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.
Bill Murray agreed to omit his name from the opening credits to prevent audiences expecting a "Bill Murray" movie along the lines of Meatballs (1979) or Caddyshack (1980).
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.
The film's working title was "Would I Lie to You?".
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.
The crew would only give bad news to Dustin Hoffman if he was in drag. They said he was "much nicer as a woman".
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.
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.
In the first scene where Michael Dorsey is waking up to dress as Dorothy, there is a picture of Dustin Hoffman's mother next to the alarm clock.
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.
The bit where Jessica Lange's character reaches behind her and accidentally grabs a corn cob instead of the phone was a genuine mistake in blocking. The director decided to leave it in.
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."
The movie's line "I was a better man with you as a woman than I ever was with a woman as a man. Know what I mean?" was voted as the #61 of "The 100 Greatest Movie Lines" by Premiere in 2007.
The movie's line "That is one nutty hospital." was voted as the #44 of "The 100 Greatest Movie Lines" by Premiere in 2007.
The greatest challenge for Dustin Hoffman was getting Dorothy's voice right - he reportedly received help and coaching from Meryl Streep (with whom he had just co-starred in Kramer vs. Kramer (1979)). He would read the role of Blance DuBois in A Streetcar Named Desire (1951) and she would offer feedback.
Southwest General is a parody of "General Hospital" (1963), even referencing the "Sally Armitage is Max Hedges!" storyline plot twist.
In 2007, the American Film Institute ranked this as the #69 Greatest Movie of All Time.
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.
Dustin Hoffman's "breasts" were custom-fitted prostheses purchased from an outlet specializing in post-mastectomy products, at a cost of $175 each.
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.
In Sydney, Australia, director Sydney Pollack commented "No one ever laughed during the shooting of any scenes of the film. It's only funny because of its story structure."
Cameo: [Gina Gershon] Seen in the beginning at Dustin Hoffman's acting class.
Cameo: [Julie Kavner] Sitting in the waiting room while Teri Garr's character enters to audition for the soap opera.
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.
At one point in development Hal Ashby was attached to direct.
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.