Tootsie (1982)

Sydney Pollack's 1982 comedy stars Dustin Hoffman as an unemployable actor who disguises himself as a woman to win a soap opera role — and is ranked number 2 greatest comedy of all time by the AFI. It was nominated for 10 Academy Awards, with Jessica Lange winning Best Supporting Actress, and grossed 177 million dollars, making it the second highest-grossing film of 1982 behind E.T.