Musical Interlude: Top Ten

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…”


Musical Interlude

I don’t have my usual resources to fall back on for this month’s entry, so I shall instead provide my top twenty list of songs about cross-dressing, some of which you might not have expected or even heard of. Just don’t assume that this selection represents the totality of my musical tastes! (Links to songs were correct and working at time of writing.)

This will be the list of #20 to #11; my top ten can be found in the next post.

(EDIT: other songs that have been suggested to me since I first posted include Nancy Boy by Placebo, The Saga Of Jesse Jane by Alice Cooper and Arnold Layne by Pink Floyd; I tend not to count Ob-la-di Ob-la-da by The Beatles on the grounds that I’m not sure if the lyric “Desmond does his pretty face” was deliberate or just a flubbed line…)

20) Shania Twain, Man I Feel Like A Woman

OK, so it’s not specifically about cross-dressing, but it just as easily could be:

“The best thing about being a woman is the prerogative to have a little fun, oh oh oh, go totally crazy, forget I’m a lady…”

19) Lady Gaga, Born This Way

Again, not specifically about cross-dressing, but it does include cross-dressers in the extensive list of differences to be celebrated:

“Don’t be a drag, just be a queen, whether you’re broke or evergreen…”

18) Emerson, Lake and Palmer, Jeremy Bender

Not entirely keen on this one; the lyrics tell of a transvestite nun which seems to reinforce that whole ‘weirdo transvestite’ stereotype:

“Diggin’ the sister, she was a mister; shouldn’t’ve kissed her but he couldn’t say no…”

17) Monty Python, Lumberjack Song

Yes, it’s a comedy song, but let’s face it – this list wouldn’t be complete without it:

“I cut down trees, I wear high heels, suspenders and a bra…”

16) Weird Al Yankovic, Truck Driving Song

Cross-dressing is quite frequently seen as comedy fodder, but that doesn’t mean you have to get in a huff about it; it can be fun, too:

“Wearing feather boas with sequins and chiffon, driving a truck with my high heels on..”

15) Green Day, King For A Day

The story of a boy who began cross-dressing early:

“Who put the drag in drag queen? Don’t knock it until you’ve tried it on…”

14) Led Zeppelin, Royal Orleans

It’s the 1970’s and you’re in a band. One of your band mates takes a transvestite back to his hotel room, who then accidentally sets fire to it. Naturally, you’re going to write a song about it:

“When I step out, strut down with my sugar, she’d best not talk like Barry White!”

13) The Cramps, I Wanna Get In Your Pants

With the song title being played literally, this may well count as a comedy song (judge for yourself):

“I got this burning desire… to don that darling attire.”

12) David Bowie, Rebel Rebel

Even at an early age, he was defending the right to go against ‘gender-appropriate’ fashions. This song features another example of androgyny from his Ziggy Stardust alter-ego:

“You’ve got your mother in a whirl, she’s not sure if you’re a boy or a girl…”

11) The Beatles, Get Back

Apart from being a classic tune, it also tells the story of a trans woman told to ‘get back where she belongs’:

“Sweet Loretta Martin thought she was a woman, but she was another man…”

My top ten can be found here.

Just don't expect me to sing any of these...

Just don’t expect me to sing any of these…