Johnny Depp in Drag
Johnny Depp played cross-dressing director Edward D. Wood Jr. in the eponymous Tim Burton film 'Ed Wood,' about the man dubbed the world's worst director who also had a penchant for pink cashmere sweaters.
The script called for Depp to dress in women's clothing on a regular basis when portraying the director of the so-bad-it's-funny 'Plan 9 From Outer Space' and followed his career from his first film 'Glen or Glenda' (about a transvestite played by Wood himself) all the way through his work with the then-aging and out-of-work Bela Lugosi. True story.
If you want to see Johnny Depp in a pink fluffy sweater that he stole from Sarah Jessica Parker's closet, this is the movie for you. If not, it's still a great film about the worst director (ever) and the last days of famed Dracula actor Lugosi.