Dear Sir or Madam.....

It’s an idea that dates back centuries.  A character in a play – comedy or drama – will dress as a member of the opposite sex.  Sometimes it’s for money.  Sometimes to trick another person for a noble cause.  Sometimes just to hide out for a while.  Shakespeare was fond of having a strong female character disguise herself as a man, often with amusing results.  Charley’s Aunt, a play from the late 19th century, had a young man pretend to be a middle-aged female chaperone for some courting couples.  Most of the time, the disguise is played for laughs.  In some plays and movies, such as The Merchant of Venice, it’s a pretty serious undertaking.

Now I’m not talking about movies where a man plays a female character (Tyler Perry in his Madea films or John Travolta in Hairspray) or a woman plays a male (Linda Hunt in The Year of Living Dangerously).  No, I’m thinking more in terms of, well, the following movies.

Women Dressed as Men

Albert Nobbs (Glenn Close)
Game of Thrones (Maisie Williams)
Mulan (voice of Ming-Na)
National Velvet (Elizabeth Taylor)
Shakespeare in Love (Gwyneth Paltrow)
She’s the Man (Amanda Bynes)
Sylvia Scarlett (Katharine Hepburn)
Victor Victoria (Julie Andrews)
Yentl (Barbra Streisand)

Men Dressed as Women

Big Momma’s House (Martin Lawrence)
The Birdcage (Nathan Lane and Gene Hackman)
The Glass Bottom Boat (Paul Lynde)
I Was a Male War Bride (Cary Grant)
Mrs. Doubtfire (Robin Williams)
Some Like It Hot (Tony Curtis and Jack Lemmon)
Thoroughly Modern Millie (James Fox)
Tootsie (Dustin Hoffman)
White Chicks (Shawn Wayans and Marlon Wayans)

Shakespeare plays – to see where it mostly began…

As You Like It
The Merchant of Venice
Twelfth Night
Two Gentlemen of Verona