Comedy Is a Drag

Was Jack Lemmon the Funniest Man in Drag? Vote for Your Favorite Cross-Dressing Comic

By Buck Wolf

June 29, 2001 — 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.