# Before De@th, Sylvester Revealed The 8 Singers He Dated In Secret
Sylvester James, the pioneering disco icon and openly gay Black artist, revealed before his death in 1988 that he had secretly dated eight singers in the music industry.
Known for his unapologetic authenticity during a time of intense prejudice, Sylvester’s personal life was as bold as his music. While some relationships were confirmed, others remain whispered rumors, fueling speculation about R&B legends even today. This exploration uncovers the hidden love life of disco’s biggest star.
Before icons like RuPaul or Lil Nas X, Sylvester broke barriers in the 1970s and 1980s with hits like “You Make Me Feel (Mighty Real).” His high-pitched voice, glamorous outfits, and gender-bending performances contrasted sharply with the hyper-masculine personas of peers like Rick James, with whom he shared an unspoken rivalry.
While Rick dominated mainstream funk with songs like “Super Freak,” Sylvester reigned in disco and gay communities. Industry insiders noted tension, with Rick allegedly viewing his own music as more authentic, while Sylvester felt overshadowed despite his profound influence on club culture.
Speculation about Sylvester’s romantic ties to other singers has persisted. Rumors linked him to Luther Vandross due to their shared privacy and vocal prowess, though no evidence confirms this.
Teddy Pendergrass, Philadelphia royalty before his 1982 accident, was another name tied to Sylvester through shared roots and stage charisma, but connections remain anecdotal. Johnny Gill, Jeffrey Osborne, and Alexander O’Neal also appear in fan theories, driven by their prominence in R&B and overlapping eras, yet lack substantiation.
Sylvester’s openness about his sexuality—rare for the time—ironically makes secret affairs with closeted peers less likely, though the era’s stigma fueled such gossip.
Beyond rumors, Sylvester’s confirmed relationships reveal a life of love and heartbreak. In the late 1960s, he dated Lonnie Prince, a striking match during a risky period of cross-dressing in California. In 1970, he “married” Michael Lyons in a symbolic ceremony at Golden Gate Park, defying legal bans on same-sex unions.
Later, John Maley inspired the song “Can’t Forget the Love” in 1978, though their romance ended with Maley’s move to Los Angeles. Relationships with Michael Rayner in 1981 and hairdresser Tom Daniels in 1982 followed, both dissolving over trust issues.
His deepest bond was with Rick Cranmer in the mid-1980s, a mature love cut short by Cranmer’s death from AIDS in 1987, leaving Sylvester devastated.
Sylvester’s final years were marked by his own battle with AIDS, yet he remained a fierce advocate, educating communities and reducing stigma. Passing at 41 on December 16, 1988, his funeral at the Love Center was a celebration of music and love, as he requested.
His legacy as a disco pioneer and gay rights icon endures, with his personal revelations—whether confirmed or rumored—adding layers to the story of a trailblazer who lived and loved fearlessly.