Kind of Blue sold more copies than any other jazz album ever made. It continues to sell. It was recorded in 1959, appeared on countless year-end lists in 2024, and will be recommended to first-time jazz listeners for as long as people listen to music.

Its ubiquity is deserved. It is a great record: spacious, melodic, and constructed from an approach — modal improvisation rather than chord-change-based improvisation — that makes it more accessible to the first-time listener than almost any jazz of equal quality.

The problem is that many listeners hear Kind of Blue and treat it as the destination rather than the entrance. The musicians who made it — Miles Davis, John Coltrane, Bill Evans, Cannonball Adderley, Paul Chambers, Jimmy Cobb — went on to make other records just as good. Some of those records are more demanding. All of them reward the listener who arrives at them through Kind of Blue.

Follow the Sidemen

The most direct path from Kind of Blue is to follow the musicians who played on it into their own work.

Bill Evans heard something in the modal approach that he took in a different direction from Miles. Where Miles used modes to create spaciousness and rest, Evans used them as a starting point for a more intimate kind of harmonic exploration — one that drew as much from the classical piano tradition as from jazz. Portrait in Jazz (1960), recorded right after the Kind of Blue sessions with Scott LaFaro on bass and Paul Motian on drums, is the best starting point: a trio record that shows Evans’s approach in full development.

John Coltrane took the modal vocabulary of Kind of Blue and pushed it further and further until it broke. The arc from Kind of Blue through My Favorite Things (1961) to A Love Supreme (1964) to Ascension (1965) is the most concentrated development in any individual jazz musician’s recorded history. My Favorite Things is the most accessible next step; the soprano saxophone version of the Rodgers and Hammerstein standard introduced a quality of sustained intensity that is different from Kind of Blue but grows directly from it.

Cannonball Adderley took the modal vocabulary back toward the blues and gospel roots that hard bop had developed from. Somethin’ Else (1958, recorded before Kind of Blue but released after) is the essential Adderley record — Miles Davis appears as a sideman, inverting the usual dynamic.

Stay with Miles

Miles himself made records after Kind of Blue that extend the modal approach in different directions.

Sketches of Spain (1960), with arranger Gil Evans, applies modal thinking to an orchestral context — Miles plays against elaborate arrangements that use Spanish folk music as their modal source material. It is slow and strange and very beautiful.

Kind of Blue was the high-water mark of the first great quintet. The Prestige sessions from 1956 — Cookin’, Relaxin’, Workin’, Steamin’ — document the same quintet with Coltrane, Red Garland, Paul Chambers, and Philly Joe Jones in a harder-swinging, more blues-rooted mode. They show you what Kind of Blue grew out of.

Make a Wider Turn

Kind of Blue emerged from a specific moment in jazz — the late 1950s, when bebop had been established for a decade and musicians were looking for what came next. Understanding that moment more broadly means hearing the other records that surrounded it.

Thelonious Monk’s Trio recordings — particularly the Prestige sessions from the early 1950s — show the harmonic audacity that made Kind of Blue’s modal simplicity possible: Monk’s approach to the piano was so idiosyncratic that it cleared a space for the more spacious playing that followed.

Charles Mingus’s The Black Saint and the Sinner Lady (1963) and Mingus Ah Um (1959) show what a composer-bandleader was doing with jazz at the same moment Miles was recording Kind of Blue — denser, more complex, more explicitly rooted in the African American musical tradition.

Sonny Rollins’s Saxophone Colossus (1956) offers a different kind of development from Kind of Blue: formal rigour through thematic improvisation rather than through modal spaciousness. The two records represent different solutions to the same question of how improvisation can achieve structural coherence.

What Lies Beyond

The further you follow any of these paths, the stranger the music becomes. Coltrane’s late work, after A Love Supreme, is genuinely difficult. Ornette Coleman’s free jazz — which was developing at exactly the same moment as Kind of Blue and in direct conversation with it — requires different listening skills than anything on that album.

The strangeness is not a barrier. It is an invitation. The musicians who made Kind of Blue were working at the edge of what was possible. The music they made in the years after it pushed further. Following them is the most rewarding thing a jazz listener can do.