Concluding my list of songs about cross-dressing, some of which you might not have expected or even heard of. (Links to songs were correct and working at time of writing.)
This will be the top ten; #20 to #11 can be found in the first post.
10) Madonna, What It Feels Like For A Girl
OK, so it’s another song that isn’t specifically about cross-dressing, but the opening lines do touch on a topic I’ll be blogging about at some point in the future:
“..But for a boy to look like a girl is degrading, ’cause you think that being a girl is degrading…”
9) Lords of Acid, I Like It (It’s Kinky In A Way)
It’s not the best song about cross-dressing out there, but it’s a fun little ditty about a playful, cross-dressing relationship with an incredibly catchy chorus:
“I found my boyfriend in my clothes, in my brand new panty hose – It struck me crazy, so to say, but he kinda looked good in a way…”
8) The Who, I’m A Boy
This song could also describe the experience of a trans boy sick of being treated as a girl; judge for yourself?
“Yeah I feel lucky if I get trousers to wear; spend ages taking hairpins from my hair…”
7) Aerosmith, Dude Looks Like A Lady
I’ve mentioned before about how some guys can be petrified of being ‘fooled’ by a transvestite; this is a song about it:
“She had the body of a Venus, Lord imagine my surprise.”
6) The Rocky Horror Picture Show, Sweet Transvestite
Because cross-dressers are bound to hear it anyway at some point…
“Don’t get strung out by the way I look; don’t judge a book by its cover…”
5) James, Laid
I include this with fond memories of… ah, never mind… 🙂
“Dressed me up in womens’ clothes, messed around with gender roles, line my eyes and called me prettyyyyyyyy…”
4) Blur, Girls And Boys
If ever a song needed a Venn diagram to help you figure it out, it’s this:
“Girls who are boys, who like boys to be girls
Who do boys like they’re girls, who do girls like they’re boys…”
3) Suzanne Vega, As Girls Go
Quite a mellow one, this; it’s a good description of cross-dressing in the uncanny valley (no that’s not a euphemism).
“Still kind of look like a guy; I never thought to wonder why”
2) Lou Reed, Walk On The Wild Side
Mellow, seedy, and an eye-opener when I first heard it, I can only imagine how it must’ve been received in the 60’s.
“Plucked her eyebrows on the way, shaved her legs and then he was a she…”
1) The Kinks, Lola
Yeah, it’s probably a bit of an obvious choice (believe it or not, I heard the Weird Al Yankovic version before I heard the original). Unlike Aerosmith’s take on the subject, this song is sung from the point of view of someone who doesn’t care about being ‘fooled’:
“Girls will be boys and boys will be girls; it’s a mixed up muddled up shook up world except for Lola…”