Sylvester (singer)

Sylvester James was born on September 6, 1947, in the Watts district of Los Angeles, California,[3] into a middle-class family.[4] His mother, Letha Weaver, had been raised near Palestine, Arkansas, into a relatively wealthy African-American family who owned their own farmland.[5] Letha's biological mother, Gertha Weaver, was unmarried and too sickly to care for her child, so Gertha's sister Julia, known to the family as JuJu, became Letha's adoptive mother.[3] In the late 1930s, Julia and her husband took part in the Great Migration of African-Americans out of the Southern United States, relocating to Watts.[3]

It was here that Letha was largely raised and where she met and married her first husband, Sylvester "Sweet" James, with the couple moving into a small cottage owned by Letha's parents. Their first child, named Sylvester after his father, was followed by the birth of John Wesley in 1948 and Larry in 1950.[6] Sylvester and his brothers became better known in their predominantly African-American community by their nicknames, with Sylvester's being "Dooni".[7] Sylvester considered his father to be a "lowlife" because he was an adulterer and left his wife and children when the boys were still young.[8] Letha and her three sons moved to a downtown housing project at Aliso Village before moving back into her parental home at 114th Street in Watts.[9]

Letha was a devout adherent of the Pentecostal denomination of Christianity, regularly attending the Palm Lane Church of God in Christ in South Los Angeles. Sylvester and his brothers accompanied her to the church's services, where he developed a particular interest in gospel music.[10] Having been an avid singer since the age of three, Sylvester regularly joined in with gospel performances; he sang the song "My Buddy" at the funeral of one of the other children in the Park Lane congregation.[11]

The women at his church described him as "feminine" and "as pretty as he could be, just like his mother. He wasn't rough like the other boys. He was prim and proper. We were always hugging on him and kissing on him, because he was so cute."[12] Family members also described his as "his own kind of boy - 'born funny'"[12] - preferring the company of girls and women like his grandmother to that of other boys. "He stayed inside a lot, reading encyclopedias, listening to music, and playing his grandmother's piano."[12] When Sylvester would turn down the boys' invitations to play with them, they would say things like, "He act like a girl!" or "He's going to be a girl."[12] But his mother would defend him, including his joy at dressing up in her and his grandmother's clothes, saying that he was not a girl, just a different kind of boy, and a valued part of their family.[12]

At the age of eight, he was sexually molested by a man at the church—at the time rumored to be the church organist; although Sylvester would always maintain that this interaction had been consensual and not sexual molestation, Sylvester was only a child at the time of this incident while the assailant was an adult.[13] Sylvester was taken to a doctor after receiving injuries when this man subjected the child to anal sex. It was this doctor who informed Letha that her son was gay, something that she could not accept, viewing homosexual activity as a perversion and a sin.[13] News of Sylvester's "homosexual activity" (actually, having been raped) soon spread through the church congregation and, feeling unwelcome, he ceased his attendance at age 13.[14]

During Sylvester's childhood, his mother gave birth to three more children by different fathers before marrying Robert "Sonny" Hurd in the early 1960s, with whom she adopted three foster children. A supervisor at aerospace manufacturer North American Rockwell, Hurd's job increased the family income and they were able to move into a more expensive, predominantly white neighborhood north of Watts.[15] The relationship between Sylvester and both his mother and stepfather was strained; in the midst of one argument with his mother, Sylvester decided to leave their house permanently.[16]

Now homeless, Sylvester spent much of the next decade staying with friends and relatives, in particular, his grandmother Julia, who expressed no disapproval of his homosexuality, having been a friend of a number of gay men in the 1930s. On occasion, he returned to his mother and step-father's house for a few days at a time, particularly to spend time with his younger sisters, Bernadette and Bernadine.[17] Aged 15, he began frequenting local gay clubs and built up a group of friends from the local gay black community, eventually forming themselves into a group which they called the Disquotays.[18] Sylvester's best friend among the Disquotays was a trans woman named Duchess, who earned her money as a prostitute, a job that Sylvester refused to engage in.[19] 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.[20]

Sylvester's boyfriend during the latter part of the 1960s was a young man named Lonnie Prince; well-built and attractive, many of Sylvester's friends described the pair as being "the It couple".[22] Sylvester often hitchhiked around town while in female dress; such activity carried a risk of arrest and prosecution, for cross-dressing was then illegal in California.[22] Although avoiding imprisonment for this crime, he was arrested for shoplifting on several occasions.[23] He found work in a variety of professions, including cooking in McDonald's—where he was fired for refusing to wear a hairnet—cashier at an airport parking garage, working in a hair salon, at a department store, and as a make-up artist at a mortuary, preparing the corpses for their funerals.[24] In the 1960s, the Civil Rights Movement was at its peak, but Sylvester and his friends did not take an active role within it. During the Watts riots between members of the black community and the predominantly white police force, they joined in with the widespread rioting and looting, stealing wigs, hairspray, and lipstick.[21]

Although he had little interest in formal education and rarely attended classes, Sylvester was enrolled at Jordan High School. He graduated in 1969 at the age of 21; in his graduation photograph, he appeared in drag wearing a blue chiffon prom dress and beehive hairstyle.[18] By the end of the decade, the Disquotays had begun to drift apart, with a number of them abandoning cross-dressing and others recognizing that they were trans women and undergoing sex reassignment surgery. Sylvester always considered himself male and began to tone down the feminine nature of his clothing, aiming for a more androgynous look which combined male and female styles and which was influenced by the fashions of the hippie movement.[25]

At Los Angeles' Whisky a Go Go bar, Sylvester met Reggie Dunnigan, who invited him to move to the city of San Francisco in Northern California to join the "Chocolate Cockettes"—black members of an avant-garde performance art drag troupe known as the Cockettes.[27] Founded by drag queen Hibiscus in 1970, the Cockettes parodied popular culture, were involved in the Gay Liberation movement, and were influenced by the ethos of the hippie movement, living communally, embracing free love, and consuming mind-altering substances such as marijuana and LSD.[28] With the Disquotays disbanded, Sylvester had tired of Los Angeles, and was attracted by San Francisco's reputation as a gay and counter-cultural haven. Arriving in the city, he stayed in the Cockettes' communal home for several days. They were impressed with his falsetto singing voice and his ability to play the piano, asking him to appear in an upcoming show, Radio Rodeo.[29] Sylvester agreed, and one of his first performances involved singing the theme song of The Mickey Mouse Club while dressed in a cowgirl skirt.[30] Moving into the Cockettes' communal residence, he soon found the flat too crowded and had difficulty with the lack of privacy; after a year he moved into a new house on Market Street with two fellow Cockettes.[31]

Although a significant member of the troupe, Sylvester remained a relatively isolated figure; not only was he one of very few African-American members, he eschewed the group's more surrealist activities for what he saw as classier, more glamorous performances onstage.[32] In the Cockettes' performances, he was usually given an entire scene to himself, often with little relevance to the narrative and theme of the rest of the show, although through doing so, he gained his own following.[33] 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.[34] Adding to his image, Sylvester used the pseudonym "Ruby Blue"[35] and described himself as "Billie Holiday's cousin once removed".[36] Fascinated by black musical heritage, he read up on the subject and became a collector of "negrobilia"; in some of his Cockette performances, he played up to racial stereotypes of African-Americans to ridicule the stereotypes themselves.[37]

Palace Theater, where Sylvester performed a one-man show

In 1970, Sylvester entered into an open relationship with Michael Lyons, a young white man, and soon proposed marriage to him. Although same-sex marriage was not legally recognized in the US, the couple held a wedding in the Shakespeare Garden of Golden Gate Park.[38] At the invitation of the manager of the Palace Theater, Sylvester appeared in a spoof film, Tricia's Wedding, which parodied the marriage of Tricia Nixon Cox, daughter of President Richard Nixon. In the film, Sylvester played the role of both Coretta Scott King and the African ambassador Uma King.[39] In 1971, Sylvester was given a one-man show, Sylvester Sings, at the Palace Theater, for which he was accompanied by Peter Mintun.[40] He nevertheless remained a part of the Cockette troupe during their divisive split, in which Hibiscus and his followers left to form the Angels of Light. 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".[41]

The success led the troupe to take their show to New York City, a city with a long history of drag culture. Arriving in November 1971, they immersed themselves in the city's avant-garde, attending parties held by Andy Warhol and Screw magazine. Spending so much of their time partying, most of the Cockettes did not rehearse, the exception being Sylvester, who wanted to perfect his act.[42] Although the Cockettes' performance at the Anderson Theater was panned by critics, Sylvester's act was widely praised as a highlight of the show. 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.[43]

Returning to San Francisco, Sylvester was offered the opportunity to record a demo album by Rolling Stone editor Jann Wenner. Financed by A&M Records, the album featured a cover of Bonnie Bramlett and Leon Russell's song "Superstar", which had been a recent hit single for the Carpenters. Nevertheless, A&M felt that the work was not commercially viable and declined to release the album.[44] 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. After A&M's initial rejection, the band provided two songs for Lights Out San Francisco, an album compiled by San Francisco's KSAN radio and released on the Blue Thumb label.[45] Gaining a number of local gigs, they were eventually asked to open for English glam rock star David Bowie at the Winterland Ballroom. The gig did not sell particularly well, and Bowie later commented that San Francisco did not need him, because "They've got Sylvester", referring to their shared preference for androgyny.[46]

In early 1973, Sylvester and the Hot Band were signed by Bob Krasnow to Blue Thumb. On this label, they produced their first album, in which they switched their sound from blues to the more commercially viable rock, while the Pointer Sisters were employed as backing singers. Sylvester named this first album Scratch My Flower due to a gardenia-shaped scratch-and-sniff sticker adhered to the cover, although it was instead released under the title of Sylvester and his Hot Band.[47] The album consisted primarily of covers of songs by artists such as James Taylor, Ray Charles, Neil Young, and Leiber and Stoller.[48] Described by one of Sylvester's biographers as lacking in "the fire and focus of the live shows",[49] it sold poorly on release.[50]

Sylvester and his Hot Band toured the United States, receiving threats of violence in several Southern states, where widespread conservative and racist attitudes led to antagonism between the band and locals.[51] In late 1973, the band recorded their second album, Bazaar, which included both cover songs and original compositions by bassist Kerry Hatch. Hatch later commented that the Hot Band found the album more satisfactory than its predecessor, but nevertheless it again sold poorly.[52] 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".[53] Finding Sylvester difficult to work with, and frustrated by his lack of commercial success, the Hot Band left Sylvester in late 1974, after which Krasnow canceled his recording contract.[50] At the same time, Sylvester's relationship with Lyons ended, with Lyons himself moving to Hawaii.[54]

Now without the Hot Band or a recording contract, Sylvester set himself up with a new band, the Four As, and a new set of backing singers, two black drag queens named Gerry Kirby and Lady Bianca. 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.[55] 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. Nevertheless, although he performed at such events as the 1975 Castro Street Fair, success continued to elude him, and he eventually fired Elzie, Davis, and Kirby.[56]

Sylvester employed Brent Thomson as his new manager; she suggested that he rid himself of his androgynous image and wear more masculine clothing to gain a recording contract; as she put it, "nobody is giving out recording contracts to drag queens".[58] Thomson opened auditions for new backing singers, with Sylvester being captivated by one of those auditioning, Martha Wash. Sylvester asked her if she had another large black friend who could sing, after which she introduced him to Izora Rhodes. Although he referred to them simply as "the girls", Wash and Rhodes named themselves the Two Tons O' Fun (and much later, when they achieved mainstream success, as the Weather Girls), and continued to work with Sylvester intermittently until his death, developing a close friendship with him.[59] They were soon joined by bassist John Dunstan and keyboard player Dan Reich.[60]

Playing gay bars such as The Stud and The Endup, in September 1976 Sylvester and his band gained a regular weekend job at The Palms nightclub on Polk Street, performing two or three sets a night; most of these were covers, but some were original compositions by Sylvester and his then-guitarist Tip Wirrick.[61] It was through this show that Sylvester came to the attention of Motown producer Harvey Fuqua, and Fuqua subsequently signed Sylvester onto a solo deal with Fantasy Records in 1977.[62]

In the middle of that year, he recorded his third album, the self-titled Sylvester, which featured a cover design depicting Sylvester in male attire. The songs included on the album were influenced by dance music, and included Sylvester's own compositions, such as "Never Too Late", as well as covers of hits such as Ashford & Simpson's "Over and Over". 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. Released as a single, Sylvester's "Over and Over" proved a minor hit in the US, but was more successful in Mexico and Europe.[63] Building on the album's release, Sylvester toured Louisiana and then Mexico City.[64]

San Francisco's Castro neighborhood, where Sylvester regularly performed and socialized among the LGBT community. Biographer Joshua Gamson described him as Castro's "undisputed First Lady".[65]

Sylvester's fame increased following the release of his solo album, and he was employed to perform regularly at The Elephant Walk gay bar in the Castro, an area of San Francisco known as a gay village. 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.[66] In the spring of 1978, Sylvester successfully auditioned for a cameo appearance in the film The Rose starring gay icon Bette Midler. In the film, he plays one of the drag queens singing along to Bob Seger's "Fire Down Below", in a single scene that was filmed in a run-down bar in downtown Los Angeles.[67]

Sylvester released his second solo album, Step II, in September 1978. For this release, he was particularly influenced by the genre of dance music known as disco which was then becoming increasingly popular across the Western world. Disco was closely associated with the gay, black, and Latino communities in the US and dominated by black female artists such as Donna Summer, Gloria Gaynor, and Grace Jones, with Sylvester initially being unsure that it was a suitable genre for him to work in; he nevertheless recognized its increasing commercial potential.[68] During production of the album, Sylvester invited the musician Patrick Cowley to join his studio band, being impressed by Cowley's innovative techniques using synthesizers. The album landed Cowley a job as a back-up musician on Sylvester's subsequent worldwide tours, and the two started a close friendship and collaboration.[69] Once again co-produced by Harvey Fuqua and released on Fuqua's Fantasy label, Step II contained two disco songs that were subsequently released as singles, "You Make Me Feel (Mighty Real)", written by James Wirrick, and "Dance (Disco Heat)", written by Eric Robinson.[70]

Both singles proved commercial hits both domestically and abroad, topping the American dance chart and breaking into the US pop charts.[71] The album itself was also a success, being certified gold,[72] and was described by Rolling Stone magazine as being "as good as disco gets".[73] In his history of disco, Shapiro described "You Make Me Feel (Mighty Real)" as Sylvester's "greatest record", "the cornerstone of gay disco", and "an epochal record in disco history".[74] Shapiro noted that Sylvester's work brought together elements from both of the main strands of disco; the "gospel/R&B tradition" and the "mechanical, piston-pumping beats" tradition, but that in doing so he went "way beyond either".[4] 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".[4]

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.[75] It was while in the city that he filmed the music video for "You Make Me Feel (Mighty Real)".[76] Back in the US, Sylvester began to appear on television shows to advertise his music, appearing on Dinah Shore, American Bandstand, Rock Concert, and The Merv Griffin Show.[77] He also undertook a series of tours across the country, opening for both the Commodores and Chaka Khan, and performing alongside the O'Jays, War, and L.T.D.[78] As a result, he earned a number of awards and performed at several award ceremonies.[79] Through this developing public presence, Sylvester, alongside other visibly queer performers such as the Village People, helped to solidify the connection between disco and homosexuality within the public imagination; this however furthered the anti-disco sentiment among rock music fans which would emerge as the Disco Sucks movement.[80]

Sylvester followed the success of Step II with an album entitled Stars. 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.[82][83] He premiered the album's four tracks on March 11, 1979, at a sold-out show in the San Francisco War Memorial Opera House. The performance was attended by a number of senior figures in local government, and halfway through, Mayor Dianne Feinstein sent her aide, Harry Britt, to award Sylvester with the key to the city and proclaim March 11 to be "Sylvester Day".[82][84] The Opera House gig was recorded, and subsequently released as a live album, Living Proof. Sylvester thought very highly of the album, but it did not sell well.[85] A single released from this album, "Can't Stop Dancing", was a hit in the disco clubs but not in the pop music charts.[86]

Despite increasing mainstream success, Sylvester continued to reaffirm his connection to the gay community of San Francisco, performing at the main stage at the 1979 Gay Freedom Day parade.[87] Further, during his summer 1979 tour of the UK, he performed at the London Gay Pride Festival in Hyde Park.[88] That same year, Sylvester met the singer Jeanie Tracy through Harvey Fuqua, and they immediately became friends. A large black woman, Sylvester felt that Tracy would work well with his Two Tons O' Fun, and invited her to join his backing singers, which she proceeded to do. Subsequently, befriending the Tons, she would work for Sylvester for the rest of his life.[89] 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.[90] In some interviews he would express bitterness at their departure, while in others he stressed that he had no bad feelings toward them.[91]

In 1980, Sylvester also reached tabloid headlines after he was arrested on a visit to New York City, accused of being involved in the robbery of several rare coins. After three days of incarceration, he was released on a police bail of $30,000. Sylvester was never charged, and police later admitted their mistake after it was revealed that the real culprit had posed as Sylvester by signing cheques in his name.[93] Returning to San Francisco after this event, it was here that Sylvester produced his next album for Fantasy Records, Sell My Soul. Largely avoiding disco after the genre had become unpopular following the much publicized Disco Sucks movement, Sell My Soul instead represented a selection of soul-inspired dance tracks. Recorded in two weeks, Sylvester worked largely with backing singers and musicians whom he was unfamiliar with, and regular collaborators Rhodes and Cowley were entirely absent. Reviews were generally poor, describing the album as being average in quality.[94] The only disco song on the album, "I Need You", was released as a single, but fared poorly.[95]

Sylvester's fifth and final album for Fantasy Records was Too Hot to Sleep, in which he once again eschewed disco for a series of groove soul tunes, ballads, and gospel-style tracks.[96] Missing the Two Tons entirely, Tracy was instead accompanied by a new backing singer, Maurice "Mo" Long, and because the three of them had all grown up in the Church of God in Christ, they decided to refer to themselves as the "C.O.G.I.C. Singers".[97] The album also featured a number of tracks in which Sylvester avoided his usual falsetto tones to sing in a baritone voice.[97] The album sold poorly.[98]

Both the Two Tons and Sylvester came to suspect that Fantasy Records had failed to pay them all of the money that they were owed from the sale of their records. Sylvester left Fantasy and in November 1982 he filed a lawsuit against them; it ultimately proved successful in establishing that the company had been withholding money from him totaling $218,112.50. Nevertheless, Fuqua proved unable to pay anything more than $20,000, meaning that Sylvester never saw the majority of the money that was legally owed to him. Sylvester grew to despise Fuqua, and forbade his friends from ever mentioning his name.[99]

Closely associated with the now unpopular disco and having had no hit singles in the preceding few years, after leaving Fantasy Sylvester was not a particular draw for major record labels. Recognizing this state of affairs, in 1982 Sylvester commented that "there's nothing worse than a fallen star" who still has "illusions" of their continuing fame. Rather than chasing major chart success, Sylvester wanted to focus on retaining creative control over his music.[100] Hiring his former tour manager and longstanding friend Tim McKenna as his new manager, Sylvester decided to produce his next album with Megatone Records, a small San Francisco company that had been founded in 1981 by Patrick Cowley and Marty Blecman and which catered largely to the gay club scene.[101] The result was All I Need (1982), on which James Wirrick had written most of the songs, which were dance-orientated and influenced by the new wave music then in vogue. Sylvester insisted that he include several ballads on the album, which featured cover art by Mark Amerika depicting Sylvester in ancient Egyptian garb.[102]

The Castro Theatre in San Francisco, where Sylvester performed his "One Night Only" retrospective

One of the best known Sylvester songs of this period was "Do Ya Wanna Funk", a Hi-NRG dance track co-written with Cowley which was released as a single in July 1982, topping the US dance charts and entering the pop charts in a number of countries across the world.[103] 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.[104] Sylvester continued touring, and it was while in London, preparing to perform at the Heaven superclub, that he learned of Cowley's death on November 12, 1982. He went onstage, informing the crowd of Cowley's passing and then sang "Do Ya Wanna Funk" in memory of him.[105]

In 1983, Sylvester became a partner of Megatone Records.[98] That year he also brought out his second album with the company, Call Me, but it was not a commercial success. Four songs from the album were released as singles, although only "Trouble in Paradise" entered the top 20 of the US dance charts; Sylvester later related that the song was his "AIDS message to San Francisco".[106] Sylvester was emotionally moved by the HIV/AIDS epidemic, and began helping out at the Rita Rockett Lounge for patients of the disease at the San Francisco General Hospital as well as performing at various benefit concerts to raise money and awareness to combat the spread of the disease.[107] In February 1984 he also performed a "One Night Only" retrospective of his work at the prestigious Castro Theatre.[108] 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.[109]

His next album, entitled M-1015 (1984), was more frenetic and pumping than his previous releases, having embraced the recently developed genre of Hi-NRG, but it also included elements of electro and rap. The major figures behind the album had been Kessie and Morey Goldstein, and Sylvester himself had not written any of the tracks.[110] The album also contained increasingly sexually explicit lyrics, in particular in the songs "How Do You Like Your Love" and "Sex".[111] 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.[112] In 1985, he fulfilled a lifelong ambition by working with the singer Aretha Franklin; he and Jeanie had been invited to provide backing vocals on Franklin's album Who's Zoomin' Who?.[113]

Sylvester's final album, Mutual Attraction (1986), was produced by Megatone but licensed and released by Warner Bros. On the album, Sylvester had worked with a wide number of collaborators, and included new tracks alongside covers of songs by Stevie Wonder and George Gershwin. Reviews of the album were mixed, with many claiming that it was a poor release.[114] One of the album's singles, "Someone Like You", proved more successful, reaching number one on the Billboard dance charts.[114] Warner Bros booked him to appear on the New Year's Eve edition of The Late Show Starring Joan Rivers, during which Joan Rivers described him as a drag queen; visibly annoyed, he corrected her by stating that he was not a drag queen, proclaiming simply "I'm Sylvester!"[115] The appearance was also notable for Sylvester publicly declaring his relationship with Rick Cranmer despite the fact that Cranmer's family were largely unaware of either the liaison or his sexuality.

In 1985, Sylvester's boyfriend, Rick Cranmer, became aware that he had become infected with HIV. With no known medical cure, his health deteriorated rapidly and he died September 7, 1987. Sylvester was devastated, and although recognizing that he too was probably infected, he refused to have his blood tested, only noticing the virus' first symptoms when he developed a persistent cough.[116] 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.[117] Eventually diagnosed with AIDS, he was hospitalized for sinus surgery in late 1987, and upon returning to his apartment, he began to be cared for by his mother and Tracy, before being hospitalized again in May 1988, this time with pneumocystis pneumonia. Returning to his flat, he gave away many of his treasured possessions and wrote his will.[118]

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.[119] The subsequent 1988 Castro Street Fair was named "A Tribute to Sylvester", and although he was too ill to attend, crowds chanted his name to such an extent that he was able to hear them from his bedroom.[120] He continued to give interviews to the media, being open about the fact that he was dying of AIDS, and sought in particular to highlight the impact that the disease was having in the African-American community.[121] In an interview with the NME, he stated, "I don't believe that AIDS is the wrath of God. People have a tendency to blame everything on God."[122]

For Thanksgiving 1988, his family spent the holiday with him, although he had developed neuropathy and was increasingly bed-ridden and reliant on morphine; he died in his bed on December 16, 1988, at the age of 41.[123] 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. He wanted Tracy to sing at his funeral, accompanied by choirs and many flowers. The whole affair took place in his church, the Love Center, with a sermon being provided by Reverend Walter Hawkins. The event was packed, with standing room only, and the coffin was subsequently taken and buried at his family's plot in Inglewood Park Cemetery.[124] An album titled Immortal was posthumously released; it contained Sylvester's final studio recordings and was compiled by Marty Blecman.[125]

A biography of Sylvester was authored by Gamson and published in 2005.[12] 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".[148] Entertainment Weekly called the book "playful and furious" and awarded it a B+ rating,[161] The Boston Globe suggested that it was "as engaging as the times it so energetically resurrects",[162] 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".[163] The Fabulous Sylvester won the 2006 Stonewall Book Award for nonfiction.[164] In 2015, Sylvester's publicist Sharon Davis published memoirs of the time that she spent with Sylvester, noting that she planned for it to appear in 2013 to mark the 25th anniversary of Sylvester's death.[130][165]

In 2010, the TV series Unsung aired an episode on Sylvester, that was later made available through YouTube.[148] Sylvester: Mighty Real, an official feature-length documentary on the life and career of Sylvester, entered production; it featured interviews with members of Sylvester's family and other artists and musicians who have been inspired by, but by 2012 the film's progress had halted.[148]

In August 2014, an Off-Broadway musical titled Mighty Real: A Fabulous Sylvester Musical opened at Theatre At St. Clement's in New York City. It was co-directed by Kendrell Bowman and Anthony Wayne, the latter of whom also performed as the titular character.[166][167] Wayne stated that he discovered Sylvester's story through a television documentary, and was subsequently "inspired by his drive to be who he was regardless of what he went through", performing a concert of Sylvester's songs with friends Anastacia McCleskey and Jacqueline B. Arnold as the Two Tons o' Fun before deciding to begin work on the musical.[166] 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".[167] The Huffington Post review noted that the musical largely avoided dealing with the decline in Sylvester's musical success during the 1980s, and that although " anyone seeking an exhaustively researched play-by-play of the star's life would be better off waiting for a documentary", the musical "succeeds as a collection of infectious performances by a truly gifted cast".[168]

In 2014 Sylvester was one of the inaugural honorees in the Rainbow Honor Walk, a walk of fame in San Francisco's Castro neighborhood noting LGBTQ people who have "made significant contributions in their fields".[169][170][171]

• ^A Credited as Sylvester & the Hot Band.

• ^A Credited as Sylvester & the Hot Band.