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Barbra Streisand in 'Yentl' (1983) -

Barbra Streisand plays a Jewish girl in Poland who disguises herself as a boy so that she can enter a religious school. Streisand also directed, co-wrote, and co-produced the film.

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Jared Leto in 'Dallas Buyers Club' (2013) -

Leto won an Academy Award for Best Supporting Actor for his role as trans woman Rayon.

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Julie Andrews in 'Victor/Victoria' (1982) -

Julie Andrews plays a woman who pretends to be a man impersonating a woman. And for her efforts, she was nominated for the Oscar for Best Actress.

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Elle Fanning in '3 Generations' (2015) -

The actress plays a teen called Ray, who decides to transition. Naomi Watts stars as his mother, and Susan Sarandon as his grandmother.

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Glenn Close in 'Albert Nobbs' (2011) -

The veteran actress plays the titular Albert Nobbs in this film set in late-19th-century Ireland. Close was nominated for the Academy Award for Best Actress for the role.

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Linda Hunt in 'The Year of Living Dangerously' (1982) -

Linda Hunt plays a Chinese-American photographer with dwarfism in this Australian movie. The role earned her an Oscar for Best Actress in a Supporting Role.

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Robin Williams in 'Mrs. Doubtfire' (1993) -

The late actor played Daniel, a divorced actor who disguises himself as a housekeeper so that he can spend time with his children while working for his ex-wife.

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John Lithgow in 'The World According to Garp' (1982) -

The actor plays Roberta Muldoon, a transgender resident of a woman's shelter. Lithgow was nominated for the Academy Award for Best Supporting Actor for his efforts.

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Tony Curtis and Jack Lemmon in 'Some Like It Hot' (1959) -

This iconic movie starring Marilyn Monroe has Tony Curtis and Jack Lemmon playing two musicians who disguise themselves as women. For his efforts, Lemmon was nominated for the Oscar for Best Actor.

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Hilary Swank in 'Boys Don’t Cry' (1999) -

The actress plays real-life transgender man Brandon Teena, who lives in rural Nebraska. Swank won her first Oscar for the role.

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Tilda Swinton in 'Orlando' (1992) -

Swinton plays an androgynous young nobleman, who later in the movie becomes a woman.

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John Travolta in 'Hairspray' (2007) -

This remake of the 1988 John Waters' movie stars John Travolta as the protagonist's mom, Edna Turnblad.

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Martin Lawrence in 'Big Momma’s House' (2000) -

Martin Lawrence plays FBI agent Malcolm Turner, who disguises himself as an elderly woman in order to solve a crime. The film spawned two sequels.

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The Wayans Brothers in 'White Chicks' (2004) -

Probably one of their most famous performances, the movie is about two undercover FBI agents who disguise themselves as women to solve a crime.

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Dustin Hoffman in 'Tootsie' (1982) -

In this film, Dustin Hoffman plays one of his most iconic roles as a failed actor, who disguises himself as a woman to land a role. For his efforts, he was nominated for the Academy Award for Best Actor.

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Amanda Bynes in 'She's the Man' (2006) -

In this movie, we can see Amanda Bynes as Viola, a girl who disguises herself as her brother so that she can play soccer on her college's men's team. The film was inspired by William Shakespeare's 'Twelfth Night.'

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Tyler Perry in 'Diary of a Mad Black Woman' (2005) -

Tyler Perry plays Mabel "Madea" Simmons, a character based on the actor's mother and aunt. Of course, the character has made appearances in countless plays, movies, and on TV,

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Cillian Murphy in 'Breakfast on Pluto' (2005) -

The actor plays a trans woman named "Kitten" Braden, who moves from Ireland to London in the 1970s.

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Patrick Swayze in 'To Wong Foo, Thanks for Everything! Julie Newmar' (1995) -

The late actor played drag queen Vida Boheme (left) in this 1995 comedy.

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Wesley Snipes in 'To Wong Foo, Thanks for Everything! Julie Newmar' (1995) -

But there were more drag queens played by famous actors. One of them was Noxeema Jackson, played by Wesley Snipes.

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John Leguizamo in 'To Wong Foo, Thanks for Everything! Julie Newmar' (1995) -

And then we have John Leguizamo as Chi-Chi Rodriguez.

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Eddie Murphy in 'The Nutty Professor' (1996) -

Eddie Murphy plays a number of characters in this movie and its sequels. One of them is Mama Anna Klump.

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Eddie Murphy in 'The Nutty Professor' (1996) -

Another female character played by the actor is yet another family member: Granny Klump.

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Eddie Redmayne in 'The Danish Girl' (2015) -

Eddie Redmayne plays real-life painter Lili Elbe, in 1920s Copenhagen. She was one of the first known individuals to undergo sex reassignment surgery. Redmayne was nominated for the Oscar for Best Actor for the role.

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Cate Blanchett in 'I'm Not There' (2007) -

The actress plays iconic singer-songwriter Bob Dylan in this film. She was even nominated for the Oscar for Best Supporting Actress for the role.

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Rupert Everett in 'St. Trinian's' (2007) -

St. Trinian's, a school for poorly behaved young women, is run by headmistress Camilla Dagey Fritton, played by Rupert Everett.

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Adam Sandler in 'Jack and Jill' (2011) -

Adam Sandler plays twins Jack and Jill in this comedy. But the movie wasn't very well received, is and considered by many to be one of (if not the) worst film Sandler has ever starred in.

Sources: (Instantly Modern)

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