A guided listen. Roughly three hours, in order, with the story attached.
There’s a problem with an artist like Miles Davis, and it isn’t that the music is hard. The problem is that there are about fifty studio albums, another seventy live and posthumous releases, and no obvious door. So most people put on Kind of Blue, agree that it’s beautiful, and stop there. Which is a bit like watching one quarter of one game and saying you know basketball.
This is the other way in. Nine eras, thirty tracks, in chronological order, with what was happening around the music at the time. Because the fun part is never just the notes, it’s that the piano player on the record had quit the band two months earlier and came back only for the session, or that the drummer was seventeen years old.
Three hours, give or take. You can do it in one sitting, but I’d spread it over a week, one era at a time, and go dig into any album that grabs you. That’s the whole point of ordering it this way.
Era 1: The kid who wasn’t Dizzy (1945 to 1948)
Miles arrives in New York in 1944, eighteen years old, son of a well-off dentist in East St. Louis. He enrolls at Juilliard, which was mostly the excuse. What he actually did was walk 52nd Street every night until he found Charlie Parker.
By 1945 he has Dizzy Gillespie’s chair in Parker’s quintet, and he isn’t ready for it. Dizzy played fast, high, and huge. Miles couldn’t do that, at least not then, and you can hear him know it. So he did the thing that ended up defining his entire career: he stopped trying to win on speed. He stayed in the middle register, played fewer notes, and left space. What started as a limitation became the sound.
Listen to:
- “Now’s the Time” - Charlie Parker, Savoy session, November 1945 (3:15)
- “Billie’s Bounce” - same session (3:10)
- “Embraceable You” - Charlie Parker, Dial, October 1947 (3:40)
What to listen for: a nervous, thin tone, and a nineteen-year-old thinking very hard about what to leave out. Keep this sound in your ear. In about fourteen years it becomes “So What.”
Era 2: Nine pieces and a Chinese laundry (1948 to 1950)
Gil Evans had a basement apartment on 55th Street, behind a Chinese laundry, one room, a bed and a piano and a cat. It became a salon. Gerry Mulligan, John Lewis, George Russell, and Miles all hung out there arguing about arrangement.
What came out of it was a nine-piece band with French horn and tuba, trying to get the orchestral colors of the Claude Thornhill band into something small enough to work a club. Miles fronted it, and he fought for the billing, a twenty-two-year-old Black trumpeter leading a mostly white band in 1948 and insisting his name go on the marquee.
The records sold badly. Then they got collected in 1957 as Birth of the Cool and turned out to have quietly launched the entire West Coast scene.
Listen to:
- “Move” - Birth of the Cool (3:15)
- “Boplicity” - Birth of the Cool (3:00)
- “Moon Dreams” - Birth of the Cool (3:20)
Backstory detail: “Boplicity” is credited to “Cleo Henry.” That was his mother’s name. The arrangement is Gil Evans, and it starts a partnership that runs another twenty years.
Era 3: The lost years, and the way back (1950 to 1955)
Then heroin. Four years of it, roughly 1949 to 1954. He pawned the horn, missed gigs, got fired, borrowed money from everyone he knew. Bird had gotten there first and Miles followed him in.
He got out of it the ugliest possible way. He went home to his father’s farm in Illinois, locked himself in a room, and came out clean about a week later. He described it afterward as lying there sweating with his knees pulled up.
What follows is one of the great returns. 1954 gives him Walkin’, which basically starts hard bop, and the Christmas Eve session with Thelonious Monk where Miles asked Monk not to play behind his solos. The rumor went around for decades that they’d had a fistfight in the studio. Miles always denied it. He said he just didn’t want piano under him, and Monk was too big a personality to comp politely.
Then Newport, July 1955. He walks on with an all-star pickup group, plays “‘Round Midnight” with the mute, and the room stops. Down Beat writes it up, Columbia signs him, and he’s back.
Listen to:
- “Walkin’” - Walkin’, 1954 (13:25)
- “Bags’ Groove (take 1)” - Bags’ Groove, 1954 (11:10)
What to listen for: on “Bags’ Groove,” the silence. Miles takes his solo with no piano behind him and it’s one of the most famous uses of empty space in recorded jazz.
Era 4: The First Great Quintet (1955 to 1957)
Miles wanted Sonny Rollins. Sonny wasn’t available. So he took a chance on an unknown tenor player from Philadelphia with a heroin problem of his own, named John Coltrane, and got laughed at for it. Critics thought Coltrane was stiff and graceless.
The band, with Red Garland, Paul Chambers and Philly Joe Jones, was in Miles’s opinion the best he ever had. He also owed Prestige four more albums before he could go to Columbia. So in two marathon days in 1956 they went into Rudy Van Gelder’s studio in New Jersey and played their club set almost live, no retakes, no second thoughts. That’s where Relaxin’, Workin’, Steamin’ and Cookin’ all come from. Four classic albums, two days, contractual obligation.
In 1957 he fired Coltrane for the drugs and the nodding off on stage. Coltrane went to Monk at the Five Spot, got clean, had the spiritual experience he later wrote about on A Love Supreme, and came back a different musician. Miles hired him right back.
Listen to:
- “If I Were a Bell” - Relaxin’, 1956 (8:15)
- “My Funny Valentine” - Cookin’, 1956 (5:57)
- “‘Round Midnight” - ‘Round About Midnight, 1957 (5:55)
Backstory detail: “If I Were a Bell” opens with Miles talking to Van Gelder in the booth, telling him he’ll play it and explain what it was afterward. They left it on the record. That’s how casual those sessions were.
What to listen for: the Harmon mute pressed right up against the microphone. Everybody imitates it now. He invented it.
Era 5: Miles and an orchestra (1957 to 1960)
Three albums with Gil Evans, and they’re a different animal from everything else here. Gil wrote for nineteen pieces as if the whole orchestra were one instrument, and Miles plays flugelhorn on much of it, warmer and rounder than the trumpet.
Sketches of Spain took months. It’s built on Joaquín Rodrigo’s Concierto de Aranjuez, and Miles said it was the hardest recording of his life, because for once the part was written out and he had to play what was on the page instead of inventing it.
Listen to:
- “The Duke” - Miles Ahead, 1957 (3:35)
- “Summertime” - Porgy and Bess, 1958 (3:20)
- “Concierto de Aranjuez (Adagio)” - Sketches of Spain, 1960 (16:19)
Give the Concierto the full sixteen minutes with nothing else going on. It’s the one track here that doesn’t work as background.
Era 6: Kind of Blue (1958 to 1959)
The sextet: Coltrane back, Cannonball Adderley on alto, Bill Evans on piano, Paul Chambers, Jimmy Cobb.
Bill Evans is the story here. He was the only white member of the band, he took abuse from audiences and some of it from inside the band too, and after eight months he quit, worn out. But his head was full of Ravel and Debussy, and that’s where the whole harmonic world of Kind of Blue comes from. Miles called him back just for the sessions.
Two days, March 2 and April 22, 1959, in Columbia’s 30th Street Studio, a converted Armenian church with famously enormous room sound. Miles handed everyone sketches on the day. Most of what you hear is a first or second take of music the musicians had just seen. It went on to become the best-selling jazz album ever made.
The idea underneath it: stop running chord changes, play on scales, give the soloist fewer places to go and more room to go there.
Listen to:
- “Milestones” - Milestones, 1958 (5:45)
- “So What” - Kind of Blue, 1959 (9:22)
- “Blue in Green” - Kind of Blue (5:37)
- “All Blues” - Kind of Blue (11:33)
Backstory detail: Bill Evans always maintained he wrote “Blue in Green.” The credit went to Miles. Later pressings added Evans. Listen to it knowing that and it sounds like an Evans tune with Miles on top, which it probably is.
Also: Wynton Kelly, not Evans, plays on “Freddie Freeloader.” Miles wanted a bluesier touch on that one and swapped pianists for a single track.
Era 7: The Second Great Quintet (1964 to 1968)
Herbie Hancock was twenty-three. Ron Carter was in his mid-twenties. Tony Williams was seventeen when he joined in 1963, and Miles called him the center of the band, the one everyone else was reacting to. Wayne Shorter arrived in 1964 from Art Blakey and immediately became the main composer.
What they built has a name Miles gave it himself: time, no changes. The tempo and the form are there, but they keep moving underneath the soloist, so nothing sits still. It’s the most collectively adventurous music he ever made, and it’s still recognizably a jazz band, which is why some people love this era more than Kind of Blue.
At the Plugged Nickel in Chicago, December 1965, Tony Williams talked the band into a pact to sabotage their own material every night, play the opposite of whatever was expected. Miles either didn’t notice or didn’t mind. The tapes are astonishing.
Listen to:
- “E.S.P.” - E.S.P., 1965 (5:27)
- “Footprints” - Miles Smiles, 1966 (9:46)
- “Nefertiti” - Nefertiti, 1967 (7:52)
What to listen for: on “Nefertiti,” the horns just play the melody over and over and never solo. The rhythm section does all the improvising. The roles are flipped, and nobody had really done that.
Era 8: Plugging in (1968 to 1975)
In 1968 he married Betty Mabry, a young singer and songwriter, twenty-three to his forty-two. She lasted about a year as his wife and changed everything. She played him Sly Stone and Jimi Hendrix, dragged him out of his suits and into what he wore for the rest of his life, and put the idea in his head that jazz was about to be left behind by his own audience. She’s on the cover of Filles de Kilimanjaro.
In a Silent Way in 1969 is the pivot. Joe Zawinul brought in a composition, Miles crossed most of it out and kept one chord. Three keyboard players, John McLaughlin on guitar, and producer Teo Macero assembling the final record out of tape edits, which is a rock and pop technique, not a jazz one.
Bitches Brew was recorded three days after Woodstock ended and sold in numbers no jazz record was supposed to sell. A large part of the jazz world treated it as a betrayal. Then On the Corner in 1972, aimed squarely at young Black listeners, got some of the worst reviews of his career and is now cited by half of drum and bass.
Listen to:
- “In a Silent Way / It’s About That Time” - In a Silent Way, 1969 (19:52)
- “Miles Runs the Voodoo Down” - Bitches Brew, 1970 (14:01)
- “Right Off” - A Tribute to Jack Johnson, 1971 (26:53)
- “Black Satin” - On the Corner, 1972 (5:16)
Backstory detail: “Right Off” is an accident. McLaughlin was messing around in E while they waited, Michael Henderson locked in on bass, Billy Cobham followed, and Miles came sprinting out of the control room with the horn already up. That’s the take. Miles was a boxer and a lifelong fight fan, and this is his boxing record.
If you’re short on time, take the first ten minutes of “Right Off” and move on. Nobody will know.
Era 9: Silence, then the comeback (1975 to 1991)
He stopped. From 1975 to 1980 he barely left the brownstone on West 77th, in pain from his hip, deep into cocaine, not touching the trumpet for years at a stretch.
He came back in 1981, and the late period splits opinion harder than anything else he did. The bands were young and funk-based, Marcus Miller and John Scofield among them. He played Cyndi Lauper’s “Time After Time” and Michael Jackson’s “Human Nature” in concert, and when critics complained he pointed out that those were simply the standards of the moment, no different from playing a show tune in 1955.
Tutu in 1986 is almost entirely Marcus Miller: he wrote it, played most of it, programmed it. Miles is a voice laid over a produced track, and it works because the voice by then is unmistakable in two notes.
At Montreux in July 1991, with Quincy Jones conducting, he played the old Gil Evans arrangements for the first time in thirty years. He’d refused to look backward his entire life. He died two months later, on September 28, 1991.
Listen to:
- “Time After Time” - You’re Under Arrest, 1985 (3:38)
- “Human Nature” - You’re Under Arrest, 1985 (4:30)
- “Tutu” - Tutu, 1986 (5:14)
- “Portia” - Tutu, 1986 (6:15)
- “Boplicity” - Miles & Quincy Live at Montreux, 1993 (3:40)
End on that last one. It’s the same arrangement from the laundry-basement nonet in 1949, played by a sixty-five-year-old man two months from death. Put the 1949 “Boplicity” on right after it.
The short version, if you only have an hour
“Boplicity” (1949), “Bags’ Groove” (1954), “‘Round Midnight” (1957), “So What” (1959), “Nefertiti” (1967), “Miles Runs the Voodoo Down” (1970), “Tutu” (1986).
Seven tracks, forty years, and you can hear him become four or five different musicians.
Where to go next
If Era 4 or 6 was the one, go to Coltrane’s own records and start with Blue Train and A Love Supreme. If Era 7 got you, follow Wayne Shorter to Speak No Evil and Herbie Hancock to Maiden Voyage. If Era 8 did it, go to Weather Report, Mahavishnu Orchestra, and Herbie’s Head Hunters, which are all run by people who were in those rooms.
Next in this series: Louis Armstrong, who is the reason any of this exists.
This guide was written by Nova, my AI assistant, from an idea and an outline that are mine. I’m not going to pretend otherwise. The listening is all yours.