Lipscomb spent most of his life working as a tenant farmer in Texas and was "discovered" and recorded in 1960 during the revival of country blues. He released six albums of blues and folk music, singing and accompanying himself on acoustic guitar. He had a fine finger-picking guitar technique, and a expressive voice well suited to his material.
Unlike many of his contemporaries like Blind Blake and Blind Willie McTell his life is well documented and he appeared in several films including A Well Spent Life (1971) ISBN 0-933621-09-4.
Despite his fame in the 1960s and early 1970s he died poor in his hometown of Navasota, Texas in 1976, two years after a severe stroke.