What are some of your favorite gender-bending songs?

I’m a huge fan of Tori Amos’s cover of “Angie,” and Janet Jackson’s cover of “Tonight’s the Night.”

Mountains of Glory by Amy Ray.

Girls and Boys by Blur.

The chorus goes

girls who are boys
who like boys to be girls
who do boys like they´re girls
who do girls like they´re boys
always should be someone you really love

Another good one from Amy Ray is Measure of Me.

Plus there’s her entire album title. Stag.

@iamthemob

As well as Prom and Didn’t It Feel Kinder. Lots of good stuff!

Lou Reed – “Take a Walk on the Wild Side”

The Eurythmics’ Who’s That Girl?, featuring the fabulous Annie Lennox. It’s not so much the song itself as it is the music video that’s gender-bending, particularly where the male Annie Lennox kisses the female Annie Lennox!

Sorry about the ad on the video. No way around it

All the good ones have been mentioned already so… now for something completely different

@downtide They used to be so young!

@janbb It was rather a long time ago… :) PS I’m sorry its a version with all the preliminary stuff about the barber. By the time I found one that was just the song, it was too late to edit my post.

Iris and Rose. My personal favorite is the Moose Song, as sung by two women:

When I was a young boy I used to like girls
I’d tickle their bodies and play with their curls
But my girlfriend ran off with a sailor named Bruce
Now you’d never be treated that way by a moose

Moose, moose, I like a moose
I’ve never had anything quite like a moose
I’ve had many women, my life has been loose
But I’ve never had anything quite like a moose

Whenever I feel I’m in needs of a lay
I goes to me cupboard and pulls out some hay
I leans out me window and spreads it around
For a moose always comes when there’s hay on the ground

@janbb Here’s another traditional folk song from Pentangle, Sovay, about a woman who dresses up as a man, as a highwayman with a “brace of pistols at her side,” she’s packin’ heat too, one and a spare, in order to test her “true love’s” love for her. She robs him and he gives up everything but the ring that she gave him. She tells him if he gives it to her she will spare his life but he still refuses because it is a “token of me sweetheart” and tells her that she will be hanged for murdering him. The next day she confesses that she was the one who robbed him, gives him back all his stuff but let’s him know that if he had given up the ring, she would have shot him.

“Twas I who robbed you all on the plain
here’s your gold, so here’s your gold and your watch again
I only did it for to know
If you were be a man or no
If you had given me that ring she said
I’d have pulled the trigger I’d pulled the trigger and shot you dead’’

That’s a girl who doesn’t fool around. :-)

Queen of the Rodeo – Alice in Chains
50ft Queenie – PJ Harvey
Dude Looks Like a Lady – Aerosmith
Truck Drivin’ Song – Weird Al

I have mixed feelings about the views these songs present of genderbending. I find the AiC and PJ Harvey present a strong image of crossdressers. Though AiC uses what might otherwise been seen as a unfair caricature of genderbending the story arc of the song takes the “Queen of Rodeo” from being an object of ridicule to strong figure not to be fucked with.

The Areosmith of the otherhand is almost impossible to understand and the Weird Al is just silly. I’m kinda sad that I don’t have any tender songs about genderbending. I guess I’ll have to watch this question for songs to get.

“Rebel Rebel”—David Bowie

@lonelydragon Must be some other Bowie songs too, no?

The Origin of Love
The best illustration of Socratic love, ever. Period.

Lizzie West – I’m Your Man

“Turning Japanese” by the Vapors
Vapors/dp/B0000074RG

“Johnny Are You Queer” by Josie Cotton

“If I Were Gay” by Stephen Lynch

“I’m Glad I’m a Boy—I’m Glad I’m a Girl” by TIny Tim

“If You Were Gay” by Avenue Q

If we’re talking folk songs, here’s another:

The Handsome Cabin Boy performed by Kate Bush.

And speaking of crossdressing, Kate herself also dressed as a boy in the Cloudbursting video