Movies such as Priscilla Queen of the Desert, have made crossdressing (well at least in a drag sense), a lot more fun and accepting for the average person. It has spawned Priscilla Parties, which have a crossdressing theme, although the idea is to go over the top in your dressing. For the average crossdresser who is struggling to be accepted by family and friends, it hasn't done much at all.
As for a movie, I would like to see Clark Kent transform into Supergirl or Wonder Woman, but that is just me having the hots for Wonder Woman.