December 3, 2019

Miles Davis and the First Quintet



ON THE EVENING OF July 17th, 1955, Columbia Records producer George Avakian realized that he had a problem. He had just witnessed Miles Davis’ stellar performance at the Newport Jazz Festival and knew that if he did not sign the trumpeter to his label right away, another label would. Compounding the problem was the fact that Davis was already signed to an exclusive contract on yet another label.

Davis was signed to Prestige Records through 1957 — two more years in which Columbia would not have a chance at the rising star. Davis himself wanted to jump ship to Columbia, but Prestige president Bob Weinstock knew what he had and was not about to let Davis go.

On Tuesday July 19, Miles met with his lawyer as well as George Avakian and Bob Weinstock and worked out a deal that may be unique in recording history. The basics were that Miles Davis would fulfill his Prestige contract, but also be able to record for Columbia at the same time. Prestige would get several “new” LPs that it could release into the future — benefiting from Columbia’s publicity and Davis’ growing reputation – while Columbia (who would get Miles before the competition) could not release its recordings until after Miles fulfilled the Prestige contract.

There was one more catch. Davis had to form his own band and keep it together long enough to complete both the Prestige contract and tour in support of his first Columbia albums. Up to that point, Davis did not have a regular group, but would assemble one-off groups for club dates or play in front of house bands at the various clubs he appeared at.

Miles Davis - The Legendary Prestige Quintet Sessions collector's book

Miles Davis – The Legendary Prestige Quintet Sessions collector’s book

Assembling a band turned out to be a bit more difficult than Miles initially anticipated. Pianist Red Garland was easy — Garland had recorded with and played club dates with Davis regularly in recent months. Likewise bassist Paul Chambers and drummer Philly Joe Jones — having worked previously with Garland as a trio, the three made up the perfect rhythm section to back Davis and his saxophonist. For that roll, Davis had just one choice: an up-and-coming tenor player who was beginning to get a lot of attention – 25-year-old Sonny Rollins.

Rollins had recorded several times with Davis to that point and Davis counted those recordings as among his best to date. But Rollins turned out to be unavailable, as was Davis’ second choice; alto saxophonist Julian “Cannonball” Adderley. Miles briefly re-
hearsed the band with saxophonist John Gilmore (who later worked extensively with Sun Ra), but Gilmore was already heading toward a free-jazz approach that Davis did not feel fit with his own style.


It was drummer Philly Joe Jones who suggested John Coltrane for the tenor sax position. Upon arrival, it quickly became clear that Coltrane knew Davis’ repertoire and would basically be up to speed almost instantly. With the band now assembled, Miles Davis would record five albums for Prestige over just three recording sessions that would define both Davis’ style as well as the entire modern jazz form during the 1950s and early ‘60s.

Originally scattered throughout the five albums (titled Miles – The New Miles Davis QuintetCookin’, Relaxin’, Workin’ and Steamin’), the three sessions have been collected together in Miles Davis – The Legendary Prestige Quintet Sessions (Craft Recordings). This six-LP box set presents all the recordings in chronological order and features a bonus LP of early, previously unreleased broadcast performances including an early appearance on Steve Allen’s Tonight Show.

The first track, “Stable-mates” is among the strongest from the sessions and was something of a hit when it was released, while “It Never Entered My Mind” remains one of Davis’ most poignant ballad performances. While not in the modal form Davis would adopt for the famous Kind of Blue LP, this tune shows Miles inching toward that style with both grace and deep-felt emotion. Balancing out the quieter ballads were such Bop favorites as “Half Nelson” and “Woody N’ You.”

Altogether, the 32 tracks recorded for Prestige would define Davis, Coltrane and company and prove very hard to top. Columbia would ultimately only release one LP from its sessions done during the Prestige years. Round About Midnight would be the last album of this first great Miles quintet, before Columbia would record several Miles LPs with large orchestral settings with arranger Gil Evans. Other albums would re-assemble the group with other players added (notably Cannonball Adderley for Milestones) as well as major group changes for Kind of Blue.

For this new six-LP set the mastering is truly stunning and the records are spectacularly packaged in a 1950s-style 78rpm album book, complete with a twenty page hardcover linen-wrapped portfolio-style book of rare photos and extensive liner notes by noted jazz historian Bob Blumenthal.

While Miles Davis, John Coltrane, Red Garland, Paul Chambers and Philly Joe Jones would all go on to historic careers, Miles Davis – The Legendary Prestige Quintet Sessions is where that history began.

Armand Lewis buys and sells rare Jazz LPs. He can be reached at


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