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Movies: Best "cross dressing" Movies

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128 movies found (page 1/5):

White Chicks(2004)

PG-13
| 1h 49min | Comedy, Crime
3.5/5 (with 1,700 votes)

Two FBI agent brothers, Marcus and Kevin Copeland, accidentally foil a drug bust. To avoid being fired they accept a mission escorting a pair of socialites to the Hamptons--but when the girls are disfigured in a car accident, they refuse to go. Left without options, Marcus and Kevin decide to pose as the sisters, transforming themselves from black men into rich white women.

Directed by Keenen Ivory Wayans - With Shawn Wayans, Marlon Wayans, Jaime King, Frankie Faison, Lochlyn Munro, Busy Philipps, ...
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All Ladies Do It(1992)

1h 33min | Comedy, Drama
2.3/5 (with 148 votes)

Diana is a Roman wife happily married to sympathetic Paolo but she is keen on playing benign games of seduction with other men while resisting the advances of chic lingerie shop owner Silvio. She narrates her adventures to Paolo in order to stimulate their otherwise monotonous sexual life. However, under the influence of her lesbian friend Antonietta and raunchy sister Nadia, Diana starts to move the ongoings further while Paolo is still prone to believing that events narrated by her are merely fantasies.

Directed by Tinto Brass - With Claudia Koll, Paolo Lanza, Franco Branciaroli, Renzo Rinaldi, Rossana Doll, Osiride Pevarello, ...

Taboo(1977)

1h 55min | Drama
2.5/5 (with 2 votes)

Solidarity with the border people. Equal rights for the sexual deviants. Kristoffer Lohman is a young solicitor who collects stories and knowledge of different perversions. This has affected and changed his own sexual life. Sara, a young well-behaved and adorned woman, becomes interested in Kristoffer's activity.

Directed by Vilgot Sjöman - With Kjell Bergqvist, Gunnar Björnstrand, Viveca Lindfors, Heinz Hopf, Birger Malmsten, Lena Olin, ...

Some Like It Hot(1959)

NR
| 2h 2min | Comedy, Music, Romance / Love, Crime
4.1/5 (with 1,476 votes)

Two musicians witness a mob hit and struggle to find a way out of the city before they are found by the gangsters. Their only opportunity is to join an all-girl band as they leave on a tour. To make their getaway they must first disguise themselves as women, then keep their identities secret and deal with the problems this brings - such as an attractive bandmate and a very determined suitor.

Directed by Billy Wilder - With Marilyn Monroe, Jack Lemmon, Tony Curtis, George Raft, Pat O'Brien, Mike Mazurki, ...
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The Return of the Texas Chainsaw Massacre(1995)

R
| 1h 35min | Horror, Comedy
2.2/5 (with 261 votes)

Everyone's favorite chainsaw-wielding psychopath, Leatherface, is back for more prom-night gore, and this time he's joined by his bloodthirsty family. Four stranded yet carefree teens are taken in by a backwoods family, clueless of their host family's grisly habits. The terrified youths, including sweet Jenny, try to escape from Leatherface and his crazed clan, including the bionic Vilmer.

Directed by Kim Henkel - With Renée Zellweger, Matthew McConaughey, Robert Jacks, Lisa Marie Newmyer, Paul A. Partain, John Dugan, ...
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The Birdcage(1996)

R
| 1h 57min | Comedy
3.5/5 (with 479 votes)

A gay cabaret owner and his drag queen companion agree to put up a false straight front so that their son can introduce them to his fiancé's conservative moralistic parents.

Directed by Mike Nichols - With Robin Williams, Gene Hackman, Nathan Lane, Dianne Wiest, Dan Futterman, Calista Flockhart, ...
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Shakespeare in Love(1998)

R
| 2h 3min | Romance / Love, History, Comedy
3.4/5 (with 1,363 votes)

Young Shakespeare is forced to stage his latest comedy, "Romeo and Ethel, the Pirate's Daughter," before it's even written. When a lovely noblewoman auditions for a role, they fall into forbidden love -- and his play finds a new life (and title). As their relationship progresses, Shakespeare's comedy soon transforms into tragedy.

Directed by John Madden - With Joseph Fiennes, Gwyneth Paltrow, Geoffrey Rush, Colin Firth, Ben Affleck, Judi Dench, ...
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The Damned(1969)

2h 36min | War, Drama
3.7/5 (with 82 votes)

In the early days of Nazi Germany, a powerful noble family must adjust to life under the new dictatorship regime.

Directed by Luchino Visconti - With Dirk Bogarde, Ingrid Thulin, Helmut Griem, Helmut Berger, Renaud Verley, Umberto Orsini, ...

Tootsie(1982)

PG
| 1h 56min | Comedy, Romance / Love
3.6/5 (with 748 votes)

When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego - Dorothy Michaels - in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.

Directed by Sydney Pollack - With Dustin Hoffman, Jessica Lange, Teri Garr, Charles Durning, Bill Murray, Dabney Coleman, ...
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The Rocky Horror Picture Show(1975)

R
| 1h 40min | Comedy, Science Fiction, Fantasy, Horror
3.8/5 (with 1,228 votes)

Sweethearts Brad and Janet, stuck with a flat tire during a storm, discover the eerie mansion of Dr. Frank-N-Furter, a transvestite scientist. As their innocence is lost, Brad and Janet meet a houseful of wild characters, including a rocking biker and a creepy butler. Through elaborate dances and rock songs, Frank-N-Furter unveils his latest creation: a muscular man named 'Rockv'.

Directed by Jim Sharman - With Tim Curry, Nell Campbell, Peter Hinwood, Barry Bostwick, Charles Gray, Jonathan Adams, ...
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House at the End of the Street(2012)

PG-13
| 1h 41min | Horror, Thriller
2.9/5 (with 804 votes)

A mother and daughter move to a new town and find themselves living next door to a house where a young girl murdered her parents. When the daughter befriends the surviving son, she learns the story is far from over.

Directed by Mark Tonderai - With Jennifer Lawrence, Max Thieriot, Gil Bellows, Elisabeth Shue, Nolan Gerard Funk, Joy Tanner, ...
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Cannonball Run II(1984)

PG
| 1h 48min | Action, Comedy
2.7/5 (with 132 votes)

When a wealthy sheikh puts up $1 million in prize money for a cross-country car race, there is one person crazy enough to hit the road hard with wheels spinning fast. Legendary driver J.J McClure enters the competition along with his friend Victor and together they set off across the American landscape in a madcap action-adventure destined to test their wits and automobile skills.

Directed by Hal Needham - With Burt Reynolds, Dom DeLuise, Dean Martin, Sammy Davis Jr., Telly Savalas, Shirley MacLaine, ...
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100 Girls(2000)

R
| 1h 34min | Comedy, Drama, Romance / Love
2.9/5 (with 190 votes)

This sexy, teen-comedy is about a freshman, Matthew, at college who meets his dream girl in a dorm elevator during a blackout. He never sees her face, but instantly falls in love. In the morning, the power is restored, but the "dream girl" has vanished. All Matthew knows is that she lives in an all-girls dorm. He sets out on a semester-long journey to find his mystery girl amongst a hundred female suspects. Could it be Wendy? Dora? Arlene? Patty? Cynthia? Or the 95 other girls, any of whom could have been in that elevator with Matthew.

Directed by Michael Davis - With Jonathan Tucker, Emmanuelle Chriqui, James DeBello, Katherine Heigl, Larisa Oleynik, Jaime Pressly, ...
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Bringing Up Baby(1938)

NR
| 1h 42min | Comedy, Romance / Love
3.8/5 (with 442 votes)

David Huxley is waiting to get a bone he needs for his museum collection. Through a series of strange circumstances, he meets Susan Vance, and the duo have a series of misadventures which include a leopard called Baby.

Directed by Howard Hawks - With Katharine Hepburn, Cary Grant, Charles Ruggles, Walter Catlett, May Robson, Fritz Feld, ...
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Psycho III(1986)

R
| 1h 33min | Horror, Thriller, Mystery
2.8/5 (with 155 votes)

Norman Bates is still running his little motel, and he has kept the dressed skeleton he calls 'mother'. One day a nosey journalist comes to see him to ask questions about his past.

Directed by Anthony Perkins - With Anthony Perkins, Diana Scarwid, Jeff Fahey, Roberta Maxwell, Donovan Scott, Katt Shea, ...
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Psycho IV: The Beginning(1990)

1h 36min | Horror, Mystery, Thriller
2.8/5 (with 101 votes)

Norman Bates recalls his childhood with his abusive mother on a radio show about boys who commit matricide.

Directed by Mick Garris - With Anthony Perkins, Henry Thomas, Olivia Hussey, CCH Pounder, Warren Frost, John Landis, ...

Just One of the Guys(1985)

PG-13
| 1h 40min | Comedy, Romance / Love
3.2/5 (with 124 votes)

When Terry Griffith loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy, helps her pass as a guy so well that she is soon making friends with the boys at school, including the attractive Rick, who becomes her new best friend. But her gender-swapping makes things difficult when she falls in love with him.

Directed by Lisa Gottlieb - With Joyce Hyser, Clayton Rohner, Billy Jayne, William Zabka, Sherilyn Fenn, Toni Hudson, ...
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Sorority Boys(2002)

R
| 1h 33min | Comedy
2.7/5 (with 97 votes)

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.

Directed by Wallace Wolodarsky - With Barry Watson, Michael Rosenbaum, Harland Williams, Heather Matarazzo, Melissa Sagemiller, Brad Beyer, ...
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Ladybugs(1992)

PG-13
| 1h 30min | Comedy, Kids & Family
2.9/5 (with 71 votes)

To climb the corporate ladder to success, a guy agrees to coach the company's all girl soccer team with the help of his secret weapon: his fiancee's son.

Directed by Sidney J. Furie - With Rodney Dangerfield, Jackée Harry, Jonathan Brandis, Vinessa Shaw, Ilene Graff, Anne Lockhart, ...
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Dragonslayer(1981)

PG
| 1h 48min | Fantasy, Adventure
3.3/5 (with 112 votes)

The sorcerer and his apprentice Galen are on a mission to kill an evil dragon to save the King’s daughter from being sacrificed according to a pact that the King himself made with the dragon to protect his kingdom.

Directed by Matthew Robbins - With Peter MacNicol, Caitlin Clarke, Ralph Richardson, John Hallam, Peter Eyre, Sydney Bromley, ...
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Labyrinth of Passion(1982)

1h 40min | Comedy, Drama, Romance / Love
3.1/5 (with 52 votes)

An array of outrageous people, including a desperate nymphomaniac and a terrorist with an acute sense of smell, seek love and happiness in Madrid.

Directed by Pedro Almodóvar - With Cecilia Roth, Helga Liné, Antonio Banderas, Agustín Almodóvar, Imanol Arias, Pedro Almodóvar, ...
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Motocrossed(2001)

G
| 1h 31min | TV Movie, Kids & Family, Comedy, Drama, Romance / Love
3.1/5 (with 37 votes)

Motocrossed! is a 2001 Disney Channel Original Movie (based on the Shakespeare play Twelfth Night), about a girl named Andrea Carson who loves motocross, despite the fact that her father finds her unsuited for the sport, being that she is "just a girl". When her twin brother Andrew breaks his leg just before a big race, their father is forced to go to Europe to find a replacement rider. In the meantime, Andrea secretly races in Andrew's place with her mother's help.

Directed by Steve Boyum - With Alana Austin, Riley Smith, Mary-Margaret Humes, Trever O'Brien, Timothy Carhart, Scott Terra, ...
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Juwanna Mann(2002)

PG-13
| 1h 31min | Comedy
2.5/5 (with 40 votes)

A basketball star is booted out of the NBA when his on-court antics go too far, so he poses as a woman and joins the WUBA.

Directed by Jesse Vaughan - With Miguel A. Núñez, Vivica A. Fox, Kevin Pollak, Tommy Davidson, Kim Wayans, Ginuwine, ...
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My Life in Pink(1997)

R
| 1h 28min | Drama, Comedy
3.5/5 (with 46 votes)

Seven year old Ludovic (Ludo) is transgender and believes god has made a mistake. Assigned male, the film follows her difficult journey to get her family to see what seems obvious to her - that she is a girl.

Directed by Alain Berliner - With Jean-Philippe Écoffey, Michèle Laroque, Hélène Vincent, Georges Du Fresne, Daniel Hanssens, Laurence Bibot, ...
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A Night at the Opera(1935)

NR
| 1h 36min | Comedy, Music
3.7/5 (with 206 votes)

The Marx Brothers take on high society and the opera world to bring two lovers together. A sly business manager and two wacky friends of two opera singers help them achieve success while humiliating their stuffy and snobbish enemies.

Directed by Sam Wood - With Groucho Marx, Chico Marx, Harpo Marx, Kitty Carlisle, Allan Jones, Margaret Dumont, ...
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Carry On Screaming(1966)

1h 27min | Comedy, Horror
3.3/5 (with 44 votes)

The sinister Dr Watt has an evil scheme going. He's kidnapping beautiful young women and turning them into mannequins to sell to local stores. Fortunately for Dr Watt, Detective-Sergeant Bung is on the case, and he doesn't have a clue! In this send up of the Hammer Horror movies, there are send-ups of all the horror greats from Frankenstein to Dr Jekyl and Mr Hyde.

Directed by Gerald Thomas - With Harry H. Corbett, Kenneth Williams, Jim Dale, Charles Hawtrey, Fenella Fielding, Joan Sims, ...

Our Hospitality(1923)

NR
| 1h 13min | Comedy, Romance / Love
3.8/5 (with 106 votes)

A man returns to his Appalachian homestead. On the trip, he falls for a young woman. The only problem is her family has vowed to kill every member of his family.

Directed by Buster Keaton, John G. Blystone - With Buster Keaton, Joe Keaton, Natalie Talmadge, Joe Roberts, Edward Coxen

Glitch!(1988)

1h 28min | Comedy
1.0/5 (with 1 vote)

Two thieves rob a large fancy house when the owner is away. But when a visitor mistakes them for the owner, and they find out about a casting party mis-scheduled for that day, they decide to stick around for the fun. There's only one small problem, a little glitch in their plan. The real owners owe some bad dudes a lot of money, and they show up to collect.

Directed by Nikos Mastorakis

Abbott and Costello Meet the Killer, Boris Karloff(1949)

1h 24min | Comedy, Horror, Crime, Mystery, Thriller
3.4/5 (with 22 votes)

Lost Caverns Hotel bellhop Freddie Phillips is suspected of murder. Swami Talpur tries to hypnotize Freddie into confessing, but Freddie is too stupid for the plot to work. Inspector Wellman uses Freddie to get the killer (and it isn't the Swami).

Directed by Charles Barton - With Bud Abbott, Lou Costello, Boris Karloff, James Flavin, Alan Mowbray, Claire Du Brey, ...

Boarding School(2018)

R
| 1h 51min | Horror, Mystery
3.2/5 (with 98 votes)

When troubled 12-year-old Jacob Felsen is sent away to boarding school, he enters every kid’s worst nightmare: a creepy old mansion, deserted except for six other teenage misfits and two menacing and mysterious teachers. As events become increasingly horrific, Jacob must conquer his fears to find the strength to survive.

Directed by Boaz Yakin - With Will Patton
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