Retrospective gathers tracks from Smith's most influential period, between 1956, when he recorded A New Sound, A New Star, and 1963, when his initial association with Blue Note ended with Rockin' the Boat (he returned to the label in the 1980s). The set also includes portions of the albums The Champ, The Sermon (including the 20-minute title track), and the classic Back at the Chicken Shack, with tenor saxophonist Stanley Turrentine, guitarist Kenny Burrell, and drummer Donald Bailey.

Also heard on the set are such jazz giants as trumpeter Donald Byrd, alto saxophonists Lee Morgan and Jackie McLean, tenor saxophonist Hank Mobley, and drummer Art Blakey.