Dude Looks Like A Lady: Rock 'N' Roll's Top Gender Benders


By Tatiana Simonian

While it’s most closely associated with the glam rock era, androgyny and rock 'n’ roll go way back. Little Richard certainly blazed a flamboyant path (anybody care for a dish of oh-so-masculine “Tutti Frutti”?), and a good many eyeliner-daubed successors have carried his flame (so to speak) in grand fashion over the past 50 years. After all, if you’re going to look like a lady, you might as well look good, darling.
     So without further ado, here’s our salute to the men who have changed the face of rock 'n’ roll history…by making up their faces. In alphabetical order, we present our favorite gender-bending artists in modern rock history.


David Bowie has adopted many alter egos over the course of his brilliant career, but none so famous (or as controversial) as Ziggy Stardust. The androgynous alien, created for his 1972 album The Rise and Fall of Ziggy Stardust and the Spiders from Mars, was portrayed by Bowie with the help of flaming red hair, one-shouldered jump suits, sky-high platforms and a single earring. His follow-up album Aladdin Sane took the look one step further, with its now-iconic image of Bowie’s face graced by a single silvery lightning bolt. Though Bowie soon ditched Ziggy in favor of the more conservative “Cracked Actor” persona, the Ziggy look is still being poorly recreated by fans and would-be rockers around the world. And for this, Lady Stardust, we salute you.


Discovered by punk impresario Malcolm McLaren, George Alan O’Dowd — aka Boy George — was at the forefront of London’s New Romantic movement.  George and his pop group Culture Club catapulted to fame in late 1982 with their smash debut album Kissing To Be Clever, which spawned the massive hits “Do you Really Want to Hurt Me” and “Time (Clock of the Heart).” Then, like all good rock stars, Georgie developed a grievous heroin addiction; and despite brief success with his solo single “The Crying Game” (the theme from a movie about a transgendered woman, natch), it’s all been downhill ever since. These days, George looks more like a bloated version of New Romantic icon Leigh Bowery than the happy-go-lucky ‘80s icon he used to be. Oh Boy…


Back in 1985, when he first crooned the hit “You Spin Me Round (Like A Record)” — whose catchy chorus Flo Rida has would later jack for “Right Round”— the Dead Or Alive frontman’s girlish appearance was just a fraction of what it would become. The openly bisexual singer believed “make-up washes off so why not have something that doesn’t wash off.” That “something” was copious amounts of plastic surgery. The downside of this is that Burns’ had to use his entire life savings for 18 months of reconstructive surgeries to save his face (and his life), after injected fluid in his lips caused his lips to burst and spread throughout his entire face. As of press time, Burns is currently trying to assemble a band for a "reunion" tour.


If being punk means defying the norm, then AFI are still firmly punk. No stranger to adopting changes in sound or appearance, singer Davey Havok threw fans for a loop (and caused them to question his sexuality) when he began rocking not only eyeliner but metallic eyeshadow, blonde highlights and false eyelashes, and pursuing a sideline in fashion. In the band’s latest incarnation, Havok has ditched some of the makeup, thus provoking a slew of “Is he straight again?” questions. Is it that simple? Who knows; because like all good gender benders, Havok keeps mum on his personal life — and as a result, the rumors keep swirling.   


With a voice like Billie Holiday emanating from a corpulent yet dainty figure, Antony Hegarty is truly a one-of-a-kind musician. His song, “Hope There’s Someone,” a piano-based, falsetto-fueled ballad about the desire to not die alone, been known to reduce an audience to tears (and provoke standing ovations). Hegarty also serves as a powerful example that androgyny and gender bending are not necessarily synonymous with terms like “flamboyant” and “over the top.” There are no dance moves and tight pants in Hegarty’s repertoire; rather, he comes on as the sheepish chanteuse crooning torch songs with his heart on his sleeve.  


Having originally toyed with calling himself “Vip Vop” or “Raven Beauty,” Cramps frontman Erick Lee Purkhiser finally settled on Lux Interior and became a legendary figure in New York’s ‘70s punk scene. Married to bandmate Kristy Wallace aka Poison Ivy, Interior matched his wife in sex appeal and outrageous costumes. While Ivy would often be clad in patent leather boots and short dresses, it was not unusual to find Interior rocking out in…tiny undies, eyeliner and a whole lot of sweat. Even three decades into his career, the psychobilly pioneer never gave up his makeup, remaining a true gender-defying icon until his untimely passing last year.


Before Angelina Jolie, the biggest lips on the planet award belonged to hip-swinging Rolling Stones frontman Mick Jagger. The lanky singer might have started out looking like a naughty schoolboy; but as time passed, Jagger’s visage and dance moves became increasingly flamboyant, and his pants somehow magically transformed into spandex leggings. Like any proper rock icon, Jagger heeded the call of the glam era by donning eyeliner, snorting a line and perhaps hopping into bed naked with a male friend or two…like David Bowie. Of course, Bowie’s ex-wife Angela swears that it’s completely normal and platonic to catch your husband in bed naked with another male singer. Well, normal if you’re married to a rock star. 


Oh Bill, your English is bad and you wear more hair product than a beauty queen, but how the ladies love you. The Tokio Hotel frontman, who burst on the international music scene with a hairdo akin to Sonic the Hedgehog, Kaulitz is the most recent gender bending singer to cause a stir. From his requisite black nail polish to his oddly butch twin brother (who is technically identical), we expect Kaulitz to be a fixture on the androgynous heartthrob scene for quite some time. And we mean that literally — at age 19, Bill recently became the youngest celebrity ever canonized at Madame Tussaud’s wax museum in Berlin.


Most American music probably don’t remember Marilyn — but one gander at the blonde bombshell’s fabulous video for his 1983 jam “Calling Your Name,” and you’ll be convinced of his gender-bending prowess. With long flaxen hair and ultra-feminine features, the British pop singer rose to fame in the New Romantic era alongside rumored partner Boy George. However, Marilyn fell out of fame as quickly as he fell into it. And despite being a noted recluse these days, Marilyn has been brought back into the limelight over allegations that he and Gavin Rossdale had a long relationship in the ‘80s – allegations that were also brought up in Boy George’s 1995 aptly-titled autobiography, Take It Like A Man. Mr. Stefani has denied these rumors, though an old photo of the pair that seems to show a young Rossdale in makeup just might leave you wondering…


There’s something about Marilyn Manson that manages to strike fear in your nether regions. From the cover of his album Mechanical Animals (where he seemed to have transformed into a she-male) to his unabashed love of makeup, Marilyn Manson is no stranger to gender bending. If the flames of controversy have already been stoked, Manson will find a way to start a bigger fire — and if he happens to be dressed in latex and makeup while doing it, so much the better.


Isn’t it ironic that the music of one of the most flamboyant frontmen of all time regularly blares over the loud speakers of American sporting events? From anthems like “We Are The Champions” to provocative tunes like “Fat Bottom Girls,” Queen frontman Freddie Mercury managed to evoke a primal sense of masculinity even while rocking a form-fitting harlequin jumpsuits and ballet shoes. Perhaps Mercury could broach the line between masculine and feminine so well because he did it in his personal life, going from longtime girlfriend Mary Austin to the company of men, and ultimately dying with Austin by his side. When Mercury first told Austin, “I think I’m bisexual.” She replied, “I don’t think you’re gay.” Ooh proud Mary…you were wrong on that one.


On one hand, Bret Michaels ostensibly personifies the manliest of all rock stars: the guitar-slingin’ bro who wins the hearts of hoochies everywhere. The problem with Michaels, however, is that he looks like a hoochie himself. His hair has always been too long, his lips too big, his jewelry too prominent, his tan too George Hamilton, and let’s not even talk about the bandanas. Still, the bizarro persona Michaels has created is infinitely fascinating; just try to change the channel when Rock of Love is on — you can’t do it, can you? We may all snicker when the Poison front man utters cheesy one liners like, “Do you want to rock my world?” But in the end, Michaels is ultimately having the last laugh, as his success (and hoochie-magnet prowess) continues to skyrocket with every stroke of his eyeliner.


In the mid-1990s, the British music scene was all aflutter about Placebo, a new band led by a diminutive front man with delicate features, a shrill voice and a razor sharp tongue. With the brazen ego of Oscar Wilde, the openly bisexual Molko teased crowds with suggestive songs like “Nancy Boy” and fed the press cheeky comments like, “A cock in a frock still seems to upset people. The vitriolic reaction we get in the British press is probably misplaced homophobia.” However, Molko’s tendency for wearing dresses (and occasional onstage spit swapping with the band’s openly gay bassist Stefan Olsdal) proved a hit with boys and girls around the world. Placebo has amassed an enormous worldwide following — including fellow gender bender David Bowie, who duetted with Molko on a 1998 re-recording version of the Placebo track, “Without You I’m Nothing.”  


Although he was born Neil Andrew Megson, the lead singer of Throbbing Gristle and Psychic TV is far better known as Genesis P-Orridge. A veritable icon in the art world, P-Orridge took gender bending to a whole new level when he and soul mate Lady Jaye decided to become one “pandrogynous” being, getting simultaneous plastic surgeries so they could look like each other. P-Orridge underwent breast implants and assumed the pronoun of “s/he” in all referrals to herself. Sadly, Lady Jaye died of stomach cancer in 2007. In November of last year, Genesis announced her retirement from touring of any kind in order to focus on art, writing and music.


Musical genius and lover of exotic brunettes, Prince is also one of the most androgynous artists we’ve ever seen. Perhaps it’s because he literally looks like an updated version of Little Richard; or maybe it’s the waxed eyebrows and you know, that time he posed naked while superimposed on flowers. Like all great gender-bending front men, Prince’s appearance (and talent) has won him tons of lady admirers; he’s been linked over the years to everyone from Kim Basinger and Susanna Hoffs to Carmen Electra, Mayte Garcia and of course, crazy ol’ Vanity (who would later hook up with fellow gender bender Nikki Sixx, before becoming an evangelist).  Oh Purple One, you sure do know how to pick ‘em.


Pop culture phenomenon Jeffree Star isn’t so much a gender bender as he is gender-bent — ain’t no one confusing homegirl for a boy anytime soon. From his flaming (pun intended?) pink hair to his tattoo of JonBenét Ramsey, Star has set the interwebs on fire with shock rhetoric and better makeup skills than your sister. It probably comes as no surprise that one of his credos is, “Go and buy some sunglasses because the future is bright pink, bitch.”


HIM are supposed to be an intense metal band, but let’s face it: songs titles like “I've Crossed Oceans of Wine to Find You” or  “Bury Me Deep Inside Your Heart” don’t exactly drip with testosterone. Proof that one can flaunt metal stereotypes and still rise to the top, frontman Ville Valo is one lean, mean androgynous metal machine; and to thousands upon thousands of girls (and boys) out there, he’s a Finnish rock god. Valo actively contradicted notions of what it means to be “metal” by throwing on eyeliner, scarves and giving that scary old pentagram a lovely heart-shaped makeover. And just when we thought all Nordic Gods were devoted to church-burning and scaring small children…

Related Artists David Bowie AFI Antony & the Johnsons Boy George Freddie Mercury HIM Jeffree Star Marilyn Manson Mick Jagger Placebo Poison Prince psychic tv Queen The Cramps The Rolling Stones Tokio Hotel Dead or Alive


  • voxvampirica
    voxvampirica wrote: Sat. April 03, 2010 @ 03:56AM

    best article i've seen in a while on here, haha. i love me some boys that look like girls.

  • Flawlessly_Shatters
    Flawlessly_Shatters wrote: Thu. March 04, 2010 @ 10:10PM

    :) Cinema Bizzare should have been in there :)

  • Gottmorder
    Gottmorder wrote: Sun. February 28, 2010 @ 06:36PM

    one day, i will be apart of this list i hope!

  • sing_me_to_sleep
    sing_me_to_sleep wrote: Wed. February 24, 2010 @ 10:30AM

    Sweet article! I love gender bending frontmen, or really anyone stylish and outrageous enough to do it themselves. I love love love most of these artists (besides Ville Vallo, Genesis P-Orridge and Brett Michaels)so I'm happy to see this piece up. :)

  • DrTatiana
    DrTatiana wrote: Sun. February 21, 2010 @ 11:37AM

    I disagree @Ginaing - I don't think gender bending has to do with confusing gender. I view it as appropriating aspects of the other gender with your own style i.e. bending your gender style to include another. @claudia126 brett michaels may not be a pretty gender bender but he sure doesn't look like much of a dude to me :D - tatiana (the author)

  • Claudia126
    Claudia126 wrote: Sat. February 20, 2010 @ 08:50PM

    So glad to see you included Bill Kaulitz the most beautiful androgynous boy I have ever seen. And Brett Michaels? Really?

  • ginaing
    ginaing wrote: Sat. February 20, 2010 @ 06:07PM

    I think Bill Kaulitz would be very flattered to be in the company of Bowie, Brian Molko and Mick Jagger. Some of the others, eek. But simply wearing makeup doesn't make you a gender bender. All the makeup in the world won't make Prince or Marilyn Manson or Ville Valo a confusing presence to anyone. They don't have a level of beauty that is truly gender bending or confusing at all.

  • imyourheaven
    imyourheaven wrote: Fri. February 19, 2010 @ 04:45PM

    I agree with pretty much everyone except that last man, Ville Valo. He's the most beautiful on that list and the least bit deserving to be there. Yes, Valo can be feminine with the make up (that he no longer wears) but he's still striking without the it. Not his fault. Just because he's petite and hotter than a lot of men and women alike, doesn't make him a gender bender. People like Prince and Jeffrey Star who purposely alter their image to look like females, and ugly ones at that, deserve the title, not a man like Ville who still looks masculine even when wearing a purple beanie and matching scarf. Take a look at Ville in leather pants, it might make a lot of people think twice. I'm just sayin.

  • Jedidude77
    Jedidude77 wrote: Fri. February 19, 2010 @ 04:19PM


  • Cinlouxx
    Cinlouxx wrote: Fri. February 19, 2010 @ 01:44PM

    Bill Kaulitz! =D well his english may be bad (which I don't agree I think his english is pretty good) because he has an accent. You have to keep in mind that he's from Germany.