5. White Chicks (2004)

Image: Columbia Pictures

Despite White Chicks‘ status as a cult classic of sorts, its premise is exactly the sort of mindless, offensive pseudo-comedy that dominated the early ’00s.

In yet another story featuring members of the FBI (do they pay extra for all the advertising?) Shawn and Marlon Wayans star as two agents tasked with protecting the socialite Wilson sisters during a fashion event in The Hamptons.

You can essentially boil the elevator pitch for White Chicks down to one phrase: “What if we do a blackface movie… except it’s whiteface!” Even on the surface, this one is dumb, but when you scratch just a little to look underneath, it’s even more dumb and unfunny, to boot. Even more so, the movie’s “whiteface” technique is truly horrifying, making the two stars look more like the Leatherface twins than the two fictional socialite sisters they’re supposed to be.

Trying to wring comedy out of racial tension should never have been allowed, and how this awful movie has endured as a fondly-remembered “comedy”, we’ll never know.

Did it work? No. White Chicks might force an odd laugh or quotable moment, but this movie simply should never have been made.