Johnny Depp’s second appearance on this list proves both his versatility and comfort in his masculinity. Sometimes it even seems like his portrayal of Jack Sparrow has a bit of the cross-dresser in it. In Julian Schnabel’s film about gay Cuban writer Reinaldo Arenas, Depp is on screen for no more than a few minutes. He plays two roles — the first, a sadistic prison warden and the second a transvestite. His pure physical presence as the latter, the flamboyant Bon Bon, is enough to sear the image of a blond-wigged red lipsticked Depp into your cinematic memory bank forever.