Between his first recording session in 1944 and his death in 1991, Miles Davis changed the course of music many times. The first of these came with the short-lived lineups he assembled for a New York residency and three studio sessions between January 1949 and March 1950. The nine-piece lineup was unusual – few jazz bands used a French horn – and the gigs attracted little attention. The sessions produced a handful of singles for Capitol Records, later collected as an album called Birth of the Cool – these ensured the band’s shadow would prove longer than all but a handful of its contemporaries.

The recordings were the result of hanging out after hours at arranger Gil Evans’s basement flat. The punchy, brightly coloured Venus de Milo was one of three tracks the group recorded that was composed by saxophonist Gerry Mulligan. The epithet “cool” isn’t entirely helpful, suggesting a prizing of style over substance: this music is never aloof or detached. Rather, this is what you got when you tuned down the frenzy of Charlie Parker and Dizzy Gillespie and allied it to the kind of sophisticated big-band arrangements Duke Ellington pioneered. Davis was a fan – and a part – of both traditions: not for the first time, what he crafted was a fusion of preceding forms that changed what would follow.

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Touring Europe had a profound effect on Davis. In France, he felt respected as an artist without question or caveat: this had never been the case in his racially segregated homeland. Certainly, he was sure he would never have been approached by a movie director during a US nightclub residency and asked to compose music for a film. When Louis Malle made just that offer to Davis in November 1957, Davis accepted the challenge. The soundtrack to Malle’s Ascenseur pour l’Échafaud (Lift to the Scaffold) was recorded in two days in December. The band – a local pick-up group, including expatriate American drummer and bebop pioneer Kenny Clarke – were given little more than some rough ideas Davis had jotted down in his hotel room the night before. On arrival at the studio they found the film’s star, Jeanne Moreau, holding court at a makeshift bar; loops of footage from the film were projected while they improvised, with Davis suggesting that whatever they played be in counterpoint to the images on the screen. It wasn’t the first jazz soundtrack to a film noir, but it’s an exemplar of the form: Davis’s careful, vulnerable, vibrato-less playing – sometimes using his mute, at others gently enhanced with echo – was tailor-made to snake through black-and-white shots of night-time city streets and imply turbulent moods swimming through shadowy rooms and behind inscrutable faces shot in stark closeup.

Davis had already formed and fired the group that would become known as his “first great quintet” (drummer Philly Joe Jones, pianist Bill Evans, bassist Paul Chambers and John Coltrane on saxophone) when, days after returning from Paris, he re-recruited five superb musicians and began working as a sextet. Lineup tweaks were frequent, and by March 1959, the group featured Jimmy Cobb on drums, Wynton Kelly on piano, Chambers, Coltrane and additional saxophonist Cannonball Adderley. Yet for one of two sessions on 3 March, Bill Evans returned to the piano stool, so fundamental did Davis feel his style was to the material the group was about to record. The two March sessions – and another on 22 April, again with Evans taking Kelly’s place – would give the world Kind of Blue, on which Davis and friends once again upended convention and took jazz off on a new expedition. The set texts tell how Kind of Blue broke the mould, with the players rejecting chords as the basis of improvisation and adopting modes. Another way of thinking about it would be to do as Davis seems to have intended: reflect on the album’s title and listen while six master musicians reconfigure the blues for a new era.

Not content with reinventing small-band jazz with the quintet and sextet, Davis was at the same time in the middle of a series of recordings with Gil Evans that bore more similarities to classical orchestral scores than what was generally considered jazz. Sketches of Spain was the third of these releases and is perhaps the most ambitious. Davis had already begun exploring Spanish music when he was introduced to Joaquín Rodrigo’s Concierto de Aranjuez early in 1959. Davis and Evans worked up an arrangement of the second movement for trumpet rather than guitar: its ubiquity as a piece for brass bands today underlines how influential this reading would become. That it showcases some of Davis’s most confident playing is only part of the story: what matters is that he inhabits the character the notes suggest, and, through his trumpet, finds a truth in the music only the greatest artists could ever have located.

5. Yesterdays (Live at the Plugged Nickel)

There was a constant churn of collaborators through the early 60s but, with the recruitment of long-time target Wayne Shorter as the eventual replacement for Coltrane on sax in September 1964, Davis finally had what many have described as the greatest group in jazz history. That appraisal may do the “second great quintet” – Davis, Shorter, bassist Ron Carter, drummer Tony Williams and pianist Herbie Hancock – an injustice: they’re clearly one of the finest bands ever assembled, in any genre of music.

By the end of 1965, the new quintet were more than familiar with their leader’s counter-intuitive mindset, and keen to take him out of the comfort zone of a live repertoire that stuck to standards and ignored the adventurous new material they had been recording. Before a December residency at the Plugged Nickel in Chicago, and behind Davis’s back, Williams – barely out of his teens – suggested to Carter, Shorter and Hancock that from the first note of the first set they should play the opposite of what tradition, convention and their leader’s improvisations implied. The four musicians agreed, and didn’t waver even when, on arrival at the venue, they found out that the shows were being recorded by Columbia. The first night wasn’t taped – Davis was arguing with the label – but seven sets from the next two nights were.

Over the course of these performances, released in full in the mid-1990s as the box set The Complete Live at the Plugged Nickel, you can hear the band as they work out ways to become even greater than the considerable sum of their parts. It’s hard to pick a single moment to represent the combination of genius and madness all five were channelling, but by the third night, when Davis has begun to understand what was going on, the group found a way of combining the outre adventurousness of Ornette Coleman’s and Coltrane’s bands of the time with the sharp-suited cool Davis had made a visual and audible trademark. An unexpected roll through Jerome Kern’s Yesterdays from the last set finds the group in total command of this new way of working.

6. Freedom Jazz Dance (Evolution of the Groove)

The album the quintet cut during the first studio visit after the Plugged Nickel shows, Miles Smiles, wrings every last drop of creativity out of a band relishing newly unleashed senses of purpose and possibility. The sessions were quick: a few minutes’ rehearsal, then one live take. The recordings crackle with risk-taking, and it’s difficult not to get swept away by the infectious sense of unshackled creativity every player brought to the table. The way Freedom Jazz Dance emerged from the mists is particularly fascinating. The initial run-throughs (released last year on an absorbing box set, also called Freedom Jazz Dance) show Carter struggling to hear the tune anew, having played on its original recording with Eddie Harris a few weeks earlier. After he finds a fresh heartbeat, ideas quickly take shape, but it isn’t until Davis suggests to Williams that he play triplets on every beat (“I can’t play it that fast!” the drummer complains, yet barely a minute later is doing so) that the last piece of the puzzle falls in to place. Davis comes in early but they keep going, Shorter’s and Hancock’s solos conversationally addressing the questions Davis had posed in his opening bars, Carter and Williams achieving what ought to be impossible by keeping the bedrock solid while ensuring it constantly moves and changes.

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The quintet dissolved following Carter’s departure and there was never really a constant, consistent Davis studio band afterwards. The British guitarist John McLaughlin’s appearance in the studio for the sessions that became the 1969 album In a Silent Way was unplanned: he was in New York to start work with Lifetime, Tony Williams’ new band, and was invited to the studio by Davis the night before. They weren’t familiar with the material, and the version of the title track that ended up on the album is effectively the sound of the musicians gently and carefully feeling their way through the complicated melody. The results – almost unbearably fragile, and feeling all the more precious for the sense that it could all fall apart at any second – are astounding. It’s a piece of rare and intense beauty, infused with both a wonder and a gradually unfolding understanding that seem to have been as real and unexpected for those playing as they are for the listener. Miraculously, it retains this sense of revelation every time you play it. Taking advantage of every development available – from amplified instruments to multitrack recording and postproduction techniques that anticipate sampling – Davis was taking his own ideas and music through the doorways technology and culture had newly opened.

Bitches Brew was the record to really scare the jazz purists away: a chaotic, crowded, often cacophonous double LP, it was as extreme as Davis had got. That he was accused of “selling out” at the moment he pushed his music to the limits of listenability probably says more about his detractors than it does about the man or his creative output. The Jimi Hendrix influence is often cited as reaching its apogee on this track, with the title’s nod to Voodoo Child; but in truth, this is Miles, the native son of East St Louis, going back down the Mississippi to reconnect anew with his blues roots. The album version differs dramatically from the one the live band had been playing, and not just because twice as many musicians had been assembled for the session. It’s slower, anchored by a simple drum track played by Don Alias, who had been brought in to play congas: he’d heard a rhythm on a visit to New Orleans and felt it would fit this track better than the one the two drummers (Jack DeJohnette and Lenny White) had tried on earlier, aborted takes. Note, too, that title: Davis isn’t stalking or hunting his prey, hiding in the undergrowth ready to pounce – he’s out there in the open, letting his quarry know that he’s on its tail. That sense of fearless indomitability is there in every note of what is, even in a career brimming with standout moments, a notably thrilling and strident performance.

From the point where Hancock first used an electric keyboard on a quintet session, detractors had been complaining that Davis was making rock music. Among the many problems with that view was: if In a Silent Way was “rock”, what on earth was Bitches Brew? Davis was operating beyond genres, pigeonholes and categorisations. He’d been using the slogan “Directions in music” on his album sleeves for years. He remained, as the 1957 album title put it, Miles Ahead.

Yet in the first half of 1970, Davis finally made a rock album. A Tribute to Jack Johnson was released in a muddle and failed to replicate the impact of Bitches Brew – partly, its maker intimated, because it was the soundtrack to a film about the controversial black heavyweight boxing champion and was suppressed by those who still felt threatened by the thought of black success in a white-dominated world. There were only two tracks, both Teo Macero-edited patchworks, both clocking in more than 25 minutes – but there’s no arguing with the music. Again, the session relied on accident and happenstance. Herbie Hancock wasn’t supposed to be there – he only dropped in to the studio on his way home from the shops. The basic boogie riff that kicks the record off wasn’t what they’d planned to record: it was just McLaughlin, bassist Michael Henderson (a teenager Davis had stolen from Stevie Wonder’s band) and drummer Billy Cobham jamming while they waited for Miles to get ready.

In the control room, Davis heard the warmup and told Macero to run the tape: Hancock set down his groceries and was ushered to the Hammond organ stool. Davis left the control room to prowl the studio, waiting to hear where he could fit in: after couple of minutes, McLaughlin changed chord but Henderson didn’t, and Davis took his opportunity. His first note is the only one that features in both chords, its blast from his trumpet resolving the tension of the apparent mistake with a moment of astonishing musical acuity and insight. Davis proceeds to solo for the next eight minutes, some of the strongest, most strident playing of his life: as if the simple format of the rolling blues-based stomp had freed him from the uncertainties and doubts that often made his playing so emotional, yet could sometimes leave him sounding tentative. By the time McLaughlin quotes Sly and the Family Stone’s Sing a Simple Song, the track has taken us off into another galaxy of sound and imagination.

10. Prelude

Influenced by everything from funk bands to avant garde classical composers, Davis’s ensemble became ever less bound to the past, even as its reliance on grooves and cyclical riffs (particularly from the rhythm section) re-emphasised its debts to blues. But whatever this new music was, it certainly wasn’t pop.

Evidence of what his mid-70s band were up to exists in several supersized portions, doled out across three official live albums and a slew of bootlegs. Nothing sounded like what this septet were up to back then, and nothing has sounded like it since. The first track on Agharta, recorded in Osaka in February 1975, is a 35-minute collision of ideas, structures and sounds given the title Prelude on the record (but which is, in effect, a medley that includes the tracks Tatu and Maiysha as well as Agharta Prelude), that is among the most singular musical moments of the 20th century. Themes and moods are built and destroyed; ideas are assayed, discussed between the instruments, then rejected, only to be replaced by something else. It’s as if the ceaseless quest for something new, the defining characteristic of his creative life, had intensified as Davis found himself skating ever closer to the edge. Though Davis continued to record, this marked the end of the parts of the journey that took him furthest and deepest into the great musical unknown.