Top 10 list of The Best Crossdressing Movies of All Time

Top 10 Crossdressing Movies

People dressing up as the opposite sex has been part of productions dating back to the Shakespearean times. Back then, it was used as a way for female characters to move and act more freely within a story. Now films use crossdressing to highlight social issues to show how a character identifies or for comedy.

In today’s article, we take a look at the top ten Crossdressing movies of all time.

#10. White Chicks (2004)

White Chicks (2004)

In White Chicks two FBI agent brothers accidentally mess up a drug bust. As punishment, they are ordered to escort two sisters to the Hamptons, where they are going to be used as bait to catch a kidnapper.

But when the girls discover the dangerous plan, they refuse to help. Left without any other options, Marcus and Kevin decide to pose as the sisters, transforming themselves into women.

Fans of the much-loved film can rejoice. As Terry Crews has said, a sequel is in the works.

 

#9. She’s the Man (2006)

She's the Man (2006)

In She’s the Man Viola Johnson, decides to pose as her twin brother, Sebastian, to take his place at a boarding school. The only problem is Viola has fallen in love with her roommate Duke, who loves the beautiful Olivia, who has also fallen for Sebastian.

As if that weren’t complicated enough, the real Sebastian has returned from his trip to London early and has no idea that his sister has taken his place.

 

#8. To Wong Foo, Thanks for Everything! Julie Newmar
 

To Wong Foo, Thanks for Everything! 

Noxeema Jackson, Vida, and Chi-Chi Rodriguez plan on showing America how fabulous drag Queens can be. Dressed to kill, the three embark on a mission to enter the New York drag Queen beauty pageant circuit.

They hit the open road in a classic 1967 Cadillac convertible, but the trio runs into trouble when their car breaks down inside a small Midwestern town where drag Queens are not a common sight.

Despite their old-fashioned views, it doesn’t take long for the town’s eyes to be opened up by the Glamorous trio.

 

#7. Albert Nobbs (2011)

Albert Nobbs (2011)

During the 1800s, the painfully shy butler Albert Nobbs hides an incredible secret. He is really a she. Terrified that someone will discover her identity, Albert keeps a very low profile until the arrival of Hubert Page, who changes everything.

It turns out that Hubert is also secretly a woman and has managed to find a partner who helps keep the secret. Hoping to do the same, Albert begins trying to woo a hotel maid.

Despite winning twelve awards, the movie received mixed reviews from critics.

 

#6. The Birdcage (1996) 

The Birdcage (1996) 

In this remake of the classic 1978 French film, The Cage of Mad Women engaged couple Val and Barbara, nervously introduced their future inlaws to each other.

Val’s father,  Armand, is a gay Miami drag club owner who pretends to be straight so that he can hide his relationship with his club’s Flamboyant star Albert.

Upon its release, The Birdcage received positive reviews, while the Gay and Lesbian Alliance Against Defamation praised the movie for going beyond the stereotypes to see the characters deaf and humanity.

 

#5. The Adventures of Priscilla, Queen of the Desert (1994)

The Adventures of Priscilla, Queen of the Desert (1994)

When drag Queen Anthony agrees to take his act on the road, he invites fellow cross-dresser Adam and transgender female Bernadette to come along with him.

In their colorful bus named Priscilla. The performers travel across Australia, performing for enthusiastic crowds and dealing with homophobic locals.

Things turn sour when the other two performers learn why Anthony took the job in the first place, something that threatens their friendship.

Although the movie provided Australian cinema a good reputation, it has come under criticism for alleged sexist and racist elements.

 

#4. Some Like It Hot (1959)

Some Like It Hot (1959)

After being a witness to a Mafia murder, a saxophone player called Joe and his friend Jerry Cook up a plant to escape Chicago. Dressing up as women, they join an all-female jazz band and hop on a train set for Florida.

While Joe pretends to be a millionaire to win over the band singer named Sugar Kane, Jerry finds himself being pursued by an actual millionaire, which puts the pair in danger and allows the mobsters to close in.

Upon its original release, “Some Like It Hot” was banned in the state of Kansas because Crossdressing was considered too disturbing.

 

#3. Tootsie (1982)

Tootsie (1982)

Tootsie follows New York actor Michael Dorsey, who becomes frustrated that he and his agents struggle to find work. After a soap opera audition goes very badly, Michael comes up with the idea of reinventing himself as actress Dorothy Michaels and manages to get a part after all.

What was supposed to be a short role turns into a long-term contract. After a while, Michael falls in love with one of his acting colleagues, which threatens his career and future happiness.

The film wasn’t without its problems during the production, as director Sydney Pollack and Dustin Hoffman often had heated arguments on set.

#2. Mrs. Doubtfire (1993)

Mrs. Doubtfire (1993)

Mrs. Doubtfire doubtfire won an impressive array of awards, some of which include best makeup at the Academy Awards and the best motion picture at the Golden Globes.

It follows a loving but irresponsible dad called Daniel Hillard, who was separated from his partner. What makes things worse is that a court order only allows Daniel to see his children once a week.

When he learns that his ex needs a housekeeper, he disguises himself as an English nanny and gets the job, allowing him to spend time with his children and build the bonds he should have from the very start.

 

#1. The Rocky Horror Picture Show (1975)

The Rocky Horror Picture Show (1975)

In what started as a way to keep an unemployed actor busy during the winter nights, Richard O’Brien turned his homage to science fiction into a much-loved cult classic.

The film follows sweethearts Brad and Janet, who break down during a storm and have no choice but to call upon an eerie mansion. They discover that the building belongs to a transvestite scientist called Dr. Frank N. Furter.

As their innocence is slowly lost, Brad and Janet embark on a downward spiral with other strange characters who include a biker named Eddie, a creepy Butler, and a man cooked up in the lab named Rocky.

The movie was rated as 7.4 on a scale of ten on the IMDb website and was selected for preservation in the United States National Film Registry.


This was our top 10 list of the best Crossdressing movies ever made. It is a great list of the best Crossdressing movies of all time.

Do you agree with our list? If you have any suggestions or comments please shoot them down in the comments below.  

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