.

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.

“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.

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.

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.

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.

“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.

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.

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.

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.

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.

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.

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.

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.

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.

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 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.

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.

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.