2004: Philip (Peter MacNicol) in Breakin' All the Rules
It's hard to top the randomness of Peter MacNicol starring in a black comedy but here he is, fulfilling Modern Token Role #2: the nebbish white guy whose life is in some sort of specific disarray and looks to our wise, hip black hero to set him straight. Even better, the film starts with him as Foxx's boss before a windfall of fame and success flips the scales. From superior to sidekick: righteous!
It's all good, though, because MacNicol appears to be enjoying himselfâ€”we're sure this was a 180 of an experience from Ally McBeal. What's more confusing is how his character manages to land a hottie like Jennifer Esposito, no offense.