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Hollywood’s Best Gender Bending Film Comedies

by sumo nova

Hollywood loves to flip things. The film factory out of LA, CA loves to play the old shell game switch to keep us on our collective toes. Body switching romps where a Dad and son or Mom and daughter switch bodies for a few days or more are the rage sometimes. We all cheered for Trading Places, where the delightfully, snobbish Dan Ackroyd is forced to swap social places with funny man of the streets Eddie Murphy.

Then there are the Gender Benders – those cross dressing comic escapades where no character can ever be sure just what his, her or it’s wardrobe is going to be for that scene or whole film. Some call them drag movies or cross dressing comedies. Whatever your name for them, they’re plentiful and loads of fun. Here are four favorites

Some Like It Hot (1959)

This comedy classic tops AFI’s – American Film Institute – list of best comedy films. With a script by Billy Wilder and starring, Jack Lemon, Tony Curtis and Marilyn Monroe, it’s not hard to wonder why it fully delivers hard on the belly laughs. In many ways this is the film that started Hollywood’s flirtation with gender bending romps. Forced to hide in drag from mobsters on the run, Lemmon and Curtis have just as much chemistry as Lemmon and Walter Mathau would show us later in The Odd Couple. The DVD contains a great interview with Tony Curtis reminiscing on the filming of the movie and all the rumors about Marilyn Monroe being a difficult or unprofessional actress.

Dr. Jekyl & Sister Hyde (1972)

As a foreign film, this is the only non Hollywood movie on the list. This British horror outing from noted thrill studio Hammer puts a gender bending twist on the Dr. Jekyl and Mr. Hyde tale. Instead of turning into a villainous, ugly cretin after downing the noxious potion, Jekyl morphs into a feminine version of himself – a sort of soul sister who’s no less menacing and dangerous than a rampaging monster. This film inspired a slapstick, silly comedy starring Sean Young and Tim Daly, 1995’s Dr. Jekyll & Miss Hyde. Don’t confuse the two, because while the overall premise sounds preposterous, the acting and taught direction in this one creates a minor horror classic.

Tootsie (1982)

Next to Some Like It Hot, this Dustin Hoffman vehicle may be the most famous and most loved of the film gender benders. Hoffman plays an out of work actor so desperate for a gig, he’ll put on a dress and heels. Look for great supporting performances by Bill Murray and Teri Garr as Hoffman’s roommate and love interest respectively, along with a devastatingly bittersweet performance by Charles Durning who must deal with the fact that he fell in love with a man masquerading as a woman. The romantic theme song “It Might Be You” was nominated for an Oscar.

Just One Of The Guys (1985)

A once ubiquitous HBO offering and now Comedy Central staple, Joyce Heyser does a comedic drag version of Karate Kid Ralph Macchio that has to be seen to be believed. Just One Of The Guys isn’t a classic film, but it’s always an enjoyable one and more than delivers on its promise of a fun gender bender. Heyser excells in the lead role, playing both versions of herself with equal parts realism and comic flair. She’s ably assisted by actor Clayton Rohner as the James Brown obsessed high school senior whom she falls for, but must then carefully hide her affection while remaining in male guise. William Zabka, once again creates a memorable villainous punk as Greg Tolan. Zabka played the high school heavy who tormented Macchio in The Karate Kid, so at times it’s like cinematic deja-vu when we see Heyser done up like Macchio with Zabka giving her a hard time.

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