51 Actors Who Cross-Dressed for Film

by Sarah Long
Sep 18, 2017 at 4:00 p.m. ET

The fight for transgender rights is a fairly new frontier. Yes, being a trans person is nothing new, but until the past couple years, discussing transgender people's place in society was fairly taboo.

Thankfully, that is all starting to change. Sure, we still have a really long way to go in our fight for equality, but thanks to brave trans men and women who are willing to go public (we're looking at you, Laverne Cox), the trans community is definitely more visible. 

This is all very new, but gender-bending in Hollywood has been going on for a lot longer. 

Whether it's for comedic effect (like Robin Williams in Mrs. Doubtfire), or to tell gut-wrenching tale ripped straight from real life (like Jared Leto in Dallas Buyers Club), characters in literature, plays and films have been cross-dressing for centuries... and so have actors. Here are 51 of our film favorites.

Originally published April 2015. Updated September 2017.

1 /49: Gwyneth Paltrow

1/49 :Gwyneth Paltrow

Love or hate Gwyneth Paltrow, we all loved Shakespeare in Love. In the film, Paltrow plays Viola De Lesseps, a woman with a dream of taking to the Elizabethan stage in a time when only men were permitted to be actors. Using the name Thomas Kent and a little faux facial hair, she auditions for Shakespeare and gets the part!

2 /49: Ted Levine

2/49 :Ted Levine

Many of us couldn't sleep for years after seeing The Silence of the Lambs, mostly because of the psychotic Jame Gumb (Ted Levine). This guy was so desperate to be seen as a woman, he wanted to create a suit out of a woman's flesh. 

3 /49: Robin Williams

3/49 :Robin Williams

Who can forget Robin Williams as Mrs. Doubtfire? So desperate to spend time with his kids after a divorce, he disguises himself as the perfect nanny, even fooling his ex-wife (Sally Field). We miss you, Robin!

4 /49: Mulan

4/49 :Mulan

Mulan tells the story of an ancient Chinese warrior woman who disguises herself as a man and goes off to war. A live-action version of the story was recently announced by Disney. 

5 /49: John Lithgow

5/49 :John Lithgow

Based on the novel by John Irving, The World According to Garp is a complex film dealing with women's issues in the late 1970s. Lost in the melee is Roberta (John Lithgow), a transgender woman who becomes Garp's (Robin Williams) most cherished friend. 

6 /49: Jared Leto

6/49 :Jared Leto

In Dallas Buyers Club, Jared Leto plays Rayon, an ailing man with a wavering will to live. This fearless yet tragic performance by Leto rightly earned him an Oscar for Best Supporting Actor.

7 /49: Tilda Swinton

7/49 :Tilda Swinton

Orlando (Tilda Swinton) is a young man commanded by Queen Elizabeth I to remain young forever. Miraculously, Orlando survives through multiple centuries, even changing gender. This beautiful, thought-provoking film is based on the novel by Virginia Woolf. 

8 /49: Barbra Streisand

8/49 :Barbra Streisand

Barbra Streisand plays Yentl, a Jewish woman who dresses as a man to pursue her religious studies at a time when women were discouraged from doing so.

9 /49: Ed Wood

9/49 :Ed Wood

A movie ahead of its time, Glen or Glenda, from 1953, tells the story of a man named Glen (Ed Wood), who prefers to wear women's clothing but is afraid of being found out by his fiancée, Barbara (Dolores Fuller).

10 /49: Jaye Davidson

10/49 :Jaye Davidson

Many audiences were surprised when they watched The Crying Game in 1992, thinking the character Dil (Jaye Davidson) was a beautiful young woman. Turns out, Dil's situation is a bit more interesting. 

11 /49: Julie Andrews

11/49 :Julie Andrews

In Victor Victoria, Julie Andrews plays Victoria Grant, a down-on-her-luck singer who gets a job as a female impersonator. That's right: she's a woman pretending to be man pretending to be a woman. 

12 /49: Amanda Bynes

12/49 :Amanda Bynes

In She's the Man, soccer enthusiast Viola (Amanda Bynes) impersonates her brother at his boarding school, but gets more than she bargained for when she falls for her brother's hot roommate, Duke (Channing Tatum).

13 /49: John Lone

13/49 :John Lone

In M. Butterfly, a reimagining of the famous opera, Madame Butterfly, Song (John Lone) is an opera singer with a secret.

14 /49: Chiwetel Ejiofor

14/49 :Chiwetel Ejiofor

Kinky Boots explores themes of diversity and tolerance when a drag queen, Lola (Chiwetel Ejiofor), helps a young man save his family shoe business by catering to men who love fetish footwear.

15 /49: Hilary Swank

15/49 :Hilary Swank

In the groundbreaking film Boys Don't Cry, which is based on a true story, Brandon Teena (Hilary Swank) decides to live as a boy in a tiny Nebraska town with tragic consequences. Hilary Swank won an Oscar for the role. 

16 /49: Tim Curry

16/49 :Tim Curry

It's pretty amazing that The Rocky Horror Picture Show continues to run at midnight showings across the country 40 years after it was released. Its lasting popularity is largely due to the mad scientist, Dr. Frank-N-Furter (Tim Curry), who refers to himself as a "sweet transvestite from Transsexual, Transylvania."

17 /49: Billy Crudup

17/49 :Billy Crudup

In Stage Beauty, Ned Kynaston (Billy Crudup) has made a successful stage career performing as a woman in classical theatrical roles. But Ned may find himself out of work when Maria Hughes (Claire Danes) is permitted to perform as a female character onstage.

18 /49: Tony Curtis & Jack Lemmon

18/49 :Tony Curtis & Jack Lemmon

In the comedy Some Like It Hot, musicians Joe and Jerry (Tony Curtis and Jack Lemmon) hide in plain sight as women when a fearsome gangster comes after them. 

19 /49: Anthony Perkins

19/49 :Anthony Perkins

In the classic Hitchcock film Psycho, the mentally disturbed Norman Bates just can't let go of his mother and even dresses up as the deceased woman. 

20 /49: Dustin Hoffman

20/49 :Dustin Hoffman

Tootsie, from 1982, proves that some actors will do anything to get a role. Michael Dorsey (Dustin Hoffman) pretends to be Dorothy Michaels so he can get a coveted role on a soap opera. Things get complicated, however, when Michael falls for his leading lady, Julie (Jessica Lange), who thinks he's really a she.

21 /49: Samantha Barks

21/49 :Samantha Barks

With very few options to stay alive, Éponine (Samantha Barks) attempts to pass as a male soldier to join the French Revolution in Les Misérables

22 /49: Willem Dafoe

22/49 :Willem Dafoe

Dafoe plays FBI agent Paul Smecker and disguises himself as a hooker to infiltrate an organized crime member's mansion in 1999's The Boondock Saints.

23 /49: Ving Rhames

23/49 :Ving Rhames

In Holiday Heart, Rhames plays the title character, an ex-con drag queen with a big heart who befriends a single mom.

24 /49: Tyler Perry

24/49 :Tyler Perry

Perry plays Mabel "Madea" Simmons throughout the whole Madea franchise.

25 /49: Tom Hanks

25/49 :Tom Hanks

Before his career really took off, Hanks starred in Bosom Buddies, an early '80s sitcom about two male friends who disguise themselves as women so they can share an apartment.

26 /49: 'To Wong Foo...'

26/49 :'To Wong Foo...'

There was a whole lot of fabulousness in To Wong Foo, Thanks for Everything, Julie Newmar, a tale about the escapades of three traveling drag queens, played by Patrick Swayze, Wesley Snipes and John Leguizamo. 

27/49 :Stephen Dorff

Stephen Dorff as Candy Darling in 1996's I Shot Andy Warhol.

28 /49: Patrick Swayze

28/49 :Patrick Swayze

Patrick Swayze in To Wong Foo, Thanks for Everything, Julie Newmar.

29 /49: John Leguizamo

29/49 :John Leguizamo

John Leguizamo in To Wong Foo.

30 /49: Kurt Russell

30/49 :Kurt Russell

"I was looking in the mirror at a really ugly version of my mother," Russell said of dressing in drag for 1989's Tango & Cash.

31 /49: Neil Patrick Harris

31/49 :Neil Patrick Harris

NPH was nothing short of legend — wait for it — dary in Broadway's Hedwig and the Angry Inch.

32 /49: Nathan Lane

32/49 :Nathan Lane

In 1996's The Birdcage, Lane plays Albert, who dresses as a woman to mask his homosexuality from his visiting in-laws-to-be.

33 /49: Michael Rosenbaum

33/49 :Michael Rosenbaum

Michael Rosenbaum in Sorority Boys.

34 /49: Harland Williams

34/49 :Harland Williams

Harland Williams in Sorority Boys.

35 /49: Michael J. Fox

35/49 :Michael J. Fox

In Back to the Future Part II, Fox played both Marty McFly and Marty McFly's daughter, Marlene.

36 /49: Michael C. Hall

36/49 :Michael C. Hall

Hall, aka Showtime's Dexter, also took his turn as Hedwig in 2014.

37 /49: Martin Lawrence

37/49 :Martin Lawrence

Lawrence plays a master of disguise in Big Momma's House.

38 /49: Liev Schreiber

38/49 :Liev Schreiber

"I completely became giddy in a strange way the moment I put on the dress," Schreiber told People magazine of playing a cross-dressing ex-Marine in 2009's Taking Woodstock.

39/49 :Jude Law

In 2009's Rage, Law played Minx, a trans model.

40 /49: Johnny Depp

40/49 :Johnny Depp

In Before Night Falls, Johnny Depp only appears on-screen for a few minutes playing two roles: a sadistic prison warden and a blonde-wigged trans woman named Bon Bon.

41 /49: John Travolta

41/49 :John Travolta

Travolta as Edna Turnblad in the 2007 remake of the musical Hairspray.

42 /49: John Cameron Mitchell

42/49 :John Cameron Mitchell

Mitchell, who you might also know as Hannah's dearly departed boss on Girls, wrote Hedwig and was its original star.

43/49 :Guy Pearce

Guy Pearce in The Adventures of Priscilla, Queen of the Desert.

44 /49: Glenn Close

44/49 :Glenn Close

In Albert Nobbs, Close plays a woman who dresses as a man to secure employment in 19th-century Ireland.

45 /49: Gael García Bernal

45/49 :Gael García Bernal

Bernal played a drag queen in 2004's Bad Education.

46 /49: David Duchovny

46/49 :David Duchovny

On Twin Peaks, Duchovny played DEA agent Denise Bryson, a transgender woman.

47/49 :Cate Blanchett

Blanchett depicted one facet of Bob Dylan's public persona in 2007's I'm Not There.

48 /49: Arnold Schwarzenegger

48/49 :Arnold Schwarzenegger

In Junior, Schwarzenegger is a pregnant man who disguises himself as a woman so he can hide in a women's shelter.

49 /49: Angelina Jolie

49/49 :Angelina Jolie

In Salt, Jolie plays a CIA agent accused of being a Russian spy who disguises herself as a male naval officer.