Tootsie (1982)

This is actually one of the better "man dresses up as a woman" comedies. It received 10 Oscar nominations including for Best Picture Best Actor (Dustin Hoffman) two Best Supporting Actresses (Jessica Lange who won and Teri Garr) as well as for director Sydney Pollack. Hoffman plays a disagreeable actor who’s worn out his welcome such that he must dress as a woman to find a part on a soap opera as an actress. There he is pursued by a womanizing actor (played by George Gaynes) while he falls in love with another actress (Lange) who’s father (Charles Durning) also falls for him er her. Garr plays Hoffman’s girlfriend Bill Murray his roommate Dabney Colman the soap’s director. Also see Geena Davis. #2 on AFI’s 100 Funniest Movies list. #62 on AFI’s 100 Greatest Movies list.

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