Keepnews booked several sessions in October 1956 at his favorite Reeves Sound Studios in New York City. Dr Free-Zee is an interesting track on it, for its use of timpani. Roach continued to lead his own bands, and the same month he recorded with Monk he also released the album Max Roach + 4. But in June of 1956 Brown tragically died in a car accident that also killed the band’s pianist Richie Powell. During the previous two years he co-led with Clifford Brown one of the most successful jazz combos of its time, commercially and artistically. By 1956 he was a sought-after session drummer, that year alone playing on records by Sonny Rollins, Sonny Stitt, Johnny Griffin, Thad Jones and Al Cohn. Aside from performing as a sideman on numerous recordings around that time with Kenny Burrell, Milt Jackson and Phineas Newborn Jr among others, he led his own small big band with whom he released a few albums, including The Pendulum at Falcon’s Lair. Oscar Pettiford was a natural choice for a bass player, having played with Monk on his two previous Riverside recordings. The two albums, like the Prestige albums that preceded them, flopped.
Monk recorded two trio albums of well-known jazz tunes, the first with material from the Duke Ellington songbook, the second with show tune standards. Thinking that Monk’s originals are too bizarre for the jazz audience at large, Keepnews pushed Monk to play familiar pieces with the hope that this will increase his record sales.
Weinstock had more commercially successful artists to focus on, including Miles Davis and The Modern Jazz Quartet, and did not shed a tear when Monk left his label. The genius of modern jazz was an esteemed musician to all who knew him, but his albums did not sell. Weinstock was not upset over losing Monk. He paid Bob Weinstock, president of Prestige records that had a contract with Monk, a mere $108 and got Monk off that contract. When producer Orrin Keepnews signed Thelonious Monk to his newly formed Riverside label in 1955, he had to come up with a plan.