Moving to San Francisco in 1970 at the age of 22, Sylvester embraced the counterculture and joined the avant-garde drag troupe the Cockettes, producing solo segments of their shows, which were heavily influenced by female blues and jazz singers such as Billie Holiday and Josephine Baker.

[20] The group held lavish house parties, sometimes (without permission) at the home of their friend, rhythm and blues singer Etta James, in which they dressed up in female clothing and wigs, constantly trying to outdo one another in appearance.

[21] "Dooni [Sylvester] and the Disquotays wandered the streets of South Central in the 1960s done up like women, and threw ferocious gay parties in neighborhoods whose strongest institutions were conservative Black churches.

It's tempting to see them as fearless and heroic, defiant sissies who were forerunners of Stonewall and sixties counterculture, part of the dawning of gay liberation and African-American civil rights organizing."

[26] "Sylvester shared the Cockettes' affinity for outrageous flaming, their celebration of sex and gayness, their love of acid and good hash, and their bent movie-musical fantasies.

[34] With a piano player named Peter Mintun, Sylvester worked on solo scenes in which he exhibited his interest in blues and jazz by imitating several of his musical idols such as Billie Holiday and Josephine Baker.

Following Hibiscus' departure, the Cockettes began to gain increasing media attention, with celebrities such as Rex Reed, Truman Capote, and Gloria Vanderbilt enthusing about their performances.

Rolling Stone magazine singled out Sylvester's performances for particular praise, describing him as "a beautiful Black androgyne who has a gospel sound with the heat and shimmer of Aretha".

Realizing that he had far better prospects as a solo artist, on the second New York performance he opened his act by telling the audience, "I apologize for this travesty that I'm associated with", while on the seventh he announced that he would be leaving the Cockettes altogether.

[45] For the album, Sylvester and his manager Dennis Lopez had assembled a group of heterosexual white males—Bobby Blood on trumpet, Chris Mostert on saxophone, James Q. Smith on guitar, Travis Fullerton on drums, and Kerry Hatch on bass—whom he named the Hot Band.

[53] The music journalist Peter Shapiro believed that on these Blue Thumb albums, Sylvester's "cottony falsetto was an uncomfortable match with guitars" and that they both had "an unpleasantly astringent quality".

With this new entourage, he continued to perform at a number of local venues including Jewel's Catch One, a predominantly Black gay dance club on West Pico Avenue in Los Angeles, but reviewers were unimpressed with the new line-up, most of whom abandoned Sylvester in December 1974.

[56] After a brief sojourn in England, Sylvester returned to San Francisco and assembled three young drag queens to be backing singers: Arnold Elzie, Leroy Davis, and Gerry Kirby.

Many reviewers noted that Sylvester's image had been altered since his early career, moving him away from the glittery androgynous appearance to that of a more conventional rhythm-and-blues singer which would have wider commercial appeal.

He became a friend of Harvey Milk—known locally as the "Mayor of Castro Street"—who was the first openly gay man to be elected to public office in California, and performed at Milk's birthday party that year.

[5] Shapiro expressed the view that "Sylvester propelled his falsetto far above his natural range into the ether and rode machine rhythms that raced toward escape velocity, creating a new sonic lexicon powerful, camp, and otherworldly enough to articulate the exquisite bliss of disco's dance floor utopia".

[5] In both August and December 1978, Sylvester visited London, England to promote his music; he proved hugely popular in the city, performing at a number of different nightclubs and being mobbed by fans.

Consisting of four love songs, the title track – released as a single in January 1979 – had been written by Cowley, and Sylvester would proceed to tell the press that it was his first completely disco album, but that it would also probably be his last.

[90] The Tons themselves were convinced by Fuqua to produce their own self-titled album, from which came two dance chart hits, "Earth Can Be Just Like Heaven" and "Just Us"; as a result, they began to work less and less with Sylvester, only joining him on occasion for his live shows.

[104] Although he had continued working, Cowley was suffering from the recently discovered HIV/AIDS virus – at the time still referred to as "gay-related immune deficiency" (GRID) by American doctors – and was in a deteriorating physical condition.

[109] Sylvester still toured both domestically and in Europe, although he found that demand for his performances was decreasing, and that he was now playing to smaller venues and singing to a pre-recorded tape rather than to a live band as he had in the late 1970s.

[112] That year, he also entered into a relationship with an architect named Rick Cranmer, and together they moved into a new apartment in the hills, where Sylvester decorated his powder room with posters and memorabilia of Divine, the drag queen, actor and singer whom he had briefly known when they were in the Cockettes.

[117] Beginning work on an album that would remain unfinished, he moved into a new apartment on Collingwood Street in the Castro, and tried his best to continue performing in the Bay Area, even though he became too ill to undertake a full tour.

[119] Having lost a lot of weight and unable to walk easily, he attended the Castro's 1988 Gay Freedom Parade in a wheelchair, being pushed along by McKenna in front of the People with AIDS banner; along Market Street, assembled crowds shouted out his name as he passed.

[121] He appeared at the Dreamland nightclub (now The Vendry), watching the dancers from the second floor balcony, and DJ Steve Fabus put together an impromptu set of Sylvester songs.

[125] Sylvester had planned his own funeral, insisting that he be dressed in a red kimono and placed in an open-top coffin for the mourners to see, with his friend Yvette Flunder doing his corpse's makeup.

[146] "If there was one artist ... who truly exemplified disco's new language of ecstasy it was Sylvester, whose use of his gospel trained falsetto in the service of gay desire and pleasure is surely the most radical rewrite of pop's lingua franca ever attempted."

[13] Writing for the London-based LGBT magazine Beige: The Provocative Cultural Quarterly, Stephen Brogan expressed his opinion that while Gamson's biography was well researched, it had a fragmented structure and as such was "not a joy to read".

[150] Entertainment Weekly called the book "playful and furious" and awarded it a B+ rating,[163] The Boston Globe suggested that it was "as engaging as the times it so energetically resurrects",[164] and The San Francisco Chronicle reported that the author "carefully paints the shifting social tapestry into his subject's life story without ever taking Sylvester out of the foreground".

[168] A laudatory review of the musical from The New York Times noted that Wayne "certainly has the bravado, the androgynous sex appeal and the piercing voice to emulate the original convincingly".