- Bill Murray agreed to omit his name from the opening credits to prevent audiences expecting a "Bill Murray" movie along the lines of Meatballs or Caddyshack.
- Sydney Pollack had originally wanted Dabney Coleman to play Dustin Hoffman's agent. During a conversation that Hoffman had with Pollack, Hoffman wanted to know what forced his character to wear a dress and pretend to be a woman. Pollack's response was that, if he didn't, he would never work again. Hoffman replied that he wouldn't put on a dress if Coleman told him he would never work again, because Coleman was a fellow actor, and he wouldn't believe him. Because Pollack was the director, Hoffman insisted, he would convince Hoffman to wear a dress. Pollack still refused to play the part, so Hoffman sent him red roses every day with the note, "Please be my agent. Love, Dorothy" until Pollack agreed to take the role.
- Writer Larry Gelbart once said that he did not meet the other writers on this project until they were on stage together collecting their awards.
- Well known transvestite actor Holly Woodlawn was hired by the producers of Tootsie to coach actor Dustin Hoffman in his role as 'Michael Dorsey/Dorothy Michaels' in the intricate art of being a man acting as a woman in films as he prepared for this role.
View All: Trivia - Goofs - Quotes
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