Highest-Rated Movies about 'Cross-dressing', Sort by Popularity

Murder! (1930), Marilyn (2018), Venus Boyz (2002), Monty Python Live at the Hollywood Bowl (1982), Victor Victoria (1982), Tootsie (1982), Breakfast on Pluto (2005), Twelfth Night (1996) ... Let's take a look at the ranked list of the best Cross-dressing movies.

#1. Murder! (1930)

Storyline: Actress Edna Druce is found dead, and fellow thespian Diana Baring (Norah Baring) can't explanation why she's holding the murder weapon. Diana seems destined for conviction and the death penalty, but juror Sir John Menier (Herbert Marshall) thinks she's innocent. An actor himself, Sir John collects clues and revisits the crime scene in an attempt to clear Diana, but his noble efforts might finger another performer with ties to Edna and Diana's touring company.

Plot Keywords: activist, murderer, lawyer, juror, actress, actor, dark ...

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#3. Venus Boyz (2002)

Storyline: This intimate look into the real world of drag kings -- women exploring their masculinity -- crosses continents, traveling through drag king nightclubs from New York to London. Through interviews and on-stage performances, every subject reveals a different reason for choosing the gender they have. The film is less a critique than an exploration of a world that is increasingly becoming mainstream, as the featured protagonists question exactly how gender works, and should work, in modern society.

Plot Keywords: performer, transgender woman, friend, inspiring, moving, powerful, nightclub ...

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#4. Monty Python Live at the Hollywood Bowl (1982)

Storyline: A collection of skits that made the Monty Python troupe famous, performed live at the Hollywood Bowl. Included are the singing philosophers, lumberjacks, the pope, and a suspiciously-male looking seabird vendor.—Murray Chapman <muzzle@cs.uq.oz.au>

Plot Keywords: barber, lumberjack, michelangelo, son, pope, madcap, california ...

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#5. Victor Victoria (1982)

Storyline: In 1934 Paris, trained coloratura soprano Victoria Grant, a native Brit, can't get a job as a singer and is having trouble making ends meet. She doesn't even have enough money for the basics of food and shelter. Gay cabaret singer Carole 'Toddy' Todd may befall the same fate as Victoria as he was just fired from his singing gig at a second rate club named Chez Lui. To solve both their problems, Toddy comes up with what he considers an inspired idea: with Toddy as her manager, Victoria, pretending to be a man, get a job singing as a female impersonator. If they pull this scheme off, Toddy vows Victoria, as her male alter ego, will be the toast of Paris and as such be extremely wealthy. That alter ego they decide is Polish Count Victor Grazinski, Toddy's ex-lover who was disowned by his family when they found out he was gay. The Count auditions for the city's leading agent, Andre Cassell, who, impressed, gets him a gig performing in the city's best nightclub. In the audience on the ...

Plot Keywords: performer, gangster, ex-boyfriend, girlfriend, bodyguard, witty, charming ...

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#6. Tootsie (1982)

Storyline: Michael Dorsey is an unemployed actor with an impossible reputation. In order to find work and fund his friend's play he dresses as a woman, Dorothy Michaels, and lands the part in a daytime drama. Dorsey loses himself in this woman role and essentially becomes Dorothy Michaels, captivating women all around the city and inspiring them to break free from the control of men and become more like Dorsey's initial identity. This newfound role, however, lands Dorsey in a hot spot between a female friend/'lover,' a female co-star he falls in love with, that co-star's father who falls in love with him, and a male co-star who yearns for his affection.

Plot Keywords: actor, actress, agent, director, roommate, girlfriend, amusing ...

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#7. Breakfast on Pluto (2005)

Storyline: A young transwoman, Patrick "Kitten" Braden, comes of age in the 1970s. She leaves her Irish town, in part to look for her mother and in part because her transgender nature is beyond the town's understanding. She's taken in by a rock band, falls for the lead singer, has brushes with the IRA, is arrested by the London police, works in a peep show, and poses as a survey researcher for the phone company. Throughout, her nationality and her nature put her at great risk. In her search for her mother, she makes surprising discoveries of friendship and family. But, will she survive?

Plot Keywords: orphan, priest, rocker, police officer, magician, transsexual, intricate ...

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#8. Twelfth Night (1996)

Storyline: Brother and sister Viola and Sebastian, who are not only very close but look a great deal alike, are in a shipwreck, and both think the other dead. When she lands in a foreign country, Viola dresses as her brother and adopts the name Cesario, becoming a trusted friend and confidante to the Count Orsino. Orsino is madly in love with the lady Olivia, who is in mourning due to her brother's recent death, which she uses as an excuse to avoid seeing the count, whom she does not love. He sends Cesario to do his wooing, and Olivia falls in love with the disguised maiden. Things get more complicated in this bittersweet Shakespeare comedy when a moronic nobleman, Sir Andrew Aguecheek, and a self-important servant, Malvolio, get caught up in the schemes of Olivia's uncle, the obese, alcoholic Sir Toby, who leads each to believe Olivia loves him. As well, Sebastian surfaces in the area, and of course there is Feste, the wise fool, around to keep everything in perspective and to marvel, like we the audience, at the amazing things happening all around.—Gary Dickerson <slug@mail.utexas.edu>

Plot Keywords: twin, brother, duke, lady, uncle, servant, charming ...

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#9. Kinky Boots (2005)

Storyline: Charles Price may have grown up with his father in the family shoe business, but he never thought that he would take his father's place. Yet, the untimely death of his father places him in that position, only to learn that Price and Sons Shoes is failing. While in despair at his failed attempts to save the business, Charles has a chance encounter with the flamboyant drag queen cabaret singer, Lola. Her complaints about the inadequate footwear for her work combined with one of Charles' ex-employees, Lauren, leads to a suggestion to change the product to create a desperate chance to save the business: make men's fetish footwear. Lola is convinced to be their footwear designer and the transition begins. Now this disparate lot must struggle at this unorthodox idea while dealing with both the prejudice of the staff, Lola's discomfort in the small town and the selfish manipulation of Charles' greedy fiance who cannot see the greater good in Charles' dream.

Plot Keywords: entrepreneur, drag queen, fiancé, employee, charming, witty, quirky ...

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#10. The Birdcage (1996)

Storyline: Armand Goldman owns a popular drag nightclub in South Miami Beach. His long-time lover, Albert, stars there as Starina. "Their" son Val (actually Armand's by his one heterosexual fling, twenty years before) comes home to announce his engagement to Barbara Keeley, daughter of Kevin Keeley, US Senator, and co-founder of the Committee for Moral Order. The Senator and family descend upon South Beach to meet Val, his father and "mother." What ensues is comic chaos.

Plot Keywords: club owner, drag queen, senator, fiancée, housekeeper, son, hysterical ...

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#11. Madame Satã (2002)

Storyline: A story inspired by the life of one of the most remarkable figures in Brazilian popular culture, João Francisco dos Santos (1900-1976). In turn, bandit, transvestite, street fighter, brothel cook, convict and father to seven adopted children, dos Santos--better known as Madame Satã--was also a notorious gay performer who pushed social boundaries in a volatile time. The story begins in 1932, in Rio de Janeiro's bohemian Lapa district, when João Francisco is about to achieve his dream: becoming a stage star. In the sordid yet lively world of Lapa--populated by pimps, prostitutes and other denizens of Rio's underworld--João battles the streets and presides over a surrogate family that includes the charming prostitute Laurita, and her baby daughter whom everyone dotes on; the flamboyant hustler Taboo; João's teenage lover, Renatinho; and Amador, the owner of the Blue Danube club which is their second home. It is at the Blue Danube that street tough João begins to sing, and the mythic drag artiste Madam Satã is born.—Sujit R. Varma

Plot Keywords: transvestite, prostitute, performer, hustler, club owner, unrestrained, inspiring ...

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#12. Shakespeare in Love (1998)

Storyline: Will Shakespeare is a known but struggling poet, playwright and actor who not only has sold his next play to both Philip Henslow and Richard Burbidge but now faces a far more difficult problem: he is bereft of ideas and has yet to begin writing. He is in search of his muse, the woman who will inspire him but all attempts fail him until he meets the beautiful Viola de Lesseps. She loves the theatre and would like nothing more than to take to the stage but is forbidden from doing so as only men can be actors. She is also a great admirer of Shakespeare's works. Dressing as a man and going by the name of Thomas Kent, she auditions and is ideal for a part in his next play. Shakespeare soon sees through her disguise and they begin a love affair, one they know cannot end happily for them as he is already married and she has been promised to the dour Lord Wessex. As the company rehearses his new play, Will and Viola's love is transferred to the written page leading to the masterpiece that is ...

Plot Keywords: william shakespeare, love interest, actress, queen, amusing, inspiring, engaging ...

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#13. Different for Girls (1996)

Storyline: Karl Foyle and Paul Prentice were best mates at school in the Seventies. But when they meet again in present-day London things are definitely not the same. Karl is now Kim, a transsexual, and she has no desire to stir up the past while she's busy forging a neat and orderly new life. Prentice, on the other hand, has charm but is a social disaster stuck in a dead-end job. His main talent is for getting them both into trouble. Amid the squabbles, they start to fall in love. One night, Kim invites Prentice to a romantic dinner at her flat. Prentice, finding the seduction unexpectedly effective, freaks out. He proceeds to make a public display of both of them and winds up in court. Humiliated and angry, Kim runs away. Only she can save Prentice now, but will true love triumph for a new made woman and an aging punk?—<jsharp@digitus.mozart.co.uk>

Plot Keywords: transsexual, bad boy, police officer, childhood friend, touching, cheeky, catholic school ...

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#14. First a Girl (1935)

Storyline: Elizabeth, a delivery girl, dreams of being a music-hall singer but she is refused at the first casting she takes part in. A bit depressed, she gets to know Victor, a would-be Shakespearean actor and another audition victim. When Victor quite unexpectedly gets a female part in a music-hall number he unfortunately finds himself voiceless. Why wouldn't Elizabeth replace him in it? His new friend hesitates but finally makes her debut as ... a man posing as a woman! She is noticed by McLintock, an influential talent agent who hires Mr. Victoria (Elizabeth's stage name) and launches his/her brilliant international career. One day, Robert, a handsome young man engaged to Princess Mironoff, makes friends with this young man posing as a woman posing as a man ...—Guy Bellinger

Plot Keywords: aspiring actor, aspiring actress, talent scout, young man, princess, trainer, hilarious ...

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#15. Outrageous! (1977)

Storyline: Robin Turner is a gay hairdresser. He hates his job. He loves old movies and will do his customers' hair in the style of an iconic movie star if they'll let him, and even if they don't. At his apartment, he is harboring his medically diagnosed schizophrenic friend, Liza Connors, who can no longer stand being institutionalized. After Liza convinces Robin to attend a drag ball dressed as Tallulah Bankhead, Robin begins to feel liberated. On Liza's further urging, Robin accepts a local club's offer to work as a female impersonator, he doing his own singing unlike most drag queens. As he progresses with his female impersonation work to great aplomb, he takes a shot at making it big in New York City. The money will have to come in since despite medical warnings to her not to do it, Liza has become pregnant (not Robin's baby), she deciding to have and keep the baby.—Huggo

Plot Keywords: hairdresser, drag queen, schizophrenic, agent, cab driver, positive, emotional ...

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