[3] Much of his life remains a mystery, but his draft card lists his birthplace as New Orleans, Louisiana, and his death certificate states that he died in Chicago, Illinois, on May 7, 1938.

Among his recordings are several in which he accompanied classic female blues singers, such as Ida Cox, Hattie McDaniel, and Ma Rainey.

[3] According to the blues writer Bruce Eder, Jackson achieved "a musical peak of sorts in September of 1929 when he got to record with his longtime idol, Blind Arthur Blake, often known as the king of ragtime guitar during this period.

'Papa Charlie and Blind Blake Talk About It' parts one and two are among the most unusual sides of the late '20s, containing elements of blues jam session, hokum recording, and ragtime.

The Carolina Chocolate Drops recorded "Your Baby Ain't Sweet Like Mine" on their Grammy Award–winning 2010 album, Genuine Negro Jig, and often played the song in interviews after its release.