“Cross-dressing” is currently highly controversial, and it’s often associated with “gender swapping” but it’s nothing new. Our best record of it is in popular media throughout the ages.

The image, “The Cross-Dressing Zone”, is created and copyright (c) by Alden Loveshade 2024.

Tennessee became the first American state to explicitly ban most if not all drag shows in public spaces, reportedly to prevent minors from seeing them, particularly to prevent them from seeing a show that involves flirting, romance, or the like (the courts applied a permanent injunction preventing that law from taking effect). While there have been serious challenges to such laws, other states have followed. The constitutionality of these laws is being challenged in the courts. In Texas, a similar law has been ruled unconstitutional by a federal judge.

But is cross-dressing some new, radical, 21st-century phenomenon?

In the Beginning

The Bible, Torah, and Qur’an each have a version of Adam and Eve, the “first man and first woman.” They all mention the couple covering themselves with leaves and imply that the first man and woman dressed the same.

However, while this may be implied, there is disagreement over the exact interpretation. Much of the current controversy is about minors seeing someone cross-dress, and we don’t know how old Adam and Eve were when they got caught wearing clothing. So, is minors seeing cross-dressers a new, 21st-century phenomenon?

Cartoons

Not the first time Bugs Bunny would show up in drag to get laughs, and it wouldn’t be the last. This image hails from the classic Looney Tunes cartoon titled “A Corny Concerto” (1943). That’s his brazierre on Porky and the hound dog’s heads.

One of the most iconic cartoon characters of all time is Bugs Bunny. Created in the late 1930s, he seldom wore clothes—except when he was dressed as a female, which he did dozens of times. While dressed that way, he often flirted with males and even kissed some of them. Sometimes, when pretending to be female, he let them—and the kids watching—see him wearing a bra and panties, or even less.

Bugs’s cross-dressing Warner Bros./Looney Tunes cartoon co-stars include Elmer Fudd, Daffy Duck, Wile E. Coyote, Porky Pig, and Sylvester the Cat.

Did cartoon cross-dressing end there? No.

In later years, Hanna-Barbera featured cross-dressing characters associated with Yogi Bear, The Flintstones, Huckleberry Hound, Scooby-Doo, and many more.

There’s also 20th-century Disney’s The Jungle Book, Robin Hood, Aladdin, The Lion King, and Mulan. In fact, the 1998 Academy Award-nominated coming-of-age action-adventure film Mulan features cross-dressing throughout much of the movie.

In King of the Hill, the animated sitcom that first aired in the 1990s, even the “straight man” Hank Hill dresses in drag. Several characters in some versions of the adventures of the schoolgirl Sailor Moon, including in comic books, cross-dress. Not to mention earlier appearances of the comic book character, the all-American Superman’s male pal Jimmy Olsen, dressing as a girl.

But what about real human beings who aren’t voicing cartoons or creating comic books but are seen as human beings?

The Renaissance

Do a search for the greatest love stories of all time. If a list includes fiction, it will almost certainly include William Shakespeare’s play Romeo and Juliet. The couple is frequently considered the archetypal young lovers. But who first played the female Juliet? The identity of the actor isn’t certain, but it was very likely the boy actor Robert Gough. By historical records, it was decades before a female played Juliet.

In the British and European context, theatrical troupes were all-male, with the female parts played by boy actors. So yes, one of the most famous romances in the world was first portrayed for an audience by a man romancing a character played by a boy.

Cross-dressing was the norm not only in English Renaissance theatre. It was also used in French, Japanese, Indian, and Ethiopian theatre. This doesn’t even mention its use in Ancient Greece, often called the cradle of both democracy and western civilization.

Later, many of America’s “Founding Fathers” wore makeup and wigs with help from professional hairdressers.

But what about the women?

Women Dressed as Men

The United States Library of Congress lists a number of famous women who dressed as men. These include Hatshepsut, one of the few female pharaohs of ancient Egypt. There are also famous cross-dressing women from the 17th to 18th centuries. These include the British army dragoon Kit Cavanaugh/Christian Davies, the British warship gunpowder deliverer Mary Read, and the pirate Anne Bonny.

Then there’s the 18th-century British Royal Marine Hannah Snell, the American revolutionary Deborah Sampson aka Robert Shurtleff, and the 19th-century stagecoach driver Charley Parkhurst. The list of women who became successful while dressed as, and even pretending to be, men goes on.

At times, there were laws forbidding women from wearing trousers in public. But such laws didn’t stop Peter Pan. The boy who became a cultural icon symbolizing youthful innocence was traditionally portrayed for adults and children by a female.

But what about cross-dressing boys?

Boys Dressed as Girls

It was common in many countries, both before and during the early 20th century, for young boys to be dressed as girls. In the Western World, young boys from the mid-16th century through the early 20th century commonly wore gowns or dresses. In America, boys dressed as girls include the famed 20th-century American war correspondent and fiction author Ernest Hemingway. This list also includes the World War II American President Franklin D. Roosevelt.

The American law enforcement administrator who served both as the final Director of the Bureau of Investigation (BOI) and as the first Director of the Federal Bureau of Investigation (FBI), J. Edgar Hoover, reportedly continued cross-dressing as an adult.

But what about 20th-century musical performances?

It’s in the Music

In 1942 during World War II, Irving Berlin and James McColl’s famed musical This Is the Army was performed on Broadway. It opened on Independence Day, the 4th of July. The musical revue was intended to boost morale in the United States during WWII. In fact, it was produced by the U.S. Army with a cast of U.S. soldiers. It became the basis for the 1943 musical comedy movie of the same name, which features then-future U.S. President Ronald Reagan. So it was about as “all-American” as one could possibly get.

And what was one of the things it featured? Male American soldiers parading on stage while wearing women’s clothing—including fake breasts.

The one on the right would go on to be the 40th President of the United States of America in 1981: Ronald Reagan.

Two of the most popular musical groups for teenagers and children in the 1960s were The Beatles and The Monkees (although much of the latter’s work was performed by studio musicians). Both groups had forays into at least part of the realm of fantasy/science fiction/superheroes.

Both had songs about mixing gender. The Beatles’s “Get Back” includes the line, “Thought she was a woman, but she was another man.” Their song “Polythene Pam” includes, “Well, you should see Polythene Pam. She’s so good-looking, but she looks like a man. Well, you should see her in drag dressed in her polythene bag.” The Monkees’s best-selling album More of the Monkees includes the song “Laugh.” The song’s lyrics say, “And you can’t tell the boys from the girls.”

This doesn’t even include cross-dressing-related songs, performances, and/or appearances by David Bowie; Bob Dylan; Marc Bolan; Boy George; Emerson, Lake & Palmer; The Velvet Underground; and Elton John. Others include Van Morrison; Aerosmith; Pink Floyd; Red Hot Chili Peppers; Sweet; Led Zeppelin; Lou Reed; and Nirvana. The list continues with The Who; Motley Crue; Alice Cooper; The Hollies; The Kinks; The Rolling Stones; and, yes, the male bands Queen; New York Dolls; and Barenaked Ladies. And Yes.

There are dozens of movies that include both music and cross-dressing. For one, there’s the 1959 film Some Like It Hot, which features dressing in drag throughout. It has been named one of the best comedy films of all time. The movie, with its men dressed as women, won the Academy Award for Best Costume Design – Black-and-White. The film was produced without approval from the Motion Picture Production Code, i.e., Hays Code, because it features cross-dressing. Ironically, the film’s overwhelming success helped lead to the end of the Hays Code in 1968.

More than one version of the cross-dressing musical comedy Victor/Victoria won a major award.

Then there’s the 1975 musical comedy horror film The Rocky Horror Picture Show. It is considered the longest-running release in film history. It had so much influence that the famous Chicago Sun-Times movie critic Roger Ebert considered it more a “long-running social phenomenon” than a movie. One of its major characters is a scientist who’s a transvestite.

Comedy with humans playing humans is not limited to musicals.

20th Century Comedy

After the Great Depression and World War II, America strove to return to “normalcy,” even in its humor.

A comic icon of those days was Milton Berle. He earned the nicknames “Mr. Television” and “Uncle Miltie.” The latter was from a brief ad-lib to children in a 1949 broadcast: “Listen to your Uncle Miltie and go to bed.” What was one of Uncle Miltie’s most famous bits? Dressing as a woman in a dress.

Joining Berle in dressing that way was a man who would be given five honorary Academy Awards. This man not only frequently entertained American military troops but was named an honorary veteran of the Armed Forces by the United States Congress: Bob Hope.

That’s Milton Berle (TV’s “Uncle Miltie”) on the left, Bob Hope on the right.

Carol Burnett acted in the only television episode of the highly imaginative The Twilight Zone that includes a laugh track. Later, her imaginative variety/sketch comedy television program The Carol Burnett Show aired in the 1960s to 1970s. It, along with The Twilight Zone, is frequently listed as one of the greatest television shows of all time. Popular with adults, teens, and children, Burnett’s show won 25 Primetime Emmy Awards. What was one of its most popular bits? Male cast member Harvey Korman dressed as a woman. When it wasn’t the male Tim Conway. Or, on at least one occasion, the male Lyle Waggoner.

Moving forward to the 1980s, there was Bosom Buddies, an entire TV program about cross-dressing. It featured then-future Emmy Award winner Peter Scolari (who appeared in a later version of The Twilight Zone). It launched the career of Oscar winner Tom Hanks.

In film, 1993’s Mrs. Doubtfire featured actor Robin Williams portraying a man who dresses as, and pretends to be, a woman. (Williams was also the actor who played Mork in Mork & Mindy, the science fiction comedy that was a spin-off of the set-in-the-1950s family comedy Happy Days.) Why did Williams’s male character dress in drag? To be able to spend more time with children. In the film, that was a good thing. The movie earned a number of awards, including the Academy Award for Best Makeup.

Mrs. Doubtfire is a comedy-drama. But were there any non-comedy dramas made in the 20th century that featured dressing in drag?

20th Century Drama

In 1953, the docudrama Glen or Glenda was released. It was directed, written by, and starred the science fiction, crime, and horror filmmaker Ed Wood. The film follows the life of a man who likes dressing in women’s clothing.

David Lynch, co-creator with Mark Frost of the 1990s surrealistic mystery series Twin Peaks, mentioned Glen or Glenda as one of his favorite films. While the exact connection is uncertain, Twin Peaks features the then-future star of the science fiction-drama television series The X-Files. In Twin Peaks, David Duchovny portrays an FBI agent who’s transgender.

For the reverse, many 1950s and 1960s American Old West TV series have at least one episode where a girl dresses like a boy, or a woman dresses like a man. The first episode of the second season of Tales of Wells Fargo features a fictional version of the famed female outlaw Belle Starr. The series’ regular character Jim Hardie says the woman is “beautiful”—while she’s shown dressed like a man. He even kisses her romantically—while she is dressed like a man.

In drama that’s also musical, there’s the 1980s theater production turned film M. Butterfly. Apparently inspired by a combination of the opera Madame Butterfly and the real-life cross-dressing opera singer and spy Shi Pei Pu, the stage production earned a Tony Award for Best Play. It was a finalist for a Pulitzer Prize for Drama.

There’s also the 1980s American dramatic and romantic musical cross-dressing film Yentl. It won several awards, including an Academy Award.

In award-winning science fiction programs, a 1989 episode of television’s Quantum Leap features the male Sam in the body of someone else named Sam—only she’s a woman. The 1990s Star Trek: Deep Space Nine features a regular character who is a cross-dresser (and/or gender swapper, depending on how you look at it). Jadzia Dax, the station’s science officer, is a Trill woman named Jadzia sharing symbiotic existence with a long-living symbiont named Dax. Dax, joined with the previous host, Curzon, lived as a male diplomat and womanizer. So the male Commander Sisko often calls the female Jadzia “Old Man.” Later, Dax joins with another to become Ezri Dax.

Two actresses played Dax on Deep Space 9.
That’s Terry Farrel on the left as Jadzia Dax, and Nicole De Boer on the right as Ezri Dax.

But what about the original Star Trek? William Shatner has not been entirely consistent about his “favorite” episode of Star Trek. The actor famous for portraying Captain James T. Kirk has joked about that himself.


Two male performers putting on female costumes prior to a theatre performance, the one on the left wearing a mask.
Made around 430 BCE, featured in Museum of Fine Arts, Boston. Dressing in drag has been around for a long — long — long time.

At one point, Shatner hinted that his true favorite is “Turnabout Intruder.” That 1969 episode is the final one of the original series. In it, the male Captain Kirk and female Dr. Janice Lester, with whom Kirk had been romantically involved, switch bodies. So Kirk, one of the most iconic characters in all of science fiction, is essentially cross-dressing/gender-swapping through much of the final episode. That’s both as a male in a female’s body/clothing and as a female in a male’s body/clothing.

Perhaps the ultimate cross-dressing/gender-swapping in science fiction television history happened in a British program. The show started in the 20th century but still has new episodes today, over 50 years later. The program was designed to appeal to adults and children, and one of its original regular cast members was described by the program’s founding producer as a young girl. Rolling Stone magazine said the show “is as hallowed a British institution as the monarchy.” For over a dozen times, the program’s title character was portrayed by a man. Then, in the early 21st century, along came the female Jodie Whittaker as the title character in, yes, Doctor Who. While Whittaker was the first female regular in the role, she was not the first female to play the Doctor for the BBC. That happened in the 20th century.

There’s much more cross-dressing/gender-swapping in cartoons, comedies, dramas, science fiction/fantasy/horror/superhero films and TV programs, music, not to even mention novels…

Conclusion

So no, dressing in drag is not new. Yes, it’s had some historical controversy, but it’s also been an acceptable part of a variety of cultures for hundreds or, in some cases, thousands of years. It’s been acceptable for adults and children to see—and to do.

Remember that the next time you hear of a drag show, bump into a ponytailed man, or see a woman or girl publicly wearing a pair of pants.

Alden Loveshade has a degree in theatre and a minor in the area of women’s and ethnic studies. He’s written, directed, and acted in productions that dealt with history and/or cross-dressing, and wrote about the largest sex discrimination case in American history for Yahoo! News.

Alden Loveshade
Alden Loveshade

Alden Loveshade first thought of emself as a writer when in 3rd grade. E first wrote professionally when e was 16 years old, and later did professional photography and art/graphic design. Alden has professionally published news/sports/humorous/and feature articles, poems, columns, reviews, stories, scripts, books, and school lunch menus.

http://AldenLoveshade.com