Tootsie

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Tootsie is a 1982 film starring Dustin Hoffman, Sydney Pollack, and Jessica Lange. It was nominated for 10 Oscars and won 1 (Jessica Lange - Best Supporting Actress), as well as garnering Dustin Hoffman a BAFTA and Golden Globe.

Michael Dorsey (Dustin Hoffman) is a struggling actor in New York City who, despite being very talented, can never get work because he's too much of a perfectionist and consequently very difficult to work with. Desperate for money to finance a play written by his roommate Jeff (Bill Murray), Michael goes to his agent (Sydney Pollack, also the director), who tells him that no one in New York will hire him. After taking his friend Sandy (Teri Garr) to an audition for the part of a female hospital administrator in a soap, he decides to dress in drag and go for the part himself. After at first being told he was too feminine, Michael lands the part (as Dorothy Michaels) and gains immense popularity with the fans.

The romantic relationships in the film are very convoluted, since the same person is two completely different characters, a fact known only by his roommate. Michael falls in love with Julie (Jessica Lange), one of his co-workers on the show, who knows him only as Dorothy. As the two grow closer, Julie invites Michael (as Dorothy) to spend the holidays with her family, and her father (Charles Durning) ends up falling for Dorothy. Michael, meanwhile, is technically dating his friend Sandy, whom he slept with to avoid telling her his secret when she catches him nearly naked in her bedroom sizing up her clothes. Julie is going out with the film's misogynistic director, Ron (Dabney Coleman); it is through observing this relationship as Dorothy that Michael realizes he's treated Sandy as badly as Ron treats Julie. Dorothy also attracts John Van Horn, one of the soap's has-been stars, who thinks she's dating Michael's roommate Jeff.

The film was well received by both critics and the public, becoming the second highest grossing film of 1982 and winning many awards. It was praised for its innovative take on gender relations, showcased through the things Michael learns about men and women by living both lives.

Has nothing to do with the rolls, the pops, or those guys who got their shit wrecked by the Hutus.

Tropes used in the original movie:

"George: Michael, no one will hire you
 * Answer Cut: Technically not a question, but close enough

Michael: Oh, yeah?

Cut to Michael dressed as Dorothy walking down a crowded New York sidewalk."

"Dorothy: Now how much trouble can a baby be?
 * Also, when Dorothy is babysitting Julie's daughter Amy

Cut to Dorothy running around desperately trying to quiet Amy crying"

"Michael: I was a better man with you, as a woman... than I ever was with a woman, as a man. You know what I mean?"
 * Attractive Bent Gender: Although not all characters find Dorothy attractive, she is proposed to by one man and nearly sexually assaulted by another.
 * Award Bait Song: "It Might Be You"
 * Bill Murray: Plays Michael's roommate Jeff, an aspiring playwright. Most of Murray's lines in this film were improvised.
 * Disguised in Drag
 * Gender Bender Friendship: One of the most notable and well-done examples of this trope, Michael falls in love with Julie as a woman, and learns valuable things about himself as a man through his relationship with her.

"Michael: Where will I say I got the money? What am I going to do? Tell [Sandy] somebody died and left it to me?
 * Gilligan Cut: Michael ponders what to tell Sandy about the money he's gotten from his job on Southwest General

cut to Sandy's apartment

Sandy: My God! When did she die?"

"Sandy: No, we are not friends. I don't take this shit from friends. Only lovers."
 * Hospital Hottie: Jessica Lange as Julie and Geena Davis as April both play hot nurses on Southwest General. Subverted with John Van Horn, who plays an over-the-hill, over-sexed doctor.
 * I Have Nothing to Say To That: When Sandy asks Michael about some flowers he's received.
 * Just Friends: Subverted with Michael and Sandy, who aren't in love with each other, yet sleep together and start dating because Michael doesn't want to tell her his secret. Michael proceeds to be a much worse boyfriend than he was friend.

"Michael: You should have seen the look on her face when she thought I was a lesbian.
 * Love Dodecahedron: Michael loves Julie, who knows him only as Dorothy, and has hit on her in both guises and been rejected . Michael is dating Sandy, who is convinced that he's cheating on her with Dorothy. Dorothy meanwhile is wooed by both Julie's father Les and John Van Horn, an actor on the soap. Julie, meanwhile, is dating Ron, the soap's director, a charming, but misogynistic jerk.

George: "Lesbian"? You just said gay.

Michael: No, no, no - SANDY thinks I'm gay, JULIE thinks I'm a lesbian.

George: I thought Dorothy was supposed to be straight?

Michael: Dorothy IS straight. Tonight Les, the sweetest, nicest man in the world asked me to marry him.

George: A guy named Les wants YOU to marry him?

Michael: No, no, no - he wants to marry Dorothy.

George: Does he know she's a lesbian?

Michael: Dorothy's NOT a lesbian.

George : I know that, does HE know that?

Michael : Know WHAT?

George : That, er, I... I don't know."

"George: I can't even set you up for a commercial. You played a tomato for 30 seconds - they went a half a day over schedule because you wouldn't sit down.
 * Live Episode: In-universe. It is during the live episode of Southwest General that Dorothy Michaels reveals herself to be Michael Dorsey, or rather Emily Kimberly reveals that she is really her brother, Edward Kimberly.
 * Oh Crap: Michael is informed that Emily is going to be made a regular character, meaning he'll be stuck pretending to be a woman for the foreseeable future. He gulps while keeping a smile frozen on his face.
 * Playing a Tree: George mentions that Michael was given a role of a tomato in a commercial:

Michael: Of course. It was illogical.

George: YOU WERE A TOMATO! A tomato doesn't have logic! A tomato can't move!

Michael: That's what I said! So if he can't move, how's he gonna sit down, George? I was a stand-up tomato: a juicy, sexy, beefsteak tomato. Nobody does vegetables like me. I did an evening of vegetables off-Broadway. I did the best tomato, the best cucumber... I did an endive salad that knocked the critics on their ass."


 * Real Life Writes the Plot: The character of George was written and/or cast with Sydney Pollack, the director, playing the part at Hoffman's suggestion, to incorporate some of the real-life tension between the two of them into the movie itself.
 * Reality Subtext: Michael Dorsey is Dustin Hoffman. All the insane ways Dorsey gets fired or quits from a production? They really happened.
 * The Reveal: The big reveal for both the fictional soap and the actual movie, when Michael takes off his wig and many of his feminine touches and reveals himself to be a man during a live taping of Southwest General
 * Ripped From the Headlines: The reveal of Emily Kimberly to be her brother Edward Kimberly on Southwest General was based on a real plot twist on the soap General Hospital, in which the character Sally Armitage was revealed to really be Max Hedges.
 * Self Deprecation: Let's just see it's easy to see a lot of Michael's behavior in Dustin Hoffman's career.
 * Soap Within a Show: During his tenure on Southwest General, people fall in and out of comas, nurses have passionate affairs with both doctors and patients, and characters die because the actors asked for more money.
 * Throw It In: Most of Bill Murray's dialogue was improvised.
 * Title Drop: Ron calls "Dorothy" this once, which causes Michael to snap.
 * Twelfth Night Adventure: Since no one in New York will hire him, Michael Dorsey dresses as a woman and gets a part on a popular soap. As a man acting as a woman, he brings a unique perspective to the part of Emily Kimberly, and she becomes an inspiration to women everywhere.
 * Wholesome Crossdresser: Dorothy Michaels is a very convincing woman (Dustin Hoffman apparently tried her out at his daughter's parent-teacher night and no one suspected) and a good person, fiercely devoted to both acting and those in her life and feeling like she has something to say about being a woman.
 * Wig Dress Accent: Michael uses all of these when becoming Dorothy, transforming himself into a middle-aged Southern woman.
 * Your Other Left: When Dorothy is doing her camera test for "Southwest General," she mistakenly thinks the director is speaking to her when he is telling the cameras to turn left and right.