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.

#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 ...

Movie Details Click Here!

#2. The Handmaiden (2016)

Storyline: 1930s Korea, in the period of Japanese occupation, a new girl (Sookee) is hired as a handmaiden to a Japanese heiress (Hideko) who lives a secluded life on a large countryside estate with her domineering Uncle (Kouzuki). But the maid has a secret. She is a pickpocket recruited by a swindler posing as a Japanese Count to help him seduce the Lady to elope with him, rob her of her fortune, and lock her up in a madhouse. The plan seems to proceed according to plan until Sookee and Hideko discover some unexpected emotions.

Plot Keywords: lesbianism, female nudity, repeated scene from a different perspective, lesbian sex, lesbian cunnilingus, sex scene, explicit sex ...

Movie Details Click Here!

#3. I Vitelloni (1953)

Storyline: Fausto Moretti, having seduced Sandra Rubini, the sister of his friend and companion Moraldo Rubini, is forced to marry her. After their honeymoon, he takes a job as a salesman of religious objects in a small shop. He isn't changed by his marriage and still looks for women, with his friends, when and where they can find them. He even tries to seduce the wife of his boss and is fired. After each episode, Sandra forgives him. He and his friends of similar temperament are content to be idle, chase girls and leave the work and job-hunting to others. After spending the night away from home with a girl, Sandra cannot forgive anymore and runs off with their child. Fausto and his friends search all over for them, fearing the worst.

Plot Keywords: unfaithfulness, beauty contest, beauty queen, bicycle, boardwalk, boat, borrowing money ...

Movie Details Click Here!

#4. Three Nuts for Cinderella (1973)

Storyline: The film stars Libuse Safránková as the title character, a young woman who is put upon by her stepmother and stepsisters. The film employs a twist, though, when a handsome prince comes knocking. Cinderella does not simply fall into the prince's arms. In this version, he must actively pursue the young woman who is a skilled sharpshooter prone to wearing hunting outfits. Cinderella also has three wishes at her disposal, gained from three magic nuts.—Ørnås

Plot Keywords: prince, magic, riddle, princess, bully, female bully, outcast ...

Movie Details Click Here!

#5. Laurence Anyways (2012)

Storyline: The movie highlights ten years in the life of a literature teacher named Laurence who transforms himself into a woman after years of concealing his feelings. Her tremulous relationship with her family is further complicated by revealing herself to them while she struggles to find comfort with her significant other Frédérique. Though others may not initially accept or understand Laurence in her true form, those who knew her before her transformation still know her as Laurence, anyways.

Plot Keywords: character name in title, title spoken by character, sex change, two word title, cigarette smoking, hugging, fired from the job ...

Movie Details Click Here!

#6. 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 ...

Movie Details Click Here!

#7. 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 ...

Movie Details Click Here!

#8. Tomboy (2011)

Storyline: A family moves into a new neighborhood, and a 10-year-old born Laure deliberately presents as a boy named Mickäel to the neighborhood children. It is heavily implied that Mickäel is a closeted transgender boy. This film follows his experiences with his newfound friends, his potential love interest, Lisa, his younger sister and his parents. It focuses in on the significance of gender identity in social interaction from an early age, the difficulties of being transgender and young, and how Mickäel navigates these in the background of childhood play and love.

Plot Keywords: false name, tomboy, driving, necklace, spaghetti, washing hair, paris france ...

Movie Details Click Here!

#9. Phantom of the Paradise (1974)

Storyline: Evil record tycoon Swan has sold his soul to the devil for eternal youth and success - 20 years ago. Swan's current scheme is to steal the music from composer Winslow Leach to celebrate the opening of his rock palace, The Paradise. While trying to stop Swan, Leach was framed and convicted for drug dealing, and becomes the victim of a freak accident that leaves him horribly disfigured. He takes refuge in the cavernous Paradise, hiding his mangled face beneath an eerie mask and planning gruesome vengeance upon Swan - and everyone else who has hurt him. However, Leach signs a contract with Swan to complete his rock opera based on the legend of Faust for an aspiring singer - Phoenix.

Plot Keywords: black comedy, independent film, deal with the devil, rock star, masked man, rock 'n' roll, cult favorite ...

Movie Details Click Here!

#10. 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 ...

Movie Details Click Here!

#11. Beauty and the Beast (2017)

Storyline: Disney's animated classic takes on a new form, with a widened mythology and an all-star cast. A young prince, imprisoned in the form of a beast, can be freed only by true love. What may be his only opportunity arrives when he meets Belle, the only human girl to ever visit the castle since it was enchanted.

Plot Keywords: beast, disney, female protagonist, gay subtext, four word title, heroine, fairy tale ...

Movie Details Click Here!

#12. 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 ...

Movie Details Click Here!

#13. Filth (2013)

Storyline: Scheming Bruce Robertson (James McAvoy), a bigoted and corrupt policeman, is in line for a promotion and will stop at nothing to get what he wants. Enlisted to solve a brutal murder and threatened by the aspirations of his colleagues, including Ray Lennox (Jamie Bell), Bruce sets about ensuring their ruin, right under the nose of unwitting Chief Inspector Toal. As he turns his colleagues against one another by stealing their wives and exposing their secrets, Bruce starts to lose himself in a web of deceit that he can no longer control. His past is slowly catching up with him, and a missing wife, a crippling drug habit and suspicious colleagues start to take their toll on his sanity. The question is: can he keep his grip on reality long enough to disentangle himself from the filth?

Plot Keywords: male frontal nudity, death of protagonist, bare breasts, fellatio, rough sex, woman on top, sex from behind ...

Movie Details Click Here!

#14. 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 ...

Movie Details Click Here!

#15. 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 ...

Movie Details Click Here!