In the fall of 2009, I was forty-three years old and had never owned a jazz record. I don’t say this with any particular pride or shame. I say it because it’s the relevant fact for what comes next.
A colleague was cleaning out his office (he’d taken a job elsewhere) and left a stack of old records by the door with a sign that said “take what you want.” I took Saxophone Colossus because I liked the way Sonny Rollins looked on the cover. He had the posture of a man who had arrived somewhere and wasn’t going to explain it. I took it home to my study in Indianapolis, put it on at eleven at night while I was finishing a piece about pattern recognition in expert decision-making, and intended to not quite listen.
Rollins opened the album with “St. Thomas,” a calypso, absurdly cheerful, running at a tempo that seemed to be conducting a quiet argument with itself about whether to slow down. I didn’t finish my piece that night.
The next week, I went to a record store for the first time in probably fifteen years. A friend who had grown up on jazz told me to start with Kind of Blue. “That’s where everyone starts,” he said, with the authority of someone passing along received wisdom. I asked him: where did you start? “Kind of Blue,” he said. “Someone gave it to me.” I asked who told that person. He didn’t know.
That’s the question I’ve been thinking about for sixteen years.
Kind of Blue came out in August 1959. It has sold more than four million copies in the United States, which almost certainly makes it the best-selling jazz album in history. It has topped virtually every major critical list since at least the late 1980s. If you ask someone with a passing interest in jazz to name an album, they’ll name Kind of Blue. If they can name two, the second will probably be A Love Supreme. That’s the canon in two records, handed down with remarkable consistency.
This didn’t happen naturally. Canons never happen naturally.
In January 2001, Ken Burns’s documentary Jazz arrived on PBS, nineteen hours spread across ten episodes, the most comprehensive television treatment the music had ever received. The documentary organized jazz history around a specific set of heroes: Louis Armstrong, Duke Ellington, Charlie Parker, Miles Davis. It covered the first six decades of the form with considerable depth, and gave the music’s evolution after 1960, including free jazz, fusion, and the avant-garde, proportionally less space. The documentary had been shaped with the involvement of several prominent critics and musicians, Wynton Marsalis a prominent presence among them, and it carried a clear thesis about where jazz’s essential tradition resided.
A generation of listeners came to jazz through that documentary and through the wave of Blue Note reissues that had been reaching record stores since the early 1990s. They received a particular map of the territory. They were told, in effect, that Kind of Blue was the center. And they passed that along, the same way my friend passed it to me.
The same mechanism governs the books that last. A handful of titles get onto enough syllabuses, enough critical lists, enough “essential reading” compilations, and they achieve a kind of gravitational mass. The titles that arrive first become harder to question. People stop asking whether the ranking reflects reality and start treating it as given.
The question worth asking about jazz isn’t whether Kind of Blue belongs near the top. It does, and for real reasons. The question is what you miss if you stop there.
Kind of Blue is the right starting point for one specific and defensible reason: Miles Davis designed it to be accessible. He’d spent the late 1950s reading and thinking about music theory, including George Russell’s Lydian Chromatic Concept, which proposed organizing improvisation around scales rather than chord changes. The result was jazz that gave the players more room to search. Harmonic movement slows. The underlying scales are familiar. You can follow what each player is doing without years of bebop fluency.
What Kind of Blue teaches you is what space sounds like in music. Cannonball Adderley plays with a warmth that feels nearly conversational. Coltrane plays with a searching quality you can hear developing in real time. Bill Evans, who wrote the liner notes using an extended painter’s palette analogy, brings an impressionistic piano touch that makes the silences feel earned rather than accidental. The album doesn’t demand fluency. It rewards attention. That’s a genuine and uncommon achievement, and it explains why a forty-three-year-old who’d never owned a jazz record could sit with it for an hour and feel like he’d learned something true about how music works.
But Kind of Blue teaches you one thing about jazz. To understand what Davis was reacting against, you need to hear bebop at its most demanding.
Thelonious Monk’s Brilliant Corners, recorded for Riverside Records in 1956, sounds strange the first time and correct on the fourth. Monk wasn’t playing wrong notes. He was playing notes nobody else had thought to include, arriving at rhythmic displacements that felt like a sentence landing in exactly the right place through a route you hadn’t anticipated. His playing teaches you that jazz has a grammar and that the interesting musicians have internalized it well enough to break it deliberately. The break means nothing without the grammar. You can’t appreciate what Kind of Blue gave up to get its openness until you’ve heard what Monk could do with the constraints it removed.
John Coltrane’s A Love Supreme, recorded in a single session on December 9, 1964, with McCoy Tyner, Jimmy Garrison, and Elvin Jones, teaches something different: what happens when a musician finds a subject and refuses to approach it halfway. The album is a four-part suite, Acknowledgement, Resolution, Pursuance, Psalm, and Coltrane’s playing on the final movement, in which his horn traces the arc of a written prayer, is one of the stranger and more affecting pieces of music in the American tradition. You don’t have to share the spiritual intention to hear the commitment. The commitment is audible. A Love Supreme teaches you that jazz can carry weight the way a cathedral wall can.
Charles Mingus’s Mingus Ah Um, also from 1959, teaches you that jazz doesn’t have to be elegant. “Goodbye Pork Pie Hat,” a lament for Lester Young written in mourning after his death that March, is one of the most dignified pieces of grief I’ve heard in any form. “Better Git It in Your Soul” sounds like a congregation that decided the sermon wasn’t getting the job done. Mingus believed music should feel like something was at stake, and the best tracks on this record do feel that way. Not everything in the jazz canon is beautiful. Some of it is necessary, which is a different thing.
The conversation about the best jazz albums consistently undersells vocal jazz, which is where the canon has a genuine gap.
Billie Holiday’s Lady in Satin, recorded in 1958 near the end of her life, doesn’t ask you to forget what her voice once was. Ray Ellis’s orchestral arrangements give her wide space, and she sings through it with a diminished instrument and total command of what that diminishment means. Holiday’s phrasing, the way she moved behind and ahead of the beat, using the lyric as material to reshape rather than text to deliver, was the most sophisticated rhythmic intelligence in the American popular song tradition. Lady in Satin teaches you that phrasing is where the meaning lives. You understand something about musical time after listening to it that you didn’t understand before.
Sarah Vaughan with Clifford Brown, recorded in 1954 for EmArcy Records, teaches you something different: what jazz sounds like when two musicians of extraordinary technical command are working at the outer edge of what they can do. Vaughan’s range was exceptional, her control almost unsettling. Clifford Brown, who died in a car accident two years later at the age of twenty-five, plays with a confidence that has nothing to prove. The two of them together are an argument between equals about who gets to set the tempo of the conversation.
Ornette Coleman’s The Shape of Jazz to Come, recorded for Atlantic Records in 1959, is where a significant portion of the jazz establishment had its first serious argument about whether what Coleman was playing counted as jazz at all. He had dispensed with a piano player entirely. His quartet improvised collectively, without the harmonic center that bebop relied on. Critics called it chaos. Coleman said he’d removed the scaffolding to see what the building actually was. The album teaches you that the boundaries of any genre are imposed from outside, not discovered inside the music. If you sit with it long enough, The Shape of Jazz to Come doesn’t sound like chaos. It sounds like a different kind of order.
Two albums teach something I’d call the aesthetics of intimacy.
Bill Evans’s Waltz for Debby, recorded live at the Village Vanguard on June 25, 1961, with bassist Scott LaFaro and drummer Paul Motian, is what a small group sounds like when all three musicians are fully listening rather than performing. LaFaro, who died in a car accident less than two weeks after this session, was in the process of redefining what a bass player did, less keeping time, more entering the conversation as an equal voice. The album has a conversational quality that’s distinctive even among piano trio recordings. You can hear the audience between tracks, glasses, ambient noise, the room itself. The room is part of the record. Evans teaches you that jazz at its best isn’t performance. It’s thinking done in public.
Wayne Shorter’s Speak No Evil, recorded in December 1964 on Blue Note with Herbie Hancock, Ron Carter, Elvin Jones, and Freddie Hubbard, teaches you what post-bop looked like after the modal lessons of Kind of Blue had been absorbed and musicians were deciding what to do with them. Shorter’s compositions are built on unusual structures and his tenor saxophone has a quality that resists easy description. Searching is the closest I can get, like a writer who knows the thought but hasn’t found the sentence yet and is genuinely enjoying the looking.
And then there’s Bitches Brew. Miles Davis, recorded in August 1969, released the following year, the album that the jazz establishment spent most of the 1970s arguing about and that the Burns documentary gave comparatively limited treatment. Electric instruments, studio editing, rhythmic structures borrowed from rock and funk, running times that bear no relationship to anything bebop established. The album is difficult and occasionally uncomfortable and it is one of the most consequential records the form has produced. It teaches you that the tradition doesn’t end at any particular date. It keeps moving, and some of the people doing the most important work are the ones the canonical mapmakers weren’t quite ready for.
So does the consensus hold? Kind of Blue at the top, A Love Supreme not far behind?
In some respects, yes. They’re there for reasons that are real. They reward the attention you bring them. Kind of Blue remains the most elegant introduction to modal jazz ever recorded. A Love Supreme remains the most complete document of what it sounds like to bring total commitment to a piece of music. That’s not a small thing.
But the canon is also a set of choices made at a particular historical moment by particular people with particular convictions about what jazz’s essential tradition was. It reflects those convictions. It’s better at the 1950s than the 1970s. Better at New York than Los Angeles. Better at the acoustic small group than the electric ensemble. You can love the canon and still understand that treating it as a boundary rather than a starting point is the mistake.
The best jazz listeners I’ve met share one quality: they treat every album on the canonical list as a door, not a destination. Historical fiction works the same way, the recognized masterworks function as entrances into a territory that’s considerably larger than the assigned list suggests. The reader who stops at the titles they were handed has made the list into a wall.
Start with Kind of Blue. Follow wherever Coltrane leads you. Find out why Monk sounded wrong to people the first time they heard him, and why that wrongness has exactly the right shape. Sit with Lady in Satin long enough to hear what Holiday is doing with time.
Know that someone decided where you were supposed to start. The music itself doesn’t have a gate.
