I never thought David Bowie would ever die. He was otherworldly in ways that made him seem outside the stream of time or reality. His morphing into multiple characters made his art more than just music and was stunning, puzzling and intriguing to those of us watching and listening in the 1970s.

But most dramatic was his willingness to present himself as sexually ambiguous. With full facial make up; his lithe figure draped in space costumes or skin tight fabrics he seemed to say “Whatever you think I am, be aware you’re probably wrong.” This was at a time when women were trying to break the bondage of femininity and mainstream culture was trying to convince us we were imagining our oppression.

But Bowie was the mirror that confirmed what we were thinking: being feminine is a mask and at the same time not a joke—see how hard they want to keep women in it and men out of it! His look—both cool and hot—left many people with their mouths open in disbelief.

Illustration by Mark Ashkenazi

His early music was often experimental; his words were provocative; and his voice was thin but emotional effective. When he sang with Freddie Mercury on Under Pressure it was like the queens had gone wild. He liked to create visual surprises from his orange hair to engaging Aboriginal children to be the identity of the video for his pop hit, Let’s Dance; and seemed surprised when he realized he could make music that was popular.

Bowie, of course, was the more recognized but we can’t forget gay icon Sylvester (born the same year -1947) with his clear falsetto that could crack the mirrors on a disco ball. Not to mention his perfectly feathered makeup and glittery costumes. There was something in that moment (the feminist and gay movements I’m guessing) which made men’s experimentation possible. Listening to the music of the past couple of decades Bowie’s and Sylvester’s legacy is writ large.

Certainly before them Smokey Robinson reigned supreme with his poetic lyrics and sweet sound but he always landed very clearly in the tradition of Black masculinity. He and Little Anthony were never going to be mistaken for anyone other than strong (maybe sensitive) Black men.

Michael Jackson was, of course, in a category by himself. His voice could ring a chapel bell and was pitch perfect from childhood. So he seemed to develop a persona to match his Peter Pan-like vocal range. But even Michael, like his older musical brothers, opted for a masculine identity.

But feminizing the masculine—that is males embracing their masculinity and femininity both in their appearance and their vocal performance—is another arena. Little Richard, who remains an enigma was, is perhaps the quintessential fore figure in this mode.

I would count several contemporary male singers in the category of feminizing the masculine—not surprisingly many of them are gay. Elton John, who tends to sing in a middle range, does, however, wear enough huge jewelry to make Run DMC envious. That along with period wigs and sparkling costumes made coming out as gay for Elton almost redundant.

George Michael is not as visually adventurous, but he eschews the solidly masculine stance. He is the master of the whispered voice which leaves the listener feeling he’s as breathless as a woman.

Most recently and successfully is Grammy and Oscar winner Sam Smith. He stretches up unapologetically into the highest reaches of his vocal range and spirals down like silk. That he acknowledged his break up with a male lover inspired his break out album was amazing to an activist like me who kept hoping to hear something like that from Luther Vandross.

Male singers who embrace that complexity of masculine and feminine are intriguing and sexy. Girls are screaming for Sam Smith when he hits the high notes despite knowing the story that lies behind his lyrics. The combination of his maleness and femaleness, as with Bowie, makes him irresistible. Maybe not to everybody but there’s a quality of omni-sensuality (like Little Richard, but calmer!) that lives inside those high notes that isn’t just musically compelling. It also implies that there are different ways of being a man. A guy in a truck and coveralls is fine if that’s who he is. (A girl in the same is even more fine!) But the revolution is also a guy who’s not afraid to look like a girl if only because it makes everyone have to stop and think.

That’s why I’ve always favoured men with long hair or wearing skirts. They are breaking the binary expectations of what men are supposed to look and act like and that further undermines the patriarchy for me. Men (or women) who won’t stay on their ‘side’ can be the most threatening for the mainstream. So every time I see guy wearing mascara and eye shadow or a woman wearing a suit and tie I want to dance under the serious moonlight.

Jewelle Gomez is a writer and activist and the author of the double Lambda Award-winning novel, THE GILDA STORIES from Firebrand Books. Find out more about Jewelle Gomez HERE