Through his connections on the Gary, IN music scene he was acquainted with Joe Jackson, patriarch of the musical Jackson family, and Littlejohn and his band reputedly served as an occasional rehearsal band for the Jackson 5 in the mid to late '60s. Littlejohn played regularly in Chicago clubs (he was filmed by drummer Sam Lay playing with Howlin' Wolf's band c. 1961) but did not make any studio recordings until 1968, when he cut singles for several record labels. Later that year he recorded an album with Arhoolie Records and four songs for Chess Records, though the Chess tracks were not issued at the time. Although he recorded a few singles for small local labels, Littlejohn did not record another album until 1985, when Rooster Blues issued So-Called Friends. Soon after, he fell into ill health, and died of renal failure in Chicago 1994, at the age of 62.
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