Song: N/A (Battle Freestyle)
Level Of Embarrassment: High
"I may be white, but inside my soul is black as night." So begins Brad Gluckman's (Jamie Kennedy) battle freestyle in Malibu's Most Wanted. Gluckman is the son of a Senator, and identifies in superficial ways with rap culture. He becomes a cartoon of a white wannabe, and this battle is his lowest moment. He punctuates his final bars with the n-word, and is dragged from the establishment kicking and screaming like a scared and confused child.
The scene is mostly embarrassing because Jamie Kennedy (who has a credit on the screenplay) thinks he's provocatively skewering race and privilege, when he's really just hammering away at leaden ideas with fists of ham. —RS