20. Bags’ Groove (1957)

In the end, Miles Davis would fascinate jazz, rock and classical fans alike. But in the 1940s he had been a teenage trumpet hopeful partnering Charlie Parker and by 1954, when this session was recorded, he had an understatedly personal version of the revolutionary bebop sound. Alongside Sonny Rollins and Thelonious Monk, he reveals it here.

19. Miles In the Sky (1968)

A patchily intriguing set from the next decade, flagging the ever-changing Miles’ migration from free-swinging jazz to rock. The saxophonist Wayne Shorter broods, the embryonic soul-star George Benson plays terse guitar, Herbie Hancock debuts the formerly unjazzy Fender Rhodes and Tony Williams drums up a perfect storm.

18. The Man with the Horn (1981)

Miles comprehensively burned out in 1975, but while his comeback six years later was uncertain, his 1970s edginess was now softened by the rediscovery of his early lyricism. Good originals such as Back Seat Betty, with its wistful trumpet and hard-thumbed Marcus Miller bass hooks, entered the repertoire.

17. Amandla (1989)

Marcus Miller, Miles’s 1980s svengali, scored and glossily produced this late-career set dedicated to South Africa’s liberation from apartheid. It’s a bit lightweight for its subject, but the Jaco Pastorius tribute is both swinging and soulful, and the title ballad is bittersweet acoustic Miles at his most poignant.

16. Panthalassa: The Music of Miles Davis 1969-1974 (1998)

Audacious but sympathetic remixes by imaginative producer/player Bill Laswell, of music from Miles’s heavily experimental 1970s period, including In a Silent Way. While Laswell’s echoey, bass-pumping, beat-swelling treatments sometimes twist the originals way out of shape, their creator’s spirit runs through it all.

15. L’Ascenseur Pour L’Echafaud (1958)

The director Louis Malle hired a Paris-loving, 31-year-old Miles and a French/US band including the bebop drummer Kenny Clarke to improvise a soundtrack for his noirish 1958 thriller L’Ascenseur Pour L’Echafaud (Lift to the Scaffold). Going only by the visuals, the trumpeter reflected the movie’s desolate romanticism perfectly.

14. On the Corner (1972)

Bill Laswell, Miles’s posthumous remixer, called 1972’s On the Corner “mutant hip-hop” – others have heard dub, pre-punk, drum’n’bass and more in its oceanic, thick-textured, harmony-purged turmoil of multiple keyboards, overdubs, saxes and percussion. Long ignored, the session is on its way to rehabilitation.

Facebook Twitter Pinterest Miles Davis during rehearsals for an episode of The Robert Herridge Theatre, New York, 1959. Photograph: CBS Photo Archive/Getty Images

13. Miles Davis: Vol 2 (1956)

Miles preferred patience, tension, release and expressiveness of tone to the torrents of notes that often characterised bebop. This classy 50s compilation, including the saxophonist Jackie McLean, pianist Horace Silver and drummer Art Blakey, features both his ballad elegance and some of his most surefooted improv over a bop groove.

12. Relaxin’ with the Miles Davis Quintet (1958)

Miles buffs refer to his “first and second great quintets”. The second was the 1960s group including Wayne Shorter, Herbie Hancock, Ron Carter and Tony Williams. This, with saxophonist John Coltrane, is the dazzling first. The contrast between the reticent, incisive trumpeter and the unquenchable Coltrane is mesmerising.

11. Aura (1989)

In 1985, Denmark’s government awarded Miles Davis its normally classical Sonning prize, and Danish trumpeter Palle Mikkelborg wrote an orchestral suite for the star and – somehow – persuaded him to play on it. Superb solos from an engaged and attentive Miles, navigating Mikkelborg’s references to all kinds of 20th-century music.

Facebook Twitter Pinterest Time After Time, live in Munich, 1988.

10. You’re Under Arrest (1985)

Miles’s last session for Columbia Records, notably including beautiful interpretations of two pop songs – Cyndi Lauper’s Time After Time and Michael Jackson’s Human Nature. Also striking is guitar newcomer John Scofield’s fast and convoluted title-track blues, one of the great original compositions for a late-period Miles lineup.

9. Bitches Brew (1969)

The dense, dark, Latin-fusion epic Bitches Brew was a landmark of production as well as musicianship from a superb band including Wayne Shorter, John McLaughlin, Chick Corea and Jack DeJohnette. The players improvised for hours; the producer, Teo Macero, and Miles cut-and-pasted the results into distinct tracks later.

Facebook Twitter Pinterest Photograph: Picasa/PR Company Handout

8. Milestones (1958)

Along with Kind of Blue, Milestones is a masterpiece from the 1950s quintet including John Coltrane – expanded to a sextet here by gospel-y alto saxophonist Julian “Cannonball” Adderley. The springy, airborne title track is a standout, as is the leader’s incisive improv on Thelonious Monk’s Straight, No Chaser.

7. Sketches of Spain (1959-60)

Most at ease in small groups, Miles Davis was also a poetic soloist in concerto-like roles with a big band. His long and fruitful relationship with the Canadian composer/arranger Gil Evans gets a spectacular airing on Spanish themes including the smouldering Concierto de Aranjuez, and the quietly conversational Solea.

6. The Complete Live at the Plugged Nickel (1995)

Maybe the best-ever representation of “the second great quintet” at work. Superbly recorded live at Chicago’s Plugged Nickel club, the set finds Miles, Wayne Shorter, Herbie Hancock, Ron Carter and Tony Williams reinventing small-band jazz with an all-but-psychic flexibility of timing and on-the-fly harmonising.

50 great moments in jazz: How Miles Davis plugged in and transformed jazz ... all over again Read more

5. Birth of the Cool (1957)

The young Miles wanted to play bebop’s revolutionary conceptions in a more ethereal, less impatient way than its first pioneers. With likeminded souls including saxophonist Gerry Mulligan and Lee Konitz, and the composer/arranger Gil Evans, he formed this delicately groundbreaking chamber ensemble, an influence on the jazz sound still.

4. Porgy and Bess (1959)

A beautiful makeover of the Gershwin opera – give or take a little shaky section playing in the under-rehearsed band – with Miles’s trumpet soaring over a Gil Evans-arranged orchestra. His exhortations over the shouts of the band on Prayer, and his supple, gliding solo on Summertime are standouts.

3. Jack Johnson (1970)

From a film-score assignment about boxing legend Jack Johnson, Miles launched a new band (hiring Stevie Wonder bassist Michael Henderson among others) and built a thrillingly hard-rocking sound out of long studio jams and radical editing. The seeds of his next five years are in this uncompromising music.

2. In a Silent Way (1969)

Time stands still on this 1969 Davis classic. Electric sounds and textures (notably from new guitarist John McLaughlin and keyboardist Joe Zawinul) make clear breaks from the trumpeter’s acoustic bands – but Miles’s horn and Wayne Shorter’s keening soprano sax sketch passages of an exquisite, irresistible tranquillity.

Facebook Twitter Pinterest So What, from Kind of Blue (official video).

1. Kind of Blue (1959)

Revered by pundits and fans, radiating an enduringly contemporary sound, and with un-jazz-like sales of 4 million plus at the last count, Kind of Blue – the 1959 session recorded in just a few hours and with minimal rehearsal – changed the way listeners and practitioners everywhere heard and made music. The Milestones band, with John Coltrane and Cannonball Adderley on saxes, was the core, with the graceful pianist Bill Evans added, and the use of modes rather than song chords throughout gave the music an ethereal, free-associative spaciousness that draws new audiences to jazz to this day.