When Miles Davis Burned

Revisiting Miles' most exciting album

Welcome music lovers again to ‘Listening Sessions.’

About a year ago, I wrote some reflections on nearing a quarter-century of being a jazz collector. In the piece, I noted that Miles Davis’ Milestones was one of the very first jazz recordings that I bought. Recently, I re-listened to the album after not playing it for a very, very long time. That plus some very interesting chatter on Twitter inspired me to put some thoughts down in the below essay on why Milestones represents a very special place in Miles’ recorded legacy. I hope you enjoy it.

Later this month, I will be writing some thoughts on a great soul album from 1973 with multiple connections to Bill Withers that recently appeared on streaming services and then at the end of June, there will be an essay on Marty Robbins and his songs of the American cowboy.

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Jazz in the second half of the fifties belonged to Miles Davis. Yes, there was also Sonny—both Rollins and Stitt, Ellington at Newport, the Modern Jazz Quartet, Moanin’, Mingus, Time Out, Horace Silver, Ella and her songbooks, Ahmad Jamal and Ornette Coleman ultimately showing The Shape of Jazz to Come. Yet, Davis still defines the age. The age of cool, the age of hip, the age of aloofness; if Julian “Cannonball” Adderley’s maxim that “hipness is not a state of mind. It’s a fact of life” is taken as gospel, Davis in the late fifties was its’ leading apostle. Both the man and the music.

His performance at the 1955 Newport Jazz Festival with an all-star band was the culmination of his resurrection from heroin addiction and set a chain of events in motion that saw him move from the indie jazz label Prestige Records to one of the era’s esteemed major labels, Columbia Records. It was George Avakian, a visionary record producer and executive, who signed Davis and who also crafted his first two releases on Columbia: ’Round About Midnight, featuring his classic quintet of John Coltrane, Red Garland, Paul Chambers and “Philly” Joe Jones, and Miles Ahead, an orchestral recording with arranger and conductor Gil Evans, with whom Davis worked with for his seminal Birth of the Cool recordings in 1949 and 1950 and who was a major force in Davis’ music and life.

What distinguishes these two recordings, both released in 1957, beyond the supreme quality of their contents and their endurance as touchstones of the early LP era, is the deliberate care and calculation that went into their creation. ’Round About Midnight, which Davis began recording while still under contract with Prestige, is programmed as a musical palindrome. Side one’s modern jazz ballad, classic bebop line and standard leads to side two’s standard, classic bebop line and modern jazz ballad. The unforgettable fanfare by Davis on open horn after his theme statement on ‘’Round Midnight’ leading into Coltrane’s solo is a declaration that Miles Davis had arrived and was leading the charge of the jazz mainstream, or to borrow the title of his follow-up album, he was Miles Ahead (the title that Avakian came up with before Davis and Gil Evans had recorded even a bar of music) of his contemporaries.

The feeling that Davis and, by extension, Columbia Records were leading the way forward remained ever present in subsequent albums released in the late fifties into 1960: Porgy and Bess, a sumptuous interpretation of portions of Gershwin’s opera (my favourite Davis album and of all time, too), Sketches of Spain, an even-more daring fusion of Spanish classical music and the jazz big-band idiom and dear, sacred Kind of Blue, all mysterious modalism and bohemian blues (not to mention the most famous jazz album period!). Then there’s Milestones, recorded and released in 1958. Its’ existence seems almost miraculous, if only that it exists amidst a series of albums that prioritize space, control, mood, balladry and precision and Milestones offers little of any of these qualities. Instead, it cooks, races, thrills, burns. Oh my, does it burn!

By the time of the first recording session on February 4, 1958 at Columbia’s legendary 30th Street Studios, David had fired and rehired Coltrane and Jones (both were let go due to issues related to drug use), added Cannonball Adderley and turned his first great quintet into a fearsome sextet—an aggregation that lasted only a few months and whose recorded legacy consists of just Milestones.

The best jazz from the late fifties has an attitude. The declarative lines of such pieces as Coltrane’s ‘Blue Train,’ Bobby Timmons’ ‘Moanin’,’ Charles Mingus’ ‘Nostalgia in Times Square,’ Jackie McLean’s ‘Hip Strut,’ and Sonny Clark’s ‘Cool Struttin’’ suggested a new aesthetic direction for the music, innovations percolating partly because of the freedom afforded by the long-playing, 12-inch album (so long the time restrictions of the 78 and the ten-inch album), the maturation of the hard bop movement—jazz inflected with gospel and blues hues—and a explosion of jazz talent—heirs to the bebop explosion of Dizzy Gillespie, Charlie Parker and others. Milestones is the sound of these possibilities played by six virtuosi.

“Milestones is the definitive jazz album. If you want to know that jazz is, listen to that album. It embodies the openness of everyone who plays jazz.” - Tony Williams

Drop the needle or press play on Milestones and immediately plunge in. Davis and band dispatch the main theme of Jackie McLean’s ‘Dr. Jackle’ in an efficient 18 seconds before Davis is off on a fleet-footed solo that even at the torrid tempo that Jones maintains, utilizes spaces and pauses for dramatic impact. The recurring use of one of his patented licks (first heard about 55 seconds in) foreshadows the aggressiveness that would characterize much of his work in the sixties. Yet here, even in the sections of his solo with long, rapid lines, Davis’ tone: round, rich and robust, is the focus of attention. No matter how fast the tempo, Davis will not be rushed when he doesn’t want to be rushed. He’ll take his time.

It’s a profound contrast to his partners in the front line. Once Davis completes his improvisation, Adderley and Coltrane take over for what is not so much a duel as it is a conversation straight out a Preston Sturges motion picture—the cadence of the dialogue relentless, the rhythm staccato, Adderley and Coltrane each beginning a phrase as the other is completing his. Sullivan’s Travels, jazz style. The transitions are so seamless that it becomes more and more challenging to know who is soloing at any exact moment. Both have limited time but so much to say. Chambers’ bowed bass solo keeps the temperature red hot as does a brief return by Davis at full gallop leading to a brief drum break by Jones before a swift return of McLean’s bebop theme.

If ‘Dr. Jackle’ looks back, ‘Sid’s Ahead’ is pointed tentatively forward. It's a laid-back blues previously recorded by Davis as ‘Weirdo’ that also bears more than a passing resemblance to ‘Walkin’,’ a line that Davis memorably put on wax in 1954. It also foreshadows Kind of Blue’s ‘Freddie Freeloader,’ especially during Davis’ solo. His considered approach, prioritizing an economy of line, signified an approach to the trumpet that deemphasized the pyrotechnics of Gillespie and Clifford Brown in favour of a lyricism that others such as Chet Baker, Kenny Dorham, Donald Byrd and Art Farmer were also exploring. Davis’ work here is the most compelling aspect of ‘Sid’s Ahead,’ an otherwise somewhat meandering performance uncharacteristic of his concept at the time.

There is a pulse that runs throughout Milestones that is built upon the drums of “Philly” Joe Jones, named as such both in recognition of his hometown (Philadelphia) and to distinguish himself from Jo Jones, the legendary drummer in Count Basie’s “first testament” band. Jones was a dancer on the kit, employing a light touch to conjure rhythms seemingly on the fly, moving around the drums with the grace that Sammy Davis Jr. or the Nicholas Brothers brought to tap dancing. Even at breakneck tempos, Jones maintained an unflappable sense of swing.

Hear him step in time on John Lewis’ ‘Two Bass Hit,’ executing a thrilling pas de deux with Davis, and Adderley and Coltrane answering in unison. Jones propels both saxophonists to super-charged solos that careen through the changes. Near the end of their improvisations, Jones and Red Garland lock into a rhythmic figure, the drummer firing off snare bombs in unison with a Garland chordal pattern without missing a beat and hardly breaking a sweat, fully integrating it into the bullet-train momentum of the recording. Jones makes it all look so easy. It’s worth noting that when Davis’ band played ‘Two Bass Hit’ at the 1958 Newport Jazz Festival after Jones left the sextet for good, his replacement, Jimmy Cobb, gamefully tries to replicate Jones’ breaks but seems to be mostly hanging on for dear life in the process.

Jones’ light bounce also allows each burst of the theme of the title track to land with authority, to swing with supreme hipness. The backbeat, kept mainly by Jones on the rim of the snare, provides the space for the solos by Adderley, Davis and Coltrane to brim with affirmation in the A section and modulate to an ethereal lyricism in the B section.

Here is where Milestones’ gaze is most firmly fixed on the future—not only in terms of how the harmonically static foundation of the tune presages Kind of Blue’s modalism but also in its improvisations—impeccably conceived statements; self-contained, two-chorus works of art.

Throughout the first four tracks of Milestones, Red Garland’s piano is more of an idea than something felt (in fact, on ‘Sid’s Ahead,’ it’s Davis on piano, taking over for Garland after he left the studio in anger over Davis’ repeated dictates on how he should play). ‘Billy Boy’ is a feature for Garland, Chambers and Jones playing pianist Ahmad Jamal’s arrangement of the old folk song. Jamal was a huge influence on the direction Davis’ music took in the fifties, in terms of the use of space in his recordings, his choice of repertoire as well as in Garland’s comping and soloing. The use of repeated riffs and interludes serving as signposts for the tune’s improvisations and the contrast of vigorous chording and cocktail-ish single-note lines in Garland’s solo both point firmly in the direction of Jamal as well as that if, as previously noted, Jones’ drums were the kinetic source in Davis’ first great quintet, the triumvirate of him with Garland and Chambers gave the group’s sound its identity: bright and optimistic, providing a wide latitude for soloists as disparate as Davis, Coltrane and Adderley to express their individualism. In their way, they played jazz in Cinemascope.

This feeling pervades Milestones’ closer: a celebrated rendition of Thelonious Monk’s ‘Straight, No Chaser,’ the only track on the album in which each of group’s principal soloists improvises. After Adderley and Coltrane’s grooving theme statement, Adderley, Davis, Coltrane and Garland solo. Adderley is extraordinarily ebullient, Davis is sparse and methodical and slips in a sprightly 'When the Saints Go Marching In’ quote, Coltrane is exploratory and Garland is graciously swinging with a famous quote (about seven-and-a-half minutes into the track) of Davis’ solo from Charlie Parker's landmark recording of ‘Now’s the Time’ from 1945. Each statement contrasts with the others, each a unique impression of the blues form.

Collectively, they remind us that of all musical genres, jazz is unrivaled in its allowance for individual expression—in a word, freedom—within the group dynamic. That when the music strives for this ideal, jazz is at its most vital: a living, breathing, evolving music.

The arc of Miles Davis’ career is one of constant evolution, seized with the notion of harnessing the future in the present while letting the past remain past, unbothered with leaving those behind for whom the music no longer resonated. Rare is the Davis fan who loves all his music but rarer is the musician who contributed as much to jazz’s canon over the course of the 20th century. Milestones is certainly part of that. It may well be the most exciting album he ever made. Dig that!