Highest-Rated Movies about 'Crossdressing'

Some Like It Hot (1959), The Handmaiden (2016), I Vitelloni (1953), Three Nuts for Cinderella (1973), Laurence Anyways (2012), White Christmas (1954), The Blind Swordsman: Zatoichi (2003), Tomboy (2011) ... Let's take a look at the ranked list of the best Crossdressing movies.

#16. I Was a Male War Bride (1949)

Storyline: In post-war, French Army Captain Henrí Rochard and US Army Lieutenant Catherine Gates, stationed in Heidelberg, West Germany, are often teamed on missions. Their personal relationship teeters from being friendly enough to Catherine not sure if she wants to spend any time with him, professionally or personally, as he is the type who will chase anything in a skirt, while she knows she ultimately wants to be with the type of man who only wants one "skirt", namely hers. Their latest mission, what will be their last together before he is decommissioned, is punctuated by them getting into one misadventure after another, and despite those mishaps, they come to realize that they love each other on the fact that they would never see each other again after their return to Heidelberg, and want to get married. That want starts the bureaucratic nightmare they face, ranging the gamut of military policies and civil laws in whatever jurisdiction they are in. That nightmare culminates when Catherine's unit is being shipped back to the United States, the only way that Henrí can enter the United States as her spouse being under the War Brides Act. Henrí ends up being classified among one hundred thirty-nine other war brides, one hundred twenty-six children of war brides, nine dogs, three cats, two canaries and one parrot, none having as much trouble that he has despite he being "approved" as "Mrs. Henrí Rochard".—Huggo

Plot Keywords: military, sleeping in a chair, false accusation, black market, sidewalk cafe, kiss, marriage ...

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#17. One of Our Aircraft Is Missing (1942)

Storyline: During the Allied Bombing offensive of World War II the public was often informed that "A raid took place last night over (city name). One (or often more) of our aircraft Is missing." Behind these sombre words hid tales of death, destruction, and derring-do. This is the story of one such bomber crew who were shot down, and the brave Dutch patriots who helped them home.—Steve Crook <steve@brainstorm.co.uk>

Plot Keywords: warplane, sheep, passport, crossdressing, told in flashback, parachute, disguise ...

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#18. The Quiet Earth (1985)

Storyline: A man wakes up to find himself literally alone in the world, and goes about trying to find other survivors, as well as to find out what happened. He suspects that a government research project he was involved in had something to do with the disappearance of everyone. Eventually he finds several other people, and once they begin to trust each other they try to figure out why they were left on earth.

Plot Keywords: experiment, parallel world, love triangle, post apocalypse, campfire, cathedral, chandelier ...

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#19. 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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#20. 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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#21. J. Edgar (2011)

Storyline: Biopic of J. Edgar Hoover (Leonardo DiCaprio) told by Hoover as he recalls his career for a biography. Early in his career, Hoover fixated on Communists, anarchists, and any other revolutionary taking action against the U.S. government. He slowly builds the agency's reputation, becoming the sole arbiter of who gets hired and fired. One of his hires is Clyde Tolson (Armie Hammer), who is quickly promoted to Assistant Director and was Hoover's confidant and companion for the rest of Hoover's life. Hoover's memories have him playing a greater role in the many high profile cases in which the F.B.I. was involved, the Lindbergh baby kidnapping, the arrest of bank robbers like John Dillinger, and also show him to be quite adept at manipulating the various politicians with whom he worked over his career, thanks in large part to his secret files.

Plot Keywords: gay relationship, homosexual, ends with biographical notes, fbi investigation, fbi agent, repressed homosexual, sexual repression ...

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#22. Wild Tigers I Have Known (2006)

Storyline: Junior high in a time of rotary phones. Cougars have been spotted in the area. Logan is 13, the odd kid, with an active imagination and few friends. His young, single mother seems stressed. Latency is giving way to puberty, and Logan, who keeps a tube of lipstick in his dresser, may be gay or, more mysterious, transgender. He stares at himself in the mirror. He becomes friends with Rodeo, older and more mature, good-looking, with girlfriends. They take walks. Logan calls Rodeo and pretends to be a girl. Will he disclose himself to Rodeo? The kids at school talk. The school wants to promote kindness and tolerance. There are stories of child suicide. How do we find our way?—<jhailey@hotmail.com>

Plot Keywords: infatuation, hallucination, groceries, goggles, ghost, friendship, footprint ...

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#23. House at the End of the Street (2012)

Storyline: Newly divorced Sarah and her daughter Elissa find the house of their dreams in a small, upscale, rural town. But when startling and unexplainable events begin to happen, Sarah and Elissa learn the town is in the shadows of a chilling secret.

Plot Keywords: mother daughter relationship, stabbed multiple times, locked in a room, strapped to a bed, swimming pool, barefoot woman, police officer ...

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#24. Boat Trip (2002)

Storyline: Jerry and Nick are two best buddies whose love lives have hit rock bottom, Jerry's especially, having just vomited all over his fiancée on a hot air balloon trip prior to proposing to her. To escape their troubles and find women, they book a trip on-board a cruiseliner, unaware the travel agent has just played a horrid trick on them in retaliation for Nick offending his secret gay lover. And that's the trick; it's a gay cruiseliner for gay men to meet and mingle. Slowly but surely, the two main characters begin to realize this and in turn get into a lot of humorous predicaments.

Plot Keywords: death of mother, gay stereotype, blow job, homosexuality, pretending to be gay, catfight, two word title ...

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