In 1915, Estes' father, a sharecropper who also played some guitar, moved the family to Brownsville, Tennessee. Not long after, Estes accidentally lost the sight in his right eye when a friend threw a rock at him.At the age of 19, while working as a field hand, he began to perform professionally. The venues were mostly local parties and picnics, with the accompaniment of Hammie Nixon, a harmonica player, and James "Yank" Rachell, a guitarist and mandolin player. He would continue to work on and off with both musicians for more than fifty years. 　　Estes made his debut as a recording artist in Memphis, Tennessee in 1929, at a session organized by Ralph Peer for Victor Records.He recorded the tracks "Drop Down Mama" and "Someday Baby Blues" with Nixon in 1935. He later worked with Son Bonds and Charlie Pickett.He later recorded for the Decca and Bluebird labels, with his last pre-war recording session taking place in 1941.He made a brief return to recording at Sun Studio in Memphis in 1952, recording "Runnin' Around" and "Rats in My Kitchen", but otherwise was largely out of the public eye for two decades. 　　Estes was a fine singer, with a distinctive "crying" vocal style. He frequently teamed with more capable musicians, like "Yank" Rachell, Hammie Nixon, and the piano player Jab Jones. Estes sounded so much like an old man, even on his early records, that blues revivalists reportedly delayed looking for him because they assumed he would have to be long dead, and because fellow musician Big Bill Broonzy had written that Estes had died. By the time he was tracked down, by Bob Koester and Samuel Charters in 1962, he had become completely blind and was living in poverty. He resumed touring and recording, working with Nixon on tour and on works released on the Delmark Records label.His later records are generally considered less interesting than his pre-war output. Estes, Nixon and Rachell appeared at the Newport Folk Festival in 1964. 　　Bob Dylan mentions Estes in the sleeve notes to Bringing It All Back Home (1965). 　　Many of Estes' original songs were based on events in his own life or on people he knew from his home town of Brownsville, Tennessee, such as the local lawyer ("Lawyer Clark Blues"), local auto mechanic ("Vassie Williams' Blues"), or an amorously inclined teenage girl ("Little Laura Blues")."Lawyer Clark Blues" referenced the lawyer, and later judge and senator, Hugh L. Clarke. Clarke and his family lived in Brownsville, and according to the song let Estes 'off the hook' for an offense. 　　He also dispensed advice on agricultural matters ("Working Man Blues") and chronicled his own attempt to reach a recording studio for a session by hopping a freight train ("Special Agent (Railroad Police Blues)"). His lyrics combined keen observation with an ability to turn an effective phrase. 　　Some accounts attribute his nickname "Sleepy" to a blood pressure disorder and/or narcolepsy. Others, such as blues historian Bob Koester, claim he simply had a "tendency to withdraw from his surroundings into drowsiness whenever life was too cruel or too boring to warrant full attention".