20 Best Miles Davis Albums Ranked
Introduction: A Hundred Years of Miles
On 26 May 2026, Miles Dewey Davis III would have turned 100. That feels like the right occasion to sit down with his catalogue and try to make sense of what one trumpet player did to twentieth-century music. The short version is that he changed it five or six times, depending on how you count, and that he did so without ever sounding like he was straining for the next idea. The longer version is what follows.
There is no other figure in jazz with a discography quite like this. With each recording, Miles burnt the bridge behind him. He arrived in New York in 1944 as a teenager from East St Louis, found Charlie Parker on 52nd Street, dropped out of Juilliard, and within four years had stepped sideways out of bebop with the Birth of the Cool sessions. Then came the First Great Quintet with Coltrane, the Gil Evans collaborations, the modal jazz of Kind of Blue, the Second Great Quintet with Shorter, Hancock, Carter and Williams. Then the electric era, the funk era, the rock era, a five-year silence, then a comeback, then synthesisers and Cyndi Lauper covers, and then he was gone, in 1991, at sixty-five.
Trying to rank his albums is a bit absurd. What I have tried to do here is balance the records that genuinely changed where the music could go, the records I cannot stop listening to, and a few that are less famous than they should be. The ranking is mine, and I would happily argue any of it over a drink, but ultimately the point is the music, not the order.
What you have below is, more than anything, an argument for why this music still matters at a hundred years on from the day Miles was born. He never made the same record twice. Every one of these records contains a different theory of what jazz could be.
What Made Miles Miles
Worth saying out loud before the rankings begin, because it explains a lot of what follows. Miles was not the greatest trumpeter in jazz. Dizzy had more range, Clifford Brown more flash, Freddie Hubbard more chops, Lee Morgan more bebop fluency. Miles knew it, and he played around it. What he had instead was tone. Three notes in and you know it is him, the way you know two seconds of Billie Holiday or one bar of Coltrane. His sound was forged out of a deliberate refusal of vibrato, taught to him as a teenager by Elwood Buchanan in East St Louis, and out of a lifelong instinct for how much air to put behind a note. The Harmon mute, the slightly cracked attack, the long melodic line that floats above the chord changes rather than chasing them, that was his vocabulary, and it is one of the most recognisable in twentieth-century music.
He was not the greatest composer in jazz either. Mingus wrote more, Monk wrote stranger, Ellington wrote everything. Plenty of the tunes most associated with Miles came from other hands. Monk wrote 'Round Midnight'. Gershwin wrote 'Summertime'. Bronisław Kaper wrote 'On Green Dolphin Street'. Joaquín Rodrigo wrote 'Concierto de Aranjuez'. Even on Kind of Blue, Bill Evans's hand on 'Blue in Green' is now widely accepted as decisive. None of this matters much, because what Miles did with other people's tunes, and with the originals he did write was to make records that have outlived almost everything else recorded in their time.
His supreme gift was as a bandleader. He could hear a player nobody else was hearing and put them in front of a microphone before the rest of the world caught up. Coltrane was a struggling tenor player with a heroin problem when Miles hired him in 1955. Wayne Shorter was the music director of Art Blakey's Jazz Messengers, and Miles spent months trying to poach him before he finally said yes in September 1964. Herbie Hancock was twenty-three when Miles called. Tony Williams was seventeen. Chick Corea, Joe Zawinul, John McLaughlin, Keith Jarrett, Dave Holland, Jack DeJohnette, Marcus Miller, John Scofield, Bill Evans, every one of them passed through a Miles band and came out as a defining voice in their own right. He had a sixth sense for what a young player could do before they knew it themselves, and he put them in rooms with each other in configurations no other bandleader had thought of. Miles did not invent these musicians. He saw them earlier than anyone else did, and he gave them the platform.
And then he kept moving. This is the part of the story hardest to overstate. From the late 1940s to his death in 1991, Miles was at the front of nearly every major change of direction in jazz. He helped invent cool jazz with the nonet sessions in 1949. He helped define hard bop with the First Quintet. He helped invent modal jazz on Milestones and codified it on Kind of Blue. He fused jazz with classical across three records with Gil Evans. He pushed harmonic and rhythmic abstraction to a new limit with the Second Quintet. He brought electricity into the music and effectively invented fusion with In a Silent Way and Bitches Brew. He pulled funk and dance rhythms into the equation with On the Corner. He came back in the 80s and worked with synthesisers, drum machines, hip hop and pop production on his own terms. Nine or ten major shifts inside a single career. No one else in jazz can say that. No one in any popular music can either.
That is the case for Miles as the greatest innovator jazz has produced. The trumpet playing, the writing, the long career: all of it matters. But what puts him alone, finally, is the restless intelligence that kept finding the next room before anyone else knew there was one to find.
The Rankings
20. Dark Magus (Columbia, 1977)
Recorded: 30 March 1974 at Carnegie Hall, New York City
Released: 1977 (Japan only on CBS/Sony, US release 1997)
Personnel: Miles Davis (trumpet, organ), Dave Liebman (soprano and tenor saxophones, flute), Azar Lawrence (tenor saxophone), Pete Cosey (electric guitar), Reggie Lucas (electric guitar), Dominique Gaumont (electric guitar), Michael Henderson (electric bass), Al Foster (drums), James Mtume Forman (percussion)
This is the most extreme thing Miles ever released, and arguably the most prescient. Recorded over one night at Carnegie Hall in March 1974, by a band that mostly did not know what was about to happen, Dark Magus documents the absolute terminal point of his electric period. Three guitarists. Two saxophones. A bassist locked into one of the deepest grooves in the history of recorded music. And Miles on trumpet through a wah pedal and Yamaha organ, conducting the chaos with hand signals.
The four tracks are named in Swahili for the numbers one through four, which tells you most of what you need to know about how much Miles cared for conventional song titles by this point. 'Tatu' in particular is a 25-minute piece of jazz-rock that mutates between Sly Stone funk and something closer to noise music. Pete Cosey's guitar work, full of effects and tunings borrowed from Hendrix's playbook, sounds like an electrical storm. Azar Lawrence and Dominique Gaumont were essentially auditioned live that night, with neither having previously played a full gig with the band.
For decades only available as a Japanese import, Dark Magus sat at the edge of his discography like a rumour. Q magazine eventually named it one of the 50 heaviest albums of all time, and you can hear its DNA in everything from Sonic Youth to Squarepusher. It is not a record for casual listening but it is a record that puts you somewhere very specific, and it leaves you there.
19. Aura (Columbia, 1989)
Recorded: January to March 1985 at Easy Sound Studios, Copenhagen
Released: 1989
Personnel: Miles Davis (trumpet), Palle Mikkelborg (composer, arranger, conductor, trumpet, flugelhorn), John McLaughlin (electric guitar), Vince Wilburn Jr (drums), Marilyn Mazur (percussion), Niels-Henning Ørsted Pedersen (bass), Thomas Clausen (piano, keyboards), with the Danish Radio Big Band
In late 1984 Miles became the first jazz musician, and the first Black artist, to receive Denmark's Léonie Sonning Music Prize, an honour normally reserved for European classical composers. The prize came with a commission. Danish trumpeter and composer Palle Mikkelborg wrote Aura, a ten-part suite built around the letters of Miles's name, each section named for a colour Mikkelborg perceived in Miles's musical aura. Miles loved it enough to return to Copenhagen weeks later and record it.
A collaboration not unlike those he had with Gil Evans but with synthesisers replacing strings, and Mikkelborg's writing borrowing from Messiaen and Ives as much as from any jazz tradition. The role Miles plays inside the orchestration, that pinched, lonely tone weaving through enormous slabs of synthesised brass and woodwind, is the same role he played on Sketches of Spain twenty-five years earlier. 'Orange' is the most extroverted moment, a hard 4/4 groove that builds into a McLaughlin guitar solo straight out of the Mahavishnu years. 'Red', 'Indigo' and 'Violet' are more austere, the trumpet almost a thread of light through dense fog.
Columbia sat on the tape for four years before finally putting it out in 1989, which was part of why Miles defected to Warner Bros. He thought it was a masterpiece. He was not wrong, even if the album has remained 'underheard'. For anyone who has dismissed late-period Miles, Aura is a rebuttal.
18. Tutu (Warner Bros, 1986)
Recorded: Early 1986 at Capitol Studios, Los Angeles; Clinton Recording, New York; and Le Gonks West, West Hollywood
Released: 29 September 1986
Personnel: Miles Davis (trumpet), Marcus Miller (bass, bass clarinet, soprano saxophone, keyboards, guitar and most other instruments), George Duke (keyboards, arrangement on Backyard Ritual), Adam Holzman (keyboards), Bernard Wright (keyboards), Jason Miles (synthesiser programming), Omar Hakim (drums), Paulinho da Costa (percussion), Steve Reid (percussion), Michał Urbaniak (electric violin)
This was the album that brought Miles back to wider critical attention in the 1980s. His first record for Warner Bros after thirty years on Columbia, and a tribute to Desmond Tutu, then the Anglican Archbishop of Cape Town and one of the most visible faces of the anti-apartheid movement. The project had originally been meant as a collaboration with Prince, who later withdrew, leaving Warner producer Tommy LiPuma to bring in bassist and arranger Marcus Miller. Miller was twenty-seven. He wrote almost all the music, played almost all the instruments, and shaped the album into the cleanest, most coherent statement Miles made in the last quarter of his career.
The production is openly of its moment, full of drum machines, Synclavier programming and the kind of digital reverb that mid-80s R&B was built on. What stops it from sounding like a period piece is Miles. His muted trumpet over Miller's tracks creates a strange and very effective tension. 'Tomaas', the only track Miles co-wrote, is the most jazz-leaning piece on the record, with a slow funk groove and a darkly suggestive trumpet line. 'Portia', dedicated to Miller's wife, is one of Miles's most beautiful late ballad performances. The title track is the funkiest thing here, and the one most people who remember Tutu remember.
Critics divided on it at the time and have continued to divide on it since. Robert Christgau called it "pop-funk Sketches of Spain." Some jazz commentators thought it was Miller's record with Miles featured on top rather than the other way around. Both readings have something to them. What the album does, undeniably, is sound like a Miles Davis record that people outside the jazz world actually wanted to hear. It won a Grammy, attracted a younger audience, and stands as the most fully realised piece of late-period Miles, whatever else you want to say about it.
17. Miles Davis Volume 2 (Blue Note, 1953)
Recorded: 20 April 1953 at WOR Studios, New York
Released: 1953 (BLP 5022, 10" LP); later reissued on the 12" Miles Davis Volume 2 (BLP 1502, 1956)
Personnel: Miles Davis (trumpet), Jay Jay Johnson (trombone), Jimmy Heath (tenor saxophone), Gil Coggins (piano), Percy Heath (bass), Art Blakey (drums)
The 1953 session that gave us this 10-inch LP catches Miles at one of the lowest and most fragile points of his career. He was deep in heroin addiction. The recording itself was financed by Alfred Lion of Blue Note as much out of faith as out of business sense, a small label betting that the trumpet player who had cut Birth of the Cool was still in there somewhere. The bet paid off.
The sextet Miles assembled was extraordinary. Jay Jay Johnson on trombone is one of the great underrated voices in the bebop front line. Jimmy Heath, all of twenty-six, plays tenor with the kind of melodic concision that would mark his entire career. Behind them, Percy Heath on bass and Art Blakey on drums lay down a rhythm section that would have been hard to beat anywhere in 1953. 'Tempus Fugit', originally written by Bud Powell, is the standout. The arrangement is dense, the tempo is unforgiving, and Miles plays through both with a poise that contradicts everything else happening in his life at the time.
Material from this session, along with the 1952 and 1954 dates, would later be gathered onto the 12-inch Miles Davis Volume 2 on BLP 1502 in 1956. Either format is a key document of bebop in transition toward hard bop, and a portrait of Miles before the First Great Quintet, before Columbia, before everything that followed. It also stands as proof that even at his most personally unwell, Miles could walk into a room with the right musicians and make music that lasts.
16. Miles Smiles (Columbia, 1967)
Recorded: 24 to 25 October 1966 at Columbia 30th Street Studio, New York
Released: 16 February 1967
Personnel: Miles Davis (trumpet), Wayne Shorter (tenor saxophone), Herbie Hancock (piano), Ron Carter (bass), Tony Williams (drums)
If E.S.P. was the second quintet getting acquainted, Miles Smiles is the same group fully arrived. Recorded over two days in October 1966, it captures the band in a state of rhythmic and harmonic freedom they had not quite reached on their previous studio outing. Hancock makes a striking choice on 'Orbits', 'Dolores' and 'Gingerbread Boy', dispensing with his left hand entirely and playing only right-hand melodic lines, leaving the chord work to the bass and the drums. The result feels like the floor has been removed from under the music.
Wayne Shorter's compositions are the spine of the record. 'Orbits' opens at a sprint, all jagged angles and unexpected resolutions. 'Footprints' is the famous one, a blues whose 6/8 to 4/4 ambiguity Tony Williams plays both sides of simultaneously, and which has become one of the most studied compositions in modern jazz. 'Dolores' carries the same kind of melodic-rhythmic puzzle that Shorter brought to everything he wrote in this period. Davis's own 'Circle', the only ballad on the album, is the lyrical heart of the record, a muted trumpet performance of immense restraint.
The closing tracks, 'Freedom Jazz Dance' by Eddie Harris and 'Gingerbread Boy' by Jimmy Heath, give the band rare standards to interpret, and they tear both apart and put them back together at slightly different tempos. Miles Smiles is jazz as collective improvisation pushed almost to the limit of what could still be called bebop. Some critics at the time called it abstract. They were not wrong. They just had not realised what was about to follow.
15. E.S.P. (Columbia, 1965)
Recorded: 20 to 22 January 1965 at Columbia Studios, Los Angeles
Released: 16 August 1965
Personnel: Miles Davis (trumpet), Wayne Shorter (tenor saxophone), Herbie Hancock (piano), Ron Carter (bass), Tony Williams (drums)
E.S.P. is the first studio album by the second great quintet, and the title is the band's own joke about how they were playing together by then. Wayne Shorter had joined the previous September, completing the lineup that would dominate Miles's studio output for the next four years. The name was a wink, and also accurate. By 1965 these five musicians were already operating as a unit that responded to each other faster than most groups could think.
The whole album is original material, the first time Miles had recorded a date of compositions written entirely from within the band since Kind of Blue. Shorter contributes the title track and 'Iris', Ron Carter writes 'Eighty-One' with Miles, plus 'R.J.' and 'Mood', Hancock brings 'Little One' and Miles adds 'Agitation'. There is not a standard or a ballad in sight. Every piece is short by the standards of the era, almost all of them under seven minutes, and each one functions as a kind of structural experiment. 'Eighty-One' alternates between a soul-jazz boogaloo head and looser passages where the rhythm section drops away entirely.
This is the sound of the quintet establishing what they wanted to do. The risks they would take later, on the Plugged Nickel dates and on Miles Smiles and Nefertiti, were already implicit here.
14. On the Corner (Columbia, 1972)
Recorded: June to July 1972 at Columbia Studios, New York
Released: 11 October 1972
Personnel: Miles Davis (electric trumpet, organ), Dave Liebman (soprano saxophone), John McLaughlin (electric guitar), Chick Corea (electric piano), Herbie Hancock (electric piano, synthesiser), Bennie Maupin (bass clarinet), Harold I. Williams (organ, synthesiser), Collin Walcott (electric sitar), Michael Henderson (electric bass), Jack DeJohnette (drums), Billy Hart (drums), Al Foster (drums), Badal Roy (tabla), James Mtume Forman (percussion)
On the Corner was the most hated record Miles ever released, and it now sounds like one of the most prophetic. Trying to reconnect with a young Black audience who had moved on to Sly and James Brown, Miles described his goal as "Stockhausen plus funk plus Ornette Coleman." Whatever you call the result, it predicted a bunch of musical genres that did not yet exist. You can hear hip hop in the way the breaks are looped. You can hear drum and bass in the rhythmic density. You can hear ambient and house and everything that would eventually call itself post-rock.
The recording technique was as radical as the music. Davis and producer Teo Macero spliced together edits from hours of jamming, layering them with overdubs that sometimes treated trumpet as just another texture rather than the lead instrument. Michael Henderson's bass holds the centre with a single repeating figure that almost never changes. The drummers, plural, build a polyrhythmic field around it. Miles often plays through a wah pedal, the trumpet barely recognisable as a trumpet. The album credits no individual players, which infuriated jazz critics and was almost certainly the point.
It was Miles's worst selling album for years and his most divisive ever. Stanley Crouch decided it was the moment Miles betrayed jazz. Thankfully, the record has been critically reappraised over time and is now considered a classic. On the Corner is the moment Miles stopped caring whether what he was making was still jazz at all, and made it anyway. The fact that the music was right and the audience eventually caught up tells you all you need to know.
13. Relaxin' with the Miles Davis Quintet (Prestige, 1958)
Recorded: 11 May and 26 October 1956 at Rudy Van Gelder Studio, Hackensack, New Jersey
Released: March 1958
Personnel: Miles Davis (trumpet), John Coltrane (tenor saxophone), Red Garland (piano), Paul Chambers (bass), Philly Joe Jones (drums)
Miles needed to fulfil his Prestige contract before he could fully commit to Columbia, so in May and October 1956 he and the First Great Quintet sat down at Rudy Van Gelder's studio in Hackensack and recorded four albums' worth of material in two marathon sessions. The four records that resulted (Workin', Steamin', Cookin' and Relaxin') are among the finest small-group jazz documents ever produced, made with effectively no retakes, no overdubs, no formal preparation, just the quintet playing through its existing live repertoire.
Relaxin' is the most balanced of the four, and probably the easiest to live with. 'If I Were a Bell' opens with Miles snapping his fingers and giving Bob Weinstock his offhand "I'll play it and tell you what it is later." From there the band rolls through a programme of standards and originals with the kind of nonchalant mastery that this quintet seemed to find inexhaustible. Coltrane's reading of 'You're My Everything' is gorgeous. 'Oleo' is the perfect distillation of how this rhythm section worked, with Paul Chambers walking under Coltrane's solo and Philly Joe Jones laying out for half the track.
The tape rolled with no overdubs, no edits, no retakes. You can hear studio banter between takes. You can hear Miles telling Van Gelder to start tape. It is jazz at its most undefended. The First Great Quintet would dissolve within a year, with Coltrane heading off to Monk and eventually his own career. The Prestige marathon sessions are the most complete record we have of how they played together, and Relaxin' is the easiest of the four to fall for.
12. Nefertiti (Columbia, 1968)
Recorded: 7 June, 22 to 23 June, 19 July 1967 at Columbia 30th Street Studio, New York
Released: 15 January 1968
Personnel: Miles Davis (trumpet), Wayne Shorter (tenor saxophone), Herbie Hancock (piano), Ron Carter (bass), Tony Williams (drums)
Nefertiti is the last album Miles made on acoustic instruments. He never went back. It is also one of the strangest records in his catalogue, a place where the second quintet inverts every convention of jazz performance and somehow makes it sound natural.
The title track is the experiment in microcosm. Shorter's 16-bar melody loops through the entire piece, played and replayed by the two horns while the rhythm section solos underneath, reversing the traditional roles. There is no improvisation over the changes, no horn solo at all. Tony Williams's drums become the lead instrument, ebbing and surging beneath the fixed melodic figure, with Hancock and Carter responding in real time.
The rest of Nefertiti extends the same logic. 'Fall' is companion to the title track in mood and form. 'Hand Jive' points toward the funkier rhythmic language Williams would lean into the following year. 'Pinocchio' is a Shorter melody played at speed, the quintet opening it up live for years afterward. The whole album sits inside a kind of haunted serenity that Miles Smiles and E.S.P. did not quite reach. By the time Miles next walked into a studio, the Fender Rhodes was already plugged in. Nefertiti is the door swinging shut on the acoustic era, and one of the most quietly radical records he ever made.
11. Miles Ahead (Columbia, 1957)
Recorded: 6, 10, 23 and 27 May 1957 at Columbia 30th Street Studio, New York; trumpet overdubs 22 August 1957
Released: 21 October 1957
Personnel: Miles Davis (flugelhorn), Gil Evans (arranger, conductor), with a 19-piece ensemble including Bernie Glow, Ernie Royal, Louis Mucci, Taft Jordan and Johnny Carisi (trumpets), Frank Rehak, Jimmy Cleveland, Joe Bennett and Tom Mitchell (trombones), Willie Ruff, Tony Miranda and Jimmy Buffington (French horns), Bill Barber (tuba), Lee Konitz (alto saxophone), Romeo Penque, Sid Cooper and Eddie Caine (reeds and flutes), Danny Bank (bass clarinet), Wynton Kelly (piano), Paul Chambers (bass), Art Taylor (drums)
The first of the three Columbia collaborations with Gil Evans, recorded in May 1957 with trumpet overdubs added in August to patch up Miles's solo lines. The project came from producer George Avakian, who had heard the Birth of the Cool sessions and wanted to expand the nine-piece idea into something bigger. Miles asked for Evans to write the arrangements, and the partnership that would define both their careers properly began here.
The instrumentation is unusual for jazz. Nineteen players, with three French horns, tuba, bass clarinet, and a single small-group rhythm section underneath. Miles plays flugelhorn throughout, the only album he ever made on the instrument exclusively, and his tone on it is rounder and more melancholy than his trumpet sound. Evans arranged ten pieces from an unusually wide variety of sources: Dave Brubeck's 'The Duke', Kurt Weill's 'My Ship', Ahmad Jamal's 'New Rhumba', Johnny Carisi's 'Springsville' (originally part of the Birth of the Cool repertoire), and Evans's own 'Blues for Pablo'. The ten tracks segue into each other almost without interruption, structured as a continuous suite.
This is third stream in the literal sense, jazz reaching toward European classical orchestration without losing the rhythmic instinct of the small group. Miles is the only soloist on the album. His role to stay close to the melodies and let Evans's arrangements do most of the dramatic work. The original cover featured a young white woman and child on a sailboat. Miles was not happy about this, and later pressings used a photograph of him instead. Sketches of Spain and Porgy and Bess are the better-known Evans collaborations, but Miles Ahead is the one where the template was set. The whole partnership runs back through here.
10. Sketches of Spain (Columbia, 1960)
Recorded: 20 November 1959, 10 to 11 March 1960 at Columbia 30th Street Studio, New York
Released: 18 July 1960
Personnel: Miles Davis (trumpet, flugelhorn), Gil Evans (arranger, conductor), with a large ensemble including Paul Chambers (bass), Jimmy Cobb (drums), Elvin Jones (percussion), and a full brass and woodwind section
The last and most ambitious of the Gil Evans collaborations. Miles had been turned on to Joaquín Rodrigo's Concierto de Aranjuez and flamenco by his then-girlfriend Frances Taylor. The result is something close to a concerto for trumpet and jazz orchestra, with Evans arranging Spanish folk and classical material into vast orchestral panoramas that Miles improvises across.
The adagio from 'Concierto de Aranjuez' is the centrepiece, almost a literal transcription of Rodrigo's original but with the solo guitar line replaced by Miles's flugelhorn. He plays it with extraordinary restraint, letting the orchestration do most of the emotional work. 'Will O' the Wisp', adapted from Manuel de Falla's 'El amor brujo', is shorter and brighter. 'Saeta' recreates the processional music of Holy Week in Andalusia, with snare drum rolls and a trumpet line that sounds like a muezzin's call. 'Solea' closes the album with twelve minutes of slow flamenco-derived modal improvisation.
Evans's writing is the densest he ever did for Miles. There is no rhythm section in the conventional sense across most of the album. The whole orchestra is the rhythm section. Miles afterward said he had "nothing inside" of him when the sessions ended, which gives some sense of how much he poured into the playing. Sketches of Spain opened the door to a kind of cinematic jazz that no one had quite made before. Sixty-six years on, there's still nothing else that sounds like it.
9. 'Round About Midnight (Columbia, 1957)
Recorded: 26 October 1955 at Columbia Studio D; 5 June and 10 September 1956 at Columbia 30th Street Studio, New York
Released: 4 March 1957
Personnel: Miles Davis (trumpet), John Coltrane (tenor saxophone), Red Garland (piano), Paul Chambers (bass), Philly Joe Jones (drums)
This is the album where Miles introduces the First Great Quintet to a major-label audience. It is also the cover photograph that essentially invented the public image of Miles Davis, the trumpeter behind sunglasses, hands raised to mute the horn, swathed in red club light, all withdrawal and cool. The image and the music landed together in March 1957, and modern jazz had its first proper crossover star.
The title track is the version that turned a Thelonious Monk composition into a jazz standard. Miles's Harmon-muted reading of the melody, with its mournful arranging by Gil Evans, is one of the most recognisable performances in jazz. Coltrane comes in on tenor for the second chorus and the dynamic between the two horns, the muted introvert and the searching extrovert, becomes the template for everything they would do together. 'Ah-Leu-Cha' takes a Charlie Parker line at speed and lets the quintet show off its bebop chops. 'Bye Bye Blackbird' is the lighter side, the standard reworked at a strolling tempo with Miles in his most romantic mode.
The sound of this band, Garland's block chords behind Miles's spaces, Chambers walking with a singing tone, Philly Joe's rimshots on the back beat, would become the default texture of hard bop for years to come. 'Round About Midnight is where you can hear it being established. It is also where Miles's signature Columbia sound, recorded by Frank Laico at 30th Street, started to take shape. Hard bop's golden era effectively begins here.
8. Birth of the Cool (Capitol, 1957)
Recorded: 21 January 1949, 22 April 1949, 9 March 1950 at WOR Studios, New York
Released: February or March 1957
Personnel: Across the three sessions, Miles Davis (trumpet), Gerry Mulligan (baritone saxophone), Lee Konitz (alto saxophone) and Bill Barber (tuba) play on every date. Other contributors include Kai Winding and Jay Jay Johnson (trombone), Junior Collins, Sandy Siegelstein and Gunther Schuller (French horn), John Lewis and Al Haig (piano), Joe Shulman, Nelson Boyd and Al McKibbon (bass), Max Roach and Kenny Clarke (drums). Arrangements by Gil Evans, Gerry Mulligan, John Lewis and Johnny Carisi.
The sessions that became Birth of the Cool were recorded in 1949 and 1950 by a nine-piece band that played live exactly twice in its entire existence. Miles was twenty-two. The arrangements came out of the famous salons at Gil Evans's basement apartment behind a Chinese laundry on 55th Street, where Mulligan, John Lewis, Konitz and others gathered to figure out what an alternative to Charlie Parker's bebop might sound like. They built a small group with French horn and tuba and no drum solos, took the Claude Thornhill big band as their textural reference point, and made some of the most influential jazz recordings of the post-war era.
The compositions are tight, the arrangements are dense, and Miles's trumpet sits at the centre of an unusually voiced ensemble that gives him space to play short, melodic statements without the harmonic clutter of bebop chord changes. Lee Konitz's alto solo on 'Move' remains one of the freshest moments in early modern jazz, a player from outside the Parker school finding his own way through. Gerry Mulligan's baritone is the rhythmic and tonal anchor of the whole project.
The sessions were released piecemeal on 78s, gathered onto a 10-inch in 1954, and only collected as Birth of the Cool on a 12-inch LP in 1957, by which time the cool jazz movement they had helped create was a fully established West Coast scene. Miles never went back to this exact sound, but you can hear its DNA in everything Gil Evans wrote for him afterward, and in much of the modern jazz that has followed.
7. Porgy and Bess (Columbia, 1959)
Recorded: 22 and 29 July, 4 and 18 August 1958 at Columbia 30th Street Studio, New York
Released: March 1959
Personnel: Miles Davis (trumpet, flugelhorn), Gil Evans (arranger, conductor), with a large ensemble including Cannonball Adderley (alto saxophone), Paul Chambers (bass), Philly Joe Jones and Jimmy Cobb (drums), and a brass and woodwind section featuring Ernie Royal, Bernie Glow, Johnny Coles, Louis Mucci, Frank Rehak, Jimmy Cleveland, Gunther Schuller, Bill Barber and others
The middle of the three Gil Evans collaborations, and to my ear the most consistently extraordinary. Frances Taylor, Miles's wife, was performing in a New York production of George Gershwin's Porgy and Bess in 1958, and the Sam Goldwyn film adaptation was due the following year. Several jazz versions of the opera were being announced. Evans took the project and turned it into something none of the others approached.
His arrangements slow the harmonic motion of the original songs almost to a stop, leaving Miles with single modes to improvise across rather than the conventional chord changes Gershwin wrote. That is essentially the modal jazz that Kind of Blue would crystallise six months later. 'Summertime' is the most famous track, but 'Bess, You Is My Woman Now' and 'Gone' (a Gil Evans original built on Gershwin material) are deeper performances.
What you hear is the meeting of two musical sensibilities at full strength. Evans's orchestration is dark and lush, full of low brass and bass clarinet, with the rhythm section largely buried in service of the larger texture. Miles plays the melodies with extraordinary control, sometimes muted, sometimes on flugelhorn, always leaving more space than seems possible. Some critics call it the best of the Davis-Evans collaborations. I would not argue. It is also the album that made Kind of Blue possible, which is more than enough by itself.
6. The Complete Live at the Plugged Nickel 1965 (Columbia/Legacy, 1995)
Recorded: 22 to 23 December 1965 at the Plugged Nickel, Chicago
Released: First released complete in 1995 (a 1976 Japanese double LP, Live at the Plugged Nickel, contained a partial selection)
Personnel: Miles Davis (trumpet), Wayne Shorter (tenor saxophone), Herbie Hancock (piano), Ron Carter (bass), Tony Williams (drums)
Two nights in a Chicago jazz club, just before Christmas 1965, captured across seven sets by Columbia engineers without the band initially knowing the tape was running. The second great quintet had been touring the same standards for over a year, and Tony Williams, by then all of twenty, was bored. On the plane to Chicago he proposed to Wayne Shorter, Herbie Hancock and Ron Carter what he called "anti-music." Whatever any of them expected to play, they would play the opposite. They did not tell Miles. Herbie Hancock stated: "Some people have suggested that Tony was trying to sabotage the band by doing this, but really he was only trying to sabotage our comfort level, to break us open again. It was just another step in trying to push our boundaries as musicians and as a band."
What unfolds across the resulting seven hours is one of the most extraordinary live documents in jazz, the sound of four musicians actively trying to dismantle the music they have been hired to play, in real time, while the trumpet player whose name is on the marquee figures out what is happening and decides to ride it. Standard tunes the band had played a hundred times ('My Funny Valentine', 'Stella by Starlight', 'If I Were a Bell') are deconstructed and reassembled in ways that change from set to set. Two performances of the same tune the same night can sound like different compositions.
For decades only fragments circulated. A pair of Japanese LPs in the 1970s, a double album in 1982. The full 1995 box set, eight CDs across seven sets, is one of the great archival releases in jazz history. It catches Miles's trumpet not always at its strongest, since he had been recovering from hip surgery for most of that year, but it catches Shorter, Hancock, Carter and Williams at the absolute peak of their collective imagination. For me, the most exciting jazz performance ever committed to tape.
5. Milestones (Columbia, 1958)
Recorded: 4 February and 4 March 1958 at Columbia 30th Street Studio, New York
Released: 2 September 1958
Personnel: Miles Davis (trumpet, piano on Sid's Ahead), John Coltrane (tenor saxophone), Cannonball Adderley (alto saxophone), Red Garland (piano), Paul Chambers (bass), Philly Joe Jones (drums)
The first Miles Davis album with the full sextet, Cannonball Adderley having joined Coltrane in the front line in late 1957, and the album where modal jazz arrives in the catalogue. The title track is the moment. Built on just two scales it strips away the harmonic complexity of bebop and gives each soloist a wide-open framework to improvise across. Miles had been reading George Russell's Lydian Chromatic Concept. He had been thinking about getting away from the dense chord changes of contemporary jazz. Milestones, the composition, is where the thinking became music.
The rest of the album is hard bop at the height of its powers. 'Dr. Jackle' and 'Two Bass Hit' are fast, propulsive performances. 'Straight, No Chaser' is the Monk composition reimagined by a sextet that knew how to push it harder than any group before or since. 'Billy Boy' is a Red Garland trio feature, an old folk song turned into a piano vehicle. 'Sid's Ahead' is the one ballad-tempo track, and the only one where Miles plays piano, after Red Garland walked out of the session over an argument that history has not recorded.
This is the bridge between two eras. Coltrane and Adderley together on the front line, Garland and Philly Joe still in the rhythm section, all of them about to scatter into their own enormously consequential careers. And in the middle of it all, the title track that gave Miles the framework he would build the rest of the decade on. Milestones sometimes gets overshadowed by the album that came next. It should not.
4. Bitches Brew (Columbia, 1970)
Recorded: 19 to 21 August 1969 at Columbia Studio B, New York
Released: 30 March 1970
Personnel: Miles Davis (trumpet), Wayne Shorter (soprano saxophone), Bennie Maupin (bass clarinet), Chick Corea (electric piano), Joe Zawinul (electric piano), Larry Young (electric piano), John McLaughlin (electric guitar), Dave Holland (bass), Harvey Brooks (electric bass), Jack DeJohnette (drums), Lenny White (drums), Don Alias (drums, congas), Juma Santos (congas, shakers), Billy Cobham (drums on later overdubs), Airto Moreira (percussion)
Three days in August 1969, six weeks after Woodstock, in Columbia's Studio B. The record that came out of those sessions has done as much to shape the second half of the twentieth century in music as any single album in any genre. Miles assembled an absurdly large band, gave them tempo counts and chord hints and almost nothing else, and let the tape roll. What Teo Macero then did with the resulting hours of music, splicing, looping, repeating, building two LPs worth of material out of edited fragments, is as central to the album as anything the musicians played.
The title track is the strangest thing on the record, a 27-minute piece that surges between slow ambient sections and full-band crescendos, Miles often barely audible in the mix, the three electric pianos creating overlapping clusters of texture. 'Pharaoh's Dance' by Zawinul opens the album with twenty minutes of similar density. 'Spanish Key' and 'Miles Runs the Voodoo Down 'both lean harder into rock and funk rhythms, with John McLaughlin's guitar pushing in the direction of what he would soon do with Mahavishnu Orchestra.
The decision to put electricity at the centre of the music was the most contested thing he ever did. Jazz purists were horrified but younger audiences now found him via rock radio stations. The truth is that Bitches Brew is neither rock nor jazz in any conventional sense, but a new thing constructed in the studio out of long collective improvisation and aggressive editing. It is the founding document of fusion. It is the most physically present recording in Miles's catalogue. And it sits this high on the list because almost everything that has happened in jazz and adjacent music since 1970 has had to deal with it in one way or another.
3. A Tribute to Jack Johnson (Columbia, 1971)
Recorded: February to April 1970 at Columbia 30th Street Studio, New York
Released: 24 February 1971
Personnel: Miles Davis (trumpet), Steve Grossman (soprano saxophone), Bennie Maupin (bass clarinet), John McLaughlin (electric guitar), Sonny Sharrock (electric guitar), Herbie Hancock (organ), Chick Corea (electric piano), Michael Henderson (electric bass), Dave Holland (electric bass), Jack DeJohnette (drums), Billy Cobham (drums), with narration by Brock Peters
Conceived as a soundtrack for a Bill Cayton documentary about the first Black world heavyweight boxing champion, Jack Johnson turned into the toughest, most focused statement of Miles's electric period. Two side-long tracks, 'Right Off' and 'Yesternow', edited together from multiple sessions by Teo Macero, anchored by Michael Henderson's bass on 'Right Off' and built around John McLaughlin's guitar work on both.
The story of how 'Right Off' came together is now famous. McLaughlin was killing time in the studio waiting for Miles, started riffing on a boogie in E, Billy Cobham picked up the rhythm, Henderson joined on bass, and the take was running before Miles even walked in from the control room. When he did walk in, McLaughlin shifted to B flat, Miles raised his horn, and eight minutes of some of the most aggressive trumpet playing of his career poured out. Herbie Hancock got drafted in mid-take to play a Farfisa organ that was not even plugged in until an engineer noticed. It is one of the great accidental masterpieces in recorded music.
'Yesternow' is more abstract, looser in form, structured around a slightly modified version of the bassline from James Brown's Say It Loud, I'm Black and I'm Proud. It closes with Brock Peters reading a Jack Johnson speech as a kind of benediction. The whole album moves with an aggression and a forward momentum that Miles never quite captured in the studio again. He thought it was his best jazz-rock record. He was probably right. McLaughlin called it the moment Miles "wanted to play rock and roll," but that does the music a disservice. Jack Johnson is its own thing, harder than fusion, looser than funk, the sound of a band trying to keep up with one of the great trumpet performances of the late twentieth century.
2. In a Silent Way (Columbia, 1969)
Recorded: 18 February 1969 at CBS 30th Street Studio, New York
Released: 30 July 1969
Personnel: Miles Davis (trumpet), Wayne Shorter (soprano saxophone), Herbie Hancock (electric piano), Chick Corea (electric piano), Joe Zawinul (organ), John McLaughlin (electric guitar), Dave Holland (bass), Tony Williams (drums)
Recorded in a single session on 18 February 1969, In a Silent Way is the moment Miles plugs in for good. The session lasted three and a half hours. The musicians played what amounted to forty minutes of music, much of it loose and exploratory. Teo Macero then took the tapes and assembled the two side-long tracks that make up the album, editing repeated sections and looping passages in a way that had simply never been done in jazz before.
Joe Zawinul wrote the title track, a slow modal piece that Miles stripped down to an arrangement so spare it sounds almost weightless. McLaughlin had been in the US for less than two weeks when Miles called him for the session, and was so nervous he asked Miles what to do. Miles told him to play like he did not know how to play the guitar. The opening figure McLaughlin produced, a hesitant, single-note line shimmering against Tony Williams's hi-hat pulse, became one of the most quietly influential moments in modern music.
'It's About That Time', which follows the title track on side two and returns to it at the end, builds a deeper groove around a Wayne Shorter melody and Dave Holland's pulsing bassline. The whole album sits in a kind of suspended state, almost ambient, not quite jazz, not quite rock, definitely not what anyone had been making the previous year. In a Silent Way is where the editing room becomes part of the music. It is also one of the most beautiful records Miles ever made. Calm before the storm of Bitches Brew, certainly, but a calm worth living in.
1. Kind of Blue (Columbia, 1959)
Recorded: 2 March and 22 April 1959 at Columbia 30th Street Studio, New York
Released: 17 August 1959
Personnel: Miles Davis (trumpet), John Coltrane (tenor saxophone), Julian "Cannonball" Adderley (alto saxophone, omitted on Blue in Green), Bill Evans (piano on all tracks except Freddie Freeloader), Wynton Kelly (piano on Freddie Freeloader), Paul Chambers (bass), Jimmy Cobb (drums)
The most important jazz record ever made, and Miles's most important record by a margin. Two sessions, two months apart, in March and April 1959. Five tracks, almost no rehearsal. Miles gave the musicians sketches of scales rather than chord charts, walked them through the basic shapes, and rolled the tape.
'So What' opens the record with that quiet, two-note response from the horns answering the bass figure, then unfolds across nine minutes of Dorian modal improvisation that has informed practically every modal jazz solo recorded since. 'Freddie Freeloader' brings Wynton Kelly to the piano stool for a blues that grooves harder than anything else on the album. 'Blue in Green' is the ballad, a Bill Evans piano piece adapted as a sextet performance, six and a half minutes of melancholy that has somehow never lost its weight. 'All Blues' is the 6/8 modal blues that became a jazz standard within months of release. 'Flamenco Sketches' closes the record with five scales played in turn by each soloist for as long as they want, an act of trust that sounds spontaneous because it is.
Everything about Kind of Blue has been talked to death. It is the best-selling jazz record of all time. It is on more all-time greatest album lists than any other jazz record. Miles himself, in his autobiography, called it a failed experiment, because he had heard something different in his head before the sessions began. None of that has dimmed it. Put it on this evening and the first eight bars will sound exactly as fresh as they did the first time you heard it. Sixty-seven years after the fact, on the centenary of the trumpet player who made it, Kind of Blue is still the album. There is no other album that could be number one for me.
A century in, Miles Davis is the most fully realised musical life of the twentieth century. Cool jazz, hard bop, modal, third stream, the second quintet's post-bop, electric fusion, ambient, funk, hip hop. He invented much of it, influenced all of it and stayed mobile through every shift. The twenty records above are markers on that journey, not a definitive map. The catalogue is large enough that someone else's twenty would look quite different and would still be defensible.
What strikes me, returning to these records again to write this piece, is how present the man is in all of them. The aloofness he was famous for on stage is not in the music. The music is exposed, attentive, deeply felt. He spent fifty years figuring out how to play less, and how to make every note matter. We are unlikely to see a career like it again.
If anything here has sent you back to the records, or made you want to start a Miles collection from scratch, you can find what we currently have in stock at the Lush Life Records Miles Davis collection. Sometimes original Columbia six-eyes, vintage Japanese pressings for everything else, and a good selection of modern reissues across the period.
Happy hundredth, Miles.
