101 Funniest Screenplays

The elevator pitch – an out-of-work actor becomes a cause célèbre while disguised as a woman on a soap opera – fails to capture what made Tootsie feel hilarious and monumental. “'In my very first meeting with Larry Gelbart, I said, `If in 1982 a man puts on a dress, he'd better become a better man for it.’ So we worked on developing that,’” director Sydney Pollack told The New York Times. The screenplay was nominated for an Oscar and won the Writers Guild Award. Pollack said that Tootsie was an amalgamation of an original screenplay by Don McGuire and a similarly themed script that Dustin Hoffman was working on with Murray Schisgal. Gelbart, the master craftsman who’d cut his teeth gang-writing for TV star Sid Caesar, told author Mike Sacks of the circumstances around Tootsie: “It was just way more help than I ever needed, and certainly more than I asked for.”

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