Sometimes a role is so good – or so bad – it requires a bit of cross-dressing. Nevertheless, it always makes for an interesting experience. Some are amazing performances like JohnCameron Mitchell in Hedwig In The Angry Inch or Johnny Depp in Ed Wood, while others may be laughably ridiculous like Amanda Bynes in She’s The Man or just horribly insulting like Adam Sandler in Jack and Jill. Why is dressing up like a woman always the punch line? Is it because being a woman is a joke? Hmm. Here are 22 roles that required a bit of drag.