Miles Davis in 1984, photo by Wikimedia Commons

Miles Davis died, aged 65, on September 28, 1991. Thirty years on, the trumpeter’s bright, dangerous flame is still undimmed in the public imagination. He remains one of the most revered and influential artists of all time.

Let’s call him Miles. Such is his fame that a first name will do. He’s widely regarded as one of the key architects of jazz, and one of a tiny handful of jazz musicians to have become a household name, known even by those with little interest in the music. What’s more, Miles’ legendary status is entirely deserved. In an intense, blinding streak of creativity from the mid-1940s to the mid-1970s, he relentlessly forged ahead, constantly reinventing his music, never stopping to look back, tirelessly exploring, breaking new ground, and changing the face of jazz over and over again. Along the way, he developed an extraordinary knack for picking younger musicians to help him realise his visions. His ever-changing bands served as both boot camp and academy for a dizzying roll call of jazz superstars – from John Coltrane and Wayne Shorter to Herbie Hancock and Chick Corea. It’s impossible to imagine jazz as we know it without the mark Miles made upon it.

Born in Illinois on May 26, 1926 into a middle class family, Miles Dewey Davis III was raised in East St Louis. He received his first trumpet at the age of 11 and, by the time he was in his teens, he had already decided to devote his life to music. In 1944 he moved to New York, attending classes in music theory at the Julliard School by day, and haunting the all-night bebop jam sessions at Minton’s Playhouse in Harlem by night. The following year he replaced Dizzy Gillespie in Charlie Parker’s band and, in the next few years, participated in epochal be-bop recordings.

At the turn of the 50s, Miles led a nine-piece group that broke away from bebop and pioneered a softer, more relaxed sound – making a major contribution to the development of the style that became known as cool jazz. In the mid-50s, he formed his first great quintet, featuring John Coltrane on tenor saxophone, Red Garland on piano, Paul Chambers on bass and Philly Joe Jones on drums. This tight, tough ensemble was one of the definitive hard bop units of the era, recording a handful of albums that remain touchstones of mid-20th century small-group jazz. In 1959, the group – extended to a sextet with Cannonball Adderley on alto sax, and with Bill Evans at the piano – recorded Kind Of Blue. Considered by many to be Miles’ greatest statement and one of the key recordings in the history of jazz, the album was a quietly radical exploration of modal jazz.

The 1960s were a period of incessant innovation for Miles. Between 1964 and 1968, he led his second great quartet, featuring four young avatars of jazz: Wayne Shorter on tenor saxophone, Herbie Hancock on piano, Ron Carter on bass and Tony Williams on drums. But it was from the end of the 60s, through to the mid-70s that Miles made his boldest statements of all. Embracing the possibilities of electric instruments and incorporating elements of funk and rock he announced the advent of fusion in an incandescent blaze of future-focused creativity. With every album he released – from 1969’s In A Silent Way and 1970s Bitches Brew to 1971’s Jack Johnson and 1972’s On The Corner - Miles pushed further and further away from traditional notions of jazz.

This furious pace couldn’t last. In 1975, burned out from three decades of non-stop invention, years of drug and alcohol abuse and various serious health issues, Miles retired from music, beginning a five-year hiatus away from public life.

When he returned, in 1980, Miles was a shadow of his former self. Albums such as 1981’s The Man With The Horn and 1986’s Tutu revealed an artist coasting on former glories, exhausted, struggling to remain relevant, and creating watered-down, pop-oriented funk that fell far short of his past triumphs. His death in 1991 – attributed to the combined effects of stroke, pneumonia and respiratory failure – marked the end of a dismal artistic coda.

And yet, those three decades of fierce, unparalleled creativity remain one of the greatest musical legacies of all time. Miles’ discography is studded with world-changing classics. Here, we examine his back catalogue and attempt to look past the obvious selections, finding less storied albums that fall in the interstices and occupy moments of transition, suggesting an alternative history of the music of Miles Davis.

Milestones (1958) instead of Kind Of Blue (1959)

Luxuriating in a laid-back, late-night vibe of soporific cool, Kind Of Blue is generally held to be Miles’ brooding modal masterpiece. Yet Milestones, recorded and released the year before, contains the seeds of this experimentation presented in a more upbeat setting bursting with brash enthusiasm. The title track, Miles’ first foray into the modal style, zips along with an irrepressible rim-shot energy, summoning the bright, bustling daytime streets of uptown 50s Manhattan. It’s set alongside a clutch of solid bop bruisers, including Dizzy Gillespie’s ‘Two Bass Hit’ and Thelonious Monk’s ‘Straight, No Chaser’ rendered in gleaming brass-heavy arrangements. Throughout, the three principal horns present a trio of boldly drawn personae: Cannonball Adderley’s alto sax is light and loquacious, John Coltrane’s tenor hints at darker depths while Mile’s trumpet maintains an spry melancholy that colours the entire session.

Ascenseur pour l’échafaud (1958) instead of Sketches Of Spain (1960)

With its sumptuous arrangements by Gil Evans, Sketches Of Spain is an ambitious evocation of an idealised, imaginary Spain, fusing elements of jazz, flamenco and European classical to create a suite as sultry and torrid as a siesta love affair. But, for a truly captivating, fully realised aural postcard – and one that allows Miles’ own personality to shine through with an air of almost heartbreaking vulnerability – turn to his soundtrack to Louis Malle’s 1958 film noir Ascenseur pour l’échafaud. Miles had fallen in love with Paris on his very first visit in 1949, when he began a long and passionate affair with actress Juliette Gréco. On a later sojourn, in December 1957, he was asked to provide a soundtrack to Malle’s taut, black and white tale of murder and thwarted passion. Together with drummer Kenny Clarke and some top French musicians, Miles spontaneously improvised to a screening of the film in the recording studio, perfectly capturing a sense of louche longing, nocturnal assignations and neon light reflected in rain-washed Parisian streets.

Seven Steps To Heaven (1963) instead of Steamin’ (1961)

Two recording sessions in 1956 – on May 11 and October 26 – yielded enough material for four albums by the classic line-up of Miles’ first great quintet, beginning with 1957’s Cookin’ and culminating in Steamin’ in 1961. These albums, which cemented the quintet’s reputation as a quintessential hard bop outfit, all featured a mix of bop favourites and standards from the Great American Songbook. By 1963, the quintet had fallen apart and Miles was looking for a new direction. Collating recordings from two separate sessions that year, Seven Steps To Heaven, reveals a moment of major transformation. Tracks recorded in April in Hollywood feature journeyman drummer Frank Butler and veteran English pianist Victor Feldman alongside saxophonist George Coleman and young bassist Ron Carter. But tracks from a session in New York the following month introduce two youthful firebrands: 23-year-old pianist Herbie Hancock and 17-year-old drummer Anthony Williams. On tracks like the perfectly formed swinger ‘Joshua,’ these youngsters inject a palpable crackle of energy that changed Miles’ sound forever. With the foundations of his second great quintet in place, the future had arrived.

Live In Europe 1967: The Bootleg Series Vol. 1 (2011) instead of E.S.P. (1965)

Across a handful of albums, beginning with 1965’s E.S,P., Miles’ second great quintet revealed itself to be a preternaturally lithe unit with an extraordinary telepathic connection. Together, they explored Miles’ conception of “time no changes” – a more free and open approach to hard bop that moved away from the strict straightjacket of chordal sequences while retaining a bullish rhythmic imperative. Nowhere is this group’s astonishing flexibility and drive more apparent than on the 3-CD box set – the first volume of the extraordinary Bootleg Series – that documents live performances in Antwerp, Copenhagen and Paris in October and November 1967. With original compositions by Miles and saxophonist Wayne Shorter to the fore, the group bend and stretch, surge and swoon, driven by Anthony Williams’ impossibly fluid, constantly mutating sense of time. Utterly modern in 1967, the music on these discs still sounds like a pinnacle of human artistic endeavour: not just the most vital and sophisticated band Miles ever led, but one of the greatest small groups in jazz history.

Live In Europe 1969:The Bootleg Series Vol. 2 (2013) instead of Miles In The Sky (1968)

When the second volume of the Bootleg Series arrived in 2013, it sent shockwaves through the jazz world, shining a light on a fascinating and previously unheard moment in Miles’ stratospheric development. Recorded in July and November 1969, it captures Miles’ legendary ‘lost quintet,’ a revolutionary and short-lived unit that never made it into a recording studio. With Wayne Shorter on sax, Chick Corea on electric piano, Dave Holland on bass and Jack DeJohnette on drums, Miles harnesses a snarling, electrified energy that shakes off vestigial traces of the blues, pushing ahead to arrive in wide open, uncharted territory. Miles frequently sits out for long stretches, allowing the four younger musicians to weave jagged webs of complex, spontaneous interplay – and bringing Miles the closest he ever came to embracing free-jazz. Corea’s electric piano is a key voice – making it hard to believe that, just the year before, Miles had made his first tentative forays into electric jazz on Miles In The Sky with Herbie Hancock supplying electric piano on the slinky boogaloo of ‘Stuff’ and guitarist George Benson adding brittle jitters to the urgent ‘Paraphernalia.’

Filles de Kilimanjaro (1969) instead of In A Silent Way (1969)

Filles de Kilimanjaro, recorded just months after Miles In The Sky, captures Miles in a moment of transition. It’s the last album featuring his second great quintet, and the first on which Chick Corea and Dave Holland make an appearance. More crucially, it documents a stylistic overlap, with one foot in the acoustic jazz tradition and the other purposefully striding forward into an electric future. While 1969’s In A Silent Way is generally held to mark the beginning of Miles’ electric period, its game-changing innovations can be heard in embryonic form on Filles…, providing a tantalising glimpse of Miles’ unfolding creative process. With electric Fender Rhodes keyboard and bass guitar high in the mix on most tracks, and a decisive move away from recognisable jazz forms, Filles… provides the first hint of Miles’ growing interest in incorporating elements of rock: ‘Mademoiselle Mabry’ is a cool abstraction of Jimi Hendrix’s ‘The Wind Cries Mary,’ while the title track is an insistent throb paving the way for the dream-like swish of In A Silent Way.

Jack Johnson (1971) instead of Bitches Brew (1970)

Assembled from a three-day recording session held in the same week as Woodstock, Bitches Brew was Miles’ most explicit attempt to tap into the vibe of psychedelic rock. But what a gloomily subterranean vision Miles conjures, with Bennie Maupin’s crepuscular bass clarinet wafting like a dark fog across John McLaughlin’s barbed wire guitar, while multiple drums and basses roil and churn. Recorded the following year, Jack Johnson is simultaneously more ambitious – with just one extended track per side – and more direct. Conceived as the soundtrack to a documentary about the first African-American world heavyweight boxing champion, it’s a punchy mix of rock heft, funk sweat and Black Power politics. ‘Right Off’ kicks in as a bluesy power-shuffle with Billy Cobham’s thumping drums, McLaughlin’s kranging chords and Miles blowing more muscular than ever before. On the flip, ‘Yesternow’ is a stealthy creep with Michael Henderson’s electric bass unfurling a slowed-down take on the hook from James Brown’s ‘Say It Loud, I’m Black And I’m Proud.’ It’s one of Miles’ toughest and most uncompromising joints.

Live-Evil (1971) instead of On The Corner (1972)

On its release, nearly 50 years ago, On The Corner caused consternation among fans and critics alike. Described by Miles as “Stockhausen plus funk plus Ornette Coleman,” it was at once cerebral and bodily: seemingly endless jams built on sinuous, Sly Stone-inspired bass lines, overlaid with pattering tabla, unfettered guitar and sax solos, and Miles alternating between buzzing wah-wah horn and stabs of glacial organ. It sounded like music made by extraterrestrials passing themselves off as humans. If On The Corner comes across as oddly cold and emotionless, Live-Evil, released the previous year, is the sweaty, joyous, thrillingly alive antidote. Mostly recorded live at the Cellar Door jazz club in Washington D.C. in December 1970, it throbs with unstoppable energy. Long jams like ‘What I Say’ ride on bass guitarist Michael Henderson and drummer Jack DeJohnette’s crunching funk-rock riffage, leaving plenty of room for Keith Jarrett’s Fender Rhodes keyboard, while Miles’ horn gleefully sprays hot testosterone all over the front row. A handful of short, pellucid studio pieces act as palette-cleansers between the live bruisers, making this double album a completely satisfying trip.

Dark Magus (1977) instead of Agharta (1975)

Add three-and-a-bit years of escalating cocaine use and spiralling mental health issues to the amped-up vibe of Live-Evil and you end up with the snarling intensity of Dark Magus. Recorded live at Carnegie Hall in March 1974, it represents the twisted conclusion to Miles’ single-minded investigation into the trance-inducing energetic properties of rock and funk. The rhythms are faster, with drummer Al Foster and percussionist James Mtume racing ahead almost into proto-jungle territory. The solos seethe and glower, with guitarist Pete Cosey tapping into a gnarled, post-Hendrix virtuosity. Miles contributes less than before, occasionally adding a jarring organ burst or spurt of wah-wah trumpet, but the whole date smoulders with his heavy-lidded, malevolent spirit. Something had to give and Agharta, recorded in Osaka, Japan in February 1975, feels like the crashing come down. Reggie Lucas’s rhythm guitar chops out a relentless churn while Pete Cosey’s lead guitar writhes in razored agony and saxophonist Sonny Fortune blows high and free – but there’s a sense of exhaustion lurking beneath the grooves. Later that year, Miles, aged 49, sought refuge in the darkened interior of his Manhattan brownstone, beginning five years of silence.

Dingo (1991) instead of Tutu (1986)

When Miles re-emerged into public view in 1980, he was clean, healed and seemingly back on track. Yet, at the same time, he was noticeably diminished – both physically frail and creatively spent. His enormous fame ensured there was no lack of work: he collaborated with Scritti Politti, contributed to the 1985 protest song ‘Sun City’ by Artists Against Apartheid, and even branched out into acting, playing a pimp in an episode of Miami Vice in 1985 among other roles. Yet, his own recording projects lacked the fire of previous years. 1986’s Tutu was hailed by some as a welcome return but was less a Miles Davis album than a showcase for the compositional and production skills of young bassist Marcus Miller who masterminded its inoffensive mix of toothless drum machine rhythms and glossy synth sheen. Yet, given the right circumstances, Miles could still burn – as on the soundtrack to the Australian film Dingo, in which Miles played a thinly-disguised version of himself. Recorded in 1990, Miles’ contributions – particularly on the extraordinary ‘Concert On The Runway,’ which opens the film – reveal an unmistakable instrumental genius. By the time the soundtrack album and movie were released, Miles had already died. A lifetime of relentless, uncompromising, endlessly inspiring creativity had come to an end.