Like in dreams, anything is possible in movies. Actors and actresses bring to life ideas that may seem wild in real life and that entertain the viewers. One of these is men dressing as women.
Cross-dressing was used in movies as early as the 1910s when actors would wear women’s clothing for its comedic value.
You can see how a man, beard and all, in a dress would be funny. The plots also enhanced jokes because these characters did not dress as women without reason: they aimed to achieve something, and they often failed, making the viewers laugh.
In the 1930s and onwards, movie-makers included cross-dressing as a non-comedic plot element. It is an excellent tool for plot development and highlighting diverse themes.
Here is a list of the top white men cross-dressing in movies from the earliest to the most recent.
1. Charlie Chaplin
- Movie Title: A Woman
- Year: 1915
- Role: Man
In 1915, Charlie Chaplin starred in a movie titled “A Woman,” where he dressed as a woman.
In the film, Charlie gets into a fight with a man for trying to seduce his daughters or his wife and daughter.
After losing his trousers in the fight, he puts on a dress, and the man who beat him tries to seduce him; admittedly, he looks better than the women in the movie.
2. Eric Idle and Robie Contran
- Movie Title: Nun on the Run
- Year: 1990
- Role: Brian Hope/ Sister Euphemia of the Five Wounds, Charlie McManus/Sister Inviolata of the Immaculate Conception
In the movie Nun on the Run, Eric Indle and Robie Cotran play criminals (Brian Hope and Charlie McManus) who want out, but their boss will not allow it. They rob him and then hide in a convent dressed as nuns—very ugly nuns.
This movie is very funny because it takes quite a bit of effort for these men to disguise their voices and act convincingly female.
3. Chad Lowe
- Movie: Nobody is Perfect
- Year: 1990
- Role: Stephen/ Stephanie
Stephen’s crush on a female teammate gets him kicked out of the tennis team because he cannot concentrate.
He dresses up as a woman to get close to her and pretends to be a female exchange student. Chad makes a beautiful woman, but it is hilarious to watch him try to act female.
4. Jonathan Brandis
- Movie: Ladybugs
- Year: 1992
- Role: Matthew/Martha
In the movie, Jonathan Brandis plays Matthew, who dresses as a girl, Martha, to play soccer with the Ladybugs. His mother’s boyfriend, Chester, is the coach, and he must make the team win to get a job promotion.
Chester teaches Matthew how to behave like a girl, which is very entertaining because he does not know much about women.
5. Jonathan Silverman
- Movie: Little Sister
- Year: 1992
- Role: Bobby/ Roberta
Jonathan Silverman plays Bobby, who dresses up as Roberta to steal a painting from a sorority in a fraternity prank.
He does not get the painting, but he is attracted to one of the girls (Diana) and continues dressing as a girl to be close to her. His attempts to appear female and conceal his true identity make this a great comedy.
6. Corey Haim
- Movie: Anything for Love
- Year: 1993
- Role: Chris/Chrissy
In the movie Anything for Love, Corey plays a teenage boy named Chris, who dresses up as a girl to avoid his bullies. He only meant to dress as a girl on the way to school, but he enjoys it so much that he does it all the time.
He joins the cheerleading squad, and watching him try to keep his secret from the other cheerleaders and his parents is hilarious.
7. Robin Williams
- Movie: Mrs Doubtfire
- Year: 1993
- Role: Daniel Hillard
In the movie, Robin Williams plays Daniel, who loses custody of his children after divorce. When he finds out that his ex-wife is looking for a Nanny, Daniel dresses up as a woman in her 50s and applies for the job.
Unfortunately, Daniel has very poor housekeeping skills. His attempts to keep his secret bring out Williams’ comedic genius.
8. David Price
- Movie: All Men Are Liars
- Year: 1995
- Role: Mick/ Michelle
In All Men Are Liars, David Price plays Mick, a teenager who wears his mother’s clothes to join an all-girl band and make money. When one of the singers starts to fall in love with him, she begins to question her sexuality.
Mick’s struggle to be a convincing woman and his crush on the lead singer makes the movie funny while ensuring that it explores LGBTQ themes.
9. Nathan Lane
- Movie: Birdcage
- Year: 1996
- Role: Albert Goldman/ Mrs Coleman
Nathan Lane plays Albert Goldman in Birdcage. In the movie, his partner’s son, Val, wants to marry Barbara, whose ultra-conservative father is a senator. There has been a scandal, and to ensure no more surprises, the senator insists on meeting Val’s family.
Unfortunately, Val’s father is gay and owns the drag club Birdcage, so Albert has to dress as a woman and pretend to be his domestic partner’s wife (Mrs Coleman).
10. Barry Watson
- Movie: Sorority Boys
- Year: 2002
- Role: Dave/ Daisy
Dave and his two friends are accused of stealing their fraternity’s funds. They join the Kappa Omicron Sorority as girls as they have nowhere else to go.
Of the three, Dave is the most convincing female and the best-looking. The humour comes from their attempts to look feminine and behave like girls: “We don’t have to be babes, just believable.”
11. Cole and Dylan Sprouse
- Movie: The Heart is Deceitful Above All Things
- Year: 2004
- Role: Mathew
Cole and Dylan Sprouse have cross-dressed for several roles over the years. In this movie, they play Jeremiah, whose mother dresses him as a girl and tells people he is her sister. This movie shows how an unfit parent can put their child at risk to get what they want.
12. Jonas Karlson
- Movie: Cockpit
- Year: 2012
- Role: Valle/Maria
In trying to empower women, society can sideline men. In the movie Cockpit, Jonas Karlson plays Valle, a pilot who loses his job and dresses as a woman to get the same job through affirmative action.
While dealing with the dark side of female empowerment, it is also a funny movie as Valle tries to be a convincing woman.