Listen to a sample of Skip James's "I'm So Glad" (1.56MB wav)

Born June 21, 1902, in Yazoo City, Mississippi, at the "colored" hospital, Skip James was raised on the Woodbine Plantation, fifteen miles south of Yazoo City and a mile and a half from nearby Bentonia. His bootlegger father left his wife and son in 1907, a step ahead of the local revenue agents. His mother bought him his first guitar for $2.50 in 1912. Henry Stuckey, a guitarist five years older who lived on nearby Sataria Plantation, taught James the venerable eight-bar staple "Drunken Spree." James's mother moved the family to nearby Sidon in 1914 in an attempt to reconnect with her husband. The reunion fizzled and fourteen-year-old James ran away from home for a year. In 1917, he returned to Bentonia, where his mother was then living. There he attended high school and worked on the weekends at Gooching Brothers sawmill. During this time James took rudimentary piano lessons from his cousin Alma Williams, a schoolteacher.

James dropped out of high school in 1919 and left Bentonia to work and live at a road construction camp near Ruleville. During the next two years he worked in various levee and lumber camps around the Delta. While working in a lumber camp James composed his first song, "Illinois Blues." On weekends, he would pick his guitar for tips in the nearby towns of Drew, Louise, and Belzoni. In 1921, James moved to Weona, Arkansas, to work as a lumber grader at a sawmill camp. There he met pianist/pimp Will Crabtree. By James's account, Crabtree was a huge man from nearby Marked Tree, Arkansas, who influenced his piano playing and lifestyle. James remained in Weona until 1923, hustling women and working as a pianist. After a dispute with one of the women, James moved to Memphis, where he worked as a pianist at a brothel on North Nichols Street.

Likely as a result of the passage of Prohibition, James returned in 1924 to Bentonia, where he remained for six years. During this time he worked as a sharecropper, but soon began bootlegging "white lightning" to pay for the fancy clothes and jewelry that he had come to enjoy during his days as a pimp. He also practiced his guitar playing, working dances with Henry Stuckey in Bentonia, Sidon, and as far away as Jackson, Mississippi. James developed his three-finger picking style, a style practiced by Charley Patton, Mississippi John Hurt, and Jackson native Bo Carter. James's trademark sound came from his E-minor tuning, which he called "cross-note tuning." His digital dexterity, unusual sound, falsetto singing voice, and proficiency with a guitar convinced Paramount Records talent scout H.C. Speir to recommend James to the label based on an audition in Speir's music store at 111 Farish Street in Jackson. In February 1931, he waxed eighteen sides at Paramount's Grafton, Wisconsin, studio that were subsequently issued. During the session James established himself at the forefront of blues musicians, evidenced by songs such as "I'm So Glad," "Devil Got My Woman," "Special Rider Blues," and "20-20 Blues."

Speir attempted to persuade James to record again in late 1931 or early 1932, but the musician had "gotten religion" as a result of a meeting with his father and refused the offer. The elder James had reformed his habits and become a Baptist minister. James followed his father to Plano, Texas, where he attended, but did not graduate from, seminary school. James remained with his father during the 1940s, returning home to Bentonia upon the death of his mother in the early 1950s. He was rediscovered in 1964 and together with Son House and Mississippi John Hurt sparked interest in the blues revival of the time. A rock version of "I'm So Glad" became a million seller, but James denounced it. He recorded and toured during the 1960s before being stricken with cancer.

Skip James died October 3, 1969, in Philadelphia, Pennsylvania. He is buried at Mercon Cemetery, Bala-Cynwyd, Pennsylvania.