2002: Isaac Rosenberg (Troy Garity) in Barbershop
Yep, that's Jane Fonda's kid in the Ice Cube flick. Stranger things have happened. Isaac fits cool white character trope #1, in that he blends in seamlessly with the rest of his colored cast. Unfortunately for Isaac, though, nobody is going to come through the barbershop and let the only white dude take a crack at their waves, no matter how many du-rags he rocks.