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Top 10 Songs About Crossdressers

It doesn’t matter if you refer to them as crossdressers or transvestites. Fact is, there’s a surprisingly huge number of songs out there about boys who like to dress as girls and girls who like to dress as boys. Some of these songs are about the crossdressers; some of them are about chance encounters with them, either intentionally or accidentally. And there’s a handful of cuts where the narrator is the crossdresser. So strap on some garters and stockings, or slide into a cozy flannel shirt, and dig into our list of the Top 10 Songs About Crossdressers.

Emerson Lake and Palmer Tarkus


‘Jeremy Bender’


From: ‘Tarkus’ (1971)

This tossed-off piano ditty from Emerson, Lake & Palmer’s second album may be the oddest song the oft-bombastic trio ever recorded. It clocks in at less than two minutes — by far their shortest song — and the springy tale of a crossdressing “man of leisure” doesn’t take itself too seriously. Which is something you definitely cannot say about the 20-minute, seven-movement title track that pushes prog into classical territory and then back again.


Velvet Underground


‘Candy Says’


From: ‘The Velvet Underground’ (1969)

Lou Reed is no stranger to tunes about crossdressing boys and girls (see No. 3 on our list of the Top 10 Songs About Crossdressers). But the opening ballad on the band’s third album takes a sensitive approach to its real-life subject: Candy Darling, a transsexual, and tragic, member of Andy Warhol’s crew who died at the age of 29.


David Bowie Hunky Dory


‘Queen Bitch’


From: ‘Hunky Dory’ (1971)

Like pal Lou Reed (see No. 9 on our list of the Top 10 Songs About Crossdressers), Bowie was fascinated by the underground culture of transsexuals. And like Reed, he wrote about them often. ‘Queen Bitch’ is a tribute to both the scene and to the Velvet Underground. The guitar riff is even borrowed from the Velvets’ ‘Sweet Jane.’


Van Morrison Astral Weeks


‘Madame George’


From: ‘Astral Weeks’ (1968)

Morrison’s gorgeous 10-minute epic, which ties into his terrific ‘Astral Weeks’ song cycle, slips in and out of its narrative, blurring its meaning along the way. ‘Madame George’ sure sounds like it’s about a cross-dresser, even though Morrison says the song is a composite of a bunch of different people he knew. We’re guessing at least one of them liked to put on women’s clothes once in a while.


David Bowie Rebel Rebel


‘Rebel Rebel’

David Bowie


From: ‘Diamond Dogs’ (1974)

Bowie again (see No. 8 on our list of the Top 10 Songs About Crossdressers), but this time he was a star and managed to score a hit single about a “hot tramp” who isn’t sure if he’s a boy or a girl. ‘Rebel Rebel’ quickly became an anthem for glam rock, a genre best known for sparkly guitar riffs and its, duh, androgynous fans.


Aerosmith Dude Looks Like a Lady


‘Dude (Looks Like a Lady)’


From: ‘Permanent Vacation’ (1987)

Aerosmith’s comeback hit takes a playful, and typically Aerosmith-like, approach to the subject of crossdressing guys. Of course, they could just as well be singing about someone who didn’t meet their rigid standards for maleness. Or maybe it’s about a drag queen they encountered during a wild night out. One thing’s for sure: That dude? No lady.


Led Zeppelin Royal Orleans


‘Royal Orleans’


From: ‘Presence’ (1976)

Say you’re a member of one of the planet’s biggest rock bands and you hook up with a fan after a show in New Orleans. Say that woman turns out to be a guy. What do you? If you’re a member of Led Zeppelin who wasn’t duped by the man dressed like a woman, you write a song about the time your bass player picked up a transsexual who accidentally burned down his hotel room. Good times.


Lou Reed Walk on the Wild Side


‘Walk on the Wild Side’

Lou Reed


From: ‘Transformer’ (1972)

Candy Darling, from the Velvet Underground’s ‘Candy Says’ (see No. 9 on our list of the Top 10 Songs About Crossdressers) makes another appearance in a Reed song. And this one somehow became a Top 40 hit — possibly the only Top 40 hit to include appearances by junkies, male prostitutes and fellating crossdressers.


The Who I'm a Boy


‘I’m a Boy’


Single (1966)

While most of the men in our list of the Top 10 Songs About Crossdressers wear women’s clothing by choice, the poor lad in the Who’s song is dressed that way by his mother, who wanted another girl (like three isn’t enough?). Still, he sure does seem to spend a lot of time putting pins in his hair, painting his nails and trying on wigs.


Kinks Lola




From: ‘Lola Versus Powerman and the Moneygoround, Part One’ (1970)

Like Zeppelin’s ‘Royal Orleans’ (see No. 4 on our list of the Top 10 Songs About Crossdressers), the Kinks’ ‘Lola’ is about an accidental hookup between straight guy and crossdressing guy. But unlike in the Zep song, ‘Lola”s narrator doesn’t seem to care about the mix-up. In fact, he seems pretty happy he’s made a new friend.


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