Songs about Cross-Dressing

   

19 comments:

Anonymous said...

Holly came from Miami F-L-A
Hitchhiked all across the U-S-A
Plucked her eyebrows on the way
Shaved her legs and then he was a she
She said, "Hey, babe
Take a walk on the wild side."

(Lou Reed)

Deborah in IL said...

Well I'm not dumb but I can't understand
Why she walks like a woman and talks like a man

Lola
The Kinks

Sally said...

For Victoria's also known as Victor
Making it tricky to depict her
Victor Victoria, Victor Victoria,
Victoria, what a victor you are!

-from "Victor Victoria," a musical about a woman pretending to be a man pretending to be a woman

Shanona Ryder said...

Sweet Loretta Martin
thought she was a woman
but she was another man...

---Beatles "Get Back"

Sandra Dodd said...

So early next morning she softly arose
And dressed herself up in her dead brother's clothes
She cut her hair close and she stained her face brown
And went for a soldier to fair London town

"Polly Oliver," a maybe 18th C ballad

Deborah in IL said...

I'll tie back my hair
Mens clothing I'll put on
I'll pass as your comrade
As we march along
I'll pass as your comrade
No one will ever know
Won't you let me come with you?
No my love no

The Cruel War

Spinning Ninny said...

I was chasin' sun on 101
Somewhere around Ventura
I lost a universal joint and I had to use my finger

This tall lady stopped and asked
If I had plans for dinner
Said no thanks maam, back home
We like the girls that sing soprano

Where I Come From
Alan Jackson

Sally said...

Oo, what a funky lady
He like it, like it, like it like that
Oo, he was a lady

-"Dude Looks Like a Lady"
Aerosmith

Sally said...

Soldier: This guy's got'em scared to death
Mulan: Hope he doesn't see right through me

-"I'll Make a Man Out of You" from Disney's "Mulan"

Elisha said...

You've got your mother in a whirl
'Cause she's not sure if you're a boy or a girl

David Bowie, "Rebel Rebel"

Heaz said...

when she got undressed
it was a big ol' mess
Sheena was a man

-Tone Loc, "Funky Cold Medina"

Meghan said...

Straight Boys I must confess.
Wanna get under my dress.
Give me a kiss kiss.

Straight Boys by Jeffree Star

Mark Horning said...

I'm just a sweet Transvestite,
from Transexual, Transelvania.

"Sweet Transvestite" - Rocky Horror Picture Show

Heaz said...

Dress me up in women's clothes
Mess around with gender roles
Line my eyes and call me pretty...

"Laid" - James

Sandra Dodd said...

When I was a young maid about seventeen
I 'listed in the Navy for to serve the Queen

(a ballad, must be from the 17th century, and... I don't know the name of it)

Pervection said...

Does his makeup in his room
Douse himself with cheap perfume

- Nancy Boy, by Placebo

Unknown said...

Well, she's got Jet Pilot eyes from her hips on down.
All the bombardiers are trying to force her out of town.
She's five feet nine and she carries a monkey wrench.
She weighs more by the foot than she does by the inch.
She got all the downtown boys, all at her command
But you've got to watch her closely
'cause she ain't no woman She's a man.

Jet Pilot
Bob Dylan

Tortus said...

My friend was kinda hurtin'
For a girl to try
He saw one that looked like Pat
On Saturday Night Live
It had a pair of thingies
But a mustache too
Not clearly male nor female
So now what to do
Offspring - Don't Pick It Up

Anonymous said...

Who are you girl?
Who are you boy?
Bet I know what you're up to
Can I come along
Your home number's on the wall
-Regular John by Queens of the Stone Age