In the spring of 1955, Miles Davis assembled a quintet. He was twenty-eight years old, recently recovered from a heroin addiction that had nearly ended his career, and he was playing better than he ever had. The group he put together would record some of the most enduring sessions in the jazz catalogue and establish the small group as the primary vehicle for jazz expression in the decade that followed.

The lineup: John Coltrane on tenor saxophone, Red Garland on piano, Paul Chambers on bass, and Philly Joe Jones on drums.

Why This Group

Miles didn’t build this quintet for comfort. He built it for friction.

Coltrane was the most obvious source of it. His approach to improvisation was the polar opposite of Miles’s — where Miles left space, Coltrane filled it; where Miles implied, Coltrane stated and restated; where Miles ended phrases early and let them hang, Coltrane extended them until they resolved on their own terms. Put the two of them on a bandstand and the contrast was structural. The music had an argument built into it.

Red Garland’s piano playing was something else entirely. His right hand floated over everything like it had somewhere better to be and wasn’t in a hurry to get there. He voiced chords in a particular way — sparse, with a lilt in the rhythm — that gave the horn players unusual freedom to ignore the harmony when they needed to.

Chambers and Jones on the rhythm section were young and explosive. Philly Joe Jones played with a crispness and a forward momentum that pushed the soloists. Chambers had a tone on the bass that could fill a room.

The Prestige Sessions

In October 1956, Miles booked two marathon days at Van Gelder’s studio in Hackensack to record enough material to fulfill his Prestige contract before moving to Columbia. The sessions produced four albums: Cookin’, Relaxin’, Workin’, and Steamin’.

They recorded the way a working band records: no excessive preparation, minimal retakes, a set of tunes they’d been playing live for months. The results sound like what they are — a band at the peak of its live chemistry, captured in a recording studio by one of the best engineers in the business.

Cookin’ opens with “My Funny Valentine,” Miles playing the ballad at a tempo so slow it sounds like he might stop altogether. He doesn’t. He holds the melody at arm’s length, bends it, circles it, treats it as a question he’s not sure has an answer. Coltrane’s solo on the same track is dense, fast, certain. The contrast is not accidental.

What Garland Brought

The Prestige sessions are sometimes described as primarily showcases for Miles and Coltrane. That undersells the piano. Red Garland’s comping on these records is one of the underrated achievements of hard bop rhythm section playing.

He had a habit of playing repeated block chords in his right hand — a rhythmic device called “shout choruses” in big band arranging, miniaturized for a trio — that created pockets of harmonic stability underneath the soloists. Miles loved it, then reportedly grew frustrated with it. The tension in that relationship (Garland was fired and rehired multiple times) gave the sessions an edge that is audible in the recordings.

Coltrane Leaves

By 1957 Coltrane was beginning to move toward something Miles couldn’t quite follow. He briefly left the quintet to work with Thelonious Monk, an experience that transformed his harmonic language. When he returned, he was playing with even greater density and searching quality.

The two men had less than two years of recording together before Kind of Blue in 1959 completed the formal argument that had been running through the quintet. That album used a different pianist — Bill Evans — and a different formal approach — modal rather than changes-based — and produced something neither of them could have made without the friction of the quintet years behind them.

Coltrane played on Kind of Blue and then left to lead his own groups. Miles assembled different musicians and moved in a different direction. The first great quintet existed for less than five years. The music it made has not dated.

What It Left

The Prestige sessions didn’t sell particularly well at the time. They have since been reissued continuously for seven decades, which is a form of critical verdict more reliable than any review.

What those albums documented was the process by which two very different musicians learned to share a bandstand. Coltrane played in dense, overlapping waves. Miles answered with space. Taken together they described the full range of what a jazz horn could do — and neither of them was close to finished.