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.

5 Unexpected True Stories Behind Famous Gender-Bending Songs
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"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."

"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.

5 Unexpected True Stories Behind Famous Gender-Bending Songs
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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.

5 Unexpected True Stories Behind Famous Gender-Bending Songs

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.


Old lady looks like a halibut.


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.

5 Unexpected True Stories Behind Famous Gender-Bending Songs

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 ...

"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.

5 Unexpected True Stories Behind Famous Gender-Bending Songs

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

5 Unexpected True Stories Behind Famous Gender-Bending Songs

"Lady Stardust"

Do you know this song? You do? Cool, then someone probably called you a faggot in junior high school. Don't worry. It happens to the best of us.


Even more so if you show up to a Halloween dance dressed like this.

Anyway, "Ziggy Stardust" is David Bowie's 1972 classic about an androgynous alien/rock-and-roll messiah. On "Lady Stardust," Bowie sings about Ziggy's androgynous appearance.

The Lyrics:

People stared at the makeup on his face
Laughed at his long black hair, his animal grace
The boy in the bright blue jeans
Jumped up on the stage
And Lady Stardust sang his songs
Of darkness and disgrace

Who It's About:

Well, when I was a kid, I always thought Bowie was singing about Bowie. I mean, as portrayed by Bowie, Ziggy Stardust looked like this:


OK, fine, that's teen me as Bowie as Ziggy. (If I use the pic one more time, I win a prize!)

But then I read that, while performing "Lady Stardust," Bowie sometimes projected images of Marc Bolan of T-Rex or Iggy Pop. It's tough to know which is more accurate. On the one hand, Marc Bolan was certainly a very pretty man.


On the other hand, all the other lyrics sound like Iggy Pop: bright blue jeans, black hair, and animal grace.


The truth is that "Lady Stardust" is what we in the writer biz like to call a composite, which means I don't actually know exactly who "Lady Stardust" is about.


Although "Jet" is a Paul McCartney song, let me take a moment to talk about David Bowie. Don't worry. It'll make sense. Then again, when it comes to David Bowie, I do all sorts of things that don't make sense.


For example, this outfit. (Winner!)

Anyway, I've had a theory for many years that David Bowie deliberately recorded the super accessible and poppy Let's Dance album in 1983 because that was the year he was finally free of his contract with the piggish Tony DeFries, who entitled himself to a whopping 50 percent of Bowie's royalties through 1982. I never wrote about it because there is absolutely no support for such a theory, even though I fully believe it to be true. Now enter young Cracked stalwart Maxwell Yezpitelok. (That might seem like a hard name, but in Max's home country, it means "man with a name that makes small children cry.") Anyway, Max had the same theory but none of the fear of writing stuff with zero contextual support.

5 Unexpected True Stories Behind Famous Gender-Bending Songs
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"Sources are for wussies!" (Pictured above: NOT Maxwell Yezpitelok)

Anyway, it was a great article, and when we got to talking, Max dropped another Bowie theory on me that has absolutely zero support and is also totally wonderful. As a Cracked upper classman, I did the only thing I could: I poached it completely and told him if he squealed to the editors I'd tell everyone he secretly hates Teddy Roosevelt and Nikola Tesla (that shut him up).

OK, so Max's theory is about the 1974 hit song "Jet" by Paul McCartney.

The Lyrics:

Jet, I can almost remember their funny faces
That time you told them that you were going to be marrying soon
And Jet I thought the only lonely place was on the moon
Jet Jet Jet
Jet was your father as bold as the sergeant major
How come he told you that you were hardly old enough yet
And Jet I thought the major was a lady suffragette
And Jet you know I thought you was a little lady suffragette
A little lady
My little lady ... yes

Who It's About:

Well, according to Paul McCartney, the song is about a pony he owned. That makes sense, right? Read those lyrics again. Not even McCartney has smoked enough weed for that to make sense. So fuck that. According to Max (and now me), the song is about David Bowie. The song came out in 1974, at the height of Bowie's androgynous glam rock phase, a phase that Macca was certainly aware of and even mimicked, to hilarious results as far as hairstyles go.

5 Unexpected True Stories Behind Famous Gender-Bending Songs

Seriously, Macca?

What other support? Well, two of David Bowie's most famous songs by the time this song were written were 1969's "Space Oddity," featuring the outer space exploits of Major Tom, and his 1972 classic rock staple "Suffragette City." Hell, "Jet" even sounds a little like "Suffragette City," stylistically. Further evidence? In the early '70s, Bowie totally looked like a lady.

Can I prove this? Of course not. Does it make more sense than Macca's theory that it's about a pony (that he apparently loves and was gonna marry and mistakenly thought was a lady?). Yeah, safe to say it makes a lot more sense.



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