Sylvester: The (Un)sung Icon of 70’s San Francisco

Before Sylvester (whom we’ll rotate between using they/him/Sylvester as the late artist would do) made their splash and ultimate legacy in the LGBTQ community (then in San Francisco, then the world), he was born into a sizable, and supportive family in the Watts neighborhood of Los Angeles. Surrounded by the civil rights struggles of the era (which would later inform his activism), he also honed his vocals in the church choir and found a hero in Billie Holiday.

Credit: Wikimedia Creative Commons

By the time Sylvester was an adolescent, he was partying with a clique of black trans women, drag queens, and gender-nonconforming people who called themselves the Disquotays. They made a big impression on the person we’d come to know and love as SYLVESTER. Yet, L.A. wouldn’t be the place where the soon-to-be disco queen would make their name.

Originally coming to the Haight in 1970, Sylvester would later move to the Castro because he felt he could be himself and with the budding acceptance of queer culture. He went on to integrate a mostly white drag-theater troupe called The Cockettes, who spent their days taking LSD, dressing up, and living their lives as one long, bizarre piece of performance art. That was all before Sylvester helped turn SF into what was lovingly known for a decade as “San Fran-disco”.

Credit: Fayette Hauser

Always the outspoken advocate, when Barbara Walters visited San Francisco on assignment, he corrected her about NOT being a drag queen but being gender fluid/nonconforming/nonbinary (terms that most viewers had never heard of before… and are still having a hard time understanding 40+ years later). He’d continue these triumphs when Joan Rivers described him as a drag queen in a 1986 interview on The Tonight Show, he rejected the label, turning up his nose and replying, “I’m Sylvester.”

From a stage standpoint, he opened for David Bowie in 1972, who became an instant admirer of Sylvester, and when returning on tour 4 years later, stated, “San Francisco doesn’t need me, they have Sylvester”. Most notably, their performance at the War Memorial Opera House would be tied to a handful of memorable moments. It was the first time ever in music history that a non-classic singer performed, with the whole orchestra, a concert on stage in an Opera House – performing with the full SF Symphony. The same day would be commemorated, and proposed by Mayor Dianne Feinstein, as ‘Sylvester Day’ and he was awarded the key to the city. This performance would be recorded and pressed as Sylvester’s only live album, ‘Living Proof’.

Not only was Sylvester a star performer he was a star reformer. He was a friend and supporter of Harvey Milk, and worked with the Mayor’s efforts towards SF’s recovery from the Johnstown Massacre and Harvey Milk assassination. Like Milk, Sylvester advocated and fought til he couldn’t do so any longer. Just months leading up to his death from HIV/AIDS, Sylvester led the People Living with Aids section of the SF Pride parade reminding the world that there are humans embodying and living with the disease to this day.

Yes, Sylvester made a forever-lasting mark on San Francisco but their legacy just doesn’t stop at the very contested Bay Area border. Here’s a list of their lasting impact:

• A truly gender-fluid Black man in mainstream music, he became an inspiration to Billy Porter, Tunde Olaniran, Mykki Blanco, Frank Ocean, and Boy George who see themselves represented positively in mainstream culture at a time when this was extremely rare.

Credit: Fayette Hauser

• In 1982, Sylvester’s rock single “Hard Up” became the THIRD video by a black artist to be featured on MTV, right behind Prince and Michael Jackson.

• Mighty Real: A Fabulous Sylvester Musical had a well-received off-Broadway run in 2014 and a celebratory outing at the Brava Theater in the town Sylvester had made his home benefitting the S.F. AIDS Emergency Fund

• Passing on December 16, 1988, Sylvester left all future royalties to Project Open Hand and PRC (which provides meals, healthcare, financial assistance, and behavioral health services to most SF’s most vulnerable)

• As quoted in the documentary, Love Me Like You Should, “As beneficiaries of Sylvester’s estate, we’re PROUD to elevate the lives of the who most need our support. We serve our community with love and nobody knew how to serve love better than Sylvester.” – POH/PRC

• Sylvester’s story would inspire a slew of books including 2020’s Penguin book, “Mighty Real: The Music That Built LGBTQ America”

• Sylvester’s way of life and career are even spoken and taught about in college music and sociology:

“This idea that people had to catch up to him was always part of his mindset,” says University of San Francisco professor Joshua Gamson, who published the biography The Fabulous Sylvester in 2005. “He was not going to be waiting for permission from people to do what he wanted to do, or for the mainstream culture to say it was OK.”Gamson adds, “He was certainly genderfluid before anybody named that, and really queer before anybody named it the way people talk about ‘queer’ in the last 25 years.”

•  Sylvester openly talked about being married to a man before it was legal/spoken about

•  His backing singers, 2 Tons of Fun, would go on and form The Weather Girls of “It’s Raining Men” fame

Credit: Author’s Personal Record Collection

•  Sylvester’s trailblazing legacy was prominently featured in a 2019 exhibit, Queer California: Untold Stories, at the Oakland Museum of California

•  For a deeper diver into all the glam (and not so glam) of Sylvester’s legacy, an entire season of Sound Barrier was dedicated to the disco diva

Credit: Spotify | Sound Barrier

If there is anything we can take away from the best, and sometimes worst, parts of Sylvester’s life, it’s the phrase they lived by most, “Be free; Be fabulous; Be real“. Perhaps you want to keep up on anything throwback or new from the life of Sylvester, there is still an active Instagram profile run by his estate/family.

At the time of this article, Eye Zen Presents has set an opening date of August 11th for the world premiere of Sylvester, The Mighty Real, fifth in the company’s OUT of Site series of performance-driven walking tours, rediscovering the hidden queer history of San Francisco.

Per usual, if you’d like to see more content like this you can join the BAS Patreon, tip your favorite gender-nonconforming writer, and donate to Project Open Hand.