Cross Dressing in Music

[Nick]

I know of a couple songs...

First one is "Bleed Like Me" by Garbage
"Chrissy all dressed up and acting coy
Painted like a brand new Christmas toy
He's trying to figure out if he's a girl or if he's a boy and he says
Hey baby, can you bleed like me?
C'mon baby, can you bleed like me?"

"Androgyny" by Garbage
"Boys in the girl's room
Girls in the men's room
You free your mind in your androgyny"

"She's Like Heroin" by System of a Down
"She's like heroin, sipping through a little glass
I'm looking for some help I need someone to save her backside
She wants nothing more but to be a little whore
He wants nothing less but to wear a little dress"

There's also "Truck Drivin' Song" by "Weird Al" Yankovic *shudders violently*
"Drivin' a truck
Drivin' a big ol' truck
Pedal to the metal
Hope I don't run outta luck
Got my 18 wheels a'rollin'
Before the break of dawn
Drivin' a truck with my high-heels on"

[LeftyRainbow(SO)]

"Halloween" by Ministry (even though it really is about dressing up as Goths...the lyrics fit for CDers)..was listening to it in the car on the way home.

"I'm a Boy" by The Who

The entire "Rocky Horror Picture Show" Album

What's the name of Iggy Pop's song that goes "And I've never known a girl like you before"?

And I always picture myself singing Bowie's "In the Heat of The Morning" to a TG girl for some reason....

[Laycee]

I don't know if this one count's because they aren't singing about crossdressing but they do wear women's clothes almost throughout the entire video but Vince Gill and Rodney Crowell (both country music stars) did a song together called "It's Hard to Kiss the Lips at Night (That Chew Your backside Out All Day Long." Won't hear it on the radio but the video is pretty funny.