Silver's break came in 1950, when his trio backed saxophonist Stan Getz at a club in Hartford: Getz liked Silver's band and recruited them to tour with him. The saxophonist also gave Silver his recording debut, in December 1950, for a quartet album. After about a year, Silver was replaced as pianist in Getz's band and he moved to New York City. There, working as a freelance, he quickly built a reputation, based on his compositions and bluesy playing. He worked for short periods with tenor saxophonists Lester Young and Coleman Hawkins, before meeting altoist Lou Donaldson, with whom he developed his bebop understanding. Donaldson made his first recording on Blue Note Records in 1952, with Silver on piano, Gene Ramey on bass and Art Taylor on drums. Later that year, another Blue Note quartet session was booked for Donaldson, with Art Blakey replacing Taylor, but the saxophonist withdrew and producer–owner Alfred Lion offered Silver the studio time for a trio recording. Most of the tracks recorded at it were Silver originals, and he went on to stay with Blue Note as a leader for the following 28 years.