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.
The character of Dorothy originally did not speak with a Southern accent, but in doing research Dustin Hoffman discovered his voice fell more closely into the range of female pitch while doing the accent.
Dustin Hoffman first got the idea to do this film while working on Kramer vs. Kramer (1979). He felt his character in that film had to be both a mother and a father, so he started thinking about how to play a man and a woman. Several scripts, several writers and a few directors later, this was the result.
Cinematographer Owen Roizman was initially opposed to Dorothy's character wearing glasses, as the reflective nature of their lenses tend to hamper lighting crews. After some tests, however, it was decided that glasses added a distinct, flattering dimension to Dorothy: Hoffman's prominent nose became less obtrusive and the glasses further feminized his personality, creating a more noticeable gender separation between the Dorothy/Michael characters. The glasses stayed, but a compromise was reached when Sydney Pollack suggested that the production try a special non-reflective coating developed by then Panavision head, Robert Gottschalk. The spray had been used to coat camera lenses, improving light transmission through the front elements. When the spray was used on Dorothy's glasses, it proved to be a godsend.
While being profiled for "The Directors" series, Sydney Pollack claimed that Dustin Hoffman refused to continue working on the film unless Pollack played his agent. Pollack refused up until Hoffman's agent Michael Ovitz intervened and Pollack reconsidered. He later agreed to play the role. The scenes featuring Hoffman's and Pollack's characters were meant to reflect what happened behind the scenes between the two when they would argue. In fact, Hoffman and Pollack quarreled so furiously during filming that they never did another film together; while they did discuss mending fences in order to work on Rain Man (1988), ultimately Pollack declined the director's spot for that film, leading to the hiring of Barry Levinson.
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.
Ellen Foley has a mostly non verbal role as the assistant to the soap opera producer. Her character originally had dialog but it was cut because Foley was recording an album that hurt her speaking voice.
During the credit sequence Sydney Pollack provides the voice of the unseen play director who tells Michael Dorsey (Dustin Hoffman), "We're looking for someone older," then, "We're looking for someone younger," and finally, "We're looking for someone else."
Dustin Hoffman allegedly tried out his role as Dorothy by passing himself off as his daughter's Aunt Dorothy at her parent's evening at school. His performance was so strong he actually convinced the teachers present. They never suspected.
During a 2008 appearance on the Late Show with David Letterman (1993), Dustin Hoffman revealed that, while dressed as Dorothy Michaels, he played a trick on legendary actor José Ferrer. While in an elevator, Hoffman introduced himself as Dorothy, a big fan and member of the Dallas Theater. Ferrer bought it and seemed flattered. Hoffman then asked if he could "suck Ferrer's c**k". After a long pause, Ferrer raised his right-hand and said, "Not right now, thank you." After Hoffman exited the elevator, Ferrer looked at assistant director David McGiffert and asked, "Who was that scumbag of a woman?" A year later, Hoffman ran into Ferrer again at a benefit and teased him for being fooled.
In an interview conducted a year before his death (in 2009), writer Larry Gelbart revealed that he nursed a grudge against Dustin Hoffman, because Hoffmann claimed that his friend, writer-producer Murray Schisgal, had conceived the movie. In his last major interview, given in 2008, Gelbart told Salon.com's Mike Sacks: "Tootsie is my vision, despite Dustin Hoffman's lifelong mission to deprive anybody of any credit connected with that movie, except for his close friend, the writer and producer Murray Schisgal. I say that because Dustin appeared with James Lipton on 'Inside the Actors Studio' in 2006 and declared that the Tootsie idea sprang from Schisgal's intestines. I don't know much about gastroenterology, but I do know that the central theme for Tootsie came from me. And the central theme was that Dustin's character, Michael Dorsey, would become a better man for having been a woman. That was the cornerstone of the film. All of the other details are just floating around that idea."