All-Time Greatest Gender-Bender Cinema

Posted on Posted in Entertainment, Film

by Zachary F. Volkert

Watching trans movies today tells us a lot about how far things have come, from the clinical shock pieces like The Christine Jorgensen Story in the 70s up until now when the hilarious all-drag cast of Girls Will Be Girls redefines the rules of what drag can and can’t do on screen. There have been mainstream successes that educated the public (Transamerica) and sex symbol actors putting on frocks to perform such ladylike acts as sneaking an entire novel out of prison up his ass (Johnny Depp in Before Night Falls), but the most exciting shift is just how developed trans films have become: they can exist in the mainstream now, and a wide range of films are available on any range of the gender spectrum, which unfortunately means that a lot of non-traditional trans icons (Buffalo Bill in The Silence of the Lambs) and classics that haven’t aged as well as some of their counterparts (To Wong Foo, Thanks for Everything, Julie Newmar and Priscilla, Queen of the Desert) have been omitted. But the snubbing of such quality cinema exposes how un-taboo the issue has become, not to mention how lucky we are to live in an era where every year sees a new trans film topping critics’ list – and the accolades couldn’t be more deserved.

20. Normal (Jane Anderson, 2003)
If there were an award for best actor whose name slips past most audiences, Tom Wilkinson would probably have it in the bag every year. But how can his performance as Roy “Ruth” Applewood go unnoticed? There is no attitude or charisma to Ruth; Wilkinson plays the everyman even though he’s really playing the transsexual woman. His family’s gradual acceptance of “Ruth” put us on the edge of our seat, as we watch the familiar all-knowing condescension of the religious town. Like a true lady, Ruth takes it all in stride, wearing earrings to work, eye shadow to the grocery store, and a negligée to bed – where he sleeps with his, the greatest symbol that even as gender changes, some things never do.

19. Some Like It Hot (Billy Wilder, 1959)
How is this here? When Tony Curtis and Jack Lemmon aren’t even drag queens by choice? When the movie’s focus is heterosexual couples? When the only diva who performs in front of a microphone is Marilyn Monroe, a genetic woman? One word: 1959. How in God’s name did Billy Wilder manage to get this irreverent comedy made back when queens were still being assaulted on their way to work? From a modern perspective, the real inquiry is how his portrayal is still so fresh and funny? Wilder really understood the comedy of drag. He isn’t just making a movie about men in dresses; he’s making a movie about the projection of gender and how its rules are so static that even mild tinkering can make life and love impossible. Before Stonewall, before Harvey Milk, before everything – Tony Curtis and Jack Lemmon showed a little leg of what was in the future.

18. Wigstock: The Movie (Barry Shils, 1995)
Drag is always a party, and what better facet of that constantly bustling celebration to zoom in on than Wigstock? Everyone from Jackie Beat to RuPaul lines up for roll call here, and those of us who haven’t seen all of the history unroll before our very eyes can catch queens we might not have heard of. Wigstock doesn’t manage to quite measure up to the icon status of Paris is Burning, but it comes damn close. Especially with moments like the one near its end, where a single wig-topped balloon floats off into the sky as a memorial to a deceased queen.

17. Ed Wood (Tim Burton, 1994)
I’m not as much of a Depp fan as many others, but the man knows how to tap into characters – and I’ve never seen him do it better than when he gets in drag. Ed Wood is a character who commands intuition. He can’t be played by anyone who doesn’t understand what his sense of humor and style was, and why those two things make him interesting. Depp takes what could have been an offensive “let’s all laugh at the drag queen” moment and instead bestows a person upon us, who we laugh with, not at.

16. The Rocky Horror Picture Show (Jim Sharman, 1975)
Tim Curry’s Dr. Frank-N-Furter is definitely on the short list of who brought the first great representation of transvestites to the screen. For unlike Jack Lemmon and Tony Curtis, Tim Curry encompassed what it means to be a man dressed a woman: the wild screams, flamboyant gesticulation, and love for everything sexy and feminine. Sure, Curry is playing a villain, but in a movie as over the top as Rocky Horror, the audience is still able to relish in his presence. After all, who doesn’t love a queen who can dance, sing, and “breathe the breath of life.”

15. Trinidad (Jay Hodges and PJ Raval, 2008)
Sex change documentaries are one of the most prolifically selected niches of the trans movie world, but many of them are plagued by the same problem, a poor balance of emotional backstory and clinical shock that ends up leaving us cold and not knowing much more at the end than we did going into it. Not so for Trinidad, the documentary giving us a close-up of the Colorado town that has become an international hub for gender reassignment. Hodges and Raval add details to the story that other filmmakers have missed – we understand the ignorant backlash of the town just as well as we understand the wave of trans immigration there – fostering understanding on a truly two-way street.

14. Beautiful Boxer (Ekachai Uekrongtham, 2004)
Thailand has long since been the mythic land of ladyboys, but Beautiful Boxer turns even the exhausted topic of the Thai trans world on its head. A boy who wants to be a girl also wants to be a boxer – how much more gender-bending can you get than that? If you’ve ever been that tranny who wished they could fight back with their fists as well as they could with their words, then this movie will be a fantasy for you. Campy superhero queens need not apply when contrasted with the fierceness of Parinaya Charoemphol, who pummels the boys without ever losing her poise…once she learns the wonders of waterproof makeup.

13. Flawless (Joel Schumacher, 1999)
It’s no surprise that one of the greatest queens on the list is played by the national treasure that is Phillip Seymour Hoffman. Flawless got snubbed by a lot of audiences and critics when it was released, but the few flaws it has (the sloppy crime subplot) can’t even be seen amidst the blinding radiance of energy that is Rusty. And who better than Robert DeNiro to reprise the role of the homophobic cop, the kind of guy the LGBT community is always trying to pull over the other wise? The stroke-victim cop learns from the vocal-coach drag queen story sounds schmaltzy on paper, and, at times, it is. But just like the subtle masculinity of Rusty, we are willing to look past these things because the overall picture tells a story that is in need of an audience – taking drag to the mainstream without losing any rhinestones in the process.

12. Pink Flamingos (John Waters, 1972)
Before I had ever heard of John Waters or Divine or Mink Stole or Edith Massey, I had seen the image of Divine eating dog feces. I don’t know what kind of preface that is for the film that defines Midnight Movie, but it definitely isn’t the most shocking thing you see during Pink Flamingos. The Marble’s underground rape-baby ring, the close-up artificial insemination, and the general shenanigans that make the characters the most disgusting people give it enough controversy to belong on any list of alternative cinema, and it earns its place here through the enigma that is Divine.

11. The Sons of Tennessee Williams (Tim Wolff, 2010)
Mardi Gras’ free for all attitude made New Orleans an open season for drag queens compared to a lot of the rest of the country at one time. That’s not to say these girls didn’t face a backlash, from family, police, and even bloodthirsty youth, but their determination in fighting against these things is more than admirable, it is heroic. Sons of Tennessee Williams is Paris is Burning’s counterpart, a film that is about the social catalyst that drag was and still is for gay rights. Instead of explaining the world of drag, we see the effect that drag has had on the world. Like every carefully selected sequin on the Mardi Gras queens, the final effect of strength, beauty, and joy scintillates before us – stunning us just like we were there.

10. Orlando (Sally Potter, 1992)
Virginia Woolf was such a feminist icon that it isn’t surprising that almost a hundred years later her works are able to be reimagined for the trans world. Tilda Swinton is androgyny, and the way she exudes it despite her Elizabethan environment makes her performance the center of a well-shot, well-acted classic. Orlando is man and woman concurrently, commanding respect and eliciting tenderness. And for a while at least, it’s the closest we’re going to get to a trans Jane Austen.

9. Cabaret (Bob Fosse, 1972)
Joel Grey’s Oscar-winning, gender-bending performance as the Master of Ceremonies in Cabaret, is the stamp that allows it to qualify as a transgender film, but it is the iconography achieved by Liza Minnelli and the ménage-a-tois that she enters into that truly make it a gender-bender classic. What time in history better foreshadows the hidden drag scene of yore than the cabarets, liberation dens where performance sought to quell fear in the face of the rise of Nazis? Cabaret in itself is a film about liberation, about being free and acceptance. Despite its dark undertones, it is impossible to walk away from it singing anything but “In here, life is beautiful. The girls are beautiful. Even the orchestra is beautiful!”

8. La Cage Aux Folles/The Birdcage (Edouard Molinaro, 1978/Mike Nichols, 1996)
Choosing between the groundbreaking French classic and its American remake comes down to a matter of taste, a stock of which is overflowing from either version’s protagonists. La Cage Aux Folles deserve acclaim for putting drag out on the line in 70s Paris, but it is undeniable how much Nichol’s mainstream adaptation opened attitudes toward drag. Whether you prefer Nathan Lane‘s Albert or Michel Serrault’s Albin, either film is a sharp comedy that manages to say something without becoming heavy-handed, resonating 20 or over 40 years respectively.

7. Boys Don’t Cry (Kimberly Peirce, 1999)
What movie has pricked the public consciousness about transsexual rights like Boys Don’t Cry: the brutal retelling of Brandon Teena’s murder featuring some of the greatest acting of all time from Hillary Swank and Chloë Sevigny? The drama deepened understanding of violence against the queer community in the year after Matthew Shepard’s murder by putting a name, face, and identity on those who suffer adversity for their gender orientation, changing hearts by wrenching them. It is as unforgettable as it is important.

6. Polyester (John Waters, 1981)
How to talk about Divine in anything but a gush of admiration: ceiling shattering, fishy-yet-funny icon, legend, and heroine? Now 20 years after her death, more people still probably know about Divine than any other queen, save perhaps RuPaul. The way that she funneled John Water’s offbeat sense of humor into a character with such a high level of charisma is still a high bar set for drag queens who want to do the same. Polyester stands between John Water’s somewhat-mainstream shift and his outrageous roots, and it is the lens that suits Divine best: big material projected by an even bigger persona, a divinity that we can’t keep our eyes off of.

5. Ma Vie en Rose (Alain Berliner, 1997)
If only the world could see the experience of growing up young and transgendered, how could anyone not understand and embrace the community? Ma Vie en Rose might be the film that came close, if it would have blown up in the United States like it did in France. The little girl in a boy’s body, Ludovich, that confronts the ignorance of his entire town and even in his own family provides a solid example of why such feelings are natural, and why seeing them happen to a 7-year-old somehow brings it all together. The fantasy of being a girl is something Ludovich is told to repress from all directions, but he never manages to lose, always living under the pink, until those around fall under its rose-colored spell.

4. Breakfast on Pluto (Neil Jordan, 2005)
Patrick “Kitten” Braden is as sprawling in his political and social commentary of Ireland as he is in his gender association. Unlike Ma Vie En Rose, we’re able to see his entire life play out, from the strong Catholic country’s barring of his transgender interests at an early age to being picked up for IRA terrorism. Trans history and Irish history coexist and manage to offer a new perspective on both. Miss Kitten is so much more than just a trans icon – she is an icon for any human, any person who has ever faced adversity, and anyone who has ever managed to look fabulous during every second of it.

3. The cinema of Pedro Almodóvar (1980 – present)
What a better setting for Almodóvar´s movies than Madrid after the fall of the ultra-conservative fascist regime of Francisco Franco? A place so celebratory of their newfound freedom that, despite being deeply rooted in Catholicism, legalized gay marriage ahead of the curb of the most of the world. The drag queens, lady boys, and other montón of transgender and transvestite characters that make up his casts are almost perfunctory: an Almodóvar movie without one would be like a mob movie without gangsters. From the John Waters-esque world of Pepi, Luci, Bom, y otras chicas del montón that exposed his face to the underground to Todo Sobre Mi Madre that won Cannes and the Oscar for Best Foreign Language Film, Almodóvar gives us some of the most accurate trans characters on film, full of emotional depth and veracity that fit perfectly into the flamboyant world that he creates around them. By placing sex symbols like Gael Garcia Bernal in La Mala Educación in drag and building Joan Crawford-esque plots of intrigue around him, Almodóvar achieves the very essence of the trans community on film: a patchwork of the camp, glamour, and shock in the drag world and the humanity, suffering, and wisdom of trans men and women – all cut together to make us laugh, cry, and be stunned by the beauty that his films exude.

2. Paris is Burning (Jennie Livingston, 1990)
Documentary greats are all about that perfect union of education and characterization, and there are few out there that succeed better in this balance than Paris is Burning. Outsiders can come in cold and leave with a piece of the trans world in their hearts; the rest of us can see the passion of female impersonation illuminated before us, realized in some of the most compelling characters ever captured on film. We see the dark side of trans prostitutes being murdered on the streets of New York: their sweet tenderness and the unforgiving world around them that tears them apart. We see the queens of the New York balls: passionate, catty, and undeniably talented. But most of all, we see a portrait of this underground world that even in 1990 made no comprises. Look at us, world – we´re fucking sickening.

1. Hedwig and the Angry Inch (John Cameron Mitchell, 2001)
How can a movie as new as Hedwig and the Angry Inch come out ahead of all the classics on this list? Well, because Hedwig isn’t really new anymore. It’s been over a decade since the film dropped, and even earlier than that when John Cameron Mitchell launched his off-Broadway one man show. But much like the gorgeous heroine herself, Hedwig has aged through struggle with dignity. It’s as fresh, funny, and sincere as it was 12 years ago. The film manages to incorporate both glam and punk rock, man-in-a-dress comedy and poignant historical drama, and, above all, has one of the most original narrative voices so far this century in cinema, trans movie or not. Hedwig is a living classic. From ¨Wig in a Box¨ to ¨The Origin of Love¨, Mitchell works the full spectrum of rock n´ roll, show tunes, and pop – in the end somehow being able to marry all three flawlessly. Much like Hedwig does between the sexes of man, woman, and ladyboy…walking away from all three at the end and still somehow never sacrificing the diva at his core.

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5 thoughts on “All-Time Greatest Gender-Bender Cinema

  1. I did not know that all of these transgender movies existed except for the Rocky Horror Pic Show and Some like it hot. I’m going to start my own collection. Thank you for the info.

  2. I’ve been collecting T girl movies ever since Bailey Jay “or Blow Job” got my attention of a teen transsexual back years ago so I heard of this new coming T girl by the name of Sienna Grace, that I’d been staying with contact with on face book but it wasn’t until I purchased my onShemale Yum DVD called Up and Cummers that took me back to when I was a teenage queen just like all of these young beautiful girls giving all of the T girls all over the movie industry some pretty stiff competition. What not only impressed me with these up and cummers was not only their ability to act the part play the role so very well but the really good ones completed the job by taking their own partiners organ deep inside of their own mouths swallowing it all down like a lady should. Grooby outdid themselve by making this Hot selling DVD to in which was a gold mind find to my own personal collect to in which it will help me to continue to write my own personal fictional stories of how I wished my life could have been like these luck girls are living today. If you ever purchase another transsesual DVD then this Third World Media T Gitl Up and Cummers is a must see movie and a collectors edition as far as I’m concerned. Thanks girls… love Albert

  3. I thouroughly enjoy watching these movies wishing that I had my youth back. You could pretty much be sure if I had my youth back I’d be either an actoress or having something to do with making these movies because they seem to make me so happy. Now that I’m older all alone I hurt because I am old all alone in my own home and it’s hurts when you have no won but the walls to talk to every day and night.

    1. I’ve only seen a hand full of these movies, myself. never seen Paris is Burning, that’s what caught my eye. I’m very interested in seeing it. I saw a couple pics from Shemale Yum on twitter from some of those weird Russian fettishists, hot pics. I used to do ‘Daytime Realness’ on a daily basis about 10 years ago. then I lost everything I owned and got really suicidal. I’ve recently bought a lace-front (Free-tress- Jealousy 1) and started putting together my new drag wardrobe. I look better than ever!
      Sorry to hear that you have no one to talk too, queen. I’ll see if I can find you on Facebook. We can type!

  4. I thouroughly enjoy watching these movies wishing that I had my youth back. You could pretty much be sure if I had my youth back I’d be either an actoress or having something to do with making these movies because they seem to make me so happy. Now that I’m older all alone I hurt because I am old all alone in my own home and it’s hurts when you have no won but the walls to talk to every day and night.

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