Sylvester Stewart was born the second of five children (Loretta, Sylvester, Freddie, Rose, and Vaetta, known as Vet) in Denton, Texas, on March 15, 1944. His devout African-American family was affiliated with the Church Of God In Christ (COGC) and took their beliefs with them when they moved to Vallejo, California, a northwest suburb of San Francisco. Reared on church music, Sylvester was eight years old when he and three of his siblings (sans Loretta) recorded a 78 rpm gospel single for local release as the Stewart Four.
A musical prodigy, he became known as Sly in early grade school, the result of a friend misspelling ‘Sylvester.’ He was adept at keyboards, guitar, bass, and drums by age eleven, and went on to perform in several high school bands. One of these groups, the Viscaynes, boasted an integrated lineup, a fact that did not go unnoticed in the late 1950s. The group cut a few singles, and Sly also released a few singles as well during that period, working with his younger brother Freddie.
Into the early ’60s, Sly’s musical education continued at Vallejo Junior College, where he added trumpet to his mixed bag, and mastered composition and theory as well. Around 1964, he started as a fast-talking disc jockey at R&B radio station KSOL. His eclectic musical tastes made Sly hugely popular, as he became an early proponent of including R&B-flavored white artists (especially British Invasion bands like the Beatles, the Animals, and the Rolling Stones) into the station’s soul music format. Sly later brought his show to KDIA, where he deejayed right up through the start of Sly and the Family Stone in 1967.
But as early as 1964, the result of a hookup with legendary disc jockey Tom Donahue, Sly had also been tapped as a producer for the San Francisco-based label, Autumn Records. The small label was known for its successes with first generation Bay Area rock bands the Beau Brummels, the Charlatans, the Great Society, and the Mojo Men, all of whom benefited from Sly’s unerring ear. Sly was paired with black singer Bobby Freeman, who had previously recorded one of the Pop/R&B crossover anthems of an era, 1958’s “Do You Want To Dance” (Josie Records). In 1964, Sly produced Freeman’s bona fide #5 Pop hit, “C’mon And Swim” (Autumn), which ironically never appeared on the R&B charts at all.
The stage was set for a quantum leap in 1966. Sly was leading a band called Sly And the Stoners, featuring African-American trumpeter Cynthia Robinson. Freddie was also leading a band, Freddie And the Stone Souls, featuring white drummer Gregg Errico. It was white saxophonist Jerry Martini who urged Sly and Freddie to combine the best of both bands, leading to the birth of Sly and the Family Stone in March 1967. Freddie took over on guitar as Sly quickly mastered the organ. Their sister Rose joined on keyboards and vocals, and bassist/vocalist Larry Graham completed the lineup.
Every band’s story includes their “discovery gig,” and for Sly and the Family Stone it was at a club called Winchester Cathedral in Redwood City, where they frequently played until dawn. They mixed cover tunes with original material, until the originals took over altogether. “When we started doing our own thing,” Freddie told rock writer Bud Scoppa, “it really was our own thing, and we threw all those other things out of the window.” A local CBS Records promotion man caught their act and alerted A&R executive David Kapralik in New York. He flew to the West Coast and wasted no time signing the band to Epic Records and becoming their manager.