EDDIE MURPHY AS RASPUTIA LATIMORE IN NORBIT (2007)
Reason for cross-dressing: Eddie Murphy was in straight cash grab mode. Complex says:Norbit has to haunt Eddie Murphy. It just has to. Murphy was damn near guaranteed an Oscar for his role as James "Thunder" Early in 2006’s Dreamgirls. Then this monstrosity of a movie was released, right around the time the Academy was making its decision. Oscar dream dead and buried. The movie was a disaster in every conceivable way. Well, except one. The shit made money—it pulled in more than $100 million in its box office run. So, actually, maybe this doesn’t haunt Murphy that much after all.