Disco Diva Sylvester Moved With an Audaciousness That Resonates Today

Sylvester James Jr., better known by his performing mononym Sylvester, was so ahead of his time when he emerged on the ‘70s music scene that culture is still catching up. As a singer-songwriter, he made his biggest splash during the disco era with a trio of Top 40 hits, including the indelible “You Make Me Feel (Mighty Real),” which recently placed No. 2 on Jezebel’s list of the greatest disco songs of all time. He sang in a piercing falsetto and presented an unabashed gayness, usually donning drag. He was queer during a time when it was considered career suicide to be so. In the ‘80s, he rode the post-disco tide, helping to innovate the particularly San Francisco-fied strain of the genre called hi-NRG (“Do You Wanna Funk?,” a collaboration with pioneering producer Patrick Cowley, featured prominently in the 1983 Eddie Murphy vehicle Trading Places). He died of AIDS at age 41 in 1988.

To some, Sylvester is synonymous with disco; to many others, he’s virtually unknown. Enter Sound Barrier, a new Spotify podcast hosted, co-written, and co-produced by writer, musician, and New York University professor Jason King. (Full disclosure: I’ve known King for years, but I also wouldn’t be writing about his show if it were just some bullshit.) Over the course of eight episodes, King and his team trace Sylvester’s history, from his days on the streets of South Central Los Angeles with queer crew the Disquotays, to his work with the San Francisco performance troupe the Cockettes, to his early rock records alongside the Hot Band, to his disco triumphs, and beyond. King shares storytelling duties alongside a host of new and archival interviews from the likes of Patti LaBelle, Martha Wash, Billy Porter, Big Freedia, Sound Barrier co-writer (and film director) Stephen Winter, and Sylvester himself.

Sound Barrier delves deeply into Sylvester’s life—“the motivations for the things that he did and for the creative choices that he made,” King explained in a call with Jezebel earlier this week. He also discussed the performer’s legacy and modern relevance: “Sylvester did many of the things that Lil Nas X is currently doing.” An edited and condensed transcript of our conversation is below.

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JEZEBEL: Sylvester is unsung but his story has been told before. In fact, Josh Gamson, who published the biography The Fabulous Sylvester in 2005, is a consulting producer here. What did you aim to do differently with Sylvester’s story?

JASON KING: The book stands, and I think it’s the definitive look at Sylvester’s life at this point. There was an opportunity to do a really entertaining podcast that walks people through Sylvester’s life and explains who he was that exceeds in some way the limitations of what a book can be. On top of that, it felt really important for me to address Sylvester as a musician. He’s often heralded as this groundbreaking cultural figure, which he was, and he deserves his due for that, but he was also an astounding musician. I wanted to really track the development of his music and to also be able to show that the success that he had in the disco era, which was his greatest success commercially, was not a fluke and actually came out of these earlier attempts to convey his musical message around Black musical excellence. He was somebody who was invested in the idea of bringing together a whole bunch of different genres. He could sing jazz and blues and gospel and R&B and rock and everything else, and he didn’t really see a difference between those musics as long as they all had a kind of blues impulse to them in some way.

To know Sylvester is to love him, but there are a lot of people who have no idea who he was. Was it difficult convincing Spotify that he’s a worthy subject?

They got it pretty immediately. They knew that this was an opportunity to tell a story about somebody who was intersectional before “intersectional” was a buzzword. The challenge in telling Sylvester’s story in 2022 is: How do you make it current? How do you make it relevant? How do you make it more than just the story of the musician who had his best work in the 1970s and ‘80s and is no longer with us? We tried to do that by connecting his story to the stories of younger artists who followed in his footsteps, whether they know or not. He opened up space for people to live authentically and to be who they truly are and to not compromise at all in terms of their identity in a public way. And while that is increasingly the way that things are now, it certainly wasn’t then. He was facing incredible stigmas around being Black, and around being gay and feminine and wearing drag.

This was an opportunity to tell a story about somebody who was intersectional before ‘intersectional’ was a buzzword

A few times during the podcast, we hear this stated amazement that Sylvester was getting away with what he did, having a viable career. How was he able to do that then?

I think it’s important to remember that he comes out of a really venerable history, maybe one that has been underwritten, but it’s a history nonetheless, of Black and POC queer men who did stage careers in the music industry, regardless of the stigmas or in spite of the stigmas—people like Little Richard and Billy Ray and Esquerita and so many others. I think he drew on that history, but he also drew on the history of the blues, all the blues women figures like Bessie Smith who were queer themselves, or bisexual. Given the fact that his music was so rooted in jazz and the blues, he saw them as a model of audaciousness that he could emulate musically, sonically, and every other way, even in terms of his look.

As a teenager, he was part of the Disquotays, this group of radical teenagers on the West Coast who walked around all day in makeup and drag, and were just fully themselves and incredible inspirations to a lot of people who faced down bullying and all kinds of other odds. Then he became part of the Cockettes, that legendary radical performance art troupe in the Bay Area in the early 1970s. He was a traditional performer who would go on stage and really sing and perform and wow an audience as a showstopper. I think those two groups became this incredible crucible for him to be able to move with an audaciousness and with a courage that lasted his entire career.

The sex life of Sylvester’s collaborator Patrick Cowley has been documented extensively (in his music as well as the 2019 release of his private sex journal), but there’s less information about Sylvester’s sex life. Did you have any sense of that?

There were times in his life he was very committed—to his partner, Rick Cranmer, for instance, in the 1980s, who passed away from AIDS before Sylvester did. He was a very committed guy who was in a relationship that he really loved, and he talked about it openly when he would go on The Joan Rivers Show, for instance. We also know that he was open and free with his sexuality, as many were in the 1970s and beyond. And while we don’t go into it in great detail on the show, I’ve heard a lot about Sylvester and his desirability and the kind of men that he desired as well. He was an openly honest guy about his sexuality, let’s put it that way. I know Barry Walters of Rolling Stone, when we did the conference on Sylvester in 2004, he had some personal information about Sylvester and his versatility, and so on. He thought that was important information to bring forward, just to show that Sylvester really blurred the binary in so many different ways, not just in his music or his look, but also even in the bedroom. We don’t go into it in detail, because we’re dealing with so much other stuff in the series.

This podcast conveys a real sense of Sylvester’s courage, and his refusal to listen to whatever voices were out there telling him to rein things in. He strikes me as a model for forging your own path.

I 100 percent agree. I think Sylvester is a model and an emblem for living your authentic life. It sounds like a cliché, but it is still one of our number one most difficult things to do in a culture and a society that still stigmatizes us. Even this whole notion of “don’t say gay” in Florida—Sylvester was not just saying it. He was living it. He was performing it, turning the dial up to 11 on it. And amazingly, he was doing all of this in the midst of disco in the ‘70s. So many people think of disco as being this totally liberatory genre of music where everyone could just be themselves. But you have to remember, even the gayest groups of all time, like the Village People, were still coded in the messages that they put out to the world. There was still this incredible homophobia, whether it was explicit or implicit, that determined how artists moved through the world. Sylvester was way ahead of his time, not just musically and not just artistically, but in terms of the way that he moved through the world, his individuality, his eccentricity, his sense of audaciousness with which he presented himself. He was unwilling to compromise. He couldn’t be bossed, he couldn’t be bought. He was just going to be himself.

That’s not to say that he didn’t face an incredible amount of pushback. One of the things we do in the podcast is document the pressures that his label put on him to be kind of normative. They wanted him to be like a Teddy Pendergrass or ultimately like a Luther Vandross figure, and there were moments in which he tried to compromise. I mean, he wasn’t somebody who was unwilling to work with others. He didn’t just have to sing in falsetto. He could also be a baritone. He listened to people who suggested to him that he should explore the totality of his range stylistically and musically and in terms of self-presentation. But ultimately, he was always himself. Always himself.

This whole notion of ‘don’t say gay’ in Florida—Sylvester was not just saying it. He was living it. He was performing it, turning the dial up to 11 on it.

Besides those fleeting concessions, did you get a sense that living his truth was any kind of struggle, or that it caused him any kind of suffering?

He definitely came from the generation where you kind of grin and bear it. So your job is to keep moving, to keep progressing, but not necessarily to be a pessimist who makes an entire critique of the system, as you’re within the system. We looked but didn’t find a lot of moments where he was deeply critical of the system in that way. We can imagine, just based on what we know about human beings, it must have been difficult for him. There’s no way that it couldn’t have been. But he seemed not to internalize a lot of it. It seems like what he did is, rather than be deterred by the pressures that he faced, he simply just moved in different directions. He found new collaborators and he started working on other kinds of songs and styles. He kept pivoting. My feeling of it is that he wasn’t deterred, and, in fact, what he did was just continue to move forward in a progressive way, which is what many artists have to do in the face of constraints and challenges.