Highest-Rated Movies about 'Crossdresser'

Some Like It Hot (1959), The Celluloid Closet (1996), White Christmas (1954), The Blind Swordsman: Zatoichi (2003), Kiss of the Spider Woman (1985), The Rocky Horror Picture Show (1975), Tootsie (1982), March of the Wooden Soldiers (1934) ... Let's take a look at the ranked list of the best Crossdresser movies.

#1. Some Like It Hot (1959)

Storyline: When two Chicago musicians, Joe and Jerry, witness the the St. Valentine's Day massacre, they want to get out of town and get away from the gangster responsible, Spats Colombo. They're desperate to get a gig out of town but the only job they know of is in an all-girl band heading to Florida. They show up at the train station as Josephine and Daphne, the replacement saxophone and bass players. They certainly enjoy being around the girls, especially Sugar Kane Kowalczyk who sings and plays the ukulele. Joe in particular sets out to woo her while Jerry/Daphne is wooed by a millionaire, Osgood Fielding III. Mayhem ensues as the two men try to keep their true identities hidden and Spats Colombo and his crew show up for a meeting with several other crime lords.

Plot Keywords: sex comedy, comedy of errors, 1920s, disguise, farce, organized crime, prohibition ...

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#2. The Celluloid Closet (1996)

Storyline: This documentary highlights the historical contexts that gays, lesbians, bisexuals and transgenders have occupied in cinema history, and shows the evolution of the entertainment industry's role in shaping perceptions of LGBT figures. The issues addressed include secrecy -- which initially defined homosexuality -- as well as the demonization of the homosexual community with the advent of AIDS, and finally the shift toward acceptance and positivity in the modern era.

Plot Keywords: gay, gay slur, film history, homophobia, gay interest, homosexuality, lesbianism ...

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#3. White Christmas (1954)

Storyline: Having left the Army following W.W.II, Bob Wallace and Phil Davis team up to become a top song-and-dance act. Davis plays matchmaker and introduces Wallace to a pair of beautiful sisters (Betty and Judy) who also have a song-and-dance act. When Betty and Judy travel to a Vermont lodge to perform a Christmas show, Wallace and Davis follow, only to find their former commander, General Waverly, as the lodge owner. A series of romantic mix-ups ensue as the performers try to help the General.

Plot Keywords: christmas, sheriff, business partner, bachelor, jeep, horseshoe, ballerina ...

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#4. The Blind Swordsman: Zatoichi (2003)

Storyline: Blind Zatoichi makes his living by gambling and giving massages. But behind his humble facade, Zatoichi is a master swordsman, gifted with lightning-fast draw and strokes of breathtaking precision. Zatoichi wanders into a town run by sinister gangs and a powerful samurai. He's destined for violent showdowns when he stumbles on two beautiful geishas avenging their parents' murder... Duels, wit and a touch of zen! Cult anti-hero Zatoichi is back in a sword-fighting adventure written, directed and starring Takeshi Kitano.

Plot Keywords: hit on the head, shot in the chest, slashing, slaughter, stabbed in the back, stabbed in the chest, stabbed in the hand ...

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#5. Kiss of the Spider Woman (1985)

Storyline: Luis Molina and Valentin Arregui are cell mates in a South American prison. Luis, a trans individual, is found guilty of immoral behavior and Valentin is a political prisoner. To escape reality Luis invents romantic movies, while Valentin tries to keep his mind on the situation he's in. During the time they spend together, the two men come to understand and respect one another.

Plot Keywords: film within a film, based on novel, psychological drama, foreign language adaptation, homosexual, revolutionary, prison ...

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#6. The Rocky Horror Picture Show (1975)

Storyline: On a wild and rain-swept late-November evening, somewhere at an empty stretch of road outside Ohio's merry Denton, the blissfully-affianced, prudish, and boringly innocent young pair of Brad Majors (Barry Bostwick) and Janet Weiss (Susan Sarandon) find themselves stranded on their way to visit an ex-tutor. Instead, the couple will inadvertently unearth the cross-dressing Dr. Frank-N-Furter's (Tim Curry's) spooky lair of inexhaustible oddities, just in time to partake in the out-of-this-world mad scientist's proud unveiling of his latest, delightfully extravagant, and most daring creation - the ultimate male and the perfect sex symbol: the flaxen-haired, Rocky Horror (Peter Hinwood). But, little by little, as the effervescent transgressive force gobbles up whole the unsuspecting visitors of the night, Brad and Janet slowly begin to embrace the potent fascinations of seduction, while an idolized Rocky roams free in the mansion. Who can interrupt man's union with the absolute pleasure?

Plot Keywords: dancer, dancing, based on stage musical, church, dark and stormy night, freezer, male underwear ...

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#7. 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: reputation, cult film, unwanted kiss, premarital sex, seduction, lesbian, woman in lingerie ...

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#8. March of the Wooden Soldiers (1934)

Storyline: Ollie Dee and Stanley Dum try to borrow money from their employer, the toymaker, to pay off the mortgage on Mother Peep's shoe and keep it and Little Bo Peep from the clutches of the evil Barnaby. When that fails, they trick Barnaby into marrying Stanley Dum instead of Bo Peep. Enraged, Barnaby unleashes the bogeymen from their caverns to destroy Toyland.—Paul Penna <tterrace@wco.com>

Plot Keywords: forced marriage, toy soldier, sheep, well, lifting someone into the air, young love, wedding ...

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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: drag queen, crossdresser, high heels, singing, gay bashing, gay interest, gay slur ...

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#10. The Longest Yard (1974)

Storyline: A football player-turned-convict organizes a team of inmates to play against a team of prison guards. His dilemma is that the warden asks him to throw the game in return for an early release, but he is also concerned about the inmates' lack of self-esteem.

Plot Keywords: warden, misogynist, bare chested male, hairy chest, american football, convict, florida ...

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#11. Mrs. Doubtfire (1993)

Storyline: Eccentric actor Daniel Hillard is an amusing and caring father. But after a disastrous birthday party for his son, Daniel's wife Miranda draws the line and files a divorce. He can see his three children only once a week which doesn't sit well with him. Daniel also holds a job at a TV studio as a shipping clerk under the recommendation of his liason. But when Miranda puts out an ad for a housekeeper, Daniel takes it upon himself to make a disguise as a Scottish lady named Mrs Doubtfire. And Daniel must also deal with Miranda's new boyfriend Stu Dunemyer.

Plot Keywords: custody battle, family reunion, impersonation, secret identity, single father, single mother, allergy ...

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#12. Sweet November (2001)

Storyline: The story centers around a man and a woman, whose fates are intertwined and will change forever. Nelson is an avid advertiser living in San Francisco. One day, during a driving test, he meets Sara, a beautiful but seemingly eccentric woman. But, she is falsely accused of cheating and ends up failing the test because of Nelson. After getting kicked out of the exam, Sara waits for him outside and starts to insult him. However, Nelson ignores her and takes off. Then, she traces him down and shows up at his place. She promises to leave him alone only if he gives her a ride. Later that night, she asks him to live with her throughout November on the promise that his life will change for the better. He turns her down saying that he has a girlfriend. On the first day of November, after being fired and dumped on the very same day, Nelson decides to give it a try and then somehow, agrees to spend the whole month with Sara and finds himself in a desperate love affair that he will remember for ...

Plot Keywords: advertising, remake, terminal illness, san francisco california, cancer, dog, vegan ...

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#13. The Snowtown Murders (2011)

Storyline: Sixteen-year-old Jamie lives with his mother, Elizabeth, and two younger brothers, Alex and Nicholas, in a housing trust home in Adelaide's northern suburbs. Their home is but one of many sun-starved houses crammed together to cater for a disenfranchised society. Jamie longs for an escape from the violence and hopelessness that surrounds him and his salvation arrives in the form of John, a charismatic man who unexpectedly comes to his aid. As John spends more and more time with Jamie's family, Elizabeth and her boys begin to experience a stability and sense of family that they have never known. John moves from the role of Jamie's protector to that of a mentor, indoctrinating Jamie into his world, a world brimming with bigotry, righteousness and malice. Like a son mimicking his father, Jamie soon begins to take on some of John's traits and beliefs as he spends more and more time with him and his select group of friends. The protection and guidance that John presents to Jamie is ...

Plot Keywords: gang, underwear, male rear nudity, male nudity, male frontal nudity, ice cream truck, shopping ...

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#14. Aloys (2016)

Storyline: Aloys Adorn is a middle aged private detective who lives and works with his father. He experiences life from a safe distance, through a video camera he keeps recording 24 hours a day, and the massive collection of surveillance tapes he organizes and obsessively watches at home. But when his father dies, Aloys is left on his own and his sheltered existence begins to fall apart. After a night of heavy drinking, Aloys wakes up on a public bus to find that his camera and precious observation tapes have been stolen. Soon after, a mysterious woman calls to blackmail him. She offers to return the tapes if Aloys will try an obscure Japanese invention called 'telephone walking' with her, using his imagination as their only connection. As he is drawn deeper and deeper, falling in love with the voice on the other end of the phone, the woman opens up a new universe that may allow Aloys to break out of his isolation and into the real world.—New Europe Film Sales

Plot Keywords: zoo, headset, hospital, shower, hospital room, tortoise, female in shower ...

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#15. She's the Man (2006)

Storyline: Here's the thing! Viola's soccer team at Cornwall gets cut. She wants to join the boys' team, but they do not allow girls. So she thinks, "If you can't beat them, join them". So she does! She disguises herself as her twin brother, Sebastian and goes out for the rival school, Illyria Boys' Soccer Team and makes it. Unfortunately, she didn't plan falling in love with her roommate Duke. But Duke has his eyes on Olivia. What makes matters worse is that Olivia starts to fall for Sebastian because he/she has a sensitive side. If things couldn't get more problematic, the real Sebastian (who was in London working on his music) comes home early. He arrives on campus and has no clue that he was replaced by his twin sister.

Plot Keywords: love triangle, invitation, insult, insecurity, impersonation, geek, friendship ...

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