It remains an all-too rare occurrence in the 80-plus year history of the Oscars that a funny film is nominated for the grand prize, let alone that one wins. The last comedy Best Picture winner was Annie Hall in 1977. And of those that have made the final cut, plenty of worthy titles have lost, including 1982's Tootsie. Looking back, it's painful that not only did Sydney Pollack's perfectly pitched, smart, grown-up and hysterically funny gender farce was trumped by well-made snoozefest Gandhi, but also that Dustin Hoffman's supreme performance — as an out-of-work actor who dons drag in order to get a job on a soap opera and ends up as daytime TV's biggest star — lost out to Ben Kingsley. Chuck in terrific support from Jessica Lange (who did win the Oscar), Dabney Coleman, Charles Durning, Bill Murray and the song stylings of Stephen Bishop, and you've got an American comedy classic. Comedy Death Ray's monthly showcase at Cinefamily pays tribute this week with Jon Hamm presents Tootsie; the dashing, talented Mad Men star — and when he isn't maneuvering the cutthroat world of '60s advertising, a damn funny guy it turns out — will be on hand to discuss his love of Pollack and Hoffman's high-concept yet hugely heartfelt tour-de-force.

Sun., May 2, 8 p.m., 2010

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