We’re not going to focus on the negative portrayals of transsexuality, like in PSYCHO and SILENCE OF THE LAMBS and last year’s thankfully cancelled WORK IT television sitcom. And we’re not focusing on the history of transitioning stories that takes us all the way back to the 1930s when an intersexed, Bohemia-born Zdenka Koubkova went from female running/jumping champion to male cabaret performer. Nor are we going to look at transgender issues in the news, like when the Girls Scouts of Colorado let their first transgender girl into the organization last year or when, two years ago, a federal court ruled in favor of a woman who was fired from her job after coming out as trangender. Nope. We’re simply looking at the top ten positively positive, purely pop-culture gender-bending movies, moments and movers & shakers of the past few decades:
10. “Lola” by the Kinks
Considered one of “the greatest 500 songs of all time” by Rolling Stone magazine, 1970’s “Lola” dealt with a straight man falling for a transgendered woman without jokes or judgment: “Girls will be boys and boys will be girls / It’s a mixed-up, muddled-up, shook-up world except for Lola / Lo-lo-lo-lo-Lola.”
Perhaps it was RuPaul’s loveableness that made 1990s America embrace him with both arms. There’s a seamlessness, a naturalness to his drag-queenness that has kept him in the pop culture limelight for twenty-years, with five albums, two hosted TV shows, countless movie and TV appearances, and even a MAC modeling contract under his bedazzled belt.
And he didn’t care if you referred to him as he or she. As he wrote in his autobiography: “You can call me he. You can call me she. You can call me Regis and Kathie Lee; I don’t care! Just as long as you call me.”
Runner-up: Amanda Lepore.
8. The movie “Boys Don’t Cry”
There are a ton of decent movies which involve issues of transsexuality — probably a lot more than you think, but frankly still not enough. Many of them involve men in drag and focus on the straight characters’ points of view, which unfortunately keeps the transgendered person squarely in the detached and alienated category of “other.”One of the most successful, almost mainstream movies to really get inside the head (and body) of its transgendered character was 1999’s BOYS DON’T CRY, based on the real life of Brandon Teena, an intersexed teen who identified and lived as a man until he was beaten, raped and killed by male acquaintances after they learned of Teena’s female anatomy. The film got critical acclaim, won 43 awards (including Oscar’s Best Actress for Hilary Swank’s portrayal of Teena), and was nominated for 27 others (including Oscar’s Best Supporting Actress for Choe Sevigny’s portrayal of Teena’s girlfriend).
By telling a heartfelt star-crossed love story that people related to on a human level, it made a convincing case for wider acceptance and tolerance of sexual diversity — in an intimate way no film had before.
Runner-up: The Crying Game (stay tuned for our Top 10 list of Transgender Films)
7. Ellen DeGeneres
It’s not just that she’s a successful lesbian celebrity. It’s that she’s America’s sweetheart and she runs a media empire that almost rivals Oprah and she’s legally married to a typically femininely gorgeous Hollywood actress and she dresses in androgynous clothing with extremely sensible shoes (this last point being the most significant and impressive).
6. Buck Angel
You know a cultural issue has become accepted and mainstream (or at least is on its way to becoming accepted and mainstream) when it gets its own successful porn star. Buck Angel, a.k.a. “The Man with the Pussy,” is a transsexual adult film producer and performer, the only FTM one who’s ever won AVN’s Transsexual Performer of the Year Award.
5. Gender-bending super models
Maybe it was inevitable that the fashion industry would be a safe haven for gender-benders, since 90-pound female models are inescapably androgynous (look ma, no boobs!) Recent and notable models include the androgynous Andrej Pejic, the transexual Lea T, and the lesbian Jenny Shimizu (who’s had relationships with Madonna, Angelina Jolie, and Ione Skye) — all of whom appeared in the fabulous gender-bending promo for last year’s “Fashion Forward” fundraiser for the Gay Men’s Health Crisis. As RuPaul would say, they workit.