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From Louisville, KY., Weaver, like his parents, lived most of his life in the Smoketown neighborhood. The financial hardship during the Great Depression; it indicates that Weaver supported his music career with employment in various blue-collar jobs. By 1949, he and his wife, Dorothy, had moved to a better neighborhood, near Cherokee Park, where they lived in a basement apartment, probably a modest accommodation. His move from Smoketown is roughly concurrent with the construction of the Sheppard Square housing project, so he and his parents may have been displaced when the project absorbed his Roselane Court and their Clay Street residences.
Weaver recorded "Longing for Daddy Blues" and "I've Got to Go and Leave My Daddy Behind" with the blues singer Sara Martin on October 23, 1923, in New York City. Two weeks later, as a soloist, he recorded "Guitar Blues" and "Guitar Rag", the first blues guitar instrumentals; released by Okeh Records. They are the first recorded country blues and the first known recordings of a slide guitar. "Guitar Rag" (played on a Guitjo) became a blues classic. A cover version recorded by Bob Wills and the Texas Playboys in the 1930s as "Steel Guitar Rag" became a country music standard.
Weaver recorded about 50 more songs, sometimes accompanied by Martin, until 1927. On some recordings from 1927 he was accompanied by Walter Beasley and the singer Helen Humes. Weaver often played his guitar bottleneck style, using a knife as a slide. His recordings were successful, but in 1927 he retired and went back to Louisville, where he lived until his death from carcinoma of the tongue (death certificate).
A revival of interest in the recordings of many country blues artists occurred from the 1950s on, but Weaver died almost forgotten. A complete collection of his recordings was released on two CDs in 1992. In the same year his hitherto unmarked grave received a headstone by engagement of the Kentuckiana Blues Society, based in Louisville. Since 1989 the society has presented its Sylvester Weaver Award annually to honor those who have rendered outstanding services to blues music. Sylvester Stewart died on April 4, 1960.