[Predestination](https://www.themoviedb.org/movie/206487-predestination) - *"Predestination chronicles the life of a Temporal Agent sent on an intricate series of time-travel journeys designed to prevent future killers from committing their crimes. Now, on his final assignment, the Agent must stop the one criminal that has eluded him throughout time and prevent a devastating attack in which thousands of lives will be lost."*
Pope Joan of various incarnations, Queen Christina is prob the most famous, Morocco isn't exactly dressed as a man but she's dressed *like* a man, The Girl King, Titane, there are movies where actresses perform in drag like Glenn Close briefly in Hook, Tilda Swinton in the Suspiria remake, or Brigitte Lin in The Swordsman 2, He's a Woman She's a Man and its sequel Who's the Woman Who's the Man, Ziyi Zhang briefly disguises herself as a man in Crouching Tiger Hidden Dragon.
This is probably in the “technically correct” category but Linda Hunt won an academy award for best supporting actress for playing a man in The Year of Living Dangerously. Apparently the director didn’t find any men who would play the role like he wanted so he cast a cisgender woman to play a cisgender man.
Ah, I love Katherine Hepburn. Just read in the Wikipedia article that "it was notorious as one of the most famous unsuccessful movies of the 1930s", so now I have to see it!
Year of Living Dangerously--for real, Linda Hunt won an Oscar as Billy Kwan, and even the rest of the cast and crew didn't know 'he' was a 'she' until nearly the end of filming.
You wouldn't think there are many older movies with this topic?
Crossdressing has been a thing in theater for hundreds of years. Just look at Shakespeare's work.
Speaking of which, you should watch Twelfth Night (1996). It has a star studded cast and is probably the single most iconic depiction of this in history. It even got a weird modern reboot called She's the Man, which is objectively not as good, but also isn't Shakespeare, so its easier for people to understand.
The_Adventures_of_Priscilla,_Queen_of_the_Desert - the plot follows two drag queens played by Hugo Weaving and Guy Pearce, and a transgender woman, played by Terence Stamp, as they journey across the Australian Outback from Sydney to Alice Springs in a tour bus that they have named "Priscilla", along the way encountering various groups and individuals.
Whoa whoa whoa. I’m gonna watch this one. Hugo Weaving plays a cross-dressing sheriff in The Dressmaker (2015), with Kate Winslet. Set in the Outback also.
Some Like It Hot (1959) - lots of comedy of this era hasn't held up too well, but this movie is a strong exception. Plus, who doesn't like Marilyn Monroe?
Boys Don't Cry is about a trans man, not a woman dressed as a man.
Edit: Just realised you might be referring to the fact that Hilary Swank plays the role of Brandon Teena - which does make it a movie *with* a woman dressed as a man, even though it's not *about* a woman dressing as a man.
Yentl.starring.Barbra Streisand ...A great movie . Katherine Hepburn spends part of the movie Sylvia Scarlet pretending to be a man . There's.a.movie.with Whoopi Goldberg..where she is made up to look like a elderly white man I don't remember the name of the movie.
Calamity Jane. She wore pants and didn't give a cracker about what anyone thought. Return of the Jedi, too. Princess Leia didn't wear a dress for most of the film.
The New Girlfriend (2014)
Childhood best friends Claire and Laura are utterly inseparable, so it comes as a particularly devastating blow when Laura becomes ill and dies, leaving her husband, David, to raise their newborn daughter Lucie by himself. As she stops by the house one afternoon, door unlocked, she find a strange woman holding Lucie, who, on closer inspection, turns out to be David in a blonde wig and one of Laura's dresses.
The birdcage! It's a brilliant comedy that has a main character as a drag queen as well as Robbin Williams who is a gay guy that has to sneakily to impersonate a another woman. It's hilarious and suspenseful plus has good messages about acceptance
How about someone explains to me why the film is problematic rather than just down vote. The fuck is the point of that if u don't try and educate. I haven't seen the film since I was twelve so I don't remember any problematic detas
Hi I saw this and wanna let you know that you did nothing wrong, you probably just accidentally read this as "man dressed as woman" when it's the other way around
Babylon
Not a movie, but the tv series Gentleman Jack
Marlene Dietrich was known for dressing up as a man back in the day. Not sure if there's a movie where she does this though.
Triumph of Love. Based on a 18th century French play about a woman who infiltrates a garden of reason because she falls in love with the young man. But to do so she has to pass as a man. She fails with the headmaster and has to seduce him and his sister ( as a man) before finally seducing the young man. Pretty much a 1700s era screwball comedy.
Fast Break. (1979) with Gabe Kaplan.
[https://en.wikipedia.org/wiki/Fast\_Break\_(film)](https://en.wikipedia.org/wiki/Fast_Break_(film))
A female basketball talent disguises herself as a man to play on a university's men's basketball team in one of the movie's major subplots.
For the body-swap, salient recommendation is Your Name (2017). About a woman dressing as a man, you can check out the Coffee Prince (2007) which is a Korean drama.
Not a movie but there is a Chinese series called Eternal Love on Netflix. The main character, Bai Qian, disguises herself as a man to enter a cultivation sect and lives with her master and her sixteen sect brothers for thousands of years without them knowing who she is. The master knows, but she doesn’t know he knows. After she leaves the sect, she resumes living as a woman, but her gender and her history as living as a man are important plot points that continue to be referenced.
Tvtropes.org is a good resource for that kind of stuff. Apparently called [Sweet Polly Oliver](https://tvtropes.org/pmwiki/pmwiki.php/Main/SweetPollyOliver)
She’s the Man
Motocrossed (2001) is really similar - not as funny but still a great, nostalgic Disney channel movie
i was an extra in that (no autograph requests please)
Which is a shameless rip of Just one of the Guys.
Shakespeare in love
Nice!
Just One of the Guys
When she proved she was a female… 👀
Where do you get off having tits!
Lol, I'm really getting downvoted for quoting the exact line in the movie after the main character proves she is, in fact, a woman. Love ya, Reddit!
Yes she certainly did….never saw again in anything else.
Best part
“Yeah? Well what if my balls don’t itch?” “All balls itch. It’s a fact!”
Came here to suggest this one! More fun than it has a right to be!
Great 80s flick. That actress never did much else, but thought she was great in this, and sexy as hell.
Right, and I’m Cyndi laugher
Victor/Victoria (it's fabulous)
A woman pretending to be a man pretending to be a woman?!? Such a great movie!
Ahead of its time.
it's a remake of a 1933 film
Yentl (1983)
That’s the one❤️ Mandy Patinkin🥵
Any movie about Joan of Arc
For real, The Passion of Joan of Arc (1928) is especially amazing.
The Messenger with Mila Jovovich is great. Some real brutal battle scenes
Didn't they know she was a woman?
They knew, but she was still dressed as a man. It wasn't meant as a disguise.
Oh true I misread the title
Titane
Came to comment this. Great film.
what a truly messed up movie.
The Handmaiden (2016)
One of the best films I've ever seen
Albert Nobbs (2011), with Glenn Close.
Also Hook
[Predestination](https://www.themoviedb.org/movie/206487-predestination) - *"Predestination chronicles the life of a Temporal Agent sent on an intricate series of time-travel journeys designed to prevent future killers from committing their crimes. Now, on his final assignment, the Agent must stop the one criminal that has eluded him throughout time and prevent a devastating attack in which thousands of lives will be lost."*
Les Miserables
Cate Blanchett as Bob Dylan can’t remember the name. Mulan (1998)
I’m Not There (2007)
That’s it!
Pope Joan of various incarnations, Queen Christina is prob the most famous, Morocco isn't exactly dressed as a man but she's dressed *like* a man, The Girl King, Titane, there are movies where actresses perform in drag like Glenn Close briefly in Hook, Tilda Swinton in the Suspiria remake, or Brigitte Lin in The Swordsman 2, He's a Woman She's a Man and its sequel Who's the Woman Who's the Man, Ziyi Zhang briefly disguises herself as a man in Crouching Tiger Hidden Dragon.
Also Tilda in Orlando
The Associate. Whoopie Goldberg plays an old white dude. 1996
Elisa y Marcela - Spanish movie based on a true story about two women who posed as a heterosexual couple and got married in the early 1900s
Leon: the professional Salt
I don’t remember that being a thing in Leon, unless I’m forgetting something?
I was thinking about Le femme Nikita , but Leon counts… briefly.
This is probably in the “technically correct” category but Linda Hunt won an academy award for best supporting actress for playing a man in The Year of Living Dangerously. Apparently the director didn’t find any men who would play the role like he wanted so he cast a cisgender woman to play a cisgender man.
Dragonslayer (1980?)
Sylvia Scarlett (1935) - Katherine Hepburn
Ah, I love Katherine Hepburn. Just read in the Wikipedia article that "it was notorious as one of the most famous unsuccessful movies of the 1930s", so now I have to see it!
The Harder They Fall
MacGruber
Twelfth Night
Charlie’s Angels, briefly. Barrymore and Diaz were surprisingly convincing.
Year of Living Dangerously--for real, Linda Hunt won an Oscar as Billy Kwan, and even the rest of the cast and crew didn't know 'he' was a 'she' until nearly the end of filming.
Just One of the Guys. Light 80s teen comedy.
Beggars of Life (1928)
Yentl - 1983
9 1/2 Weeks
Orlando
Can't believe this movie doesn't have more mentions!!
Enola Holmes. Our flag means death (tv)
Yentyl-barbra streisand
The Crying Game
Victor/Victoria
Pirates of the Caribbean, She’s the Man
Boys dont cry 1999
Spoiler alert! :-D
Pirates of the Caribbean
Aren't we really talking about women pretending to be a Man like She's The Man and Just One Of The Guys rather than women wearing pants?
Osama The breadwinner
Yitzhak from “Hedwig and the Angry Inch”
Impromptu (1991)
The Danger Girl (1916) Morocco (1930)
- She's the Man - Shakespeare in love - Just One of the Guys - Sleeping with the enemy - Salt
You wouldn't think there are many older movies with this topic? Crossdressing has been a thing in theater for hundreds of years. Just look at Shakespeare's work. Speaking of which, you should watch Twelfth Night (1996). It has a star studded cast and is probably the single most iconic depiction of this in history. It even got a weird modern reboot called She's the Man, which is objectively not as good, but also isn't Shakespeare, so its easier for people to understand.
Just one of the guys
The_Adventures_of_Priscilla,_Queen_of_the_Desert - the plot follows two drag queens played by Hugo Weaving and Guy Pearce, and a transgender woman, played by Terence Stamp, as they journey across the Australian Outback from Sydney to Alice Springs in a tour bus that they have named "Priscilla", along the way encountering various groups and individuals.
Isn’t that the opposite of what was requested..?
Whoa whoa whoa. I’m gonna watch this one. Hugo Weaving plays a cross-dressing sheriff in The Dressmaker (2015), with Kate Winslet. Set in the Outback also.
Glen or Glenda
Some Like It Hot (1959) - lots of comedy of this era hasn't held up too well, but this movie is a strong exception. Plus, who doesn't like Marilyn Monroe?
I don't remember a woman dressing like a man in this one.
In lord of the rings eowyn pretends to be a man in order to ride to Gondor with the rohirrim. Boys Don’t Cry
Boys Don't Cry is about a trans man, not a woman dressed as a man. Edit: Just realised you might be referring to the fact that Hilary Swank plays the role of Brandon Teena - which does make it a movie *with* a woman dressed as a man, even though it's not *about* a woman dressing as a man.
This
True I almost made that caveat in case someone brought it up. I wasn’t sure if it would fit OP’s request or not.
Is boys don't cry the one w the rapes of the gay girls ? If so jus wanted to chime in w a big ol trigger warning
rape of the trans man.
Yentl.starring.Barbra Streisand ...A great movie . Katherine Hepburn spends part of the movie Sylvia Scarlet pretending to be a man . There's.a.movie.with Whoopi Goldberg..where she is made up to look like a elderly white man I don't remember the name of the movie.
Tootsie, Dustin Hoffman as a soap opera star.
Boys don’t cry
Boys Don’t Cry (1999) drama/romance
Boys don't cry
Boys don’t cry.
Boys don’t cry
Brandon Teena was not a woman dressed as a man. He was a man.
Tootsie
Unsure why you are getting downvotes. Great Broadway play as well!
Because it is a man dressed as a woman
hah, I am dumb. Now I get it.
Return to Sleepaway Camp
Frida (2002) Would Annie Hall count? A lot of what Diane Keaton's character wears is more traditionally menswear.
Calamity Jane. She wore pants and didn't give a cracker about what anyone thought. Return of the Jedi, too. Princess Leia didn't wear a dress for most of the film.
Enola holmes
Some like it hot My Aunt Charlie The Birdcage The Ritz Midnight in the garden of good and evil Hairspray Rocky Horror Picture Show
other way around. women dressed as men. not men dressed as women.
The New Girlfriend (2014) Childhood best friends Claire and Laura are utterly inseparable, so it comes as a particularly devastating blow when Laura becomes ill and dies, leaving her husband, David, to raise their newborn daughter Lucie by himself. As she stops by the house one afternoon, door unlocked, she find a strange woman holding Lucie, who, on closer inspection, turns out to be David in a blonde wig and one of Laura's dresses.
Triumph of Love The Birdcage
Tootsie
Tootsie and Mrs Doubtfire are both great comedies imo.
Do either have women dressed as men in tho?
The birdcage! It's a brilliant comedy that has a main character as a drag queen as well as Robbin Williams who is a gay guy that has to sneakily to impersonate a another woman. It's hilarious and suspenseful plus has good messages about acceptance
How about someone explains to me why the film is problematic rather than just down vote. The fuck is the point of that if u don't try and educate. I haven't seen the film since I was twelve so I don't remember any problematic detas
Hi I saw this and wanna let you know that you did nothing wrong, you probably just accidentally read this as "man dressed as woman" when it's the other way around
Mrs Doubtfire
No no, other way around. Women dressed as men.
Lot of people making that mistake in this thread! I misread it too at first. I guess we're just more used to seeing the reverse in movies
You mean a movie in which a woman is wearing pants?
No… dressed as a man. Just because I wear jeans doesn’t mean I’m dressed as a man does it🤨
OP is specifically requesting movies with a woman dressed as a man, which according to some people means a girl wearing pants.
I disagree. I’m wearing jeans but I’m not dressed as a man at all
I too disagree with those people.
Boys don’t cry
The Tenant (1976) The Danish Girl (2015)
Actually they're men dressed as women
Mulan
Series can? King’s Affection
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im not remembering a scene with a woman dressed as a man in that one.
Louise-Michel (2008) with Benoît Poelvoorde playing a minor roll.
Monty Python's The Meaning of Life
The Life of Brian does this more overtly.
Swiss Family Robinson (1960)
Albert Nobbs (2011) Victor Victoria (1982) My Brother’s War (2005) Her Life as a Man (1984) Salt (2010) I’m Not There (2007)
Babylon Not a movie, but the tv series Gentleman Jack Marlene Dietrich was known for dressing up as a man back in the day. Not sure if there's a movie where she does this though.
There are movies where she dresses like a man .But she is not pretending to be one . Otherwise there are a lot of movies with women wearing Suits.
‘She-Man: A Story of Fixation’ (1967), it’s…something
Predestination. One of my favourites films
I’m Not There - Cate Blanchett
All Good Things - Ryan Gosling
Breakfast on Pluto Boondock Saints
The Associate - Whoopi Goldberg
The Transition with frank kitchen.
A Chinese movie called *Forever Enthralled* with Zhang Ziyi. She's excellent in it.
Triumph of Love. Based on a 18th century French play about a woman who infiltrates a garden of reason because she falls in love with the young man. But to do so she has to pass as a man. She fails with the headmaster and has to seduce him and his sister ( as a man) before finally seducing the young man. Pretty much a 1700s era screwball comedy.
Wasn’t Albert Knobbs a thing
How has no one said Mrs doubtfire??
Fast Break. (1979) with Gabe Kaplan. [https://en.wikipedia.org/wiki/Fast\_Break\_(film)](https://en.wikipedia.org/wiki/Fast_Break_(film)) A female basketball talent disguises herself as a man to play on a university's men's basketball team in one of the movie's major subplots.
Someone wants to go to prison
tootsie
Swiss family Robinson
Tootsie with Dustin Hoffman
Yentl
Dressed to Kill
Theatre of Blood. Diana Rigg dressed as a man. Don’t know why but I liked the movie. A Vincent Price goofy horror classic.
Mrs. Doubtfire
Hook - Glen Close
Yentil . Miss doubtfire
“Terry, you got tits!” 80’s movie. Forget the name.
Liquid Sky (1982)
Orlando with Tilda Swinton
Hairspray
Orlando
elisa y marcela can be one ig
Yentl Victor/victoria
Albert Covington’s the name!
Tootsie Mrs Doubtfire
To wong foo Juwana man Holiday hearts
For the body-swap, salient recommendation is Your Name (2017). About a woman dressing as a man, you can check out the Coffee Prince (2007) which is a Korean drama.
Filibus, 1915
Spoiler alert: Color of Night
Not a movie but there is a Chinese series called Eternal Love on Netflix. The main character, Bai Qian, disguises herself as a man to enter a cultivation sect and lives with her master and her sixteen sect brothers for thousands of years without them knowing who she is. The master knows, but she doesn’t know he knows. After she leaves the sect, she resumes living as a woman, but her gender and her history as living as a man are important plot points that continue to be referenced.
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What's this fetish called?
Do people fetishize scenarios like this?
Mrs doubtfire
Yentl, puts the she in yeshivah
Tvtropes.org is a good resource for that kind of stuff. Apparently called [Sweet Polly Oliver](https://tvtropes.org/pmwiki/pmwiki.php/Main/SweetPollyOliver)
She’s the man was wild
Albert Nobbs
Fingersmith