Born in Lake, Mississippi, United States, Littlejohn first learned to play the blues from Henry Martin, a friend of his father.
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Over the next 12 years, Rooster Blues released albums by artists like Magic Slim, Eddy Clearwater, John Littlejohn, Lonnie Pitchford, Roosevelt "Booba" Barnes, James "Son" Thomas, Larry Davis, Valerie Wellington, Carey Bell, Willie Cobbs, Super Chikan, and Lonnie Shields.