Waldron played on numerous sessions for Prestige Records from 1956 to 1958, as he was the house pianist with the label, a position he acquired after being introduced to Prestige by saxophonist Jackie McLean. Waldron appeared on several McLean-led recordings, and was praised by critic John S. Wilson for these performances as being "a consistently interesting and inventive pianist, who apparently can create fresh and provocative ideas even in the midst of a shrilling bedlam". Other leaders he worked under at Prestige included Gene Ammons, Kenny Burrell, John Coltrane, and Phil Woods. Waldron often used his own arrangements and compositions for the Prestige sessions, of which his most famous, "Soul Eyes", written for Coltrane, became a widely recorded jazz standard following its initial appearance on the 1957 album "Interplay for 2 Trumpets and 2 Tenors". He composed at night at home in St. Albans between all-day recording sessions, and in a car traveling to and from the studio in Hackensack. Waldron estimated that he composed more than 400 pieces of music during his time with Prestige.