The 150 Greatest Hip-Hop Videos of All Time

Like everything else Eric B. and Rakim did in the Eighties, their first video set a new standard for hip-hop cool and street realness. “I Ain’t No Joke” wasn’t set in a club or on a soundstage—it was right there on the street, in the same park where they hung out. No cornball comedy, no posing: Eric rocks the turntables while Rak holds the microphone like a grudge, next to a graffiti mural, a playground, a Harlem storefront on 125th Street. It made all previous rap videos look like Toys R Us. The director was Vivien Goldman, the London punk professor who’s chronicled reggae, Afrobeat, rock, and rap. There’s a scene-stealing dance cameo from a then-unknown Flavor Flav—his first time on camera. He was just hanging out that day to watch, but Goldman noticed he was “jumpy and perky and lively. And I said, ‘Oi, you over there! Can you do me a favor, will you do a bit of dancing for us?’…And that’s how sort of innocent it all was.”–R.S.

Kanye West had come across visual artist (and director of 1993’s Demolition Man) Marco Brambilla’s work while at New York’s then-hip Standard Hotel, which displayed his Inferno-inspired video collage “Civilzation” alongside elevator rides—guests ascended up to heaven and or tumbled down to hell, depending on their destination. West asked Brambilla to create a similarly life-or-death-themed clip for his King Crimson-themed My Beautiful Dark Twisted Fantasy cut. The result, a 90-second tableau focusing on a hyperstylized West, surrounded by muses and wearing a massive chain, was “not a video .. It’s a moving Painting!!!,” as West tweeted, correctly, after its release.–M.J.

When Kendrick Lamar dropped the surreal highlight reel for “Humble,” the think-piece industrial complex went into overdrive attempting to dissect the Compton MC’s curious messaging. Did Kung Fu Kenny dress like his holiness the pope only to flip to indiscriminately firing a money gun as some statement on his struggle to find balance? Is there a symbolic meaning behind taking golf swings off the roof of a run-down hooptie? What’s up with Lamar sitting in for Jesus in a wide shot re-creation of Leonardo Da Vinci’s painting of “The Last Supper”? And why is he wearing a white suit in a large group of men in black suits? As Kendrick put it, “The initial idea was to go off of one my favorite words: contradiction.” —K.M.  

Jay-Z’s “Picasso Baby” already qualified as a high-art music video, with his epic staredown of Marina Abramović at NYC’s Pace Gallery. Going several steps further, Jigga and Beyoncé donned pastel suits and shut down the world-famous Louvre museum for this Ricky Saiz-directed clip. Their unprecedented flex led to an over 50 percent uptick in Louvre visitors under the age of 30 when this dropped in 2018, with a guided tour taking Gen Z fans through all the artwork (the Mona Lisa! the Venus de Milo!) featured in the video. Strategically chosen paintings depicting royalty, status and wealth found their modern counterparts in the Carters. Setting a new bar for luxury rap, Bey even delivered a more impressive flow than her laid-back zaddy.—M.M.L.

From an opening frame centered on a photo of the late Boogie Down Productions DJ Scott La Rock and his two children, director Fab 5 Freddy ensures this clip from By All Means Necessary is all about family. A young boy in a LITTLE RED ALERT sweatshirt appears early, most likely the son of famous hip-hop DJ Red Alert (who appears several times). KRS-One’s ex-wife, the late Ms. Melodie, goads him on throughout the black-and-white clip as he cements his transition from the proto gangsta rap of Criminal Minded to this sophomore album video full of Malcolm X, Bob Marley and Marcus Garvey imagery. As an extra cradling a saxophone mimes the hook (borrowed from Stanley Turrentine’s “Sister Sanctified”), KRS rocks a golden-age hip-hop nightclub, making it clear that politically conscious rap could also rock the boulevard.—M.M.L.

“The idea was to compile Arabic references, fantasized or not, into a pop video,” said “Bad Girls” director Romain Gavras. “Pop videos usually show American kids in their element. Here, you got Arab kids in an insane car rodeo element.” Full of fast and furious drifting, M.I.A’s “Bad Girls” video mixed the beautiful desert landscapes of an epic drama with the dangerous vehicular stuntwork of an action franchise. Gavras and M.I.A. were inspired after watching YouTube videos of Saudis driving their cars on two wheels, jetting off to Morocco to film their own version. “I thought I was gonna die on the shoot when I saw the drifting. It was a four day shoot so everyone was on edge the whole time specifically ME when I had to [sing] to the camera while the cars did doughnuts on the wet road 10 feet away,” said M.I.A. “In my mind I was thinking how I was gonna deliver the video to Vice with no legs.”–C.W.

A sweeping shot takes us through 32 years of the joy and pain that Scarface has witnessed on the same Houston block. The fashions change, the haircuts change and even the cinematography changes — director Marc Klasfeld aged the film and added grain for scenes in the ’70s and ’80s. However, the core message of the video — bookended by shots of sneakers on a wire — is the exact opposite. “The whole pair of shoes over a wire is pretty indicative of somebody dying [in the projects],” Klasfeld told MTV. “I wanted to start it with one pair and then end it with many. And it was the same kid in 1968 as it was in 2002, meaning the hood is fucked up. It’s kind of hopeless and the shit never ends. It’s a cycle and it’s hard to get out.”–C.W.

“It was kind of a dumb video, but it was done in a very sophisticated way visually,” “Fight For Your Right” co-director Ric Menello told MTV News. I often say the style of the video is ‘stupidity done in an intelligent way.’” Columbia Records wanted a video ASAP for their bratty new signees and gave producer Rick Rubin a few days to make it happen. He tapped Menello, NYU film school alumni. Menello wanted someone to blame in case the video went sideways, so he wrangled Rubin’s roommate, Adam Dubin, to co-direct. With a $20,000 budget and a two-day window on Thanksgiving weekend, Menello and Dubin turned the young Beasties into pie-throwing, beer-chugging, girl-chasing Marx Brothers for the age of hip-hop and punk rock. “It was designed to be a classic comedy and it works that way,” Dubin told Beastiemania. “It is like the Beastie Boys’ version of the Beatles’ A Hard Days Night.”–C.W.

“Mo Money Mo Problems” was the first Biggie video made after he was killed. When the song hit Number One, the chart-topper it replaced was about his death: the Puffy/Faith Evans eulogy “I’ll Be Missing You.” The video could’ve been a downer, but it became a joyfully lavish tribute from Puff, Mase, and Hype Williams. They do right by Big by cranking up the Bad Boy floss all the way. Puff and Mase float in mid-air in a 2001-style spaceship wind tunnel and dance under the Unisphere in their shiniest suits, bigger than the city lights down in Times Square. Kelly Price sings the Diana Ross hook. Biggie beams in via archival footage, cut to sync with his climactic verse. In the most touching moment, Puffy and Mase throw their Rolies in the sky and wave them side to side, at Big’s command. And because Puff is Puff, there’s also a comedy golf gag where he’s Tiger Woods and Mase is Bryant Gumble.–R.S.

Directed by Video Music Box founder Ralph McDaniels, “C.R.E.A.M.” cascades between visual re-enactments of Raekwon and Inspectah Deck’s autobiographical lyrics about life in “Shaolin Land,” as Rae calls Staten Island, and wintry, iced-out nights in New York. For trainspotters enthralled with Nineties boom-bap, both techniques result in iconic images of a bygone era: young clockers running and laughing through tight apartment stairwells and fire escapes, snow-covered parking lots full of Wu-Tang-affiliated men idling in bubble goose jackets, and despondent Black boys staring sadly out of bus windows while “going upstate,” as Inspectah Deck raps. “[RZA said] I just want to do it in the streets,” McDaniels remembered in a 2016 interview with the radio show Sway’s Universe. “It was minus-20 degrees when we shot that in Staten Island.”–M.R.

Opening with a referential throw to classic Seventies NYC movie The Warriors (Sean “Puffy” Combs clinking together Coke bottles), hip-hop’s communal spirit suffused this black-and-white clip by ubiquitous director Hype Williams. Beyond the remix’s five starring MCs, cameos abounded from DJ Funkmaster Flex, Irv Gotti, Mic Geronimo, Das EFX, Doodlebug (of Digable Planets), singer Keisha Spivey (Craig Mack’s labelmate from Bad Boy Entertainment R&B trio Total) and Puffy himself—cradling a child who’s surely pushing 30 these days. (Perhaps the most noteworthy cameo? Transgender video vixen Shamika, dancing animatedly beside a smirking LL Cool J.) The monochromatic scheme of the video—all-black-everything clothes playing against an all-white soundstage—presages a hood-famous scene from Williams’s one and only feature film, Belly. Absent any frills, CGI or even a fish-eye lens, Craig Mack and company win big with minimalism.—M.M.L.

“B.I.G., he really was offended by ‘What They Do’,” Black Thought recently revealed on People’s Party with Talib Kweli. “He was rocking with the song, and then he saw the video and was devastated, because he was a huge Roots fan.” Directed by Charles Stone III, the Roots clip satirically sent up several rap clichés—champagne sipping, video vixens, rented mansions and luxury vehicles—some of which may have hit too close to home depending on one’s public image. In the mid-1990s debate concerning mainstream vs. grassroots hip-hop, the Roots unquestionably sided with art over commercialism, and this third video from Illadelph Halflife made the most convincing visual argument.—M.M.L.

For Jay-Z’s most mercilessly political moment the rapper re-teamed with Mark Romanek, the director of 2004’s “99 Problems” and 2013’s “Picasso Baby” for a caustic re-tweaking of the racist images found in cartoons of the 1930s and Forties, juxtaposing them next to more solemn material. By video’s end, the lead character, “Jaybo,” naturally a play on “Sambo,” raps while being lynched. “One thing that made me respect Jay-Z a lot as an artist is there was a moment where we had an early version of the storyboard for the music video that we gave to him. We were waiting anxiously on a response and the response he gave us was ‘it wasn’t hard hitting enough,’” lead designer Rustam Hasanov told KultureHub. “He wanted more of a gut punch with the imagery. That made me feel like, ‘Whoa, he really wants to say something intense. He doesn’t want to side step anything,’”–C.W.

There are moments in the harrowing clip for N.W.A’s “Straight Outta Compton” that resemble a stark documentary more than a music video. The camera zooms in on members “from the gang called N-ggaz With Attitude” and then cuts to a nondescript block on fire. There’s conspicuous signage that reads Welcome to COMPTON as a white mustached cop ominously looks on with flashes of a baton and gun. Ice Cube, Dr. Dre, MC Ren, and DJ Yella are thrown in the back of a paddy wagon with a brazen Eazy-E riding alongside mocking authorities. Indeed, MTV banned “Straight Outta Compton,” fearing that the World’s Most Dangerous Group’s violent lyrics and provocative imagery would terrify Reagan’s America. Mission accomplished. —K.M.

Director Jim Swaffield’s clip for “Scenario” sneaks in far more cameos than A Tribe Called Quest’s feature-filled classic song. Blink and you’ll miss Spike Lee, Redman, Kid Capri, Fab 5 Freddy and De La Soul flashing by, in a posse video that overflows with mosh pit-level rambunctious energy rivaling the track itself. Art directed to resemble the interactive desktop of a Commodore 64 or Macintosh Classic, the 16-bit computer aesthetic (hi-tech circa 1992) looks as retro as Phife’s Bo Jackson reference. A teenage Busta Rhymes also establishes his signature hyper dynamism here, soon to become a staple of his future solo videos with director Hype Williams. A Tribe Called Quest’s output always balanced bohemianism with B-boyishness, and the “Scenario” visuals brought out the latter in spades.—M.M.L.

Coming off the lukewarm reception of 1989’s Walking With a Panther, LL Cool J was at a career crossroads. He answered his critics with “Mama Said Knock You Out,” a pugnacious classic that still stands as hip-hop’s most storied comeback. Paris Barclay stylishly captured LL’s never-say-die defiance in a raw black-and-white video in which the sweat-drenched hip-hop giant spars in preparation for the fight of his life — “that Raging Bull motif,” as LL later called it. When the self-proclaimed G.O.A.T. stands in the middle of a shadowy boxing ring and roars his lyrical supremacy over a retro-styled microphone, you can’t help but root for the man. —K.M.

The video for the N.J. multihyphenate’s hit single is straight Black — no cream, no sugar. Released during the apartheid era, “Ladies First” embodies diasporic Black power and the importance of Black women banding together to keep up the good fight. Repeated shots of figures like Harriet Tubman and Angela Davis remind us the battle for equality will continue across generations. Clad in military garb with African print, Latifah replaces chess pieces with raised Black fists. It’s these scenes and the weight they bear that announced Latifah as an authoritative voice in hip-hop. “[‘Ladies First’ is] a part of the deep roots of this culture that’s pervasive 25, 30, 40 years later,” director Fab 5 Freddy said in the documentary Hip Hop: Songs That Shook America. “[Latifah and Monie Love] just laid it out there, and it resonated way beyond most people’s perception.” —J.J.

Let Jay-Z rap about “Girls, Girls, Girls,” this early Kanye West dispatch was a teary-eyed four-minute look at separation, positioning the emerging rapper as hip-hop’s sensitive, insecure, vulnerable pulse. Using a first person perspective, Kanye chases after his girlfriend (played by Clueless co-star Stacey Dash) through the airport: The viewer gets fleeting looks at our protagonist through reflections in a limousine window, a bathroom mirror and Dash’s sunglasses — not only an emotional feat, but a technical one. “There is a layer filmed for his POV, a layer for the image being reflected and a layer of his hands in front of a green screen to match his hands in the reflection,” Milk told author Matt Hanson in Reinventing Music Video. “And, truthfully, I still don’t think it’s absolutely perfect. Because of time constraints I only got to shoot two takes of each layer.”–C.W.

This multi-million dollar tribute to the post-apocalyptic visions of Mad Max Beyond Thunderdome represents the Death Row Records takeover at the peak of its might, muscle and money. “Dre just was like in a place where he wanted to make movies. This is my movie,” director Hype Williams told Red Bull Music Academy. “This is just him saying, ‘I got a ton of money and I want to go crazy.’” Working off the Mad Max treatment by Tupac’s old friend Jada Pinkett and Dr. Dre, the video features high-speed desert battles, Zapp’s Roger Troutman vocodering from a helicopter and a young Chris Tucker fresh off his star-making turn in Friday. “It was fun and dangerous at the same time. Tupac just got out of jail and Suge Knight was walking around with a Rottweiler,” Tucker recalled. “I didn’t know if I was gonna get bit or what.”–C.W.

Given the stagnant status quo of the hip-hop mainstream in the early 2010s, “Yonkers” was both audacious and necessary enough to force a tonal shift. The Tyler-directed clip (created with assists from director Anthony Mandler and cinematographer Luis “Panch” Perez) provided a look into the Odd Future leader’s boundless imagination, which has only evolved since. Perez suggested the use of a perspective control lens to create a distorted, fuzzy effect, forcing viewers to question reality. (“It was all clever old-school filmmaking, and the tilt shift is a really nice way of making people feel unsettled,” he told Respect Mag.) If the blurred look of the black-and-white visual wasn’t enough to give people the heebie-jeebies, antics like Tyler eating a roach, rapping with demonically blacked-out eyes, and his fictionalized death by hanging surely did the trick. —J.J.

Jay-Z, UGK, and friends enter the new millennium on a massive yacht surrounded by bikini-clad models and enough Champagne to fill an Olympic-size swimming pool. Just how over the top was the infamous 2000 clip for “Big Pimpin’”? Hov’s $1 million-plus video — a first for a straight-no-chaser hip-hop production — was shot during Trinidad’s iconic Carnival by director Hype Williams, featured the two most celebrated video vixens of that era, Melyssa Ford and Gloria Velez, and obnoxious Roc-A-Fella Records co-founder Damon Dash splashing bubbly over women (behavior he has since said he regretted). Yet the video’s most iconic moment remains a shirtless Pimp C rapping in a black fur coat on the beach in Miami. When asked by his UGK partner Bun B why he would wear such attire in 90-degree heat, the late scene-stealing star replied, “TV ain’t got no temperature.” —K.M.

A quarter century before Run-DMC was inducted into The Rock and Roll Hall of Fame, the kings from Queens lampooned the idea of such an honor, stalking their way through a fictional Museum of Rock. “Not only did they imagine something that didn’t exist, they imagined themselves as part of it,” Def Jam publicist Bill Adler told Craig Marks and Rob Tannenbaum for I Want My MTV. Director Joe Butt trails golden age hip-hop’s first superstars through the gallery as they stomp out Michael Jackson’s sequined glove, smash some Elton John sunglasses, smirk at old black-and-white performances of Jerry Lee Lewis and Little Richard, and rock the house with guitarist Eddie Martinez. Comedian Calvert DeForest (aka Late Night with David Letterman regular Larry “Bud” Melman) has a hearty guffaw at Run, D.M.C. and DJ Jam Master Jay bum-rushing the video’s fictive hallowed halls, but history clearly gave them the last laugh. —M.M.L.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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