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…”
Just don’t expect me to sing any of these…
Miss Twist speaks her brains 
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