Given last years gender bender movies (Sam and The Sex Trip) it may make sense to go back to one of the first ones: Goodbye Charlie.
Wikipedia has this to say about the movie:
Goodbye Charlie is a 1964 comedy film about a callous womanizer who gets his just reward. It was adapted from George Axelrod's play Goodbye, Charlie and starred Debbie Reynolds and Tony Curtis. The play also provided the basis for Switch, with Ellen Barkin and Jimmy Smits.I would say that it is better than all the other movies mentioned above. I like the script and I like the comedy.
Needless to say, Charlie comes back as a woman after being murdered. A sexy vamp of a woman. And although Charlie takes to his new life a bit too quickly in my opinion, the drama that unfolds is worth watching.
Not that everyone agrees with me. In 1964 the New York Times wrote the following:
GEORGE AXELROD'S play, "Goodbye, Charlie," was bad enough on the stage. On the screen, it is a bleak conglomeration of outrageous whimsies and stupidities. And it has Debbie Reynolds and Tony Curtis so sadly cast in distasteful roles that it causes even a hardened moviegoer to turn away from it in pain and shame.
You can watch it now, if you like, as the whole movie is available on YouTube.