5:15 by the Who mentions dressing up in drag.
Actually, it’s called “not being a flaming asshole.” Granted people can’t be exempt from all humor, but there should be consideration about topical humor. Excluded middle?
For example, normal, non-sociopathic humans don’t make Auschwitz jokes about Jewish people, nor starvation jokes about Somali refugees. Sociopaths and assholes are the ones who make those jokes, then scream “sanctification!” when others rightfully call them out.
Transgender woman slips on banana = funny. (I guess…)
Transgender woman looks like a “dude” = not funny.
Within the context of the Quadrophenia album I’d say that the lines in question:
aren’t actually about men dressing as drag queens, but about Mod guys going clubbing in their sharpest outfits, including men’s shoes with Cuban heels. However, while the album was set during the Mod era it was written a decade later, at the height of glam rock. Pete Townshend presumably understood that by mentioning drag, glitter, and high heels he’d be evoking Ziggy Stardust-like images in addition to the Mods.
There is an earlier Who song about having a gender identity that conflicts with the way others see you, although it wasn’t intended to be about a transgender character. Much of the 1966 single “I’m a Boy” seems to be about a little boy who wants to play sports and run around outdoors, but his three sisters treat him like their doll and “practice making up on my face”. However, the chorus makes it clear that his parents also see him as a girl:
This song was originally conceived as part of a rock opera set in a future world of “designer babies”. The main character’s parents wanted four daughters, but when they wound up with three girls and a boy by mistake they decided to raise their son as a girl anyway. But Townshend abandoned this idea after writing “I’m a Boy”, and if you’re listening to the song without that context it’s not clear why the parents of a cisgender boy would insist that he’s really a girl. It would be easy to interpret this as a song about a child who was born female but identifies as a boy even though that wasn’t the original intent.
Let me suggest a lesson in reading comprehension, and also a dictionary.In the latter, turn to the word “sanctification” and let me know what you find.
Dar Williams “When I Was a Boy” makes clear transgender references (“I told him I was a boy… I’m glad he didn’t check”). it’s more about societal gender roles than transgender people explicitly.
Arguably “Reflection” (the song from Mulan) has a strong transgender interpretation.
Richard Digance - “Drag Queen Blues”
My friend George is a drag queen called Nancy
Pray tell me which are you tonight?
If you’re George let’s have a game of snooker
If you’re Nancy le’ts turn out the lights…
A song about a drag queen, obviously. No actual transgender references though, just the expected gender-bending.
Ray Jessel, The Penis Song. Not so much a “reference” as a “surprise.”
Another mention,
Joaquín Sabina, Yo quiero ser una chica Almodóvar (I want to be an Almodóvar actress). The line in question is a double whammy: yo quiero ser una chica Almodóvar como Bibí, como Miguel Bosé - Bibiana Fernández, born Manuel Fernández and originally famous as Bibí Andersen, is the most famous MtF transexual in Spain; Miguel don’t-ask-about-his-private-life Bosé played a judge who’s undercover as a drag queen, both in High Heels. Bibí here, Bosé here.
“Sister Ray” by the Velvet Underground
from Lou’s mouth: “I like to think of ‘Sister Ray’ as a transvestite smack dealer. The situation is a bunch of drag queens taking some sailors home with them, shooting up on smack and having this orgy when the police appear.”
it’s also a freakin’ awesome noise jam! Some versions run up to 30 minutes.
“Les Boys” by Dire Straits - “les boys do cabaret” seems to indicate dressing in drag
It’s entirely plausible that “Killer Queen” by Queen is about a transvestite rather than Queen Mary or some other royal personage.
Thanks!
The weird thing is it never even entered my mind that it could be about either a non-XX person nor an actual Queen, but rather I always assumed it was about a regally-acting XX female, in much the same way the phrase “drama queen” could easily refer to such.
But the “Les” part is just the French definite article - so it’s straightforward gays in drag (and leather ;)) being sung about, not anyone transgender.
And to me, drag queens are not the same as transvestites.
Bob Dylan’s Temporary Like Achilles
“Drama queen” is slang for a particular type of female. “… queen” is slang for a particular type of male. Considering who wrote the song, my money is on the latter and don’t understand why that possibility would never enter your mind. Maybe you could research this online and report back.
OP specified either transgender or transvestite and started the thread off with “Dude Looks Like A Lady”. I wouldn’t assume the dude is a lady.
I wouldn’t assume the dude isn’t just a drag queen. Maybe you could do some research and report back, maybe submit an article for publication in some erudite journal.
Drag is neither.
Or you could just read the frigging lyrics of the whole song. It’s about a cabaret show.
My daddy beats my mommy, my mommy clobbers me
My grandpa is a commie, my grandma pushes tea
My sister wears a mustache, my brother wears a dress
Goodness gracious, that’s why I’m a mess
West Side Story - Gee, Officer Krupke

In the “not really about transexuals” column, there’s “Andrew in Drag” by the Magnetic Fields (video mildly NSFW due to brief butt and boobie shots). Surprised this wasn’t mentioned yet, which means it probably was and I just missed it.