Malibu's Most Wanted (2003)

Malibu’s Most Wanted (2003) stars Jamie Kennedy as Brad Gluckman, an ultra-white wannabe rapper and son of a wealthy and prominent couple Bill and Bess (Ryan O’Neal and Bo Derek), growing up on the luxurious beaches of Malibu. Brad doesn’t appreciate the silver spoon he’s been handed. Instead, the goofy Gluckman likes to pretend to be “B-Rad”, a street-smart, hardcore rapper from the underbelly of Los Angeles. When Bill begins a campaign to become the governor of California, he hires two trained actors (Taye Diggs and Anthony Anderson) to play real life gang-bangers, and kidnap his son to prevent Brad from messing up his political ambitions. When the hired hands drop Brad off in Compton, the spoiled son eventually finds his niche in the hood and develops a romance with a sexy sista. The nudity is nil in this comedic flick, but during a hilarious rap battle scene, you can see Kennedy’s can and crack, but it’s not enough to get you to whack.