"In the summer of 1955, after Davis performed at the Newport Jazz Festival, he was approached by Columbia Records executive George Avakian, who offered him a contract if he could form a regular band. Davis assembled his first regular quintet to meet a commitment at the Café Bohemia in July with Sonny Rollins on tenor saxophone, Red Garland on piano, Paul Chambers on bass, and Philly Joe Jones on drums. By the autumn, Rollins had left to deal with his heroin addiction, and later in the year joined the hard bop quintet led by Clifford Brown and Max Roach.
At the recommendation of drummer Jones, Davis replaced Rollins with John Coltrane, beginning a partnership that would last five years and finalizing the Quintet's first line-up. Expanded to a sextet with the addition of Cannonball Adderley on alto saxophone in 1958, the First Great Quintet was one of the definitive hard bop groups along with the Brown-Roach Quintet and the Jazz Messengers, recording the Columbia albums Round About Midnight, Milestones, and the marathon sessions for Prestige Records resulting in four albums collected on The Legendary Prestige Quintet Sessions."