Actors have been playing gender bending roles since the days of Shakespeare: women pretending to be young boys, men trying to pass themselves off as attractive females and always all in good fun. The fear of discovery, the glamour of over the top drag fashions and the dual nature of characters who lead two lives is the playground that some wonderful films play in. Following is a selection of some of the best films that hinge on gender bending.
6) To Wong Foo, Thanks for Everything, Julie Newmar (1995)
Drag queens are truly a whole other level of cross dressing. It is not enough to simply put on a dress and a wig but they must embody femininity in a way that few biological women can even manage to do. This oddly titled little film follows drag queens Vida, Noxeema and Chi-chi as they attempt to drive from New York to Los Angeles to compete for the national “Drag Queen of the Year” competition. When they’re classic car breaks down in a rural area they begin to bond with the townsfolk who don’t realize the true nature of their genders. Of course an earlier run in with the town’s homophobic sheriff means that the stay may not be all the relaxing.
This road comedy had the brilliance to cast some of the manliest men in film as the most fabulous of drag queens. Namely Patrick Swayze as Vida and Wesley Snipes as Noxeema. Besides just the fun of the casting each of the main characters embodies one of the three drag archetypes: the Classy Lady (Swayze,) the Diva (Snipes,) and the Sex Kitten (John Leguizamo.) While both Snipes and Swayze performer wonderfully Leguizamo makes a frankly stunningly attractive woman (regardless of how much the other two call him “just a boy in a dress.”) The movie also contains some great up-front dialogue about what it really means to be a drag queen.
5) Mrs. Doubtfire (1993)
Daniel Hillard (played by Robin Williams) is a notoriously difficult to work with voice-over actor living in San Francisco. He is constantly being fired from or quitting jobs and his disregard for order and responsibility has driven his wife (Sally Field) to file for divorce. Having no regular employment Daniel has no custody of his children but needs desperately to see them more than one time a week. When he learns that his wife plans to hire a house-keeper Daniel goes to the extreme to be with his family. With the help of his make-up artist brother (Harvey Firestein) he transforms into the elderly English house-keeper Mrs. Doubtfire.
Williams completely vanishes behind the extremely well designed make-up and spot on voice that he uses to play the titular role. Watching Daniel not only have to maintain the illusion but also learn from his time living the life of the kind of responsible person he never was is both funny and touching. In many ways this already fun and enjoyable film is elevated by its conclusion. If the movie was truly as cheesy as some of its critics claim then the judge would simply rule in Daniel’s favor and granted a joint custody after having seen the lengths he went for his children. Instead the actual ruling is much more true to the reality of the situation and deals with consequences in a way that is often glossed over in Hollywood films. While it’s true that in the very end things finish happily that is due to two adults reaching an understanding outside of the courts, which really is what should happen more often anyways.
4) Victor/Victoria (1982)
Who says that men get to have all the fun? This Julie Andrews classic stars the musical legend as Victoria, a desperate and broke soprano singer in Paris. She’s on the verge of starvation and being thrown out on the street until she meets Toddy (Robert Preston in an Oscar Nominated performance,) who recognizes Victoria’s talent and develops a mad scheme to make her the talk of Paris. Under Toddy’s guidance Victoria poses as Victor, a man who is the “world’s greatest female impersonator.” Soon this woman pretending to be a man pretending to be a woman is the most successful act in the city. This is when she catches the attention of King Marchand, a small time gangster who starts to fall for Victor/Victoria and questions if she is indeed a man.
Noted comedy film-maker Blake Edwards (best known for the original Pink Panther film series) directs Andrews, who is in fact his wife, in this enjoyable romp. Drag kings are sorely under-represented on film and on the rare occasion that they do turn up it tends to be in more somber pieces like Yentil. Julie Andrews isn’t always a completely convincing man but her theatrics when on the stage make a completely convincing drag queen. The fun banter between herself and Preston bring some of the most delightful moments and one final gender flip at the end of the film gives it a great comedic conclusion.
3) Some Like It Hot (1959)
A true comedy classic rife with screwball humor. Jack Lemon and Tony Curtis are a pair of struggling musicians who accidentally witness a mob killing. Fearing for their lives they take the first paying gig they can that gets them out of town. However when that gig turns out to be in an all women’s band the two are forced to throw on some dresses and raise their voices in order to join the band. They soon find that life has tossed them some romantic difficulties to go with their gender swapping. Both become enamored with Marilyn Monroe as Sugar Cane. Curtis actively pursues her whenever he’s able to get out as a man; meanwhile Lemon’s female persona is being courted by a millionaire.
Lemon and Curtis don’t exactly make for convincing women but then that in and of itself is all part of the joke. The two have a great chemistry together and get to play with some really wonderful banter. However some particular highlights include watching Lemon actually entertain the notion of keeping his growing relationship going and Curtis doing a Cary Grant impression in the hopes that it will help woo Monroe’s character. Monroe herself is frankly a bit of a ditz in this film but her natural charisma and stunning appearance make it work for her as well.
2) Boys Don’t Cry (1999)
While people dressing against their born gender obviously lends itself to comedy, not all stories of cross dressers are light fluff entertainment. This Oscar winning film inspired by true events dwells in a very dark space and can leave viewers shaken even now. Hillary Swank won her first Academy Award for her portrayal of Brandon, a young woman who deep down knows she’s meant to be a man. In rural Nebraska she dresses as a boy and finds that she’s able to bond and blend in with a group of men very well. However when a mutual attraction between herself and Lana (played by Chloe Sevigny) develops it threatens to expose her to the homophobes that surround her.
This was the role that made Hillary Swank’s career and deservedly so. She gives a great performance, not only in her ability to be a convincing male but in capturing the swagger of youth that Brandon had. Brandon knew from her own past how dangerous it was for her to mix with the crowds she was with. But that inherent “I’m going to be fine” arrogance of youth allows her to put herself repeatedly into a dangerous situation, ultimately at a very high price. The story is an emotionally charged one told in careful detail and through truly riveting performances. Due to the dark nature of the story it can be difficult to watch at times but it an experience that any movie lover should have at least once.
1) Tootsie (1982)
How could the number one spot be anything else? What took Robin Williams a latex face mask and a body suit to accomplish Dustin Hoffman does with a wig and some glasses, and it truly is extraordinary. Hoffman plays a spoiled actor who is talented and well trained but has developed such a reputation for being difficult to work with that nobody will hire him. So naturally he dresses as a woman to land an acting gig on a popular soap opera. What is meant to be a one time job to pay some bills becomes a full time job as Hoffman’s “Dorothy Michaels” gains more and more exposure. Complicating matters is the attraction he has to Jessica Lange as well as an older cast member’s persistent romantic advances.
Hoffman simply owns this part, the premise is rather ridiculous and it takes and actor of his skill to make this more than just a goofy little movie. Hoffman’s portrayal of a spoiled actor and then his hastily put together drag alter ego is nothing short of sublime and of course hilarious. Backing him up is a stellar supporting cast, including Bill Murray and Sydney Pollack as his friend and agent who are in on and frequently stunned by what Hoffman’s character is doing. This film truly strikes the perfect balance between witty comedy and outright farce, all of it hinging on Dustin Hoffman in a dress. He carries the movie from start to finish and brings grateful viewers along for a wonderful ride.
The Adventures of Priscilla Queen of the Desert (1994) – A quirky little gem out from Down Under. This Australian road trip movie features a number of noted Aussie actors who hadn’t hit it big in the US yet (such as Guy Pierce of Memento and Hugo Weaving of The Matrix trilogy.) Two drag queens and a transsexual work their way across the outback in a battered bus to perform at a casino run by the semi-estranged wife of one of the drag queens. While it’s a fun little film there really was only room for one drag queen road movie on the list and To Wong Foo, Thanks for Everything, Julie Newmar did it better.
Rocky Horror Picture Show (1975) – Truly a gender bending omni-sexual classic, still shown at midnight screenings across the country. While the impact and fun of this film is undeniable (and I’ll admit to having gone to a few midnight showings myself) it didn’t make the list. It’s left off mostly on technicality since no characters are cross dressing for the purpose of trying to appear as the other gender, it’s simply part of the totally free sexuality of the film.
The Crying Game (1992) – This crime thriller’s cross dressing aspect is now somewhat infamous thanks to a perfectly played reveal of newcomer Jaye Davidson’s genitalia. He plays Dil, the object of affection for star Stephen Rea and anybody seeing this film when it first released never would have suspected that Dil was not completely a woman. This one missed the list because the fact that Dil is a trans-woman maybe fascinating but it’s not a lynchpin part of the plot. The film would have been largely unchanged had the character just been a woman.