Tootsie (1982)

Synopsis
Michael Dorsey (Dustin Hoffman), a brilliant but troublesome New York actor, has managed to alienate every producer on both coasts. Michael's agent George Fields (Sydney Pollack) can't even get his client a commercial since Michael complained that the tomato he was playing wasn't properly motivated. "You were a tomato!" screams George in desperation, adding that Michael is so obnoxious that he will probably never work again. Dorsey thinks otherwise; when he hears of an opening on a popular soap opera, he applies for the job--even though the job is for a woman. Posing as "Miss Dorothy Michaels," Michael wins the part and becomes a widely-known actress. Yet complications ensue when Michael falls for his co-star Julie (Jessica Lange, in an Oscar-winning performance) but, as Dorothy, is courted by Julie's widowed father (Charles Durning). Michael ultimately finds that his disguise as a woman has made him a better man. One of the classic comedies of the 1980s, Tootsie's gender-bending premise boasts a screenplay by Larry Gelbart and Murray Schisgal, and by a host of memorable supporting comic performances from Dabney Coleman, Teri Garr, George Gaynes, and Bill Murray. Future Oscar-winner Geena Davis makes her screen debut as a daytime drama queen, which indeed she had been before Tootsie came along. ~ Hal Erickson, All Movie Guide