If black men have to wear a dress to make it in Hollywood, how did all these guys make it to the top of the industry? : r theJoeBuddenPodcast These Black actors aren't all, or even mostly, A listers. And many of these Black dress photos are MORE than a decade years old. Some are even 20 30 years old. That said, yes, From Flip Wilson to Madea, Black male comedians in dresses are a Hollywood rite of passage Luxury 3D Flowers Black Evening Dress with Cape Sleeves SS479 SHARONSAID