from 1947 to 1949, tibbs recorded for aristocrat records. his debut single was "bilbo is dead" backed with "union man blues", recorded when he was eighteen years old. the tracks were both co-written by tibbs and tom archia, and caused controversy. the a-side criticized theodore bilbo's policies, whilst the b-side caused displeasure from the chicago-based teamster's union. six further singles were released by aristocrat. following its eventual acquisition by leonard and phil chess, the newly formed chess records signed a recording contract with tibbs in 1950, but he released only one record, "you can't win", before being dismissed.