by: Violet Fenn

“Why not try to see things from a different angle?”
– “I Am What I Am” from the musical La Cage Aux Folles

Gender-bending has fascinated me since I was a kid, long before my gender transition. Maybe it was because I admired the prodigious amounts of chutzpah it takes to put oneself out there and wear makeup, heels, a wig, and fabulous clothing. Maybe it was because I was envious that whatever actor or actress I saw got the freedom to play someone completely different. I don’t know, but it’s almost always fun to watch.

As many of my friends will tell you, I am quite the movie buff and have a weird talent of absorbing vast amounts of useless trivia, not to mention the ability to remember an obscure actor or actress from a movie I’ve seen. If I really love a movie, whether most consider it a good movie or not, I watch it multiple times.
So, here’s my list of my favorite gender-bending characters from movies. In this case, I consider a gender-bending role to be one in which the particular actor or actress dresses in drag. I also give mention to one that was lauded by critics but hated by me. Since I can’t possibly rank these in order of favorites, I’ll list them chronologically.  Undoubtedly, there are more gender-bending roles that I failed to mention, but that only means they either didn’t pique my interest or I haven’t seen them.

1959:  Tony Curtis and Jack Lemmon as Geraldine and Daphne in Some Like It Hot. The American Film Institute has named this as the greatest comic movie of all time and for good reason. The plot, two members of a band witness a mob hit and flee to Florida with an all-girl jazz band, is wacky and wonderful. Billy Wilder, the director, had the film shot in black-and-white as the makeup on Lemmon and Curtis was too garish for color. They look fantastic in the film, though Tony Curtis is more passable. Combined with the talents of Curtis and Lemmon, the Jazz Age costumes and the sexy, bubbly Marilyn Monroe, this should be on the must-see list for every gender-bending movie lover.

1975:  Tim Curry as Dr. Frankenfurter in The Rocky Horror Picture Show. There’s not much I could add to the conversation about this classic role of queer cinema. Who would have thought that a guy wearing black heels, thigh-highs, a corset, and 1950’s housewife pearls could be so weirdly sexy?

1982:  Dustin Hoffman as Michael Dorsey/Dorothy Michaels in Tootsie. Hoffman was nominated for an Oscar for his performance as an unemployed actor so desperate for work that he gets himself hired on a soap opera by playing a woman. In the midst, he falls in love with one of his co-stars who has no idea that Dorothy is really Michael. Hilarious moments happen and the commentary on early eighties feminism is never preachy. Hoffman has a body that women would kill for and never looks campy in drag. This is one of those movies that I go to for a guaranteed emotional pick-me-up.

1982:  Julie Andrews as Victor/Victoria in Victor Victoria. Who would have thought that the same woman who played Mary Poppins and Maria could play a woman impersonating a man who was impersonating a woman? Julie pulls off butch nicely.

1993:  Robin Williams as Daniel Hillard/Mrs. Doubtfire in Mrs. Doubtfire. Robin Williams in drag and more quotable lines than most other movies can ever hope to have. Enough said.

1994:  Hugo Weaving, Guy Pearce, and Terence Stamp as Tick, Felicia, and Bernadette in The Adventures of Priscilla, Queen of the Desert. A cult classic from Australia, this was one of the movies I was never allowed by my Southern Baptist mother to watch, mainly because it simply screams queer. The movie won an Oscar for the absolutely fabulous costumes, my favorite being a dress made out of pink flip-flops that Tick has to wear after losing a card game to Felicia. Weaving and Peerce are fantastic, but the scene-stealer is Stamp as post-op transwoman Bernadette. While not gorgeous by any standard, she’s a badass who pops off insults like nobody’s business.

1995:  Patrick Swayze, Wesley Snipes, and John Leguizamo as Vida Boheme, Noxeema Jackson, and Chi-Chi Rodriguez in To Wong Foo Thanks For Everything, Julie Newmar. What’s not to love? Fabulous drag and a land yacht Cadillac befitting a queen. The catty one-liners are a scream, and did I mention Patrick Swayze wears Chanel? Oh. My. God. I mourned the day he died and watched this movie in memorium.

1996:  Nathan Lane as Albert in The Birdcage. An American remake of La Cage Aux Folles, this is yet another movie that I’ve watched countless times and never get sick of. While playing up on many stereotypical queer ideas, Lane’s performance is screamingly funny.  Plus, he looks better in drag than I would have thought.

2002:  Barry Watson, Michael Rosenbaum, and Harland Williams as Dave/Daisy, Adam/Adina, and Doofer/Roberta in Sorority Boys. While this isn’t a classic (it flopped at the box office), it is one of those movies so bad it’s good and one of my guilty pleasures. The plot is flimsy–three fraternity brothers get framed for stealing money from the fraternity and in order to clear their names, go in drag and join a sorority of misfit girls. In the end, they clear their names and learn about the other side. The guys in drag wouldn’t pass as women in a dark alley and the movie makes no effort to convince anyone of that. This is just nice and dirty camp humor.

2007:  John Travolta as Edna Turnblad in Hairspray. I saw Harvey Fierstein’s performance as Edna in the original stage version and hoped he was going to play her in the movie. I wasn’t happy initially about Travolta being cast, but was totally surprised by how well he did. How many other men could sing and dance while wearing a fat suit?

Now I come to the gender-bending role I hate:

2005:  Felicity Huffman as Bree in Transamerica. The first time I saw this, I loved her performance. After watching the movie, I became aware of my transgender status. Since then, I can’t help but cringe at the character of Bree. She’s presented as ultra-womanly: prim and proper to extremes, with frequent shots of her getting dressed, fixing her hair, and putting on makeup. The film tries too hard to convince the viewer that Bree is a woman, and as a result, makes her more of a spectacle of a woman.

Violet Fenn is a quirky, eccentric, proudly geeky trans woman studying theology at a seminary in Chicago. When not engaged in academia, she can be found speaking in meow to her cats, Morticia and Elphaba, handling yarn and sharp pointy sticks, flirting, and searching for the perfect cup of coffee.