In the vibrant world of music, Sylvester James Jr., known universally as Sylvester, was a true luminary whose talent spanned disco, R&B, and soul, leaving an unforgettable mark.
His story is not merely one of chart-topping hits and dazzling performances; it is a profound narrative of self-discovery, community building, and unwavering activism in the face of immense adversity. Sylvester navigated a world often hostile to his very being, yet he did so with an inimitable grace and a fierce determination to be seen, heard, and celebrated on his own terms. His life encapsulates a pivotal era in American culture, mirroring the seismic shifts in racial justice, LGBTQ+ rights, and musical innovation that defined the late 20th century.
We delve into the multifaceted layers of Sylvester’s life, from his formative years that laid the groundwork for his unique artistry to the collaborative endeavors that propelled him to international stardom. It is a journey marked by both profound personal challenges and exhilarating triumphs, revealing how a sensitive, artistic soul from Watts became the “Queen of Disco” and a fearless advocate for his community. Join us as we uncover the genesis of his iconic sound, the friendships that sustained him, and the breakthrough moments that cemented his status as an unparalleled force in popular culture.
1. **The Genesis of a Soul: Sylvester James Jr.’s Watts Roots**Born on September 6, 1947, in the vibrant yet complex Watts district of Los Angeles, Sylvester James Jr. entered a world that would both nurture his artistic spirit and challenge his burgeoning identity. His origins were in a middle-class African-American family, a foundation that instilled a sense of heritage and community. His mother, Letha Weaver, herself from a relatively wealthy African-American family in Palestine, Arkansas, brought her children to the Palm Lane Church of God in Christ in South Los Angeles, where Sylvester’s musical journey truly began.
It was within the walls of this Pentecostal church that Sylvester first discovered the intoxicating power of gospel music, a sound that would profoundly influence his vocal stylings. An avid singer from the tender age of three, he regularly participated in gospel performances, showcasing a natural talent that captivated those around him. The church environment, while fostering his early love for music, also presented the first societal friction for young Sylvester.
Though his family noticed his “feminine” nature early on, lovingly calling him “his own kind of boy,” his childhood was tragically disrupted by molestation at age eight, leading to his ostracism from his church at 13 after his mother discovered his homosexuality.
2. **The Disquotays: Forging Identity in 1960s Los Angeles**Having left home after an argument with his mother, Sylvester navigated the challenging terrain of adolescence and early adulthood, spending much of the next decade finding refuge with friends and, significantly, his grandmother Julia, who offered unconditional acceptance of his homouality. It was during this period, in the culturally charged 1960s, that Sylvester began to forge connections within the local gay Black community, culminating in the formation of a groundbreaking group they playfully named the Disquotays.
He found solace and community with a group of Black cross-dressers and transgender women, like his best friend Duchess, throwing extravagant parties and forging a vibrant subculture that was a precursor to later liberation movements.
Sylvester’s romantic life also blossomed, with Lonnie Prince becoming his boyfriend during the latter part of the decade, a relationship described by friends as the “It couple.” Yet, this era of self-expression came with inherent risks. Cross-dressing was illegal in California, and Sylvester often hitchhiked in female attire, risking arrest. Although he avoided imprisonment for cross-dressing, he was arrested for shoplifting on several occasions. Despite these challenges and various odd jobs—from a McDonald’s cook fired for refusing a hairnet to a make-up artist at a mortuary—Sylvester embraced his burgeoning identity, becoming an integral part of a community that celebrated individuality in a world struggling to catch up. He even graduated high school at 21, appearing in his photograph in drag, a bold statement of his evolving self. By the end of the decade, as the Disquotays evolved, Sylvester himself began to refine his look, moving towards an androgynous style influenced by the hippie movement, a blend of masculine and feminine that would become his signature.
3. **San Francisco Beckons: The Avant-Garde World of The Cockettes**The lure of San Francisco, renowned as a haven for counterculture and gay liberation, proved irresistible to Sylvester, who had grown weary of Los Angeles and the fading Disquotays. In 1970, an invitation from Reggie Dunnigan at the Whisky a Go Go bar to join the “Chocolate Cockettes”—Black members of the famed avant-garde performance art drag troupe—set the stage for his next transformative chapter. The Cockettes, founded by drag queen Hibiscus, were a radical collective known for parodying popular culture, embracing free love, and immersing themselves in mind-altering substances, all while being deeply involved in the Gay Liberation movement.
Upon arriving in the city, Sylvester’s undeniable talent was immediately recognized. His falsetto voice and piano skills impressed the communal residents, leading to his inclusion in their upcoming show, *Radio Rodeo*. His early performances, like singing *The Mickey Mouse Club* theme song in a cowgirl skirt, hinted at the playful yet profound artistry that would define him. While he briefly resided in their communal home, the lack of privacy prompted a move to Market Street with fellow Cockettes, highlighting his unique blend of communal spirit and personal introspection.
Within the Cockettes, Sylvester stood out. He was one of the very few African-American members, and his refined, glamorous stage presence contrasted sharply with the troupe’s more surrealist and “war paint” aesthetic. He often commanded entire solo segments, captivating audiences with his interest in blues and jazz, performing imitations of idols like Billie Holiday and Josephine Baker. Adopting the pseudonym “Ruby Blue” and playfully declaring himself “Billie Holiday’s cousin once removed,” he not only amassed his own following but also earned particular praise from *Rolling Stone* magazine, which described him as “a beautiful Black androgyne who has a gospel sound with the heat and shimmer of Aretha.” This period, though short-lived, was crucial in honing his stagecraft and establishing his unique artistic voice before his inevitable departure to pursue a solo career, famously apologizing for “this travesty that I’m associated with” during a critically panned New York tour.
4. After his electrifying performances with the Cockettes, Sylvester returned to San Francisco, attracting the attention of Rolling Stone editor Jann Wenner, which led to a demo album deal with A&M Records and the formation of his backing band, ‘the Hot Band’.
Undeterred, the Hot Band found a new home with Blue Thumb, contributing two songs for *Lights Out San Francisco*, an album compiled by local radio station KSAN. This exposure led to local gigs and, most notably, the coveted opening slot for glam rock superstar David Bowie at the Winterland Ballroom. Bowie himself acknowledged Sylvester’s magnetic stage presence, famously remarking that San Francisco “didn’t need him” because “They’ve got Sylvester,” a nod to their shared embrace of androgyny. The band’s sound began to shift from blues to a more commercially appealing rock.
In early 1973, under the aegis of Bob Krasnow at Blue Thumb, Sylvester and his Hot Band released their self-titled debut, originally intended to be called *Scratch My Flower*. Despite employing the Pointer Sisters as backing vocalists, the album, comprised mainly of covers, failed to capture the live intensity for which Sylvester was known. A subsequent album, *Bazaar*, included original compositions but also suffered from poor sales. Music journalist Peter Shapiro noted that Sylvester’s “cottony falsetto was an uncomfortable match with guitars” and that they both had “an unpleasantly astringent quality” in the records. Frustrated by the lack of commercial success and finding Sylvester “difficult to work with,” the Hot Band disbanded in late 1974, and Krasnow canceled his contract, leaving Sylvester once again at a crossroads, sans band and record deal.
5. Following the disbandment of the Hot Band and several unsuccessful attempts with new musicians, Sylvester’s manager, Brent Thomson, advised him to adopt a more masculine image, a pragmatic suggestion paving the way for a pivotal collaboration.
Thomson’s open auditions for new backing singers proved serendipitous. It was there that Sylvester was captivated by Martha Wash, a powerful vocalist whose talent was undeniable. He then posed a pivotal question, asking Wash if she knew another “large Black friend who could sing,” leading her to introduce him to Izora Rhodes. This introduction was nothing short of transformative. Though Sylvester affectionately referred to them as “the girls,” Wash and Rhodes soon christened themselves the Two Tons O’ Fun, a name that would become synonymous with Sylvester’s most iconic era and later, with their own mainstream success as the Weather Girls.
Biographer Joshua Gamson eloquently captured the magic of this union, noting that “Something clicked and sighed into place when Sylvester and the Tons got together.” This partnership was different; it tapped into a deeper wellspring of Sylvester’s heritage and identity. Gamson observed, “Izora and Martha were whom he came from and who he was… They sounded right with Sylvester, and looked just right, one on either side of him.” Their combined vocal prowess and stage presence provided the perfect foil and complement to Sylvester’s unique artistry, giving him the dynamic support he needed to truly soar. The three of them became a force to be reckoned with, creating an undeniable synergy that would soon propel them into the spotlight, laying the foundation for Sylvester’s global stardom.
6. **Solo Debut and Shifting Image: The 1977 ‘Sylvester’ Album**The electrifying partnership with the Two Tons O’ Fun swiftly bore fruit. Performing regularly at gay bars such as The Stud and The EndUp, Sylvester and his new band secured a coveted weekend residency at The Palms nightclub on Polk Street in September 1976. These nightly sets, a vibrant mix of covers and original compositions, drew significant attention, crucially catching the ear of Motown producer Harvey Fuqua. Recognizing Sylvester’s undeniable talent and the potent synergy with his backing vocalists, Fuqua extended a solo deal with Fantasy Records in 1977, marking a pivotal moment in Sylvester’s career trajectory.
In the middle of that year, Sylvester entered the studio to record his third album, the self-titled *Sylvester*. This album represented a deliberate and noticeable shift in his public presentation. The cover design itself was telling, depicting Sylvester in male attire, a conscious departure from the more glittery androgynous appearance of his earlier Cockettes days. This strategic image transformation aimed to broaden his appeal, positioning him as a more conventional rhythm-and-blues singer with wider commercial viability, a calculated move to break into the mainstream.
The musical content of *Sylvester* also reflected this evolution, heavily influenced by nascent dance music trends. It showcased Sylvester’s growing prowess as a songwriter, featuring original compositions such as “Never Too Late,” alongside astute covers of hits like Ashford & Simpson’s “Over and Over.” This particular track, released as a single, proved a minor hit in the United States and achieved even greater success in Mexico and Europe, foreshadowing his international appeal. The album and subsequent tours through Louisiana and Mexico City solidified his new direction, demonstrating that Sylvester was not only an extraordinary vocalist but also a savvy artist capable of adapting his image and sound to capture an ever-expanding audience.
