If the American Film Institute's list of the 100 funniest movies of all time proves anything, it's that a guy in a dress equals comedy. The top two films on that list? Some Like It Hot and Tootsie.

Why is a man in a dress a poular comic device, but a woman in men's clothing usually regarded as sexy? There are some rules, of course. The man cannot be a good looking woman. If he's too successful, too attractive as a woman, the comic element goes away. Generally drag (the term generally applied to a person of one gender performing as a person of the other gender) comedy borders on slapstick: stumbling in high heels, squirming to get into a corset, garish, clown-like make-up. The comedy comes when he doesn't succeed.

On the other hand, the less the woman succeeds the better. If she passes as a man, it's not sexy anymore. Lily Tomlin's portrayal of soul singer Purvis Hawkins, for example, is more akin to a Brini Maxwell or Rue Paul. It's convincing and therefore not funny.

Before exploring this topic further, it's probably helpful to distinquish it from a variety of "gender-bending" terms. Historically, the term drag was used in the gay community, primarily to refer to a drag queen, a gay man who impersonates a female. Very often, the impersonation is that of a well-known singer or movie actress. Judy Garland, Cher,

Men have been dressing as women on stage for hundreds of years, dating back to the thirteenth century when the church forbade the appearance of female actors but condoned that of men and boys disguised as the opposite sex. Forms of transvestism can be traced back to the dawn of the theater and are found in all corners of the world, notably in China and Japan.

There are many kinds of drag artists and they vary greatly from professionals who have starred in movies to people who just try it once. Drag queens also vary by class and culture and can vary even within the same city. Although many assume all drag queens are gay men or transgender, there are drag artists of all genders and sexualities who do drag for various reasons. Generally, drag queens dress in a female gender role, often exaggerating certain characteristics for comic, dramatic or satirical effect. Other drag performers include drag kings, who are women who perform in male roles, faux queens, who are women who dress in an exaggerated style to emulate drag queens and faux kings, who are men who dress to impersonate drag kings.

Not all men who dress as women are drag queens. Other categories include transvestites or cross-dressers, generally straight men who wear women's clothing for erotic reasons; preoperative male-to-female transsexuals; and transgender people who display and embrace a gender identity at odds with their biological sex, but who do not intend to undergo surgery to change their sex. Drag queens, in contrast, are gay men who dress and perform.

[from Dragalicious at MO's Universe. Check the Infamous Queens page for a list of popular drag queens.]

Comedians Famous for Performing in Drag

  • Milton Berle
  • Flip Wilson
  • Jack Benny