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Born in Kentwood, Louisiana in 1906, by the time Montgomery was aged 11 he had left school and was playing piano in Louisiana juke joints and barrelhouses. He moved to Chicago when he was twenty years old and within a few years he was recording for Paramount, "Vicksburg Blues" being one of his first releases.  During the 1930's he went on the road and he was recorded again by Bluebird in New Orleans in the mid 1930's. In the 1940's Montgomery settled down in Chicago and followed a comfortable and successful career playing the club scene. A major influence on artists like Sunnyland Slim and Otis Spann, he never allowed his repertoire to be restricted by a particular style and he moved effortlessly between the blues, jazz and even ragtime on occasions. For example he played major dates with Kid Ory's Dixieland Band and worked with artists such as Otis Rush and Buddy Guy. When he was in his sixties he formed his own record company and the first release was a reprise of "Vicksburg Blues". Little Brother Montgomery died in Chicago in 1985 aged 79 years old.