Songs About Cross-Dressing?

There’s more than that. I think there are other hints like, “You tacky thing, you put them on,” and the repeated tag of “Rebel, rebel, how could they know?” I always kind of assumed this song was about a tranny.

“The Lapdance is Always Better When the Strippper is Crying”? It includes the memorable line, “It’s hard to hide a hard-on when you’re dressed like Minnie Pearl.”

Dio, I interpreted those lines differently (e.g., “how could they know” how much the singer loves the tramp), but that makes a lot of sense. I guess a lot of Bowie’s early songs were at least arguably about cross-dressers (shocker!).

What Dio said.

The Beatles “Ob-la-Di Ob-la-da,” final verse: “Desmond stays at home and does his pretty face and in the evening she’s a singer in the band.”

“Have You Seen Jackie?” by The Dukes of Stratosphear

“Boys” by Bauhaus?
At the very least, it’s got a lot of of androgyny and makeup.

Well, in that case, just about every Orgy and Poison song gets in.

Oh, yeah, naturally cross-dressing is brought up in a couple of songs from The Rocky Horror [Picture] Show: “Sweet Transvestite” and “Don’t Dream It.”

There’s a song called “Bruce”, by John Wallowitch, one of those uber-sophisticated East Coast types. It pretends to be funny,
but it’s really just vicious.

“and who were those awful old trolls?
They looked like a bus-and-truck Cage aux Folles”

“Don’t emulate Nancy, or Jacquie,
You’re acting just as I feared.

My heart has an ache, Bruce,
For haute couture’s sake, Bruce,
Shave off your beard!”


Androgynous-- The Replacements

This may not quite fit, but, The Handsome Cabin Boy.

That’s a screw-up they decided to leave in after having done way too many takes of the song. I guess it still counts, though. :slight_smile:

Mrs Brown You’ve Got a Lovely Daughter.

On Todd Rundgren’s classic A Wizard/A True Star - You Don’t Have To Camp Around:
Save the satin undies, don’t pluck out your eyebrows*

He had lots of fun with the song, and how he dressed at the time, in his recent tour of the album.

Jesse Jane by Alice Cooper.

Lola is ambigous?

I Wanna Get In Your Pants by The Cramps. Lux sings about wanting to get into a girl’s pants…literally.

Yes, quite artfully and intentionally so. The fact that it was “inspired” by a specific incident doesn’t have any bearing on that. The purpose of art is to improve on reality.

“Looked Like a Woman (But Dressed Like a Man)” by Cowboy Mouth

The tender, sensitive story about a man meeting a cross dressing woman in a bar and going home with her.