1. C. Thomas Howell as Mark Watson in Soul Man (1986)
Forget performance, this whole premise makes us uncomfortable. C. Thomas Howell plays Mark, an atypical spoiled rich kid who suddenly finds himself faced with the prospect of paying for Harvard law school on his own. What's a yuppie to do when the best scholarships are only being offered to African-Americans? Get a job? Fuck that, instead chug some tanning pills to subvert that blasted Affirmative Action and beat em at their own game!
Even more reprehensible, we're supposed to believe that the likes of James Earl Jones and Rae Dawn Chong actually buy his shitty blackface and Jheri curls as the real deal. There's also inevitably cringe-worthy dialog like "So, do you hate The Beach Boys now?"
After the film's release, C. Thomas and Rae Dawn were briefly married, so does that give him a pass? We say, hell no. You fucked up with this one, Ponyboy.