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5 Unexpected True Stories Behind Famous Gender-Bending Songs

I made myself a challenge the other day: to write a whole article about transvestite/transgender pop songs without making one stupid cheap joke. No Crying Game references. No cutesy euphemistic witticisms about chicks with a little something extra. Why did I make this challenge? I didn't, actually. That's a total lie. I was actually talking to Maxwell Yezpitelok about a great article he wrote, and he indirectly gave me the idea for this column. I guess what I'm saying is I stole the idea for an article about transvestite/transsexual songs from a younger writer and there was nothing he could do about it but cry.

Digital Vision/Photodisc/Getty Images
"Thanks for the idea, nerd. Now get yourself one."

But having decided to write it, I then made a decision to avoid any cheap "tranny" jokes. Y'know, like using the word "tranny" like I just did. Shit! Anyway, here is the real story about the people behind five pop songs about unconventional women. Oh, one more thing. While I'm going to avoid cheap jokes, there is simply no way to avoid "Dude Looks Like a Lady." It would be like writing an article about songs about parts of a house that a Slinky works on and leaving out "Stairway to Heaven."

#5. "Dude Looks Like a Lady"

Alright, let's get this out of the way because, yes, it may be the most famous song on this list, but it's also the least imaginative and most craptastic. Hey, I like Aerosmith. They have many great songs, and when they decided to dedicate themselves to snorting cocaine and sucking, no one was more upset than I was.

Medioimages/Photodisc/Photodisc/Getty Images
OK, that's another lie. Every single person in Boston was more upset.

Regardless, I was happy that they had their comeback and scored a hit with "Dude Looks Like a Lady" in 1988, because it meant that one of the best rock bands in America was back. If by back you mean appearing on the soundtrack of a shitty Kirk Cameron movie. But I digress.

The Lyrics:

Dude looks like a lady
Dude looks like a lady
Dude looks like a lady
Dude looks like a lady
What a funky lady
She like it like it like it like that
He was a lady

Who It's About:

Well, there's actually some dispute, but I'm going to go with the reports that say the dude in question is Motley Crue singer Vince Neil. Funny thing, though -- Vince Neil claims the song came from a night where he and Steven Tyler of Aerosmith went to a New York City bar where the waiters dressed as women. Nevertheless, in his book The Heroin Diaries, Nikki Sixx of Crue claims the song was specifically about Vince Neil. Desmond Child, who co-wrote the song, agrees, saying Tyler mistook Neil for a big-haired chick at a bar.

people.com
Do you think someone who dressed like this would be upset to be mistaken for a woman?

Still, the thing that kills me about this song is ... who is Steven Tyler to be saying any dude looks like a lady? Have you seen the man? It's like your chain-smoking aunt had a baby with some sort of sucker fish devoid of testosterone.

funnyzela.com
Old lady looks like a halibut.

#4. "Lola"

Ah, "Lola." When I was a wee lad growing up in the suburbs and being nurtured on classic rock radio, "Lola" was always a fan favorite. And like most suburban little boys, I was sexually clueless. Even though I'd heard the song on the radio at least once a week, it wasn't until I was a teenager that I noticed, hey, Lola wasn't a chick!

The Lyrics:

Oh my Lola la-la-la-la Lola
Well I'm not dumb but I can't understand
Why she walked like a woman and talked like a man
Oh my Lola la-la-la-la Lola la-la-la-la Lola
Well I'm not the world's most masculine man
But I know what I am and I'm glad I'm a man
And so is Lola

Who It's About:

Well, there are two stories. The one I tend to believe states that the song was inspired by a woman the Kinks' manager was dancing with in a nightclub who turned out to be a transvestite. By the end of the evening, the manager's dancing partner started sporting a 5 o'clock shadow that everyone except the manager seemed to notice.

But there's a second story, based even more on rumor, that Lola was Candy Darling, the transsexual mainstay of Andy Warhol cinema.

wikipedia.com
And no joke, this pic was taken from her deathbed. Damn.

There's still another rumor that Ray Davies of the Kinks dated Candy and didn't know she was a transsexual, but given the state of reassignment surgery in the late '60s and the fact that Ray Davies speaks in full sentences, I'm going to pass on this one. The funny thing about Candy Darling is that she's also in our next song ...

#3. "Walk on the Wild Side"

Yep, beautiful transsexual Candy Darling is in Lou Reed's 1972 classic "Walk on the Wild Side," but here's the thing: Until I researched this article, I had no idea Candy was a transgender woman. To me, she was simply the girl who "never lost her head/even when she was giving head." So, incredibly, for the second time in one article about transvestites and transgender women, I am not talking about Candy Darling.

Nope, there is plenty of unconventional sexual identity characters to go around in this song. And today's topic is "Holly."

The Lyrics:

Holly came from Miami, F.L.A.
Hitchhiked her way across the U.S.A.
Plucked her eyebrows on the way
Shaved her legs and then he was a she
She says, "Hey, babe,
Take a walk on the wild side."
Said, "Hey, honey,
Take a walk on the wild side."

Who It's About:

Holly Woodlawn, a Puerto Rican transgender actress who appeared in the movies Trash and Women in Revolt. The story is apparently true as well. She hocked all her jewelry and got as far as Georgia before having to hitchhike all the way to New York.

Highbergermedia.com
OK, not as feminine-looking as Candy Darling, but at a least she made it into a Cracked article!

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