Dude Looks Like A Lady: The Greatest Gender-Bending Songs

on 21 September 2012 in Slideshows


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Rock N Roll has always been an outsider's game. The little corner of the music world where the rebel is the hero and the unconventional is celebrated rather than suppressed. The gender-bending song then, is perhaps the ultimate expression of this artistic rite and freedom. Men singing songs as women, dudes who look like ladies, transgender artists baring their souls and the whole entire celebration of the sexually vague. Let loose your gender restrictions, take a dose of androgynous and - in the immortal words of that immortal chorus - take a walk on the wild side, as we look through music's greatest gender-bending songs.

  • slidegender

    Rock N Roll has always been an outsider's game. The little corner of the music world where the rebel is the hero and the unconventional is celebrated rather than suppressed. The gender-bending song then, is perhaps the ultimate expression of this artistic rite and freedom. Men singing songs as women, dudes who look like ladies, transgender artists baring their souls and the whole entire celebration of the sexually vague. Let loose your gender restrictions, take a dose of androgynous and - in the immortal words of that immortal chorus - take a walk on the wild side, as we look through music's greatest gender-bending songs.

  • 00-  Antony

    “For Today I Am A Boy” (2005) – Antony & The Johnsons
    Perhaps the ultimate torchlight singer for transgender artists, it’s hard to choose just one song from Antony Hegarty’s rich catalogue, but this yearning cut from the 2005 breakthrough album I Am A Bird Now is the first that comes to mind. Singing in his haunting, distinctive vibrato, Hegarty draws a delicate slow-burn of poignant desire, intoning the hope that “One day I'll grow up, I'll be a beautiful woman/One day I'll grow up, I'll be a beautiful girl” but, “for today I am a child/for today I am a boy.”

  • 01 - thekillers

    “Somebody Told Me” (2004) – The Killers
    With lyrics like ‘Somebody told me, you had a boyfriend/who looks like a girlfriend,/that I had in February of last year’ it’s no wonder the catchy debut single from The Killers leaft many people scratching their heads. Whether frontman Brandon Flowers is singing about transvestites or transgenders, or merely making a comment about the nature of rumours doesn’t seem to matter to the thousands of fans singing along.

  • 02 - aerosmith

    “Dude (Looks Like a Lady)” (1987) – Aerosmith
    A pretty straight up rock tune that’s essentially about a man who is mistaken for a woman. The song is said to have originally started out as “Cruisin’ For A Lady” but after a run in with Mötley Crüe, the band transformed it. In Aerosmith’s autobiography, lead singer Steven Tyler explains, “One day we met Mötley Crüe, and they're all going, 'Dude!' Dude this and Dude that, everything was Dude. 'Dude (Looks Like a Lady)' came out of that session."

  • 03 - beyonce

    “If I Were A Boy” (2008) – Beyoncé
    This is the only song on Beyoncé’s third studio album I Am… that she didn’t co-write…. and it isn’t hard to tell. The song is, lyrically, far removed from those previously released by the pop diva. It deals with issues of gender swapping and misunderstanding between the sexes, as well as being a criticism of the male’s dominance in relationships, just for good measure.

  • 04 - The Kinks

    “Lola” (1970) – The Kinks
    A transgender sing-a-long if ever there was one. Lola walks like a woman but talks like a man, and The Kinks don’t seem to mind. The song is believed to be inspired by an encounter between band manager Robert Wace and a transvestite with whom he spent the night dancing. Sure is a ‘mixed up, muddled up, shook up world’!

  • 05 - loureed_wideweb__470x305,0

    “Walk On The Wild Side” (1972) – Lou Reed
    The Velvet Underground alumni’s second solo album, Transformer (1972) contained this transgender classic. This song has it all: sex, drugs, male prostitutes and, of course, transexuality. The opening verse introduces Holly from Miami who ‘shaved her legs and then he was a she’. Reed is known to be singing about Holly Woodlawn, a transgender actress, legendary drag queen and former member of Andy Warhol’s New York Studio, The Factory. Produced by David Bowie, the androgynous glam rock song was a Top 20 hit.

  • 06 - Blur

    “Boys and Girls” (1994) – Blur
    Boys and girls are being thrown around like nobody’s business in this song. “Girls who are boys, who like boys to be girls/ who do boys like they’re girls, who do girls like they’re boys.” It’s a transgender carousel of head-spinning proportions. The most surprising thing about this track is under all the gender confusion is one simple message: that, no matter the sexuality, it ‘always should be someone you really love’.

  • 07 - Garbage

    “Cherry Lips” (2001) – Garbage
    Released as the second international single off their third studio album Beautiful Garbage, “Cherry Lips” was notably a huge hit in Ausralia, peaking at #7 on the ARIA charts. Against a bouncing synth line, front-lass Shirley Manson encourages fans to be who they are and to be accepting of people regardless of sexual orientation or gender identity. “Go baby, go go/yeah we’re right behind you!”

  • 08 - ofmontreal

    “Tim I Wish You Were Born A Girl” (1997) – of Montreal
    The prolific plaything of songwriter Kevin Barnes, of Montreal have crafted a song that encapsulates the ultimate bromance. The playful tune speaks of the bond shared between ‘besties’. A bunch of people have felt this way before about their closest pal; these guys just happened to write a song about it. Following the titular line, Barnes ho-hums, “I'm not saying you can't be all these things for me/But it's just not the same because you're a man.”

  • 09 - Beatles

    “Polythene Pam” (1969) – The Beatles
    Part of the side-long medley of the legendary musicians’ 11th studio album, 1969’s Abbey Road; Polythene Pam is just “so good looking but looks like a man”. The song is linked to the narrative of the band’s song “Mean Mr. Mustard” where Pam is referred to as Mustard’s sister. In 1980, Lennon revealed that the influence behind the titular Pam, that he as simply “just looking for something to write about… perverted sex in a polythene bag.”

  • 10 - White Town

    “Your Woman” (1997) – White Town
    This one-hit wonder from the solo project of one Jyoti Prakash Mishra, was in fact a trendy reworking of the 1932 Bing Crosby standard “My Woman,” the key trumpet lick sampling from the original. Aside from its strength as a pop track, Mishra reasons its strength is in its possible interpretations: “being a straight guy in love with a lesbian; being a gay guy in love with a straight man… or the hypocrisy that results when love and lust get mixed up with highbrow ideals.” Just what you’d expect from an ex-Marxist whose first album was called Socialism, Sexism & Sexuality.

  • 11 - Bowie

    “Rebel, Rebel” (1974) - David Bowie
    With it’s powerful opening couplet: ‘You got your mother in a whirl/ she's not sure if you're a boy or a girl’ Bowie’s glam-punk hit established a definitive gender-bending mystique. Many well-known artists have covered the song since, including the likes of Duran Duran, The Smashing Pumpkins and even Bryan Adams.

  • 12 - greenday

    “King For A Day” (1997) – Green Day
    A positively catchy cross-dressing theme song, the closing number to the trio’s 1997 album Nimrod sees Billy Joel Armstrong proclaiming in a punk sneer: ‘sugar and spice and everything nice wasn’t made for only girls’. Presenting listeners with the image ‘GI Joe in panty hose’ over a jubilant horn and crashing three chord energy.

  • 13 - Discovery

    “I Wanna Be Your Boyfriend” (2009) – Discovery (ft. Angel Deradoorian)
    The side project put together by Vampire Weekend’s exotically named multi-instrumentalist, Rostam Batmanglij and Ra Ra Riot frontman, Wes Miles. Discovery’s gender swapping antics come from the fact that it features the effeminate vocals of Angel Deraddorian, a former member of Dirty Projectors, singing the titular lyric in cut-up vocal samples.

  • 14 - prince

    “If I Was Your Girlfriend” (1987) - Prince
    The Purple One has always had a penchant for androgyny, including creating a female alter-ego called Camille, that he was toying with dedicating a whole album to in the late 80s. This bizarre cut, and unlikely second single from Prince’s sprawling 1987 masterpiece, Sign O The Times is one of those Camille leftovers. As he ponders what it would be like if he was his girlfriend’s (platonic) girlfriend. Got that? “ Is it really necessary 4 me 2 go out of the room/Just because u wanna undress? he intones in his creepy treated vocal, as Prince longs to be a part of the intimate relationships that the opposite sex seems to share.

  • 15 - Against Me

    “Gender Dysphoria Blues” (2009) - Against Me!
    A simple affair of acoustic chords underlying Gabel's hoarse, shouted vocals, “Gender Dysphoria Blues” is exactly what it sounds. The subject matter is deeply personal for singer, who revealed himself as transgender earlier this year, and Tom Gabel began taking hormones in order to become Laura Jane Grace. Heart-warmingly, his wife, children and bandmates fully supported the decision, and its songs like this one that have transformed Gabel into an icon for transgender fans who are also punk as they come. As Gabel/Grace sings in the final line of the song, "you know it's obvious/ but we can't choose how we're made."

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