Sylvester: Rolling Stones #169 of The 200 Greatest Singers of All Time (2023)

Sylvester

Sylvester
Born: Sylvester James Jr.
September 6, 1947
Watts, Los Angeles, California
Died: December 16, 1988 (aged 41)
San Francisco, California, US.
Occupation: Singer, songwriter, 
composer, record producer
Genres: Dance, Hi-NRG, R&B, disco, soul, funk
Instruments: Vocals, keyboards, piano

Sylvester James Jr., known simply as Sylvester, was an American singer-songwriter of disco, rhythm & blues, and soul. Known for his flamboyant, androgynous appearance and falsetto singing voice, he was nicknamed the "Queen of Disco" in the late 1970s. San Francisco awarded him the key to the city. In 2005, Sylvester and Chic and Gloria Gaynor were inducted into the Dance Music Hall of Fame. In  2023, Rolling Stone ranked him number 169 of The 200 Greatest Singers of All Time.

Sylvester 

"If there was one artist who truly exemplified 

disco's new language of ecstasy it was Sylvester."

Peter Shapiro, publisher of Relix magazine

Born in Watts, Los Angeles, Sylvester sang in his Pentecostal church choir. When the congregation disapproved of his homosexuality, he left and befriended a group of black cross-dressers and transgender women who called themselves Disquotays. Biographer Joshua Gamson summed up that experience in the 2005 book The Fabulous Sylvester: The Legend, the Music, the Seventies in San Francisco:

Sylvester

"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."

Cockettes

"Oh God, don't ask me how I got started 

or how old I am or about The Cockettes. 

Let's just say I was the first test tube baby."

Interview with Sylvester

George Harris III, aka Hibiscus

In 1970, at 22 years old, Sylvester moved to San Francisco. He immersed himself in the counterculture movement and joined the avant-garde drag troupe the Cockettes. Founded by George Harris III, aka Hibiscus, they parodied popular culture. Though involved in the Gay Liberation movement, they were influenced by the hippies; living communally, they embraced free love and consumed mind-altering substances like marijuana and LSD. 

Sylvester performed with them but at a distance. Not only was he one of the very few African-American members,  he saw himself as a classier, more glamorous performer. Onstage, he was usually given an entire scene to himself -  channeling Billy Holiday and Josephine Baker - with little relevance to the theme of the rest of the show,  Gamson wrote in 2005:

The Cockettes 2002 documentary

"Sylvester shared the Cockettes' affinity for excessive flaming, their celebration of sex and gayness, love of acid and good hash, and bent movie-musical fantasies. Like them, he was making himself up, fantasizing about a self into existence. But he usually stood a few feet back, among the Cocket,tes but never quite one of theHishis drag and makeup were almost staid compared with the Cockettes'; they preferred facial designs that were almost like war paint and clothing that didn't make sense. Sylvester wore simple period dresses onstage and created the face of a sane, pretty woman."

During the Cockettes' critically panned tour of New York City, Sylvester left them to pursue his career elsewhere. An ad-supported 2002 documentary about CockeTVes is hosted free of charge on Tubi TV or can be rented for $2.99 on  Vimeo. 

Two Tons of Fun

"I wanted some big bitches who could wail."

Sylvester in the Times of London

Realizing the Cockettes were no ticket to stardom, Sylvester quit after the opening night in New York City. In San Francisco, he performed on the gay nightclub circuit with white male "eye-candy" backup singers. They billed themselves as the Hot Band. Not satisfied with this line-up, he hired some black drag queen entertainers and spent some time in England. Success evaded him. Then, he met Martha Wash. 

As Sylvester told the story, he was auditioning for a group of backup singers. A thin, pretty white woman performed before heavy-built Wash belted out her song choice. Sylvester dismissed the rest of the group and asked Wash if she knew another black woman her size who could sing. She recommended her friend, Izora Armstead. Sylvester hit pay-dirt. According to biographer Joshua Gamson: 

"Something clicked and sighed into place when Sylvester and the Tons got together – something that wasn't there with the Hot Band white boys, for all that they could cook; something that wasn't there with Peter Mintun, for all the beautiful oddness that he and Sylvester shared; something that wasn't even there with the black drag-queen singers, for all the fierceness they projected. Izora and Martha were who he came from and who he was. They were women who got their own. They sounded right with Sylvester and looked just right, one on either side of him. Plus, next to them, Sylvester, who had grown quite round, looked positively svelte."

Dance (Disco Heat)

A-Side: Dance (Disco Heat)

B-side: You Make Me Feel (Mighty Real) 
Single: Sylvester

Album: Step II

Released: August 1978

Genre: Disco

Songwriters: Eric Robinson, Victor Osborn

Producer: Sylvester

Although Sylvester called them "the girls," Wash and  Armstead billed themselves as Two Tons of Fun. The trio gained an LGBT following by performing in gay clubs and events around San Francisco. That led to his contract with Fantasy Records. They cut some numbers with local success until their breakout album, Step II. The track "Dance (Disco Heat)" was Sylvester's first Top 40 hit in the United States.  

A 12" single was released in 1978, with "Dance (Disco Heat)" as the A-side and "You Make Me Feel (Mighty Real)" as the B-side. The two songs held the top spot on the Billboard Dance/Disco chart for six weeks in August and September that year. "Dance (Disco Heat)" peaked at number 19 on the Billboard Hot 100 chart in the fall of 1978 and reached number 29 on the UK Singles Chart.

"You Make Me Feel (Mighty Real)"

"One of those surges of sustained, stylized
energy that is disco's great gift to pop music."
Music critic Robert Christgau on
"You Make Me Feel (Mighty Real)"

"You Make Me Feel (Mighty Real)" was Sylvester's second Top 40 hit, peaking at number 36 on the Billboard Hot 100 chart. It reached number 20 on the Billboard Hot Soul Singles chart. In 2003, Q Magazine ranked "You Make Me Feel (Mighty Real)" number 677 in their list of the "1001 Best Songs Ever." 

In 2018, Pitchfork Media featured the song in their 50 Songs That Define the Last 50 Years of LGBTQ+ Pride. In 2019, the Library of Congress selected the music for preservation in the National Recording Registry for being "culturally, historically, or aesthetically significant." A 2020 poll of 1,300 adults aged 30-55 ranked "You Make Me Feel (Mighty Real)" number 13 of the Top 50 happiest songs ever.

Weather Girls

It's Raining, Men
Album: Success
B-side: It's Raining Men (instrumental)
Released: September 10, 1982
Genre: Hi-NRG, disco, synth-pop
Songwriter: Paul Jabara, Paul Shaffer

Like Sylvester, Martha W,ash and Izora Armstead honed their vocals in the church, where they developed powerful voices. While singing backup for him, Sylvester's label signed them as Two Tons of Fun. They scored a few R&B hits before changing their name to The Weather Girls and recording "It's Raining Men." 

The song was explicitly made for the gay community. Like "YMCA" by The Village People, it became a gay anthem and, later, a mainstream hit. The song was from the perspective of women, objectifying men in a way rarely heard in popular music. This message was not lost on gay listeners.

Paul Shaffer

"It's Raining Men" was written by Paul Shaffer and Paul Jabara. Shaffer was David Letterman's bandleader. Jabara wrote "Last Dance" and "No More Tears" for Donna Summer. They offered it to Summer. She was deeply religious and thought the line, "It's raining men, hallelujah," was blasphemous. 

Jabara pitched it to Barbra Streisand and Diana Ross, but both turned it down. He then played it for Wash and Armstead, who were still recording as Two Tons O' Fun. Wash initially resisted, but the duo agreed to record it.

Patrick Cowley

Patrick Cowley & Sylvester

Birth name: Patrick Joseph Cowley
Born: October 19, 1950
Buffalo, New York, U.S.
Died: November 12, 1982USged 32)
San Francisco, California, US.
Genres: Disco, hi-NRG, synth-pop, experimental
Instruments: Multiple instruments

Born in Buffalo, New York, Patrick Cowley moved to San Francisco, where he met Sylvester in 1978. Cowley played synthesizer on Sylvester's 1978 album Step II. He joined Sylvester's live band for several world tours. 

Cowley's hits included "Menergy" in 1981 and "Megatron Man," which hit numbers 1 and 2 on the Billboard Hot Dance Music/Club Play chart. He started his own record label, Megaton, and convinced Sylvester to leave Fantasy and record with him. This resulted in  "Do Ya Wanna Funk" from the album All I Need. The song made number 4 on the Billboard dance chart the same year.

During a world tour with Sylvester in late 1981, Cowley felt increasingly unwell. Upon returning to the United States, he visited a doctor who diagnosed food poisoning. Weeks later, with his condition only worsening, doctors again failed to identify what was wrong with him. 

At the early stage in the history of HIV and AIDS, misdiagnosis was common. Cowley, who was gay, was discharged from the hospital after doctors could do nothing more for him. He died in the Castro District of San Francisco on November 12, 1982. He was 32 years old. Six years later, on December 16, 1988, Sylvester would die of the same condition at 41 years old.