Music videos of the classic Hip-Hop era are some of the most indelible ever made. One can’t imagine the 1990s without the laid-back SoCal vibes of “Nuthin’ But a ‘G’ Thang” or the hyperkinetic surrealism of “Supa Dupa Fly.” These vids didn’t just define Hip-Hop; they sit at the epicenter of pop culture and influenced a generation of artists and creators who came later. Hip-Hop’s music video directors sat at the forefront of that revolution. In the 1990s, Hype Williams shifted the aesthetic of MTV from the grimy, downbeat tones of early ’90s grunge and the straightforward documentary style of early gangsta rap into something richer and more cinematic. That approach — understanding the artist and the audience — was evident in the work of the best vid directors. But there was also the artistry and creativity that elevated rap videos from what so many had been at the dawn of Yo! MTV Raps in the late 1980s to something a bit more ambitious within a few short years. 

Paris Barclay

In the late 1980s, Paris Barclay was a Harvard alum looking to break through, and he paired with a rap superstar in a way that would redefine both men’s careers and set new standards for rap videos in a new decade. “Paris had went through a rough time, and I actually brought him into the business at that point,” LL COOL J shares. “That was one of his first things in Hip-Hop and in the game.”

LL’s videos began to become something entirely definitive toward the end of the late 1980s. The Def Jam superstar closed the decade with some of his biggest hits and opened the 1990s with the masterwork that is Mama Said Knock You Out. While LL’s videos had been stellar since his second album, Bigger and Deffer (his platinum-selling debut Radio famously had no videos at all), it was the visuals accompanying Mama Said Knock You Out that set a new standard for a new decade, and most were helmed by Barclay.

“He was focused. He was clear,” LL says of working on Mama Said… “He was open to my ideas. He was excellent to work with. A lot of people don’t think about him, but he did a piece of work that will live a long time.”

Barclay has served as head of the Directors Guild and had success on the big screen (Don’t Be a Menace to South Central While Drinking Your Juice in the Hood) and television (NYPD Blue). He co-chaired the Television Creative Rights Committee and has become one of the most influential men in Hollywood.

“He had a helluva sense of humor — always had me laughing,” LL remembers. “We worked super well together. We had real collaborative energy and it just really worked.

“You have those moments where you catch that creative lightning in a bottle and it’s amazing.”

F. Gary Gray

As the West Coast wrested mainstream attention away from New York City in the early 1990s, a bevy of Cali-themed videos became fixtures in music video rotations. Arguably the most iconic of the bunch, Ice Cube’s “It Was a Good Day” offered a literal glimpse into Compton on a lazy, feel-good afternoon. Director F. Gary Gray perfectly captured both Cube’s storytelling and the neighborhood that had served as a backdrop not only for the music of Ice Cube and N.W.A. but also for films like Colors and Boyz n the Hood. It became Cube’s most beloved single, and the video is one of the 1990s’ most memorable.

“I grew up in Los Angeles in that era,” Gray told VICE in 2015. “So a lot of things that they rapped about I witnessed and experienced firsthand.” The video made Gray a hot commodity, and he would go on to direct vids for Cypress Hill, Queen Latifah, OutKast, Whitney Houston, and JAY-Z, as well as TLC’s uber-acclaimed video for “Waterfalls” in 1995. 

Of course, Gray went on to Hollywood success in feature films, working with Cube on the stoner comedy classic Friday and other big hits, like Set It Off and The Italian Job. He eventually brought N.W.A.’s story to the big screen with the group’s Straight Outta Compton biopic. His ambition had always been to direct movies, and Hip-Hop gave him an inroad into that. “By the time I was 24 and experienced some success in videos and introducing these music artists to a different style of video, Cube called me,” Gray recalled to Deadline after the success of Straight Outta Compton. “He said, ‘Why don’t we do this feature film about two guys on the block called Friday?’”

Spike Jonze

If Gray’s approach was often deceptively literal, Spike Jonze seemed to thrive on the surreal. The New York native initially made his name directing clips for alt-rock mainstays like the Breeders and Sonic Youth, which led him to the Beastie Boys, an act that by the early 1990s was straddling the line between alternative rock and Hip-Hop masterfully. Jonze and the Beasties struck pay dirt with the Boys’ 1994 album, Ill Communication, as Spike was behind that album’s classic videos, including “Sure Shot” and “Sabotage.” The latter became one of the most celebrated videos of its era and cemented the Beasties’ oddball brilliance at the vanguard of the medium. The Beasties and Jonze also planned to do a film together.

“It would have been ridiculous,” Jonze told Indiewire. “After we did [the music video for] ‘Sabotage’…the four of us wrote a script together. It was really fun.”

Jonze would also direct the Pharcyde’s acclaimed video for “Drop,” which famously featured the quartet rapping and performing backwards, as well as a cameo from Mike D and Ad Rock of the Beasties. He also knocked out memorable clips for Puffy (the rock remix for “All About the Benjamins”) and the Notorious B.I.G. (“Sky’s the Limit”). Spike’s 1999 feature film debut Being John Malkovich is a cult classic, and his 2000s videos for superstars like Ludacris (“Get Back”) and Kanye West (“Flashing Lights”) are among the most iconic of the last 20 years. He also took home a Best Original Screenplay Academy Award for his 2013 film, Her.

In 2020, Spike got to tell the Beasties story with Beastie Boys Story.

Chris Robinson

Somewhere between the whimsical and the literal sits a Baltimore-born, ATL-bred visionary. Chris Robinson became one of Hip-Hop’s hottest directors in the late 1990s/early 2000s, when he delivered memorable visuals for hits like T.I.’s “Why You Wanna” and Young Jeezy’s “Go Getta.” His prominence with ATL rap superstars soon led to Robinson helming videos for virtually everyone; from Nas (“I Can”) to JAY-Z (“Change Clothes”) to Santana (“Cry Baby Cry.”) It was Robinson who directed the gorgeous video for Snoop and Pharrell’s monster hit “Beautiful” and gave the world its first major glimpse of Alicia Keys in her classic video for “Fallin.’” His style showcases his penchant for grandiose aesthetic beauty that’s grounded in a staid reality.

That romanticized realness was at the core of his first feature film’s appeal. Robinson famously made the jump to the big screen with 2006’s ATL, a coming-of-age dramedy starring T.I. and Lauren London. Shortly after making ATL, Robinson told NPR’s Ed Gordon that no one initially encouraged his entry into music videos.

“Why do you watch BET all day? Why are you watching Donnie Simpson? Because I had in my head what I wanted to do. And my mother kept telling me to go to the post office and get that application.” He stuck to his aspirations, though, and along the way injected a cinematic vitality into contemporary music videos.

Director X

Even back when Director X was still known as Little X, he was studying at the feet of one of the most accomplished names in music videos. Julien Lutz honed his chops working alongside the great Hype Williams, and you can see that influence throughout X’s work.

“He knew about the camera, about filming,” X told Variety. “About hair, makeup, wardrobe, editing. Learning from him, I thought that’s what a great director does. A great director understands all aspects of filmmaking. I strove to learn that same way, to really study filmmaking and all the other parts that come with it. That way, I can talk to my team about any part.”

Bryan Barber

Bryan Barber moved from Palo Alto to Atlanta to go to college, and OutKast fought for him to become their go-to video director. Their label was initially unimpressed with his reel, but the duo was steadfast. He would helm the video for their 1998 single “Skew It on the Bar-B” and became affiliated with the group’s visual aesthetic for the rest of their run.

“At that time in Atlanta no one wanted to be a filmmaker,” Barber told Boards magazine back in 2004. “I was the only one running around town with this camera. I could go to a party and people would know me by my camera — it’s not the coolest look, you know? I started shooting a lot of stuff with OutKast, who I’d met when I was in college and André [3000] was dating my neighbor. At one point he agreed to star in a film I’d written. We never shot it, but over time we just started working together more.”

Barber would go on to work with other ATL heavyweights like Jermaine Dupri and Ludacris, as well as R&B and pop stars like Christina Aguilera and John Legend. But he became most revered for his work behind the camera for some of Kast’s most memorable clips, including André 3000’s iconic video for the 2003 smash “Hey Ya!”

“I remembered when the Beatles were on Ed Sullivan. They all dressed the same and were strange to what America was used to. I suggested to Dré that because he does all the singing and instrumentals on the song, it’d be cool if I shot it as if he was every character on Ed Sullivan.”

In 2006, Barber made his feature film debut, directing the OutKast-starring period musical Idlewild. He also directed commercials for CoverGirl and worked with Nickelodeon on the Tia Mowry vehicle Instant Mom.

Benny Boom

Like X, Philly native Benny Boom is a student of Hype Williams — and of F. Gary Gray. The Temple alum broke through in the early 2000s with a style that was glossy and distinct. Amerie’s leggy video for “Why Don’t We Fall in Love” remains one of the most memorable of the era; he was a go-to for Birdman at his flossiest (“Stuntin’ Like My Daddy,” “What Happened to That Boy”); and Boom helped announce Ciara with his videos for her early hits “1, 2 Step” and “Goodies.”

In 2009, like his mentors, Boom made the leap to features. His debut was the dark comedy Next Day Air, and Boom was confident that his moment was near. “I’ve been ready,” he told Blackfilm.com before the premiere. “Hollywood better get ready for me.” Boom also directed S.W.A.T.: Firefight in 2011. He would go on to helm the controversial Tupac Shakur biopic All Eyez on Me in 2017. 

Boom told a group of Temple students in 2018:

“Know the goal that you want, and don’t waver from it. There’s always going to be someone telling you that you can’t do it, or that’s impossible. You just can’t believe that. If you believe in yourself there’s always going to be people that tell you, ‘You can’t do it,’ and they’re placed in your life to push you further, not to stop you.”

Hype Williams

The gold standard and still most legendary name in the world of music videos is Hype Williams. His use of color, his iconic work with the fisheye lens, and his gift for visual storytelling have been at the core of every Hype Williams vid. From the early ’90s until now, no one has become more synonymous with the art form itself. Hype injected so much into the world of Hip-Hop visuals that it’s impossible to imagine what the past 25 years of rap videos would have looked like without him and his influence. He directed classics: From Missy’s “Supa Dupa Fly” to Busta and Janet’s “What’s It Gonna Be” to Biggie’s “One More Chance” to LL COOL J’s “Hey Lover” and “Doin’ It.”

“‘Doin’ It’ became so well known,” LL says. “And a lot of the motifs and the vibes that we put in ‘Hey Lover’ — it was great. Paris and Hype were both a lot of fun to work with.”

Hype made the jump to features with 1998’s Belly and continued well into the 2000s with a bevy of popular videos from No Doubt (“Ex-Girlfriend”), Kanye West (“Can’t Tell Me Nothing”), Beyoncé (“Video Phone”), and an innumerable list of other stars. The Hype Williams effect on music videos has been felt for more than a generation now, and LL reflects on how the mid-1990s helped set the stage for so much.

“I think that the work that we put in inspired a lot of people,” says LL when he looks at what he was able to do with Hype. “It gave a lot of people the ideas that they ultimately wanted to run with. And it inspired a large part of Hip-Hop in general. I don’t think that’s overstatement. I think that’s a pretty fair assessment for what it did in the game. It had a real impact on how people wanted to proceed with their videos and music and where they could take it. If you can inspire people then you’ve really done something. That’s the shit. That’s what it’s about.”

* Banner Image: Director F. Gary Gray’s star on the Hollywood Walk Of Fame / Photo by Leon Bennett/WireImage