The name Miles Davis is synonymous with cool, creative and visionary. If you’re only familiar in passing, you might wonder why. Miles made a name with his emotive yet un-frilled trumpet sound, but he was more like the conductor of an orchestra than the lead singer of a band. His remarkable ability to bring the best performances out of stellar up-and-coming musicians allowed his fruitful recording career to last nearly half a century. His sound changed so many times that you might not even recognize the 1949 and 1991 Miles as the same musician.

I’ve picked out 16 classic tracks that chronicle Miles’s journey from bebop to cool jazz, avant-garde, rock fusion and beyond. The songs from this list are all available on this Spotify playlist.

Roadmap

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1. Move (from Birth of the Cool, 1949)

This track comes from Miles’s first official recording date as a band leader, in January of 1949. Big band instrumentation was a staple in jazz at this time following the success of composers like Count Basie, Duke Ellington, and Claude Thornhill. While Miles deliberately selected a smaller group for these sessions than what was in vogue, nine instruments is still a large jazz ensemble by today’s standards.

This sprightly and upbeat track is both faster and shorter than most of what follows on this list. It represents a transition point from the uptempo and danceable bebop jazz that came before to a slower and more thoughtful “cool” jazz that Miles ushered in. Young Miles’s solo at 0:35 is lyrical, but busier and more tentative than his later playing.

This and many pieces on this list follow the traditional head-solo-head format of jazz: the players introduce a main melody (the ‘head’), then take turns improvising solos before restating the head in the end.

The head that starts 7 seconds into this piece uses paired instrumentation: Miles’s trumpet and the alto sax double as the main melody on top, a countermelody from the baritone sax and tuba lurches across the bottom, and harmony from the French horn and trombone float in the middle. After a series of quick solos, the ensemble regroups at 1:30 to play a unison melody that cues a drum solo in response. The whole thing is over in less than 3 minutes.

2. Round Midnight (from ‘Round About Midnight, 1957)

The title track of Miles’s first recording with Columbia records introduced him to a wider audience and culminated a comeback from Miles’s heroin addiction in the early 1950s. Moving away from the big band sound, we can hear in detail each musician of Miles’s first classic quintet: John Coltrane (sax), Red Garland (piano), Paul Chambers (bass) and Philly Joe Jones (drums). The pensive whispering of Miles’s muted trumpet sets a candlelit tone for Thelonius Monk’s standard, while Coltrane’s solo at 2:55 injects a jolt of energy into the recording.

3. The Duke (from Miles Ahead, 1957)

The big band arrangement harkens back to the sound we heard in “Move”, and every instrument is more clearly audible thanks to improved recording quality. The tempo has slowed down and there is a greater sense of space in the music.

Miles’s own voice sounds more confident after years of professional band leading. He takes time to breathe, rather than rushing from one note to the next. The pauses between phrases of the main theme which starts at 0:23 are as important as the notes themselves. My favorite part of this piece is how the tuba answers the melody while the orchestra builds up to the theme in the beginning.

This tune was originally penned by Dave Brubeck, presumably as a tribute to big band composer Duke Ellington. The album was the first of what would be a fruitful series of official collaborations between conductor and arranger Gil Evans (who was also involved in Birth of the Cool, #1 on this list).

4. Milestones (from Milestones, 1958)

This track jumps out of the speakers with a crisp up-tempo beat you can snap your fingers too. The head is more about rhythm than melody: the horns peck out a staccato figure emphasizing the downbeats before Miles breaks away to engage in a syncopated tug-of-war with the saxophones.

Appropriately titled, this piece made history by introducing listeners to modal jazz. Skipping the technicalities, the effect of modal jazz was to make jazz musicians less confined to a certain melody or timed sequence of chord changes and give them more freedom to improvise around a theme. Comparing this bright and uptempo tune to the previous selections on this list, you should hear a more open and playful quality to the solos. Miles would continue using this modal approach to great success going forward.

5. So What (from Kind of Blue, 1959)

The modal jazz approach trialed in Milestones (#4 on this list) payed dividends on this record, as Miles, John Coltrane and Cannonball Adderly soar with lyricism and a newfound ease over a moderate tempo. Pianist Bill Evans leads us in. His delicate and classical-infused touch are a big part of the album’s success, and lovers of this music should also check out 1962’s Waltz for Debby. The solos are full of excitement, but the mood is fundamentally laid back and unhurried, the spirit of cool jazz. There is plenty of open space and not one nervous sound on the record. It’s music you can devote your full attention to or play in the background while working or socializing.

These pieces would stay in Miles’s live sets for most of the next decade, and inspire musicians for generations to come.

6. Concierto de Aranjuez: Adagio (from Sketches of Spain, 1960)

Got 15 minutes and a glass of tinto in your hand? Dim the lights and follow the fluttering harp notes, delicate clacking of castanets and gentle chorus of flutes onto the plains of old Andalusia. Miles enters like a proud bullfighter to state the melody on Fugelhorn after a minute. “The softer you play it, the stronger it gets, and the stronger you play it, the weaker it gets,” Miles said of the melody. Soft or strong, his unmuted and vibrato-less playing is bold, resonant and masculine.

The music slowly gets jazzier as a brush beat creeps in around 3:45, leading to a dramatic restatement of the melody around 4:35. The piece floats on for another ten+ minutes through peaks and valleys of intensity. Miles uses a mute for shimmering and mysterious passages like 9:45. Flutes, trumpets, french horns and clarinets among other instruments rise to prominence in the accompaniment as conductor/arranger Gil Evans keeps splashing new hues of paint onto the orchestral canvas.

I remember first discovering this record in my parents’ collection in high school and assuming the white marks of faded paint were real physical wear on the sleeve, until my friend got a CD with the same fading. The design certainly fits the rugged, vintage beauty of the music inside.

While Miles and Gil Evans made one more album together after this, a poorly reviewed collection of bossa nova covers, Sketches of Spain and this piece in particular was the height of their jazz orchestra experimentation.

7. Someday My Prince Will Come (from Someday My Prince Will Come, 1961)

This song arguably doesn’t show much musical growth from Miles since Kind of Blue, but it’s too gorgeous not to include. The intro’s cinematic ambience recalls “‘Round Midnight”. A tinkling cymbal gives way to brush strokes, tender piano and one repeated bass note until Miles enters with the melody, taken from Disney’s Snow White and the Seven Dwarves. Miles’s trumpet is muted but warm, with Wynton Kelly’s piano introducing just a hint of blues underneath. Drummer Jimmy Cobb trades the brushes for sticks and picks up the volume as Hank Mobley’s sax solo begins around 3:10.

This beautiful recording full of lyrical solos is one of Miles’s last forays in traditional cool jazz, the kind of jazz you might put on for casual or romantic ambience. Within a few years, he’d form a new group looking to stretch jazz’s boundaries once again.

Fun fact: This album’s cover is the first of several to feature a black woman, Miles’s wife at the time Frances Taylor. Miles had previously rejected the record company’s proposed album cover showing a white woman sailing in 1957, so this choice represented increased autonomy over the presentation of his art.

8. Footprints (from Miles Smiles, 1967)

You can’t tell the story of Miles Davis without Wayne Shorter. He authored this and numerous other compositions stretched to abstract frontiers by Miles’s 2nd great quintet of Shorter (sax), Herbie Hancock (piano), Ron Carter (bass) and Tony Williams (drums).

The acoustic lineup still follows the head-solo-head format, but there’s an almost rock-like intensity to the proceedings. This isn’t background music to snap your fingers to while having a candlelight conversation; it demands your full attention.

The five-note bass line, ending in an unexpected high note, is as crucial to the piece as the horns’ melody. The head paints a mysterious aura, like a bird quietly taking flight, but Miles kicks up the excitement and ignites a quicker tempo from the moment he starts his solo around 1:10. Compared with “So What” (#5) or “Someday My Prince Will Come” (#7), Miles’s playing is faster and more aggressive.

The speed and aggression is matched by Tony Williams’ activity on the drum set. Williams was just 17 when he joined Miles’s band a couple years earlier, and his chops and creativity pushed the music to more adventurous places. Having grown complacent, Miles began practicing harder after Williams joined, according to his autobiography. Notice how much quicker a tempo the cymbals set than the previous pieces on this list; they race forward rather than swing. Williams’ echoing tom toms during the solos give the piece a slightly bossa nova feel. The solos finally yield to a drum breakdown around 8:40, as if the music has boiled so hot that Williams needs to press the release valves before the band can settle back into the gentle melody it began with.

9. Nefertiti (from Nefertiti, 1968)

This Wayne Shorter composition flips the roles of horns and rhythm section in jazz. Traditionally the trumpet and sax solo, accompanied by piano, bass and drums; here the horns repeat a constant melody as the piano, bass and drums stretch out and improvise. The track epitomizes Miles’s ability to get novel performances out of his musicians and is a master class in telling the same story in endlessly different ways. Miles plays trumpet, but his real instrument here is the jazz quintet itself.

10. Frelon brun (from Filles de Kilimanjaro, 1968)

On Miles’s last album with a traditional jazz quintet, you can hear the musicians striving for something new. Chick Corea’s latin-tinged electric keyboard subtly pulls the music away from jazz past and towards the sounds of contemporary pop and rock music, which Miles had been increasingly exposed to by his new girlfriend Betty Mabry (pictured on the album cover).

Nobody’s presence is stronger on this track than Tony Williams. You can listen to it as a five-minute drum solo despite the head-solo-head structure still being followed by the rest of the band. The frantic drumming signals a breakaway from conventions of jazz rhythm like swing beats or brush strokes in favor of driving rock pulses. Similar to Nefertiti (#9), it portends an increasing role for percussion in Miles’s music, including the use of multiple drummers and percussionists over the next decade.

11. Shhh/Peaceful (from In a Silent Way, 1969)

Miles’s first fully electric album is a soother rather than a shocker, immersing the listener in a contemplative atmosphere better accompanied by a cup of tea than a cocktail.

The track opens with the distant sound of an organ warming up. A few seconds later, we’re off on a sleigh ride, whizzing past tinkling keys from Chick Corea, the warm tone of a Fender Rhodes from Herbie Hancock, and Joe Zawinul’s lush organ. Tony Williams is the sled driver, holding the hi-hats as his reins and anchoring the rhythm in Dave Holland’s hypnotic two-note bass line. Listen as they lead us back in from a pause before Miles states the theme after 1:30. The music is in perpetual motion despite feeling relaxed and meditative.

Miles’s own playing is blissful and rich as ever. He slowly whips the band into heightened activity without straining himself or losing his cool, stirring ripples in the water rather than provoking a full-on storm.

The track is full of subtly sublime performances. John McLaughlin wrings some deep melancholy out of his guitar at 6:00 before the sleigh ride picks up the pace. Wayne Shorter’s sax solo around 9:10 is so unhurried and seamless it sounds like a feather floating down from the sky.

This track is also where Miles and producer Teo Macero began restructuring the music through tape edits. Around 12:00, an edit returns us to the same few minutes that opened the piece. The result is a sonata format, where a theme is stated in the beginning and repeated in the end after going through a lengthy development section.

12. Pharaoh’s Dance (from Bitches Brew, 1970)

While the previous album indicated the same shift in a quiet if not fully silent way, Bitches Brew boldly announced electric Miles’s new direction to the world. Jazz, rock, funk, Latin and African music and more are thrown into the cauldron and brewed into a music never heard before. This landmark double album lost Miles some traditional jazz fans, but the crossover between genres welcomed a new generation of listeners and opened the door to sounds he’d continue exploring over the next half decade. It was the album that first got me, a progressive rock fan in high school, interested in Miles Davis and jazz in general.

Any notion of head-solo-head or even sonata format is abandoned. There is no single melody to characterize the song, but the track doesn’t feel aimless either. The recordings are taken from extended jam sessions cut up by Miles and producer Teo Macero to sculpt a structure out of the jamming. For example, at 1:39 you can hear the tape jump back to the same tinkling keyboards from the very beginning. Miles enters after two and half minutes as the momentum begins to build. He sounds strong and unmuted, leading the band into new territory and signaling changes in dynamics, like in his solo at 9:05.

The sound is busy, with more musicians in the house than any previous Miles record except the orchestral collaborations. Three keyboards swirl through the mix, taking turns leading and following the soloists. Jack DeJohnette, heard in the right speaker, drums at double the tempo of Lenny White in the left for most of the piece. Augmented by congas and a handheld shaker, the percussion collective gives the music a simultaneously rocking and funky feel. This many doubled or tripled musicians might easily get in each other’s way or play tentatively for fear of doing so, but thanks to clear recording and even better musical vision, each player comfortably runs in his own lane without cluttering the overall sound.

Bennie Maupin’s bass clarinet, sounding like a croaking frog, adds a bizarre dimension to the track. You can hear him take the spotlight around 5:40. John McLaughlin’s guitar plays call and response with the other instruments throughout the piece. His presence reflects Miles’s newfound interest in rock music at the time (especially Jimi Hendrix and Carlos Santana). Wayne Shorter makes some of my favorite entrances to his sax solos. The way he weaves himself to the forefront at 11:48 could be the soundtrack to arriving on a distant new planet in a Star Wars movie.

Listen closely and you can hear both acoustic and electric bass in this piece. A good place to distinguish them is at 16:30, when Dave Holland begins ascending runs on acoustic bass while Harvey Brooks anchors the rhythm by repeating a single note on electric bass. Miles leads a triumphant crescendo from there that concludes this wild opening track.

Fun fact: The same Harvey Brooks also plays electric bass on Bob Dylan’s Highway 61 Revisited.

13. On the Corner / New York Girl / Thinkin’ of One Thing and Doin’ Another / Vote for Miles (from On the Corner, 1972)

Even some fans of Bitches Brew threw their hands up and walked away after hearing this. About as far “out there” as Miles ever pushed the fusion envelope, the opening track attacks from the moment you press play. The keyboards clomp like elephant hooves as a Sisyphean succession of 16th notes on the hi-hat run headlong into a snare crack. Listen deeper to the rhythm section and you’ll hear Indian tablas spinning a polyrhythm around African congas. All of it anchored to an oozing bass pulse.

Miles initially limits himself to high pitched syncopated yelps; he doesn’t play a melody until his solo around the 7-minute mark. He had recently undergone hip surgery and was in much physical pain at the time. He sounds anguished, and his tone is clamped and metallic instead of open and booming. He shrieks and rants rather than singing with his trumpet. John McLaughlin’s angry bird guitar solo around 2:55 has always been a personal highlight. I hear the influence of the sitar in McLaughlin’s cadence and the way he accents notes, which makes sense given his lengthy involvement in Indian music.

Miles cited the funk of James Brown and Sly Stone, German composer Karlheinz Stockhausen, free jazz pioneer Ornette Coleman, and cellist/producer Paul Buckmaster as influences on this album. I find something new to pay attention to nearly every time I listen. Over 50 years later, has anyone else on any planet made music that sounds like this?

14. Prelude (Part 1) (from Agharta, 1975)

The opening rhythm makes clear that you’re not hearing a traditional jazz album. Conga drums play a similar role as in “On the Corner” (#13) or “Pharaoh’s Dance” (#12), but the beat they augment is thrashing rock, locked in tandem with wah-wah guitar. You’re more likely to bang your head to this muscular music than snap your fingers to it, or you can just let yourself be hypnotized by the dense rhythm.

Miles is first heard on organ rather than trumpet as the director of this fusion orchestra. That’s him when the rest of the band abruptly stops around 1:35. When he does pick up his trumpet, his sound is shrill, penetrating and abrasive. Miles was flailing in his personal life at this point, getting ready to enter a 5-year cocaine and alcohol-fueled hiatus shortly after this live performance. But that shouldn’t take away from the scorching brilliance of the music, which belongs in the same category as the most adventurous of 70s progressive rock.

Fun fact 1: You’re hearing James Mtume on percussion, the same Mtume who’d have a hit pop song “Juicy Fruit” in 1983, a song which became even more famous after it was sampled for the Notorious B.I.G.’s rap hit “Juicy” in 1994.

Fun fact 2: You’re hearing Reggie Lucas on rhythm guitar, who’d go on to produce Madonna’s 1983 debut album.

15. Fat Time (from The Man with the Horn, 1981)

A sauntering slap bass could be the soundtrack to Seinfeld, but this one is the sound of Miles’s comeback.

The world wasn’t the same when Miles returned from retirement in the 1980s, and neither was he. We can hear the 80s in the hip-hop aware pop beat and glitzy textures of the guitar and bass. After allegedly not touching a trumpet for five years, Miles himself sounds weaker than before, but is unafraid to immediately put himself at the center of the mix.

Miles’s comeback received much criticism for emulating the sounds of 80s pop. He responded that this was no different from a jazz player of the 1940s or 50s performing popular standards and styles of that era. Make no mistake: the music also ventures into Spanish keys, atmospheric effects, and face-melting intensity that set it apart from any typical pop radio fare of the time.

And how about Miles’s squawk to end the track?

16. Mystery (from Doo Bop, 1992)

Miles never stopped keeping up with the times. His posthumously-released final studio album is a collaboration with hip-hop producer Easy Mo Bee. Some songs include actual rapping, but I find them a bit too cringey to share. This piece is borderline electronica, the kind of song you’d be more likely to hear in a night club than a jazz lounge. There is a loose head-solo-head structure, with Miles as the only soloist.

Rhythmically, what you hear at the very start of the track is what you get for the rest of it: an electronic beat on loop accompanied by low keyboard chords and synthesizer effects. The atmosphere is dreamlike, like sleepwalking or flying by night over an urban landscape. Miles’s muted trumpet sounds tinny but still lyrical.

This track lacks the organic chemistry of a jam between live musicians, but Miles should be applauded for always trying to do things differently rather than rest on his laurels. R.I.P.

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If Miles Davis were still making music today, what would it sound like?