Men Who Played Women On The Big Screen

1. Dustin Hoffman - Tootsie (1982)

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Dustin Hoffman won an Academy Award for this role and it was well earned! He plays an out of work actor who disguises himself as a woman in order to get a job. This character of Dorothy Michaels is ditzy and completely lovable. Hoffman made this role funny but never mean spirited.

2. Robin Williams - Mrs. Doubtfire (1993)

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Arguably one of Robin William's best films. He plays a divorced dad who's desperately missing his kids. Attempting to see more of them, he disguises himself as an old woman babysitter. Williams' hilarious and touching performance earned him a Golden Globe Award for Best Actor.

3. Tom Hanks - Bosom Buddies (1980-1982)

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Tom Hanks plays Kip Wilson, who alongside his friend, dresses as woman to be able to live in an apartment available only to women. Hanks is such a lovable character in this role, he's excitable but very awkward! There's so much heart in this movie, showing the ups and downs of trying to find his place in the world.

4. Eddie Murphy - Norbit (2007)

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Eddie Murphy plays 3 roles in Norbit. He plays both Norbit and his abusive wife, Rasputia. She's a very exaggerated character and definitely annoying! Murphy does a good job still with his performance. In fact, it's been said that Murphy is the only thing that keeps this movie from being a disaster.

5. Tony Curtis - Some Like It Hot (1959)

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Curtis plays the role of Joe, who flees with his friend after witnessing a gangland massacre. Joe becomes Josephine, disguised as a woman to join an all-girl band. His performance was both funny and heartfelt. He was nominated for an Academy Award for Best Actor!

6. Jack Lemmon - Some Like It Hot (1959)

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Lemmon plays the other half of the duo with his character Jerry. Out of the two friends, Jerry is much more shy and serious. However, he brings a lot of energy and charisma to the role! Their use of wits to survive in their new disguises is comical and genius.

7. Tyler Perry - Madea series (2005-2019)

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Perry's portrayal of the iconic Madea Simmons has been loved by both critics and audiences. He even won numerous awards for this role! Madea is a no-nonsense, hard-faced, gun-toting grandma, well known for her catchphrases, such as "I don't play that".

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

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This movie definitely celebrates diversity and acceptance. Swayze's performance as Vida Boheme, a middle-aged drag queen, is the highlight of the film and helps to make it a classic. Vida is on her way to a drag pageant in Hollywood, when alongside her two drag queen friends, they find themselves stranded in the middle of nowhere.

9. John Travolta - Hairspray (2007)

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John Travolta surprised everyone with this amazing role of Edna Turnblad. He brings so much depth and humanity, whilst still making it funny! Edna's an overweight lady who's often made fun of for her size. Despite this, she's super loving and supportive of her daughter Tracy, determined to help her achieve her dreams.

10. Shawn and Marlon Wayans - White Chicks (2004)

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The Wayans brothers play Kevin and Marcus Copeland, 2 FBI agents who are given an undercover mission as 2 rich white women named Brittany and Tiffany Wilson to prevent a kidnapping. Their portrayal of the girls is simply hilarious! The brothers also co-wrote the screenplay along with director Keenen Ivory.

11. Eddie Redmayne - The Danish Girl (2015)

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This lovely but heart-wrenching movie tells the tale of Lili Elbe, played by Redmayne, as one of the first ever people to have gender reassignment surgery. Since, Redmayne has said that he would now turn down this role, believing it should have been given to a transgender actor.

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

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Wesley Snipes plays the friend of Patrick Swayze with the role of Noxeema Jackson. Noxeema is a highly confident and outgoing queen, always comfortable being herself. This character is a natural born leader and acts as the glue of the friendship group.

13. Martin Lawrence - Big Momma's House (2000-2011)

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Lawrence plays the FBI agent Malcolm, who's forced to disguise as the grandma of his ex-girlfriend in attempt to protect her and her child. Big Momma's House is definitely a classic comedy movie. It's made so much better by Lawrence's hilarious performance.

14. Billy Crystal - Soap (1977-1981)

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Crystal starred as Jodie Dallas in this groundbreaking sitcom. For it's time, it was extremely progressive and helped to open up the beginning of more LGBTQ+ representation on TV. Jodie was 1 of the first ever openly gay characters on American TV and Crystal played this perfectly. The character is relatable, funny, kind and clever.

15. Tim Curry - The Rocky Horror Picture Show (1975)

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Personally, I don't think anybody can rock the fishnet tights better than Tim Curry. This is the breakthrough role that made Curry and you can see why! He plays Dr. Frank-N-Furter, a mad scientist who works to build the muscle monster named Rocky. Curry can sing, act, dance and dress to perfection.

16. Terence Stamp - The Adventures of Priscilla, Queen of the Desert (1994)

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Stamp's character of Bernadette Bassenger is truly a masterpiece. Based in the Australian Outback, Bernadette is a trans woman travelling with 2 drag queens. Whilst the film is a light hearted comedy, it really highlights her struggles with identity and battles with her insecurities as she tries to fit in. Stamp is the perfect person for the role, bringing humour but is still able to tug at your heartstrings.

17. Nathan Lane - The Birdcage (1996)

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The character of Albert Goldman, played by Nathan Lane, is both touching and hilarious. He is the partner of gay nightclub owner Armand, who's son becomes engaged to a conservative woman. To help Armand win her parent's approval, they decide to pretend to be straight.

18. Jared Leto - Dallas Buyers Club (2013)

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If you haven't seen this movie, watch it! This heartbreaking true story follows Ron, a straight man diagnosed with HIV in the 80's. Leto plays Rayon, a trans woman who's also battling with HIV. The pair become unlikely friends and business partners, smuggling and selling unapproved HIV drugs to treat themselves and others in need. Leto lost 30 pounds and worked with trans women to research and understand the role. He was the 1st openly gay actor to win an Academy Award for acting.

19. Jamie Foxx - In Living Color (TV series, 1990-1994)

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Jamie Foxx plays a few different characters in this sketch comedy. Albeit, they are definitely controversial and likely wouldn't land well if released today! 1 of his roles was Wanda, who was self-important, bossy and foul-mouthed. Another was Ugly Wanda, a homeless lady who is also foul-mouthed, loud and opinionated.

20. Adam Sandler - Jack and Jill (2011)

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I don't know about you, but I had never even heard of this film! It's not surprising when you look at the reviews, it even won 10 Razzie Awards such as Worst Picture and Worst Actor! Definitely not one of Sandler's best roles. He plays twins Jack and Jill. Jill is ditzy and needy, always irritating Jack. Some people have found it offensive, whilst there are a few who say it is funny.

21. Cillian Murphy - Breakfast on Pluto (2005)

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Murphy brings a surprising edge to his role of Kitten, who's a trans woman living in a little Irish town in the 60's. Of course, this is shown to be highly difficult for her and she dreams of moving away to London to sing. This movie is a beautiful reminder to fight for what your heart tells you, regardless of the noise around you.

22. Divine - Hairspray (1988)

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Divine had his breakthrough when he played the role of Edna Turnblad in the 1988 Hairspray movie. He brought flamboyance, humour and humanity to the role. People consider this to be one of the best performances in film. Sadly, Divine passed away just 3 weeks after the release of Hairspray.

23. RuPaul - The Brandy Brunch Movie (1995)

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RuPaul starred as Mrs. Cummings and it's no surprise that he pulled it off perfectly. Mrs. Cummings is the mum of Jan Brady, she's supportive but super strict, pressuring Jan to follow in her sisters footsteps. Critics have said that RuPaul helped to make the character of Mrs. Cummings more sympathetic.

24. Jaye Davidson - The Crying Game (1992)

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Davidson's role is the trans woman, Dil, who's a gentle and caring character. She becomes involved with an IRA volunteer holding her hostage and helps him to view the world differently. Davidson's portrayal of Dil was groundbreaking, altering to way that many viewers saw trans people, putting them into a far more positive light.

25. Johnny Depp - Ed Wood (1994)

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Depp plays Ed Wood, also known as the drag woman Dolores. She is a struggling filmmaker, working hard to be accepted for who she is. Depp helps to portray the struggles of acceptance, love and identity, perfectly demonstrating Dolores' vulnerability.

26. Jude Law - Rage (2009)

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Jude Law completely brings his character of Minx to life. This Movie is based on the book by Sally Potter, telling the story of Russian drag queen Minx, who's an activist trying to overthrow the government. This political thriller makes you think! And, it really shows the range that Jude Law has, as he wholeheartedly commits to this role.

27. Quentin Crisp - Orlando (1992)

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Quentin Crisp was 83 when he played the role of Queen Elizabeth I in this movie. He is known as a gay icon and this performance helped to raise awareness of LGBTQ+ issues back in 1992. The movie is based on the novel by Virginia Woolf, Crisp plays a genderfluid character, who's been alive for centuries, having experienced a number of adventures.

28.  Rupert Everett - St Trinians (2007)

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Rupert Everett stars as Camilla Fritton, the lovable headmistress of the all-girls school St. Trinian's. Based in England, Camilla is eccentric and lively, but highly protective of her students, willing to go to lengths to keep them safe. Everett was highly praised for this role and was nominated for an Empire Award for Best Actor.

29. Woody Harrelson - Anger Management (2003)

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Woody Harrelson acts as Galaxia in this movie, who's a transvestite prostitute. The character of Galaxia is extravagant and camp, full of energy and humor. However, the movie shows that she is often misunderstood. Harrelson makes her a highly lovable character.

30. Arnold Schwarzenegger - Junior (1994)

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This movie was nominated for multiple awards. Schwarzenegger's role is Dr. Alexander Hesse, who is working as a fertility researcher. His experiment proves successful and he is able to become pregnant and give birth to a healthy baby. Despite being ridiculed, Dr. Hesse ignores the noise. It's said that this movie helped raise awareness of LGBTQ+ issues.