A friend had once given me an mp3 of a weird song. It was sung by a guy and it was about cross-dressing. I’d like to hear it again, but I’m not in talking terms with that guy and Google hasn’t really helped me.
So name a few songs about cross-dressing. 
Cross-dressing is brought up (or heavily implied) in these songs:
“Lola” by the Kinks
“Arnold Layne” by Pink Floyd
“Walk on the Wild Side” by Lou Reed
Van Morrison’s “Madame George”
I’m guessing it was “Walk on the Wild Side”…
“Jane Says” by Jane’s Addiction
“Where’s the Dress” by Moe Bandy and Joe Stampley
Monty Python’s “The Lumberjack Song”?
Weird Al’s “Truck Driving Song”?
Doesn’t Brad Paisley have a song about wearing lady’s clothes?
“Lola”
Isn’t “Jane Says” about a heroin addict who used to be Farrell’s roommate?
Might have been Wig in a Box from Hedwig and the Angry Inch?
And a transvestite, yes.
Nothing I’ve ever read about Jane Bainter indicates she has ever been a transvestite. Washington Post article (reprint), Wikipedia article, picture of Jane Bainter then, picture of Jane Bainter more recently. IIRC, the wig was worn due to her involvement in the LA club scene.
Dude Looks Like a Lady - Aerosmith
“I’m Wishing You a Drag Queen Christmas”
and
“I Am What I Am” from la Cage aux Folles
Isn’t “I’m A Boy” by The Who about forced cross-dressing?
“Out of the Wardrobe” by the Kinks–none of the ambiguity of “Lola” there!
“Rosie” - Joan Armatrading
“Woman or a Man?” - Richard Thompson
There’s “Queen of the BBQ” by 80s Austin punk band The Hickoids (“he looks much better in a dress than you”), which is pretty obscure but not too obscure to be on a MySpace page: !!!
These songs mention cross-dressing or cross-dressers but may not, strictly speaking, be about them:
King For a Day - Green Day
Nancy Boy - Placebo
Funky Cold Medina - Tone Loc
Get Back - The Beatles
Laid - James
Where I Come From - Alan Jackson
Rebel Rebel - David Bowie
There are lots about women dressing as men to join the army:
Sweet Polly Oliver (English folk song)
The Cruel War - Peter, Paul & Mary (among others)
“You’ve got your mother in a whirl / She’s not sure if you’re a boy or a girl”? I’m not sure it’s about cross-dressing per se, or androgyny, or just a “your folks don’t understand you” kind of thing (lyrics here). Lady Stardust is another song toying with gender identity, but not explicitly about cross-dressing.
I thought Bowie’s Queen Bitch was about cross-dressing, but reviewing the lyrics, I’m not sure. Is the “queen” who pushes “ahead of the dames” a drag queen, or just a pushy broad? When the singer says “I can do better that,” is he saying he could find a better lover than her, or he could dress better than her, or he could please her man better than her? I find it all very confusing.
Oh, Bowie’s She’s Got Medals* fits in that category. No ambiguity there, except for the part about picking up girls. Whatever do you suppose she did with them?
