The Miles Davis Quintet, active from 1955-1957, is hailed as a standout bebop ensemble of the 1950s, showcasing the contrasting yet complementary styles of Davis and Coltrane. Davis, known for his cool-toned trumpet, and Coltrane, with his passionate tenor saxophone, created a dynamic front line within the group. The quintet, featuring a solid rhythm section and pianist Red Garland, produced several acclaimed albums during its brief existence, including memorable recordings on Prestige and Columbia. Although officially disbanding in 1957, the quintet briefly reunited in 1958 for the recording of "Milestones" before Coltrane departed to form his own group in 1960.

The Miles Davis Quintet's legacy lies in its innovative and cohesive sound, showcasing the unique musical personalities of its members. Davis' economical playing style, influenced by cool jazz, contrasted with Coltrane's more expansive solos, yet the group maintained a unified and engaging sound throughout its recordings. The quintet's impact extended beyond its dissolution, with Davis and Coltrane continuing to collaborate on influential projects such as the modal classic "Kind of Blue" in 1959. Despite the group's relatively short existence, the Miles Davis Quintet remains a pivotal ensemble in the history of bebop and jazz music.