Born into a musical family in 1895 near Navasota, the son of an ex-slave and a half Choctaw Indian mother, Lipscomb spent much of his life as a tenant farmer in his home state of Texas. Both of Lipscomb's brothers were guitarists, his dad played fiddle and his uncle banjo. By age 11, he began playing guitar and before long was accompanying his father at local events and dances
Unlike many of his contemporaries, Lipscomb did not record during the early blues era, but he had direct exposure to early Texas recording artists like Blind Lemon Jefferson, Blind Willie Johnson, and the groundbreaking country star, Jimmie Rogers. A traveling performer invited Lipscomb to go on the road as far back as 1922, but he declined touring invitations until the blues revival of the late 1950s and early 1960s, rarely leaving home.
Although he performed often, most of these performances were for his own community at local functions. Remaining married to his wife Elnora throughout his life, with whom he raised a son and three adopted children, Lipscomb led a responsible hard-working life and did not fit the blues musician stereotype of the roving gambler or hard drinking musician.
During the late 1950s, Lipscomb relocated to Houston, where a local lumber company employed him during the day. He spent his evenings performing for local audiences, often with Sam "Lightnin'" Hopkins, whom Lipscomb had become friends with 20 years prior, when they first met in Galveston. It wasn't until 1960 that Lipscomb encountered the music researchers Chris Strachwitz and Mack McCormick, who would soon be recognized for discovering him.
They met on a job site, while Strachwitz and McCormick were trying to locate Lightnin' Hopkins, who had recently left the area. Strachwitz was in the initial stages of forming his record label, Arhoolie, and Lipscomb convinced the researchers to listen to his music instead.
This chance encounter would mark the beginning of Lipscomb's recording career and a decade of involvement in the folk and blues revivals. Well into his 60s, it was those first recordings for Arhoolie and live performances like this one that won Lipscomb acclaim and recognition for his skill and technique as a guitarist and for the breadth of his wide-ranging repertoire.
Lipscomb achieved what only a select few of the greatest musicians ever attain—the ability to infuse his personality into every song he plays. As an artist who predated the development of the blues, Lipscomb represented one of the last remnants of the 19th century songster tradition.
Although his recording career was limited to the later years of his life, his influence is wide ranging, having a significant impact on countless blues artists to emerge in the 1960s and being one of the only leading lights of the folk and blues revival to boast a repertoire spanning two centuries of music.