- AFI's 100 Years... Series:
- Creative Differences: Dustin Hoffman and Sydney Pollack reportedly fought often and loudly over the shape of the story and the approach to the material. Hoffman was said to favor an outrageous comic exploration of the craft of acting, while Pollack was more attuned to the relationships and didn't believe audiences cared much about an actor's life and work.
- The Danza: Amy Lawrence plays...Amy.
- Deleted Scene: In a deleted scene, film critic Gene Shalit interviews Dorothy Michaels. A photo of them together appears on one of the magazine covers in the finished film, while the original scene appears as a bonus feature on the Criterion DVD release.
- Dueling Movies: With Victor/Victoria, which is about an unemployed female singer who disguises herself as a man to get work as a drag queen. It premiered the previous winter and directly went up against this film in the Best Supporting Actress category at the Academy Awards (Tootsie won, for Jessica Lange), both films getting a clutch of nominations. While Tootsie was ultimately the more successful of the two with critics and audiences, Victor/Victoria also did very well. Interestingly, both films later received Screen To Stage Adaptations, but were separated by years instead of months.
- Descended Creator: Sydney Pollack plays Michael's agent, largely as a way of venting his issues with Dustin Hoffman.
- Harpo Does Something Funny: Most of Bill Murray's dialogue was improvised.
- Playing Against Type: Charles Durning to that point was exclusively a hard-nosed heavy. Here, he got to play an unambiguously sweet Nice Guy in a comedy. (His comedic chops led to his Academy Award-nominated role in To Be or Not to Be.)
- Production Nickname: The film's tense production caused the crew to dub it "Troubled Tootsie".
- Reality Subtext: Michael Dorsey is Dustin Hoffman. All the insane ways Dorsey gets fired or quits from a production? They really happened.
- Troubled Production: The film was often referred to this way while it was being made. There were script problems aplenty, even during shooting, until Elaine May fixed them (and came up with Bill Murray's part). Hoffman and director Sydney Pollack feuded so intensely over small things that Hoffman ended up suggesting that Pollack play his agent so they could get that into the film (and, perhaps, give Pollack a chance to vent). It became one of the rare instances where the drama behind the drama resulted in a better film.
- Uncredited Role:
- What Could Have Been:
- Michael Caine, Chevy Chase, George Hamilton, Dudley Moore and Peter Sellers were considered for Michael Dorsey.
- Cher was up for the role of Julie Nichols.
- Hal Ashby was assigned as director, but he was forced to leave the project by Columbia Pictures because of the threat of legal action if his post-production commitments on Lookin' to Get Out were not fulfilled.
- Writing by the Seat of Your Pants: The script was still being rewritten as filming began. In fact, so many writers appeared before the Writers' Guild panel seeking to be credited that the arbitration over it delayed the release.
Trivia / Tootsie