Songs About Cross-Dressing

Like anything, when bands write songs about something, occasionally you find yourself rocking out to some good music. These are the only songs we can find.
Know of others? Please indulge us. (and please no Rocky Horror Picture Show songs – those will kill yah).

Drag King Bar – The Bitch & Animal

A fun song about lesbians. Here’s the only video I could find featuring the song.

King for a Day – Green Day

Not anyone’s favorite Green Day song by a long shot, except for maybe people who can actually relate. I’m told it’s a good song to hear in concert.

Dude Looks Like a Lady – Aerosmith

This song is so good that it makes people forget what it’s about, but I think it’s about Glam Rockers in the 80s.

Lola – The Kinks

The guitar riff stands out the most in this song, even more than the dude dressed like a lady.

I met her in a club down in old Soho
where you drink champagne and it tastes just like Cherry Cola
C-O-L-A Cola.
She walked up to me and she asked me to dance.
I asked her her name and in a dark brown voice she said, “Lola”
L-O-L-A Lola, lo lo lo Lola
Well, I’m not the world’s most physical guy,
but when she squeezed me tight she nearly broke my spine
Oh my Lola, lo lo lo Lola, lo lo lo Lola
Well, I’m not dumb but I can’t understand
why she walks like a woman and talks like a man
Oh my Lola, lo lo lo Lola, lo lo lo Lola
Well, we drank champagne and danced all night,
under electric candlelight,
she picked me up and sat me on her knee,
She said, “Little boy won’t you come home with me?”
Well, I’m not the world’s most passionate guy,
but when I looked in her eyes,
I almost fell for my Lola,
Lo lo lo Lola, lo lo lo Lola
I pushed her away. I walked to the door.
I fell to the floor. I got down on my knees.
I looked at her, and she at me.
Well that’s the way that I want it to stay.
I always want it to be that way for my Lola.
Lo lo lo Lola.
Girls will be boys, and boys will be girls.
It’s a mixed up, muddled up, shook up world,
except for Lola. Lo lo lo Lola. Lo lo lo Lola.
Well I left home just a week ago,
and I never ever kissed a woman before,
Lola smiled and took me by the hand,
she said, “Little boy, gonna make you a man.”
Well I’m not the world’s most masculine man,
but I know what I am and that I’m a man,
so is Lola.
Lo lo lo Lola. Lo lo lo Lola.

Funky Cold Medina – Tone Loc

Rap, too, covers this subject:

So I took her to my crib, and everything went well as planned
But when she got undressed, it was a big old mess, Sheena was a man
So I threw him out, I don’t fool around with no Oscar Meyer wiener
You must be sure that the girl is pure for the Funky Cold Medina

Walk on the Wild Side – Lou Reed

The Frankenstein Drag Queens From Planet 13: Crossdressing G.D.S.O.B.

I wear lipstick and I wear a dress,
High heels I stand when I piss,
And I don’t wanna shave and I don’t wanna bathe,
‘Coz I’m a transvestite from Planet 13

Looked Like a Woman – Cowboy Mouth

There was a girl uptown, she kept her lights down low.
She kept her breasts taped down, so they did not show.
She had a daytime job, she had a daytime name.
But her nightlife baby was a different game.
Never the kind to wear a thrift store dress, she did it better in a suit and vest.

Nancy Boy – Placebo

And it all breaks down at the role reversal,
got the muse in my head she’s universal,
spinnin’ me round she’s coming over me.
And it all breaks down at the first rehearsal,
got the muse in my head she’s universal,
spinnin’ me round she’s coming over me.

Sheryl Lee Ralph – In the Evening

Also see: 5 Unexpected True Stories Behind Famous Gender-Bending Songs