If the history of American comedy has taught us anything, it's that boys will be girls and that seeing a man in woman's clothing is hardly a drag.
With the passing of Jack Lemmon, it's fitting to recall the great job he did in lipstick and a wig in Some Like It Hot, rated No. 1 on the American Film Institute's list of 100 best comedies.
If you take a look at the list, you'll see it's full of cross-dressing classics. The No. 2 all-time comedy is Dustin Hoffman's Tootsie. Lower down, you'll find Robin Williams' Mrs. Doubtfire (No. 67) and Julie Andrews' Victor/Victoria (No. 76).
The Bustier Boost
If you still think it's lowbrow for a man to slip on a skirt and apply makeup for giggles, you might want to consider the work of Charlie Chaplin and Cary Grant — or just about any comedian for that matter.
Just about every comedian has gotten a career boost with a bustier (or some other article of female attire). Jerry Lewis showed off his womanly side in 1966's Three on a Couch. Steve Martin got dolled up for the cover of his record Comedy Is Not Pretty. Even double Oscar-winner Tom Hanks is in the club (remember TV's Bosom Buddies?).
While some people may call cross-dressing a perversion, it's a gag you'll see in Shakespeare and Chaucer. Huck Finn certainly slipped on girlie clothes, just as certainly as Martin Lawrence and Eddie Murphy still do.
What were the sensors and morality police thinking at the dawn of the TV? Ricky and Lucy — husband and wife both in real life and on screen — were shown sleeping in separate beds. Discussions of pregnancy were verboten. And yet Milton Berle had a full-time job as America's most preposterous female impersonator.
Actresses sometimes pose as the opposite sex. But it's rarely put to comic effect. Two great exceptions — Gwyneth Paltrow in Shakespeare in Love, and Julie Andrews in Victor/Victoria, where she played a woman who posed as a male actor who impersonated women.
Why do men do better than women in cross-dressing comedies? The Wolf Files has a theory: Men look funny in dresses.
But what was the all-time funniest gender-bending role? Certainly, Lemmon was great. He even earned an Oscar nomination. But who was the best? Take a look and vote. If your choice isn't on the survey, fill out the e-mail form at the bottom. The Wolf Files will report the results soon.
Top Gender Bender Comedies
Jack Lemmon and Tony Curtis in Some Like It Hot: — After witnessing a gangland murder, two out-of-work musicians, Lemmon and Curtis, join an all-girl band led by Marilyn Monroe. Lemmon might not be the most comely of creatures, but he sure has a hard time fending off the guys.
He finally tells a would-be Romeo that he's just a female impersonator, but the suitor doesn't let up. He assures Lemmon that "Nobody's perfect." Film buffs, please note: Director Billy Wilder originally wanted Frank Sinatra and Mitzi Gaynor to play the roles that eventually went to Lemmon and Monroe.
Dustin Hoffman in Tootsie — If you can't get work as an actor, maybe you can become an actress. That's what Hoffman does, and he masquerades as soap opera sensation Dorothy Michaels. But getting in touch with his feminine side doesn't make it easier to lay his hands on Jessica Lange, who mistakes him for a lesbian.