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Taylor was born in Natchez, Mississippi, in 1915, though some sources say 1917. He initially played the piano and began playing the guitar when he was 20. He moved to Chicago in 1942. 

He was famous among guitar players for having six fingers on both hands, a condition called polydactyly. As is usual with the condition, the extra digits were rudimentary nubbins and could not be moved. One night, while drunk, he cut off the extra digit on his right hand using a straight razor.

He became a full-time musician around 1957 but remained unknown outside the Chicago area, where he played small clubs in black neighborhoods and at the open-air Maxwell Street Market. He was known for his electrified slide guitar playing (roughly styled after that of Elmore James), his cheap Japanese Teisco guitars, and his raucous boogie beats.