In 1951, Mr. Jamal first recorded 'Ahmad's Blues' on Okeh Records. His arrangement of the folk tune 'Billy Boy', and 'Poinciana' (not his original composition), also stem from this period. In 1955, he recorded his first Argo (Chess) Records album that included 'New Rhumba', 'Excerpts From The Blues', 'Medley' (actually 'I Don't Want To Be Kissed'), and 'It Ain't Necessarily So' —all later utilized by Miles Davis and Gil Evans on the albums Miles Ahead and Porgy and Bess. In his autobiography, Mr. Davis praises Mr. Jamal's special artistic qualities and cites his influence. In fact, the mid-to-late 1950's Miles Davis Quintet recordings notably feature material previously recorded by Mr. Jamal: 'Squeeze Me', 'It Could Happen To You', 'But Not For Me', 'Surrey With The Fringe On Top', 'Ahmad's Blues', 'On Green Dolphin Street' and 'Billy Boy'.
In 1956, Mr. Jamal, who had already been joined by bassist Israel Crosby in 1955, replaced guitarist Ray Crawford with a drummer. Working as the house trio at Chicago's Pershing Hotel drummer Vernell Fournier joined this trio in 1958 and Mr. Jamal made a live album for Argo Records entitled But Not For Me. The resulting hit single and album, that also included 'Poinciana' — his rendition could be considered his signature. This album remained on the Ten Best-selling charts for 108 weeks — unprecedented then for a jazz album. This financial success enabled Mr. Jamal to realize a dream, and he opened a restaurant/club, The Alhambra, in Chicago. Here the Trio was able to perform while limiting their touring schedule and Mr. Jamal was able to do record production and community work.