Danny Hoch, Dash Mihok, and Mark Webber as Flip, James, and Trevor in Whiteboyz (1999)
Song: N/A (Freestyle)
Level Of Embarrassment: Extremely High
Depending on how you look at it, Whiteboyz is either a scathing satire about how middle- to upper-class Caucasians are easily swayed by the rap lifestyle or a spot-on, hilarious look at that subject. Our interpretation: It's both, though mostly the latter.
It's the ultimate wannabe-gangster story: Flip Dog, Trey Dog, and Jay Dog are three well-off teenagers living in Holyoke, Iowa, who fancy themselves as "down" hip-hop heads and desperately want to be black. Whenever they're not air-rapping along with music videos, or working dead-end fast food jobs, they're holding awkwardly imposing and horribly lyrical freestyle ciphers in Flip's basement bedroom.
Flip, who's the most serious about becoming a rap superstar, carries himself like former Hypnotized Minds' associate Lil Wyte, not Eminem. It's too bad that he's barely even Milkbone on the mic. â€”MB