33. Dustin Hoffman as Michael Dorsey/
      Dorothy Michaels 
      Tootsie (1982)

Conceived as a semiautobiographical satire of an actor’s life by Hoffman and playwright Murray Schisgal, this is, as Hoffman observes, “a movie about a man who becomes a better man by having been a woman.” In simple terms, it’s the story of an actor so frustrated that he’ll cross-dress to go from playing a tomato in ads to becoming the middle-aged cynosure of what his roommate (Bill Murray) calls “one nutty hospital” on a soap opera. Hoffman expertly shifts between a guttural-voiced, street-smart New York tough guy and a wispy-voiced steel magnolia whose walk alone is a Chaplin-esque tour de force. The actor and director Sydney Pollack had legendary battles from the outset. “But [Pollack] has wonderful taste and he wanted it real,” Hoffman says. “We came to what I called the freebie agreement, which was if I got an idea, I would get a freebie [take]. That happened a lot, and some of it [e.g., the scene in which Dorothy brusquely keeps a cab that a man tries to usurp] is in the movie.” The “long, hard shoot” produced one of cinema’s best-loved romantic comedies—thanks largely to a Hoffman performance that unerringly skates between poignancy and hilarity.

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