9 Worst Cross-Dressing, Transgender Villains

January 28, 2014

Since Cautionary Women believes in equality, this site's coverage of villainesses also extends to transwomen and male characters who happen to be in ladies' clothing. Sashay through some of the most villainous, anti-heroic transsexuals and transvestites in fiction:

9. Fish Eye, Sailor Moon

via Forgotten Toon Guys

Sailor Moon has not been one to cower from depicting LGBT characters, to think this animated series first ran in the homophobic, transphobic 1990s. Japanese animé has a long history of celebrating androgyny but Fish Eye was an iconoclast. 

8. Paul, Sometimes Aunt Martha Does Dreadful Things 

via The Dead Next Door

Stanley is chick magnet par excellence. Paul is psychotically clingy to Stanley. As 'Aunt Martha,' Paul kills the competition one by one. 

7. Dawn Davenport, Female Trouble

via The Red List

In this comedic gem, legendary drag queen Divine plays a character based on murderer Charles Watson. 

6. Angela Baker, Sleepaway Camp

via Diabolique Magazine

Before Scream, before I Know What You Did Last Summer, there was Angela Baker in this cult slasher series. 

5. Ava Moore, Nip/Tuck

via Unwelcome Commentary

Unrequited love causes Avery Tanner to transform himself from just another gay escort to the incestuous statutory rapist Ava Moore, played by Famke Janssen. 

4. James Gumb, The Silence of the Lambs

Wait for the famous peen tuck. Via The Retro Guy

Plagued by mommy issues, Buffalo Bill skins overweight women to create "woman suits." Ted Levine breathes life into the serial killer in the Oscar-winning adaptation of the bestselling Thomas Harris novel. 

3. Bobbi, Dressed to Kill

Look out, Nancy Allen! Via Zombie Hamster

Carrie director Brian De Palma treats fans to another obra maestra in Dressed to Kill. 

2. Him, The Powerpuff Girls

It's...Him! The running gag is that this thigh-high-boot-loving villain embodies an evil so unspeakable that no one in Townsville can speak his name. Looks like Voldemort has competition.

1. Norman Bates, Psycho

via The Truth Inside the Lie

One of the greatest villains of all time needs no introduction. 


Media portrayals have a crucial role in shifting the tide of public favor toward the LGBT community. But as you may have read, some of the most visible villains in fiction are characters whose genders, and their attendant roles, are in transit, a fact that GLAAD has bemoaned. You should not wonder then why transwomen and transvestites get a bad rep not only in heterosexual society, but also in a patriarchal gay male community. 

In life as in art, crimes offer a level playing field for all sexes and sexual orientations. But the number of accurate and positive roles for transsexual and transvestite characters is disproportionate enough to facilitate hate in everyday life. That kid who grew up on Powerpuff Girls? He or she may not be far away from thinking a bearded man in girly clothes is the Devil herself.

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