Then again, as the central character of Malibu's Most Wanted is fond of reminding us, "The name is B-Rad/Not Robbie Van Winkle/I like my latte nonfat/And don't forget the sprinkle!" The rhymes in Cool as Ice were definitely dope by comparison. B-Rad (Jamie Kennedy), otherwise known as Brad Gluckman, is merely dopey, a white boy who lives "up in the 'bu," where he hangs with phony gangs who wear designer colors. Their idea of trouble is when a scented-candle store accidentally gives them the wrong merchandise or "when the public be all up on yo' private beach!"
Hardly a hangable offense, that. Part of the benefit of being rich is the ability to be obnoxious and/or moronic with impunity. The problem is that B-Rad still lives with his strait-laced parents (Ryan O'Neal and Bo Derek), and while they aren't the harsh disciplinarians seen in more serious culture-clash teen fare like crazy/beautiful, dad is running for governor. He'd love to score more points with minorities, but having his pale-skinned son constantly crashing his rallies with inept rhymes about bitches and hos, however well-meaning, doesn't quite curry favor with that all-important soccer-mom demo. Therapy is tried, with shrink Jeffrey Tambor concluding that B-Rad suffers from "an advanced case of gangstaphrenia," a condition that will require intense therapy for at least five years.
The campaign doesn't have that long, so campaign manager Tom (as in "Uncle") Gibbons (Blair Underwood) comes up with a more radical notion to scare B-Rad straight: Hire actors to pretend to be real thugs and have them carjack B-Rad and take him on a tour of the real 'hood. The actors, who take on the nicknames of Bloodbath and Tre, are even less "real" than their target -- pompous Sean (Taye Diggs) has to buy a dictionary of hip-hop slang to get into character ("Weak: of poor quality"), while cowardly PJ (Anthony Anderson, in his third major screen role of the past four months) relies on his hairdresser cousin Shondra (Regina Hall) for insight.
Unlike such run-of-the-mill race-based comedies like Bringing Down the House, Malibu's Most Wanted thankfully avoids the cliché of exalting stereotypical "blackness" as inherently cool, and it also steers clear of implying that any race behaves in a uniform manner. Underwood's ruthless bureaucrat is vaguely implied to be a sell-out, but Sean and PJ aren't -- they're ridiculed for being untrue to themselves, not for being unable to embody gangsta cool.
But the film does run into tricky territory with this theme. Kennedy and the filmmakers (including a director with the amusing moniker of John Whitesell) ask us to understand that B-Rad is, in his own way, genuine, even though the character's about as believable and subtle as Jar Jar Binks. By movie's end, and this spoils nothing, he hasn't somehow become a good rapper or developed much of an idea of how the ghetto really is. In one scene that hilariously parodies the rap battle climax of 8 Mile, the realization appears to sink in that he's wack on the mic and has no credibility, but he later regains his confidence without the skills and knowledge that such a development should require.
He's a caricature, and that's fine for comedy purposes, as Kennedy knows from having already used the character in standup routines and his prank-comedy TV show The Jamie Kennedy Experiment. This doesn't make him easy to identify with, though, as Kennedy seemingly wants us to do here. Though never as flagrantly unrealistic as Danny Hoch in Whiteboys -- who looked way too old in a similar role despite being the same age as the more baby-faced Kennedy -- B-Rad, while funny, doesn't ring true in any way. Like Dana Carvey or Dennis Miller, Kennedy often seems to be laughing at his own jokes even as he's performing them.
Diggs and Anderson, on the other hand, are funny and believable, at least to the extent that any such characters can be in a high-concept comedy. There's likely some truth to their portrayals -- Diggs' character's lament that he only ever gets cast as hoodlums could apply to Diggs' real-life career. If the movie had revolved around Bloodbath and Tre, in the vein of The Ransom of Red Chief or Ruthless People -- films that centered on kidnappers baby-sitting tremendously annoying "victims" -- the movie could've gone over the top as a real winner. It's still a fun diversion but unlikely to challenge the box office of the latest Chris Rock and Adam Sandler flicks.