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1957 was a very productive year for Waldron who, recorded no fewer than nine studio albums with The Prestige All Stars. This included the highly-regarded After Hours, for which the pianist composed all four of the tracks featured. Waldron would go on to compose over 400 pieces in all while at Prestige. He became Billie Holiday's pianist from August 1957, accompanying her on her television appearance for The Sound of Jazz. Following her tragic death at the age of 44, his album Left Alone - released in Holiday's honour - featured a title track for which Billie composed the lyrics. Waldron then teamed up with vocalist Abbey Lincoln and her then-husband, famed jazz drummer and bandleader Max Roach. He remained highly active towards the turn of the decade, forming a group with Eric Dolphy and Booker Little which lasted until Little's premature death in 1961, and recording several more albums as bandleader. He even performed on a number of play-along educational records for the Music Minus One publishing company. In 1963, following a heroin overdose, Waldron suffered a major breakdown which left him unable to play the piano. His work was put on hold for the next three years as he undertook shock therapy to help regain control of his hands, and a year later he began to slowly regain his abilities teaching himself solos from his own records. He began recording again in 1966, having been invited to France by director Marcel Carné to score the 1965 film Three Rooms in Manhattan. Waldron would continue to do soundtrack work for film and television over the next several years, as well as appearing on albums by Ben Webster and Kenny Clarke. He was also by now back into full swing with his own work as bandleader, and recorded the debut albums for two new European jazz labels - Free At Last and Mal Waldron Plays The Blues.

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