Highest-Rated Movies about 'Cross-dressing'

Cabaret (1972), Victor Victoria (1982), The Adventures of Priscilla, Queen of the Desert (1994), Breakfast on Pluto (2005), High Heels (1991), Shakespeare in Love (1998), First a Girl (1935), Mrs. Doubtfire (1993) ... Let's take a look at the ranked list of the best Cross-dressing movies.

#1. Cabaret (1972)

Storyline: Cambridge University student Brian Roberts arrives in Berlin in 1931 to complete his German studies. Without much money, he plans on making a living teaching English while living in an inexpensive rooming house, where he befriends another of the tenants, American Sally Bowles. She is outwardly a flamboyant, perpetually happy person who works as a singer at the decadent Kit Kat Klub, a cabaret styled venue. Sally's outward façade is matched by that of the Klub, overseen by the omnipresent Master of Ceremonies. Sally draws Brian into her world, and initially wants him to be one of her many lovers, until she learns that he is a homosexual, albeit a celibate one. Among their other friends are his students, the poor Fritz Wendel, who wants to be a gigolo to live a comfortable life, and the straight-laced and beautiful Natalia Landauer, a Jewish heiress. Fritz initially sees Natalia as his money ticket, but eventually falls for her. However Natalia is suspect of his motives and cannot ...

Plot Keywords: musical, song and dance, germany, 1930s, nazis, cabaret, berlin ...

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#2. 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: musical, comedy, romance, paris, cabaret, song and dance, gender issues ...

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#3. The Adventures of Priscilla, Queen of the Desert (1994)

Storyline: Two drag-queens (Anthony/Mitzi and Adam/Felicia) and a transgender woman contract to perform a drag show at a resort in Alice Springs, a resort town in the remote Australian desert. They head west from Sydney aboard their lavender bus, Priscilla. En route, it is discovered that the woman they've contracted with is Anthony's wife. Their bus breaks down, and is repaired by Bob, who travels on with them.

Plot Keywords: comedy, drama, musical, lgbtq+, australian film, road movie, homosexuality ...

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#4. 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: drama, comedy, romance, lgbt, coming of age, 1970s, identity ...

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#6. 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: romance, historical, drama, comedy, period piece, shakespeare, theater ...

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#7. 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: comedy, musical, romance, british film, black and white, classic film, musical comedy ...

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#8. 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: family, comedy, drama, divorce, father, humor, heartwarming ...

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#9. Freak Show (2017)

Storyline: In the vein of CLUELESS and NAPOLEON DYNAMITE, FREAK SHOW tells the moving, heartwarming, and hilarious story of Billy Bloom, a boldly confident, wildly eccentric teenager, who faces intolerance and persecution at his ultra conservative high school, and decides to fight back on behalf of all the misunderstood freaks of the world by running for the title of homecoming queen.

Plot Keywords: coming of age, lgbtq+, high school life, bullying, social prejudice, family conflict, friendship ...

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#10. Yentl (1983)

Storyline: Eastern Europe, 1904. A Jewish woman, Yentl, has a thirst for knowledge but is prohibited from learning due to the restrictions of her religion. When her father dies, she sets off to increase her knowledge, posing as a man in order to gain admission to a Jewish religious school.

Plot Keywords: musical, drama, romance, jewish, feminism, religious conflict, coming of age ...

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#11. Just One of the Guys (1985)

Storyline: Terry Griffith has got it all -- looks, popularity, the perfect college boyfriend, and an article that's a shoo-in to win her a summer internship at the local newspaper... or so she thinks. When Terry's journalism teacher passes her article up in favor of a couple of pieces written by boys, Terry is convinced that sexism is to blame. Determined to win the internship at any cost, Terry goes undercover at a rival high school to resubmit her article... as a boy. But Terry gets more than she bargained for when she finds herself fending off a bully and the advances of an oversexed female admirer, and falling for her new pal Rick.

Plot Keywords: comedy, teen, high school, 1980s, american film, coming of age, romance ...

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#12. Sorority Boys (2002)

Storyline: After being falsely accused of stealing the budget for their annual cocktail cruise, three very different fraternity brothers are kicked out of their dorm. In order to clear their name and to secure their future careers, the three dress up in drag and pledge the sorority next door where they learn a few valuable - and hilarious - lessons about themselves and the female species.

Plot Keywords: comedy, college life, prank, disguise, american movie, 2000s, brotherhood ...

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#13. Big Momma's House (2000)

Storyline: FBI agent Malcolm Turner is known best for being a brilliant, master of disguise. Malcolm's latest assignment sends him to small-town Georgia, where he's assigned to trap a brutal bank robber (and a recent prison escapee) who they suspect will be coming down to visit his ex-girlfriend Sherry and her son. Malcolm sets up a stakeout across from the home of a larger-than-life southern matriarch known as Big Momma, who's about to be visited by Sherry. It's a simple plan, but there's one big problem: Unbeknownst to Sherry, Big Momma has unexpectedly left town. So Malcolm, decides to impersonate the cantankerous Southern granny. Using a few tricks of disguise, he completely transforms himself into Big Momma, even taking on the corpulent septuagenarian's everyday routine-from cooking soul food to delivering babies to "testifying" at the local church. In the mean time, Malcolm starts falling for Sherry, who may or may not be hiding some stolen cash. Now, Malcolm/Big Momma must somehow find a ...

Plot Keywords: comedy, action, crime, family, humor, undercover, police ...

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#14. Juwanna Mann (2002)

Storyline: Juwanna Mann follows the story of Jamal Jeffries, the reigning 'bad boy' of basketball, whose undisciplined on-court antics land him out of the league and without any prospects. Financially strapped and untrained in anything but basketball, Jamal comes up with a plan so outrageous it just might work: dress up like a woman and try out for the woman's basketball league. To his surprise, he makes it, but now the real challenge begins - to cease being Jamal and start new life as Juwanna. Matters become even more complicated when Juwanna realizes that he is falling for his teammate Michelle, who shows him that there is more to women than meets the eye.—<gsm1224@ix.netcom.com>

Plot Keywords: comedy, sports, disguise, humor, romance, love, drama ...

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#15. Big Momma's House 2 (2006)

Storyline: Undercover Agent Malcolm Turner is back and this time he's out to expose the suspected designer of a deadly computer "worm" that would allow outside forces access to sophistical and critical government intelligence files. But unfortunately, the only way the crafty agent can get next to the worm's creator, Tom Fuller, is to access the programmer's Orange County home as the new "nanny" to Fuller and his wife Leah's children: toddler Andrew and his two older sisters, Carrie and Molly. This means that Malcolm must once again rely on his sure-fire alter ego, the take-no-prisoners Hattie Mae Pierce, a.k.a. "Big Momma," to bring down the bad guys and prove that a woman's work is never done! But once undercover, the job proves another tough juggling act for Big Momma as "she" must manage the hectic lives of the three Fuller kids, keep up with their myriad of daily activities, and handle the many household chores, all while secretly trying to dig up information on Tom's computer virus. Of ...

Plot Keywords: comedy, action, crime, family, disguise, fbi, undercover ...

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