9. Godfrey Cambridge as Jeff Gerber in The Watermelon Man (1970)
We're equal opportunity critics, so far be it from us to let Melvin Van Peebles' The Watermelon Man slide just because it flips the script and features whiteface instead of black. Cambridge plays Jeff Gerber, a plucky suburban husband who's white as can be, until one day he inexplicably wakes up black.
Apparently studio heads flirted with having a white actor execute the bizarre premise in blackface for the majority of the film, but it was Van Peebles' idea to do the inverse. Either way, it's still jarring and weird, especially when Cambridge essentially continues playing the Caucasian Gerber in essence even after he loses the make-up.