Hype Williams' 11 Best Rap Videos of the '90s

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The music may be the straw that stirs the drink in terms it being the driving force behind hip-hop's popularity, but when it comes to culture as a whole, there are many facets the culture, which have been documented throughout its history.

One way that the world was introduced to B-Boys, break-dancing, graffiti and urban street fashion was through pictures, but the most visceral conduit was through music videos, which captured the rap artists up close and personal, helping to put a face and style to the voice you'd been listening to for months on end.

As the '80s would progress, music videos would become staples rap culture and a pretty big deal, with artists and directors taking pride in their work, resulting in some the more memorable and iconic videos the '80s.

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However, the '90s marked the arrival Hype Williams, a Queens native fresh out Adelphi University who helped revolutionize the way we see hip-hop and what a rap music video could be. Influenced by the art Keith Haring and Jean-Michel Basquiat, Hype would get his start in hip-hop as a graffiti writer before linking with Lionel "Vid Kid" Martin and VJ Ralph McDaniels Video Music Box fame.

Starting his own video company, Filmmakers With Attitude, Hype Williams got his feet wet directing music videos for acts like Main Source, Zhigge, Cutty Ranks and BWP before hitting his stride in 1994, with now-legendary clips for Wu-Tang Clan, Craig Mack, Mary J. Blige and Usher, making him one the most sought-out directors in rap. By 1997, Hype was regarded as the most prolific and influential music director in the history hip-hop— a crown he still holds to this day.

In celebration his excellence behind the camera, The Boombox handpicked 11 the most iconic visuals from his catalog that helped define an entire decade.

  • 1

    "Flava in Ya Ear"

    Craig Mack featuring Notorious B.I.G., LL Cool J, Rampage & Busta Rhymes

    In 1994, Hype Williams ficially set f what would be considered the genesis the Bad Boy era with the visual to Craig Mack's "Flava in Ya Ear (Remix)." Shot in black-and-white with close-up shots all the rappers involved, the "Flava in Ya Ear (Remix)" music video would cement Hype Williams as hip-hop's "it" boy in terms captivating visuals, and go down as one the best clips its era.

  • 2

    "Can It Be All So Simple"

    Wu-Tang Clan

    One the first music videos that put Hype Williams on the radar the greater hip-hop community was the visual for Wu-Tang Clan's 1994 single "Can It Be All So Simple," which showcased the director's knack for encapsulating the vibe and aesthetic the inner-city. From Raekwon's iconic Snow Beach jacket to a cameo from Compton's Most Wanted frontman MC Eiht, "Can It All Be So Simple" was a gritty precursor to his more glossy clips that would shift the paradigm '90s rap vids.

  • 3

    "One More Chance/Stay With Me (Remix)"

    The Notorious B.I.G.

    In 1995, Bad Boy Records released the music video for The Notorious B.I.G.'s smash single "One More Chance/Stay With Me (Remix)," which featured cameos from Uncle Luke, Heavy D, Spike Lee, Da Brat, Jermaine Dupri, D-Nice, Queen Latifah, Cypress Hill, Tyson Beckford, Aaliyah, Changing Faces, Kid Capri, and Zhane, among others. Introducing the world to what a true Brooklyn house party looks and feels like, Hype Williams knocked it out the park with this classic music video, gifting the Biggie and company with another gem a visual

  • 4

    "Gimme Some More"

    Busta Rhymes

    Released as the lead-single from his third solo album E.L.E. (Extinction Level Event): The Final World Front, "Gimme Some More" be accompanied by a zany video. Nominated for "Breakthrough Music Video Of The Year" at the 1999 MTV Video Music Awards, "Gimme Some More" would strengthen the Flipmode general's case for having the most captivating music videos in hip-hop, or all music for that matter.

  • 5

    "California Love"

    2Pac featuring Dr. Dre and Roger Troutman

    After being released from prison and signing with Death Row Records, 2Pac came back with a big splash in the form his Dr. Dre produced single "California Love." Directed by Hype Williams, the accompanying music video was inspired by the film Mad Max Beyond Thunderdome and included cameos from Chris Tucker, Tony Cox and Roger Troutman

  • 6

    "The Rain (Supa Dupa Fly)"

    Missy Elliott

    Missy Elliott helped shift the paradigm in the world music videos with her Hype Williams-directed epic for her 1997 hit single "The Rain (Supa Dupa Fly)." The classic over-sized hefty bag was enough to put this vid in rap lore, but cameos from Puff Daddy, Timbaland, Lil' Kim, Total, 702, Da Brat, Tamara "Taj" Johnson-George SWV, Yo Yo, and Lil' Cease made the visual even more memorable and help it earn a nomination for Best Rap Video at the 1997 VMAs.

  • 7

    "Put Your Hands Where My Eyes Could See"

    Busta Rhymes

    Hype Williams and Busta Rhymes gave the classic film Coming To America a modern twist with the music video for his Grammy-nominated single "Put Your Hands Where My Eyes Could See," which would be among the first to make Busta a conceptual vanguard. "Put Your Hands Where My Eyes Could See" earned nominations for Best Male Video and Best Rap Video at the 1998 MTV VMA's and remains one the signature moments from his career.

  • 8

    "Sock It 2 Me"

    Missy Elliott featuring Da Brat

    Released as the album's second single, "Sock It 2 Me" would help push Supa Dupa Fly past the platinum mark and continue Missy and Hype Williams' streak groundbreaking music videos.

  • 9

    "Mo Money Mo Problems"

    The Notorious B.I.G. featuring Puff Daddy & Mase

    The Notorious B.I.G.'s death shook the rap world to its core and put the culture in a state uncertainty, but Hype Williams helped counter the mourning with the celebratory visual to the late rapper's Life After Death single "Mo Money Mo Problems," which captures Puff and Ma$e living adventurously, expenditures aside, in the memory the King New York.

  • 10

    "Hate Me Now"

    Nas featuring Puff Daddy

    Catching backlash for making a more mainstream-friendly album with It Was Written, Nas clapped back in epic fashion with his fiery 1999 single "Hate me Now," from I Am..., the QB deity's third solo release. The Hype Williams-directed music video created controversy and lead to an altercation between Puff and Steve Stoute, but it's ultimately remembered as one the finer examples the decadence that defined hip-hop in the late '90s.

  • 11

    "What's It Gonna Be?"

    Busta Rhymes featuring Janet Jackson

    Hype Williams ended the '90s in grand fashion with his music video for Busta Rhymes' Janet Jackson-assisted single, ""What's It Gonna Be?" Costing upwards $2 million dollars, "What's It Gonna Be?" was one the most expensive music videos ever made, and stretched the limits what a rap visual could be.