Last year at the final NASCAR event at Homestead I stayed in Miami Beach, one of the trendiest gay areas in America. Realizing a few of my friends are en route to Miami Beach next week for the final NASCAR race of the season, I got to wondering how many of them will end up getting hit on by a tranny. The next logical step was to rank memorable cross-dressers in cinema.
Criteria: Men only (women will constitute a separate list); cross-dressing must have played an integral part of the movie or of a main character.
To Wong Foo Thanks for Everything, Julie Newmar — Patrick Swayze, Wesley Snipes and John Leguzama are drag queens traveling from New York to Los Angeles in a convertible. They find themselves in a tiny town after their car breaks down and as expected have all types of interesting encounters. What’s especially entertaining to see is how comfortable these action actors look in womans wear.
Glen or Glenda — The movie itself isn’t exactly the best (nothing by Ed Wood ever was), but for this type of list I simply have to pay tribute to him. Here he plays a man keeping his cross-dressing a secret from his fiancé. It is said to be loosely based on his own love of getting dressed in the clothes of the opposite sex.
The Adventures of Priscilla, Queen of the Desert — Guy Pearce and Hugo Weaving play dress up and Terence Stamp is a transsexual who have a cabaret act in Sydney, Australia. When an opportunity comes to take the show on the road, they jump into a bus and travel across the Australian Outback. Along the way they run into some interesting situations.
The Birdcage — Nathan Lane is an out of his mind drag queen living with his boyfriend, played by Robin Williams. Things go further haywire when he must play it straight so Williams’ son can introduce them to his fiancé’s parents. Lane plays an exceptional feminine character.
Sorority Boys — After getting kicked out of their frat house for theft, Harland Williams, Barry Watson and Michael Rosenbaum dress up like chicks so they can crash at a local sorority. The premise is as absurd as it gets but it is funny as hell. The drunken frat party alone makes this a worthwhile watch.
Flawless — If you want to be frightened, check out Philip Seymour Hoffman as a pre-op transsexual. Scary. In this feature, he is a flamboyant, drag-act singer who, for extra cash, helps a homophobe (Robert DeNiro) with vocal lessons. They make the perfect Odd Couple and Hoffman shines as an openly gay man (a precursor to his Oscar win for his role in Capote).
Mrs. Doubtfire — Robin Williams dresses up as an elderly British woman and poses as a nanny so he can circumvent the bitter custody battle he has with his wife. This is one of the few roles where Williams acting like a hyperactive idiot actually adds character to his female persona.
Some Like It Hot — One of the classics. In this oldie but goodie, Jack Lemon and Tony Curtis dress like women to avoid getting knocked off by the mob. Curtis falls for Marilyn Monroe (who wouldn’t) while Lemon is chased down by Joe E. Brown. This movie is a comedy gem.
Tootsie — Dustin Hoffman can’t find work as an actor, so he comes up with an elaborate plan to dress up as a woman to find work. Needless to say, he makes the ugliest woman alive. But amazingly enough, he lands a dream gig and soon finds himself stuck when he falls for the lead Jessica Lange. Hoffman is great.
The Crying Game — This is the movie that had everyone and their mother fooled. Jaye Davidson is so convincing as a woman that it is impossible to not give this movie the top spot. Even without the shocking twist, this movie has plenty to offer. It is a must see.
I really wanted to add The World According to Garp but Lithgow’s character is a transexual and never reverts back to being a man. Nonetheless, you should watch this movie anyway.
Below is where you tell what movies I’ve excluded.