Though many may not realize that crossdressing and transgender characters have been present for a very long time first in print and then in the visual mediums, film and television.  We are to be found in the works of Virginia Wolfe, Shakespeare, Byron, Bronte, Twain, Tolkien in some form or other as well as in a myriad of more recent books.  The characters tend to be used mainly in comedy, but do exist in drama, thrillers, horror, and suspense. In this first Media Review article, we would like present some characters that you may or may not know or have forgotten about.  And since all things must have a place to start, the age of television seems to be a great place to begin. Fair warning there are spoilers ahead!

During the 1950’s and 1960’s, the rise of television would expose a wider audience to different cultures, worlds, people, and ideas, as well finding new way to advertise.  The tradition of the trope man in a dress was still popular as a comedic prop. You could see “Uncle” Milton Berle in a dress telling jokes or Curly dressed as a woman in earlier Three Stooges shorts in syndication. Or in “McHale’s Navy”, someone dresses as a woman as part of a scheme.  In the United Kingdom, Monty Python’s Flying Circus has the male cast play various “pepper pot” ladies and other female characters. At the same time the movies show Gary Grant wearing a dress in” I was a Male War Bride” (1949) trying to sneak onto a ship or Jack Lemmon and Tony Curtis in “Some Like It Hot” (1958) hiding out from the mob as women musicians, or a movie like “Kind Hearts and Coronets”, where Alec Guinness plays the character of Lady Agatha D’Ascoyne among his 9 roles.

To this day they continue but in the 1970’s we begin to see more sympathetic characters as well as horrendous ones. But we will leave those ones alone.  We had Geraldine on “The Flip Wilson Show” or Maxwell Klinger on “M.A.S.H.” and even a show like “The Love Boat” had a transgender character (played by Mackenzie Phillips) in an episode where she and Gopher have a history prior to her transition and now what their friendship means.  On season 6 of “All in the Family” Archie saves the life of a passenger, Beverly LaSalle who Archie does not realize is a Drag performer, played wonderfully by Lori Shannon (nee Don Seymour McLean). She makes 2 more appearances and again there is the comedy of the situation, the character is shown to be a warm, confident and loyal friend.   In the movies, we have Chris Sarandon in “Dog Day Afternoon” (1975) playing the love interest of Al Pacino and the catalyst for the story.   We may not be sympathetic to her boyfriend’s decision to rob a bank but we can at least understand his motives.  In “The Pink Panther Strikes Again” (1976) Inspector Clouseau follows a suspect, Ainsley Jarvis the butler to a nightclub where it’s learned that he performs as a cross-dressing lounge singer, the song is sung by Julie Andrews.  Or we can look at Stan/Loretta in “Life of Brian” (1979) and though played for a laugh with her declaring that she wants to be a woman is shown to be accepted as still an important member of her group.

And then comes the 1980’s, on the small screen crossdressing or trans characters continue to show up in sitcoms, such as “Bosom Buddies” (1980-1982), a show that’s original premise is 2 men dressing as women in order to have a place to live.  Though their exploring of gender identity is eventually played down, I remember being very interested in what they would wear when “Buffy and Hildy” were on screen.  In TV drama, the ground breaking “Hill Street Blues” (1982-1987) had Alan Wachtel, an attorney later judge who is openly a crossdresser, played by Jeffrey Tambor. The character begins as stereotypical sleazy attorney and grows into a cynical by the book judge, but at least we are seeing someone willing to openly express despite the world around him.  It is in this time period, a Japanese Anime series appeared on television, called “Robotech” (1985), it was made up of 3 separate series but combined into one for American viewers. During the 3rd story arc, we meet Lancer, a soldier who disguises himself as Yellow Dancer, a popular female singer that is born out of necessity and by the end of the series, continues to perform as his alter ego.  There are many more characters like this in Anime that we hope to cover and introduce to our community.

On the big screen, some very memorable appearances occur in main stream comedies that inadvertently portray cross-dressing as necessity to survive.  Blake Edwards “Victor/Victoria” (1982) has Julie Andrews as Victoria, a woman posing as a gay man performing in drag in 1930s Paris. There are scenes showing other cross-dressers in the audience while Robert Preston performs “Gay Paree”.   Edwards showed a glimpse into a world that most people would have never have seen.  In “Tootsie” (1982) Dustin Hoffman is Michael Dorsey/Dorothy Michaels, an out of work actor who dresses to get a soap opera role, and experiences the trials and tribulations of being a woman in show business as well as in life.   A year later, Barbara Streisand plays a young woman passing herself off as man to get an education in “Yentl” (1983).  Her character refuses to except the gender roles assigned in her world and to find a way to forge her own path.  Cross-dressing is used once again as tool to achieve ones goals and brings attention to the restrictions in place to define our roles in society.

Never mind the 80’s here comes the 1990’s! There are 2 characters that I would like to mention from 90’s television.  The first is Steve Carey from “The Drew Carey Show” (1995-2004). Steve (John Carroll Lynch) was the straight crossdressing brother of the title character of the show.  Steve is comfortable being who they are and finds love. Though they remove the crossdressing in later episodes, it was someone who many had not seen before on television.   The other is Denise Bryson (David Duchovny, yes Fox Mulder) from “Twin Peaks” (1990-1991).  A former Drug Enforcement Administration Agent who worked with FBI agent Dale Cooper, in the past but sent to investigate allegations against him.  She tells Cooper about how working undercover as a crossdresser led to her dressing.  Dale’s acceptance of his friend’s new identity is refreshing.  She works to help clear Dale of the charges. All the while, she is taken seriously as an agent by Cooper and the local law.  She returns in “Twin Peaks” (2017) and has had a career advancement to FBI Chief of Staff along with coming out as a transwoman.

Ah the movies of the 90’s.  We will see drag queens, crossdressers, transmen and transwomen. In 1992, Neil Jordan’s “The Crying Game” was released.  A thriller with a twist about a Fergus Maguire (Stephen Rae), IRA member in Northern Ireland promises a British soldier prisoner, Jody (Forest Whitaker), that he will find tell Jody’s girlfriend back home what happened if he should die.  Not only does Fergus find Jody’s girlfriend, Dil (Jaye Davidson) but falls for her as well. As you may guess the twist, Dil is a transwoman, hairstylist by day and performer by night. From there it is a story of the past catching up with Fergus and Dil.  The following year “Mrs. Doubtfire” (1993) is released with Robin Williams playing a failing actor in work and home dressing to become a nanny to his children.  It highlights, Williams’s incredible quick wit and acting skills for laughs and drama.  Eugenia Doubtfire is a smart, sassy woman who seems to take on a life of her own.    Then in 1994, Tim Burton’s “Ed Wood” is released with Jonny Depp playing the title character.  Some of you may never have heard of Ed Wood, a b-movie director from the 50’s and 60’s who crossdressed. The movie has a fun scene that mimics, Wood’s “Glen or Glenda” as a tribute to the director.  As we get into the middle of the 90’s “Priscilla, Queen of the Desert” (1994) and “To Wong Foo, Thanks for Everything! Julie Newmar” (1995) both gave us the trope of buddy road movie. The first features Terrance Stamp/Guy Pearce/Hugo Weaving as Drag performers on a quest.  Stamp plays Bernadette a seen it all and bored transwoman but loyal to her performing partners, Felicia and Mitzi.  In “To Wong Foo” we have A list actors Patrick Swayze, John Leguizamo, and Wesley Snipes as drag queens travelling cross country to get to a contest in California and the adventure getting there. On the dramatic side, “Boys Don’t Cry” (1999) a biographical movie about Brandon Teena played by Hilary Swank maybe tough to watch but it is also showing that trans people exist. And then we come to today….

…. Of course, there are many we haven’t named or remembered and that is why we are counting on you.

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Michelle Liefde

When I was young , I loved Deborah Harry. I thought it was just a crush, but realized not only did I find her attractive but what she would wear. When I was 11, I first tried on a dress, pantyhose and bra. I had waited for my family to go out and finally decided to try. We had a storage area in our garage where my mom had some of her old clothes. I would go out there a much as I could. Eventually, I was found out. I buried this part of myself for over 30 years. I spent that time being happy, sad and repressed. Then about 2-3 years ago, I finally admitted to myself that I wanted to try again. After a little time, I told my wife and luckily she has been growing with me as I figure learn more about Michelle. I smile everytime Michelle comes out. I feel happier when I look in the mirror and see her.

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Mitzi May

That is an awesome article! There are so many you discussed there, it’s hard to know where to start.

I’m intrigued by the mention of Tolkien. It reminded me that many mythical stories have characters who are cd or switch genders. Thor disguises himself as a woman to deceive a giant; Loki changes gender; Arjuna lives as a woman while in exile; Tiresias dresses as a woman to worship Dionysus.

It’s such a rich history. Thank you for summing that up so well, the bad and the good. Please continue with this!

skippy1965 Cynthia
Active Member

Clarence/Clarice on Boston Legal was another character. Great article Michelle! Looking forward to future ones!

Rhonda Roe...
Managing Ambassador

Love the Article Michelle….So much history in media….Helped to promote and normalize cross dressing…Good work Hon

Sarah Daniels

Fabulous…..some there for me to watch.

The danish Girl is also one to see (athough its a later movie) about Transwoman Lily, and her trying to find her self and the first gender reassignment surgery.


Dame Veronica Graunwolf
Active Member

Michelle…..As I read your article, I was stunned by your memory!!! I remember all of this items you mentiond after you mentioned them LOL.

I look forward to more tales of the movies….you are definity the new Gene Siskel!

Dame Veronica

Trusted Member

Michelle, it’s Scarlett! I loved your entire article and thanks for the TV and movie lesson on when cross dressing was in display! And my bio story is very similar to your’s. Wish I had the time right now to share the details with you but I don’t!

XOXOXO Scarlett

Bianca Everdene
Active Member

Fantastic article Michelle, well done for all the work you have put in pulling together many instances of cross dressing being a part of film and TV. Still sad that cross dressing has not really broken free in TV and the media except for fictional characters, occasional historical stories based on fact, or treating a cross dresser like some kind of curiosity in a documentary. I Long for the day a male News reporter or weatherman rocks up in a red tailored dress, with matching heels and lipstick. Or a male presenter of a chat show, or Dancing on Ice… Read more »

Dawn Wyvern

Wonderful write up ! I remember the time that it ‘clicked’ with me was watching ‘Freebie and the Bean’ where the stunning Christopher Morley played the assassin … I went to see the film 4 times in one week just to watch that part… I had been dressing for several years but was totally fooled at the time ! Chis did a great part in the telly show ‘Vega$$’ not long after and once again was amazing! (the ‘General Hospital series was not broadcast over here in the UK .. so only seen him in this recently ..) Mike Hammer… Read more »

Wanda Full
Managing Ambassador

Wow! what a great article Michelle. That brought back a few memories. Thank you, that was well put together and I enjoyed it very much. Looking forward to the next one.
Hugs, W

Lucinda Hawkns
Active Member

Michelle Liefde yes this was a very interesting article to read and knowing the history of x dressing. way back in the 50s but it goes back further i would say but this is a very good article, well put. we all watch it and never gave it a thought about it as being a x dresser, so why is society so not understanding about it all? woman wear men clothing all day long to work and nothing is said about that, so why cant us men dress up in what society calls female clothing and go out shopping and… Read more »

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