The fight for transgender rights is a fairly new frontier. Yes, being a trans person is nothing new, but until the past couple years, discussing transgender people’s place in society was fairly taboo.
Thankfully, that is all starting to change. Sure, we still have a really long way to go in our fight for equality, but thanks to brave trans men and women who are willing to go public (we’re looking at you, Laverne Cox), the trans community is definitely more visible.
This is all very new, but gender-bending in Hollywood has been going on for a lot longer.
Whether it’s for comedic effect (like Robin Williams in Mrs. Doubtfire), or to tell gut-wrenching tale ripped straight from real life (like Jared Leto in Dallas Buyers Club), characters in literature, plays and films have been cross-dressing for centuries… and so have actors. Here are 51 of our film favorites.
Originally published April 2015. Updated September 2017.