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1* ActorInspiredElement: Creator/DustinHoffman suggested the title. "Tootsie" was the name of his mother's dog.
2* CastTheExpert: George Gaynes, playing soap opera star John Van Horn, was best known at that point for playing mob boss Frank Smith on ''Series/GeneralHospital''.
3* CastTheRunnerUp: Creator/DabneyColeman was originally cast as George, but when Creator/DustinHoffman insisted on Pollack playing the part, Coleman was cast as Ron, the director of ''Southwest General'', instead. It ended up being TypeCasting, since Coleman had just played Franklin Hart in ''Film/NineToFive''.
4* CreativeDifferences: Creator/DustinHoffman and Creator/SydneyPollack 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.
5* TheDanza: Amy Lawrence plays...Amy.
6* DeletedScene: 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.
7* DuelingMovies: With ''Film/VictorVictoria'', 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 Adaptation}}s, but were separated by years instead of months. (Another transgender role was nominated by the Academy Awards in 1982 against ''Victor/Victoria'' that year as well, with John Lithgow for ''Film/TheWorldAccordingToGarp''.)
8* DescendedCreator: Creator/SydneyPollack plays Michael's agent, largely as a way of venting his issues with Creator/DustinHoffman.
9* HarpoDoesSomethingFunny: Most of Creator/BillMurray's dialogue was improvised.
10* MissingTrailerScene: One of the movie's main trailers includes some pick-up shots such as of actorial promotional photographs of Michael Dorsey and film footage not seen in the final cut.
11* PlayingAgainstType: Creator/CharlesDurning to that point was exclusively a hard-nosed heavy. Here, he got to play an unambiguously sweet NiceGuy in a comedy. (His comedic chops led to his UsefulNotes/AcademyAward-nominated role in ''Film/ToBeOrNotToBe''.)
12* ProductionNickname: The film's tense production caused the crew to dub it "Troubled Tootsie".
13* RealitySubtext: Michael Dorsey ''is'' Creator/DustinHoffman. All the insane ways Dorsey gets fired or quits from a production? They ''really'' happened.
14* TroubledProduction: The film was often referred to this way while it was being made. There were script problems aplenty, even during shooting, until Creator/ElaineMay fixed them (and came up with Creator/BillMurray's part). [[Creator/DustinHoffman Hoffman]] and director Creator/SydneyPollack 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.
15* UncreditedRole:
16** Creator/BillMurray agreed to omit his name from the opening credits to prevent audiences expecting a "Bill Murray" movie.
17** Creator/AndyWarhol has an unbilled cameo as himself.
18** Robert Garland did uncredited work on the script.
19* WhatCouldHaveBeen:
20** Creator/MichaelCaine, Creator/ChevyChase, Creator/ElliottGould, Creator/GeorgeHamilton, Creator/DudleyMoore, Creator/GeorgeSegal, Creator/PeterSellers and Creator/RobinWilliams were considered for Michael Dorsey.
21** Creator/DustinHoffman wanted Creator/GoldieHawn to co-star as Julie Nichols. Music/{{Cher}} was interested in the role.
22** Creator/SydneyPollack offered the role of Ron to Creator/PeterBogdanovich, who declined, feeling that the part should go to an actor.
23** Creator/HalAshby 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.
24* WorkingTitle: ''Would I Lie to You?''
25* WritingByTheSeatOfYourPants: 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.

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