On a February afternoon in 1958, at the end of a session lasting four and a half hours in a deconsecrated Armenian Orthodox church on East 30th Street in New York City, a sextet led by the trumpeter Miles Davis recorded two takes of a newly composed tune called ‘Milestones’. Here was the first fully realised evidence that Davis was pursuing an interest in moving the basis of his improvisations away from the harmonic obstacle course of bebop – the form of modern jazz identified with his mentor, the saxophonist Charlie Parker – and towards less enclosed structures based not on repeated cycles of chord sequences but on scales just about as ancient as music itself.

The first take of the tune would have passed muster on most occasions but in this case turned out to be just a run-through, a test of pacing and trajectory. The second attempt, lasting just under six minutes, is as exquisite in its balance of calculation and spontaneity as Louis Armstrong’s ‘West End Blues’ or Coleman Hawkins’s ‘Body and Soul’, two other recordings that, in 1928 and 1939 respectively, gave jazz a shove into its future. Fore-and-aft iterations of Davis’s simple but indelible four-note melody enclose improvised solos by each of the sextet’s three horn players. First comes the alto saxophonist Cannonball Adderley, whose habit was to turn the blues into a shout of optimism as endlessly inventive and joyously unpredictable as a blackbird’s song. Then Davis arrives to change the weather, his phrases shaped with poised restraint and extruded with a feline elegance. Third up is John Coltrane, whose tenor saxophone had acquired a slate-grey tone that compelled attention as much as the convoluted lines with which he seemed to be mapping the furthest reaches of harmony. The three solos, so disparate in emotional temper, were linked as if by an intuitive thread, something more than mere composed source material. Unusually for the era, the track was faded out at its conclusion – not unresolved, but heading into infinity.

Perfection? Well, almost. Davis’s momentary fluffed note on the bridge of the closing theme statement is the fumbled knot in an otherwise flawless Persian rug, left there by its weaver to acknowledge that perfection belongs to Allah. There’s also the matter of its tempo. The take begins at a briskly swinging but unhurried sixty-four bars per minute. By the time it finishes, it has slowed naturally and almost imperceptibly to sixty bars per minute, a reversal of the common tendency to speed up and a further sign that human beings are at work, responding to each other rather than to a conductor or a metronome.

The tune was released later that year on an album named after the track, its cover featuring an early example in jazz of carefully styled iconography. In a picture taken by Dennis Stock, a celebrated Magnum photographer, Davis perches on a 1950s modern chair, possibly Swedish, a cigarette in one hand and his trumpet in the other, wearing a green button-down shirt and dark slacks, staring down the camera, his expression impassive and uningratiating – a new definition of cool.

A year later, in the same studio, Davis made a more extended bid for perfection by recording Kind of Blue, destined to become the biggest selling album in the history of jazz and still, sixty-five years later, the one most likely to be in the collections of people who are not otherwise committed fans of the genre. In the album’s five tracks, Davis pursued the thinking behind ‘Milestones’ within an ambience modified by the presence of Bill Evans, a young white pianist who combined advanced jazz skills with an interest in Ravel, Debussy and other classical composers. Thanks to Evans’s influence, Kind of Blue’s special allure resides in its carefully cultivated air of introspection. 

In turning jazz from hot to cool, infusing it with an air of civilised melancholy, Davis had found a way to renew the appeal of a music that, through its move from the dance hall to the concert platform, was forfeiting the broad popular appeal it had acquired in the 1920s and exploited during the subsequent swing era. What Kenneth Tynan called the ‘little boy lost’ sound of Davis’s trumpet brought him fame at the end of the 1950s and the start of the 1960s, when Kind of Blue and an orchestral album of similar temperament titled Sketches of Spain became as much a part of the furnishings of sophisticated homes as a cocktail bar or an African mask on the wall. 

Nothing comes more naturally, however, than a desire to halt artists at a certain point in their development, and many of his admirers wanted Davis to exist forever in the zone defined by ‘Milestones’ and Kind of Blue. Like his 20th-century near-contemporaries Pablo Picasso and Bob Dylan, he provoked enduring exasperation, even wrath, by refusing to stand still. (‘I have to change,’ he once said. ‘It’s like a curse.’) He moved on, engaging with younger musicians and newer styles, leaving behind the ‘empire of cool’ to which James Kaplan refers in the subtitle of 3 Shades of Blue.

Kaplan, whose previous subjects include Frank Sinatra and Irving Berlin, is not the first writer, or even the second or third, to build a book around Kind of Blue. Instead of concentrating on Davis, or on the album and its lasting influence, he constructs a triple portrait of Davis, Coltrane and Evans before and during the years in which they worked together, then follows them through their subsequent careers. As with his two-volume study of Sinatra, he makes frequent and scrupulously attributed use of the works of those who went before, particularly the biographers of Davis (notably John Szwed and Ian Carr), Coltrane (Lewis Porter and Ben Ratliff) and Evans (Peter Pettinger). To these sources, and dozens of others, he brings a handful of his own interviews, including one with Davis (for Vanity Fair) from 1989, when the author was a young journalist who, as he admits, didn’t know a lot about jazz.

While his enthusiasm and his diligence are not in question, Kaplan has little of interest to say about the music itself, and what he does say is sometimes plain wrong. It’s hard to imagine anyone actually listening to Ornette Coleman’s ‘free jazz’ and concluding that, whatever else had been jettisoned, it was characterised by the absence of a ‘recognizable rhythmic pulse’. Occasionally, he describes events through the eyes of others who, like himself, were not present at the time, rather than trusting his own powers of imaginative reconstruction and interpretation. While he is undoubtedly sympathetic towards his protagonists, his lengthy descriptions of the drug addiction that shaped their lives, and their markedly different ways of dealing with it, can seem both obsessive and superficial. He is incurious, for instance, about the supply networks underlying the plague of heroin use among jazz musicians of the postwar decades.

As in his study of Sinatra, however, the occasional fresh-minted coinage shines through. ‘Like Charlie Parker, like Sonny Rollins and Dexter Gordon,’ he writes, ‘Adderley was a jazz magpie, fond of inserting bits and scraps of familiar melodies into his solos; Coltrane seemed to quote only from God.’ There’s a good extended riff on how improvisation based on modes reflected the uncertainty of the times, and another on the Beatles’ negative impact on the jazz economy, shifting the focal point of hipness to long-haired boys with guitars. 

If Kaplan has given us a conventionally readable portrait of jazz musicians, The Notebooks of Sonny Rollins offers an unstructured sequence of views from inside the mind of one of jazz’s most remarkable practitioners, a tenor saxophonist noted not just for his virtuosity and creative imagination but also for his lifelong self-questioning. Now aged ninety-three and recently the subject of a thorough biography (Aidan Levy’s Saxophone Colossus), Rollins is pretty much the last surviving figure from the Mount Rushmore of jazz’s first century, a man who played with Parker and Davis and rid himself of a heroin habit in the 1950s before emerging as a master of thematic and free-associative improvisation, with a special fondness for wandering out of a club into the street while still playing. 

The extracts from his notebooks published here, some of them from the period between 1959 and 1961, in which he disappeared to reassess his life and music, include thoughts on saxophone embouchure and fingering, the shortcomings of nightclub owners and the correct posture for shaving. There are snatches of dreams, lists of favourite films and records, haiku-like fragments of advice (‘This Golden Rule/We must obey/Always end a phrase of playing/In its perfected corrected way’), a reminder to bathe and wash socks before setting off for a tour of Europe, indications of his interest in Eastern philosophy, and a note from 1963 on the importance of his quartet beginning a set together in the dressing room, thereby arriving on stage already in a state of performance. And a final instruction: ‘No matter how you feel, get up, dress up, and show up.’