The Records of Miles Davis' Sidemen, Part I: The First Great Quintet

For the concluding half of this two-part feature, read "The Records of Miles Davis' Sidemen Part II: The Second Quintet."

In 1955, after years as a sideman and apprentice to the bebop masters—not to mention a long, dark period of drug addiction and dependence—Miles Davis was about to conquer the world.

But world conquest takes a while. Davis first needed to get his act together and establish his name as a leader. He already had a recording contract with Prestige Records—one of the few labels willing to risk signing him despite his reputation as an addict—and he recorded with bands assembled ad hoc for the various sessions, but he didn’t have a regular working group. For a short period, he traveled with drummer Philly Joe Jones to different cities and played pickup gigs with local musicians, which, he notes in his autobiography, was frustrating.

But that was about to change.

That summer, July 1955, Davis played two songs as part of an all-star lineup at the Newport Jazz Festival. The set was a tribute to his mentor, Charlie Parker, who died earlier that year. Davis played on Parker’s classic, "Now’s the Time," and the Thelonious Monk tune, "‘Round Midnight."

It was his breakout moment.

"I played it with a mute and everybody went crazy," Davis says in his autobiography about his solo on "‘Round Midnight." "It was something. I got a long standing ovation. When I got off the bandstand, everybody was looking at me like I was a king or something—people were running up to me offering me record deals."

John Coltrane, Cannonball Adderley, Miles Davis, and Bill Evans

One of those people was George Avakian from Columbia Records. Davis was interested—especially when he found out how much money Columbia was offering—but he still had a one-year/five-and-a-half album commitment to Prestige. To honor that obligation, Davis put together a group, which in addition to himself and Jones, included John Coltrane on tenor sax, Red Garland on piano, and Paul Chambers on bass. He brought that group into the studio for two marathon sessions—first on May 11 and then again on October 26, 1956—and that resulted in four epic releases: Cookin’, Relaxin’, Steamin’, and Workin’ with the Miles Davis Quintet.

That lineup would later be known as Davis’ first great quintet, and with those sessions out of the way, Davis was not only done with Prestige, but was on his way to becoming a major force in jazz.

His next releases were on Columbia and included ‘Round About Midnight, Milestones, and Kind of Blue. But that first, classic lineup was already starting to morph into something else. Alto player Cannonball Adderley was added to the group for Milestones—making it a sextet—and on Kind of Blue, which many consider Davis’ era-defining statement, Bill Evans replaced Garland and Jimmy Cobb took over for Jones (Wynton Kelly also plays on one track and would soon replace Evans).

By decade’s end, Davis’ first great group was no more. Chambers stayed the longest and didn’t leave until 1963, but by then, the others were already long gone. As leaders, Coltrane and Evans became bonafide legends, Adderley scored Top 40 hits on the singles’ charts, and Garland had a long and distinguished recording career. Chambers and Jones only led a handful of sessions as leaders, but worked steadily as sidemen and appear on hundreds of albums. The profiles below focus on Coltrane, Garland, Adderley, and Evans’ output as leaders.

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John Coltrane

John Coltrane—who went on to become a cultural icon in his own right—joined Davis’ group in 1956. He was somewhat unknown, despite about 10 years in-and-out of various ensembles, and not yet the powerhouse he would become, but Coltrane already had something. That something—his intensity, adventurousness, excitement, and edge—was the missing piece that transformed Davis’ group.

But Coltrane didn’t come without baggage. He was addicted to heroin, which—in addition to the havoc it wreaked on his personal life—made him unreliable and disheveled, and, much to Davis’ chagrin, spaced out and drowsy on stage. Davis fired him twice, and it was during his second hiatus, while working with Thelonious Monk, that Coltrane kicked his habit and put his life together.

Coltrane rejoined Davis’ group in 1957, but now—drug-free and making up for lost time—he had too much to say. With Davis’ encouragement, he signed a deal with Atlantic Records, and released a string of albums that would redefine jazz.

John Coltrane - "On Green Dolphin Street" (Live, 1960)

Coltrane released seven albums on Atlantic. The first was Giant Steps, which—not to overstate the point—rivaled Charlie Parker’s output in terms of influence. Giant Steps was recorded two weeks after the final sessions for Davis’ Kind of Blue, and although the harmonic language of Kind of Blue—modal, spacious, somewhat open-ended—would inform most of Coltrane’s ‘60s output, Giant Steps is nothing like that. Giant Steps, especially the title track, relies on rigid, complex structures (known by jazz nerds as “Coltrane Changes”—chord changes moving in major thirds) and overwhelms your senses with an abundance of harmonic information. He also made his debut on soprano sax with the 1961 release, My Favorite Things.

Impulse! Records bought Coltrane’s contract in 1961, and that’s where he remained until his death in 1967. His first albums on Impulse!, especially Impressions and Crescent, find him exploring modal concepts, pushing traditional frameworks, and experimenting with less chordal accompaniment from the piano. That period culminated with his magnum opus, A Love Supreme, released in 1965.

After that, Coltrane took it outside. He obliterated traditional forms, harmony, melody, and experimented with extended techniques like overblowing and multi-phonics. His albums from this period were too avant-garde for jazz traditionalists, but made a major impact—especially on younger, rock audiences already enamored with free jazz radicals like Albert Ayler—and feature standout sessions like Interstellar Space, his duets with drummer Rashied Ali.

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Red Garland

William “Red” Garland joined Davis’ group in 1955. Garland had once been an amateur boxer and even lost a fight to Sugar Ray Robinson, which for Davis, a lifelong boxing enthusiast, was a big deal.

But Garland’s thing was piano, not fighting, and his light touch, à la Ahmad Jamal, was the reason Davis wanted him in his band. “Red knew I liked Ahmad Jamal,” Davis says in his autobiography. “That was the type of piano player I was looking for, and so I asked him to give me Ahmad’s sound, because Red played his best when he played like that.”

Garland’s tenure with Davis ended during the Milestones sessions in 1958. Garland walked out mid-session—Davis even plays piano on “Sid’s Ahead”—but following that incident, Davis opted not to bring him back. Davis’ reasons, however, were musical—he was moving in a different direction—and not because of bad blood between him and Garland.

Red Garland - "Halleloo-Y'-All"

Garland cut a number of albums for Prestige while still working with Davis, which often featured Paul Chambers on bass and Art Taylor on drums, and he continued with the label until 1960. In addition to his trio recordings, as well as numerous sessions as a sideman, he also recorded albums like Manteca, featuring Ray Barretto on conga, and Halleloo-Y’-All, on which he plays organ.

Garland continued playing and recording—although he was semi-retired for a few years in the early ‘70s—and even reunited with Philly Joe Jones on Crossings in 1977, until his death in 1984.

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Cannonball Adderley

Julian “Cannonball” Adderley was a high school band director from Florida. (His nickname, “Cannonball,” is a play on words, derived from “cannibal,” because he often overate.) He moved to New York City in 1955, sat in with bassist Oscar Pettiford at the Café Bohemia—a club Davis often played as well—and caused a stir. As Davis notes in his autobiography, “Everybody knew right away that this big motherfucker was one of the best players around. Even white critics were raving about his playing. All the record labels were running after him. Man, he was hot that quick.”

Adderley joined Davis’ group in 1957 and, with Coltrane’s return later that year, Davis’ first great quintet became a sextet. He stayed in the band through 1959 and appears on Milestones and Kind of Blue.

Cannonball Adderley Quintet - "Jeannine" (Live, 1962)

Following his stint with Davis, Adderley signed with Riverside Records and released a string of albums that, in contrast to Coltrane’s embrace of the avant-garde, moved in a more soulful and ultimately assessable direction. In 1964, when Riverside went out of business, he signed with Capitol Records and his single, “Mercy, Mercy, Mercy,” (written by his then-sideman, Joe Zawinul) was a legitimate hit. It peaked and Number 11 on the Billboard Hot 100 charts in February 1967. According to the New York Times, his mainstream success was anomalous for the times. “Over the years, [Adderley’s] group continued to turn out an unusual number of hits for a jazz group during a period when rock rather than jazz was the hit‐making music. Among these was ‘Work Song,’ ‘Sermonette,’ ‘African Waltz,’ ‘Jive Samba,’ and ‘Mercy, Mercy, Mercy.’”

Adderley continued recording and touring until he suffered a stroke in 1975. He died a few weeks later at the age of 46.

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Bill Evans

Pianist Bill Evans replaced Red Garland after the Milestones sessions. Composer and jazz theorist George Russell recommended him and his style—what Davis characterized as a rhythmically underplayed “quiet fire”—complimented Davis’ new, modal direction.

Evans’ tenure with Davis was brief—he only appears on Kind of Blue and Jazz Track, an album later reissued as 1958 Miles—but his impact, which included introducing Davis to classical composers like Ravel and Rachmaninoff, was significant. He left in 1959 and started recording with his acclaimed trio featuring bassist Scott LaFaro and drummer Paul Motian. It was a creative peak and included the albums Waltz for Debby and Portrait in Jazz, but came to an abrupt end with LaFaro’s death in 1961.

Bill Evans - "My Foolish Heart"

But Evans kept at it. He worked in small groups and as a soloist and continued to record as well. He won his first Grammy—he won seven in total—for his 1963 release, Conversations with Myself, which, unusual for jazz, features three interconnected, overdubbed piano parts. His 1967 release, A Simple Matter of Conviction, is his first in what would become a longterm association with bassist Eddie Gomez and he won another Grammy the next year for his solo release, Alone.

But Evans was plagued by health issues, drug addiction, and other demons, and died in New York in 1980.

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