For decades, pop musicians have been trying to push the boundaries. Not only in terms of music genres and their capabilities as performers, but also with their appearance and sexuality.
With a lot of pop and rock music, image is a great portion of their performance, as well as their marketing standpoint among the industry.
This list is dedicated to a handful of people that decided their sexuality was anyone’s guess, and how they blurred that tricky line between what’s female and male.

Suggested soundtrack while reading this: Dude Looks Like a Lady – Aerosmith

10. Brian Molko

While it’s not hard to guess that Molko is a man simply by listening to his oddly nasal monotone voice throughout his tracks, but it’s his dress and terribly well applied makeup that fooled us all for quite some time. During several performances, Molko sported sequined red skirts, bejewlled cowboy hats and boots. While typically, you’re going to see some crazy outfits (Twisted Sister, anyone?) but it was the fabulous makeup that put together the androgynous veil. White powder foundation, sparkly black eyeliner and a well suited red lipstick caused the confusion and helped blur that line just a little bit further.

9. Kevin Barnes

Of Montreal front man has a tendency to embrace the theatrical. With heavy emphasis on theatre based performances, as well as skits and slow movement sword fights between songs on stage, he employs his talents of all things arts as closely as possible. While doing this however, he also sports a short haircut, with amazing bone structure. David Bowie-esque makeup, and short red dresses, the line begins to blur occasionally.

Well, only until he pulls his dress up to reveal he’s not actually wearing underwear. That’s when you figure out his gender.

8. Bill Kaulitz

Early last year, the world started to hear rumblings of a band called Tokio Hotel. While their name lends no meaning to the fact they’re German, they took over the world with their different music, as well as different dress style. The lead singer, Bill Kaulitz, a sprite young 20 year old tends to bend his gender a little bit too much. With his amazingly feminine eyes, tendency to overuse the “guy-liner”, and a figure which any woman would kill for.

His ever changing hair style, and well executed makeup only plays into his feminine side, despite the fact he has one of the largest female fan populations in the world currently.

7. Annie Lennox

Our favourite Scottish lass had her music career take off in 1975, she’s been turning corners for music direction every few years or so, changing our perspective. With her short cropped hair that she’s sported for the majority of her career, with that intense bone structure and physically beautiful face, she definitely carries that androgynous feel to her image. Her music too, with her strong voice and different styling of music, she’s pushing that envelope and allowing us to enjoy her strong sexuality. Whatever it may be.

6. Eddie Izzard

If you were wearing a pair of beer goggles, from a distance, Mr Izzard might actually just catch your fancy. The only actor/comedian/cross dresser to make the list – he qualifies simply for his terrible love of transvestism. With constant dressups being played, and very little definition of his sexuality his gender bending performance always brings a smile to the faces of his audience.

5. Grace Jones

I’ve been puzzled as to how to put this into a paragraph, but I think saying: Bitch is fierce, sums it up pretty well. This amazing woman is a model, singer and actor, with an incredible voice, incredible body, and the most interesting facial structure you’ll ever see. Her gorgeous dark skin with that fierce razored haircut added to the allusion that she might be male – the fact that she wore well tailored suits and rarely ever conformed to a typical female sexuality is the reason why she graces our list.

4. Boy George

Well, Mr Karma Chameleon certainly turned heads in his hay-day. Unfortunately for him now, he’s probably just turning heads in the communal prison shower. Remember the coloured hair, with the braids. The sparkling suits, the hats, the makeup that stretched beyond the confinements of a normal humans face?

Boy George’s commitment to looking like a boy trying to look like a girl, who really just looks like a boy, is outstanding.

3. Prince

It’s amazing how much action this man got during his rise to fame, despite the fact his hair was so well quaffed, his jeans were so tight, and his abundance of purple clothing and décor was almost sickening. Yet, despite the fact he embodied all these attributes one would suggest belong to a woman, he pulled it off in such a theatrical array of performances and videos, that it further amped up his sex appeal. Maybe it was his tight pants, maybe it was the fact women thought they could share makeup tips with him post coitus – but this man has it all.

2. David Bowie

This list is absolutely impossible without David Bowie. The man pioneered androgynous makeup through his career, with the invention of several characters, videos that defied sexuality, and live performances that included so many theatrics and a heavy team of makeup artists, it’s great to see a man bending gender so effortlessly.

His style had become iconic, and is still often copied in film and fashion today. Who could forget Drew Barrymore in the unfortunate event that was the Charlie Angel’s films – but decked up in David Bowie makeup? Hot.

1. JD Samson (Le Tigre)

Well Ms. Samson. Or Mr. We’re not actually sure anymore.

Playing for electro pop band Le Tigre, JD Samson started off as a lesbian woman. Slowly, but surely, she started to take male hormones which gave her a slight moustache. For months a great debate brewed over “Is that a chick, or a dude?” Her performance style left no clues, as well as her dress sense. When she finally admitted she was in fact taking hormones, everyone got some clarity, and we loved her performance and sexuality even more. Her disregard to see gender and sexuality as a defining attribute to a person makes us love her even more, mostly for cutting through the bullshit and enjoying her life for what it is.

Plus, have you seen Le Tigre live? Fun! Dancing, and fluro lycra everywhere. There is not a second to be missed of that unique performance.