Five most outrageous instances
of men impersonating women in
literature, film, and song
5
Edward Rochester:
Jane Eyre
Mr. Rochester throws a party at Thornfield Hall. He wants to know what the ladies—especially Jane—think of him, so he does
what any sensible man would do: straps on a black bonnet, poses as a fortune-teller, and chats them up. This fools everyone,
including Jane. If Rochester were a real fortune-teller, this is what he would tell her: “You will fall in love with a married
man who keeps his pyromaniac wife locked in the attic. Run. Now.” Oddly enough, this tradition of the host crashing his own
party as a cross-dressed clairvoyant to find out who has the hots for him is no longer in vogue.
4
(tie) Michael Dorsey, Daniel Hillard:
Tootsie
,
Mrs. Doubtfire
Dustin Hoffman plays an actor who wants to work; Robin Williams is a divorced dad who wants to spend time with his kids: hello
Dorothy Michaels and Euphegenia Doubtfire.
Tootsie
is probably the better movie, but that scene in
Mrs. Doubtfire
where chunks of Robin Williams’s lemon meringue facial mask keep plopping into Mrs. Sellner’s tea makes me laugh till my
head hurts. Every time. Even when I know what’s coming.
3
Norman Bates:
Psycho
He seems like a nice guy: soft-spoken, polite, boyish in a way. Till he puts on a wig, grabs a knife, and visits you in the
shower.
Mamma mia!
2
Joe and Jerry:
Some Like It Hot
Tony Curtis and Jack Lemmon get dragged into drag in this classic from Billy Wilder. After witnessing the St. Valentine’s
Day Massacre, bass-playing Joe and saxophonist Jerry slip into hiding—and high heels—as Josephine and Daphne, members of an
all-girl band. They get pinched and ogled and fix each other’s torn-off breasts. Watching Curtis as a faux Cary Grant millionaire
seduce ukulele-playing Marilyn Monroe is hilarious; watching Jack Lemmon’s Daphne gush about his/her fiancé Osgood Fielding
III is even better.
1
Steven Tyler: lead singer, Aerosmith
The tights. The scarves. The hair. The eye makeup. Those
lips
. Dude
definitely
looks like a lady.