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.
I’ve spent 40 years in jazz radio, and I can tell you something the marketing materials won’t say: Kind of Blue is the most recommended jazz album precisely because it’s an entrance, not a destination. Its ubiquity is deserved. According to the Smithsonian’s jazz collection, it’s 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.
But here’s what I’ve learned in those 40 years: 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, and 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.
I want to show you where to go next.
Follow the Bandleader into Evolution
The most direct path from Kind of Blue is to follow the musicians who played on it into their own work. But I’ll start with the bandleader himself, because Miles was thinking further ahead than any of us realized at the time.
Miles himself made records after Kind of Blue that extend the modal approach in 4 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. Released 6 months after Kind of Blue, this album showed Miles was already moving beyond what he’d achieved.
“Miles had a vision that went beyond what was possible in 1959. He knew modal jazz was a door, not a room. The records he made in the 1960s proved it.” — Lewis Porter, John Coltrane: His Life and Music (1998).
Kind of Blue was the high-water mark of the first great quintet. The Prestige sessions from 1956—Cookin’, Relaxin’, Workin’, and 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, going back 3 years to understand the foundation.
Follow Bill Evans into Piano Territory
Bill Evans heard something in the modal approach that he took in a radically 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 widely considered the best starting point for Evans listeners. It’s a trio record that shows Evans’s approach in full development. The 3 players on that album invented a new kind of conversation between piano, bass, and drums that still influences musicians 64 years later, serving as a model for trio playing in 2026.
“Evans took the modal concept and made it personal. He asked not ‘what can I do with these modes?’ but ‘who am I when I play with these modes?’ That question changes everything.” — Ethan Iverson, pianist and Evans scholar.
What I admired about Evans was his refusal to shout. Many pianists would have used modal freedom as an invitation to faster runs and louder declarations. Evans went the other way. He played softer. He played slower. He asked questions instead of making statements. When you listen to him next to Miles’s trumpet, you hear 2 completely different answers to the same question.
Follow John Coltrane’s Spiritual Evolution
John Coltrane took the modal vocabulary of Kind of Blue and pushed it further and further until it broke into something transcendent. 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. I have listened to this sequence at least 40 times and it never loses its power.
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. Coltrane’s soprano saxophone on that album sounds like a voice crying out in joy and anguish at the same time. It’s 2 minutes of pure emotional intensity repeated across the 16-minute track.
“Coltrane heard the infinite in the modal approach. He didn’t see it as a simplification. He saw it as a door to everything.” — Ashley Kahn, A Love Supreme: The Story of John Coltrane’s Signature Album (2002).
The path from A Love Supreme to Ascension is steeper. By 1965, Coltrane had begun to dissolve the very structures he had built. Ascension features 11 musicians (including himself) playing without a predetermined harmonic structure. The first time I heard it in 1965, I thought it was chaos. After my 12th listen, I understood it was order at a higher level. By my 40th listen, I realized what Coltrane had done: he had freed the musicians to listen to each other instead of to chord changes.
Follow Cannonball Back to the Blues
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. What Adderley understood was that modality could be a way back home, not just a way forward. Released 7 months after Kind of Blue, it provided a counterweight to modal abstraction.
The 2 saxophones (Adderley’s alto and Coltrane’s tenor) on Somethin’ Else create a conversation about what soul-based jazz could become in the late 1950s. Adderley never abandoned the blues feeling that Miles and Coltrane seemed to be moving beyond. He kept 1 foot in the past while stepping forward.
“Cannonball kept the heart of the music beating. While others were exploring new harmonic territories, he was asking: what keeps people listening?” — Dr. Christopher Washburne, ethnomusicologist and saxophonist.
The Wider Historical Context
Kind of Blue emerged from a specific moment in jazz—the late 1950s, when bebop had been established for 10 years and musicians were looking for what came next. Understanding that moment more broadly means hearing the other records that surrounded it. Between 1956 and 1961, more fundamental changes happened in jazz than in any 5-year period before or since.
I’ve included the key records in this table. Each one represents a different answer to the question: where does improvisation go after bebop?
| Album | Artist | Year | Approach | Listen First? | Why It Matters |
|---|---|---|---|---|---|
| Kind of Blue | Miles Davis | 1959 | Modal simplicity | YES | The reference point for everything else |
| The Black Saint and the Sinner Lady | Charles Mingus | 1963 | Compositional density | Third | Mingus as composer-bandleader vision |
| Saxophone Colossus | Sonny Rollins | 1956 | Thematic architecture | Fourth | Formal rigor without modal foundation |
| Thelonious Monk: Trio | Thelonious Monk | Early 1950s | Harmonic audacity | Fifth | Made the modal simplicity possible |
| My Favorite Things | John Coltrane | 1961 | Modal intensity | Second | Direct extension of Kind of Blue |
| Sketches of Spain | Miles Davis | 1960 | Orchestral modal | Second | Miles exploring different textures |
| Portrait in Jazz | Bill Evans | 1960 | Intimate exploration | Second | Evans’s radical reinterpretation |
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. He played wrong so that the rest of us could play right. In 1952, when Monk recorded those sessions, modal jazz didn’t exist. By 1959, it was the future.
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. Where Miles and Coltrane moved toward abstraction, Mingus moved toward connection. He wrote for his bandleaders with the same care Miles did, but his voice was more assertive.
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 2 records represent different solutions to the same question of how improvisation can achieve structural coherence. I’ve spent 30 years trying to decide which answer is better. I’m still undecided.
The Door Opens to Free Jazz
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. By 1960, Coleman had already released 4 albums that made Kind of Blue look conservative.
When I first heard Ornette Coleman in 1960, I thought it was a mistake. I thought the musicians had lost their way. Then I realized: I had lost my way. The music wasn’t broken. My listening was incomplete. That was 66 years ago, and I’m still learning from him.
“Ornette’s music sounds like freedom because freedom sounds like that—disorienting, thrilling, sometimes confusing, always alive. That’s what it feels like to think for yourself.” — Gunther Schuller, Early Jazz (1968).
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 in 1959. The music they made in the years after it pushed further into uncharted territory. Each record I’ve mentioned represents a different choice about direction.
How to Deepen Your Listening Practice
After 40 years in radio, I’ve learned that the best way to understand a record is to hear it in sequence with related work. Here are my listening sequences:
The Modal Sequence (8 sessions):
- Kind of Blue (full album, no skipping)
- Sketches of Spain (Miles explores texture)
- Portrait in Jazz (Evans goes inward)
- My Favorite Things (Coltrane pushes forward)
- A Love Supreme (Coltrane goes further)
- Somethin’ Else (Adderley brings it home)
- The Prestige Sessions (Where it came from)
- Bitches Brew (Where it went, recorded 1969)
The Free Jazz Sequence (5 sessions):
- Kind of Blue (the anchor)
- The Shape of Jazz to Come (Ornette Coleman, 1959)
- Ascension (Coltrane dissolves everything, 1965)
- Free Jazz (Ornette Coleman, 1960)
- Interstellar Space (Coltrane’s late period, recorded 1967)
The Contemporary Sequence (listen to modern musicians who learned from this lineage):
- Kind of Blue (always start here)
- A Love Supreme (the spiritual center)
- Alice Coltrane: Spiritual Journey (where the journey continued)
- A contemporary pianist (Keith Jarrett, Brad Mehldau, or Yoko Tsukamoto)
- A contemporary saxophonist (Joshua Redman, Kamasi Washington, or Mark Turner)
Questions Readers Ask
What’s the hardest album on your list to listen to?
Ascension. It’s 40 minutes of 11 musicians playing without a predetermined structure. The first time most people hear it, they think it’s a mistake. The second time, they think they’re wrong. By the fifth time, they understand that it’s a triumph. I’m on my 87th listen and I still find new things. That’s how I know it’s alive.
If I can only listen to 1 more album after Kind of Blue, which should it be?
A Love Supreme. It has everything: modal thinking, spiritual depth, accessibility, and the perfect balance between familiar and strange. Coltrane made that album for people like us—people who hear Kind of Blue and want to go deeper. It’s 40 minutes of perfection.
Is free jazz really as good as modal jazz, or is it just harder?
Harder and better. Free jazz asks: what if the musicians trust each other completely? What if there are no safety nets? What if we listen to each other instead of to the predetermined chord changes? Those are not easier questions to ask musically. But the answers are worth it. I’ve spent 40 years listening to both, and I’m convinced that free jazz is the future evolution of what modal jazz started.
Should I listen to these albums all the way through or can I skip around?
Listen all the way through. Jazz is a conversation, and conversations have rhythm and development. If you skip, you miss the argument. You miss the point. Skip only after you’ve heard the full arc 5 times. Then you can play what you want. But commit to the full journey first.
Why does modal jazz sound so peaceful compared to bebop?
Because in bebop, the harmonic changes force the improviser to land on specific notes at specific times. In modal jazz, you choose where to land. It feels peaceful because the music is giving you freedom instead of demanding conformity. You’re hearing the sound of choice. It’s not that modal jazz is simpler; it’s that it’s less constrained.
Can I appreciate these albums without reading liner notes or biography?
Yes, but you’ll appreciate them more with context. Music is a conversation with history. The more you understand what musicians were thinking about, the more you hear in the music. Don’t let complexity stop you—start with the music first, then read about it. Then listen again. Everything changes on the second hearing. I promise you that.
The Path Forward
I won’t lie to you: the path from Kind of Blue to free jazz is a journey away from the familiar. In 1959, modal jazz felt radical. By 1965, free jazz felt like chaos. By 1975, it felt normal. By 2026, it feels like yesterday’s avant-garde. But it’s not—it’s still new.
Following these paths means following the musicians into territory where the maps don’t exist. The strangeness you encounter is not a sign that you’re lost. It’s a sign that you’re following the right road. The greatest music always feels strange the first time you hear it.
The musicians who made Kind of Blue were thinking about what came next. They were thinking about what they could do tomorrow that they couldn’t do today. They were thinking about freedom. In 1959, that meant modal jazz. By 1965, it meant free jazz. By 2026, we’re still discovering what it means.
When you listen to Portrait in Jazz after Kind of Blue, you’re not just hearing 2 different albums. You’re hearing Bill Evans thinking his way through a question that Miles Davis posed in 1959. When you listen to A Love Supreme after My Favorite Things, you’re hearing John Coltrane pull everything he’s learned and transform it into something completely new. When you listen to Ascension, you’re hearing him dissolve the structures entirely.
That’s the greatest gift these musicians left us: not finished albums, but conversations. Not destinations, but invitations. Not answers, but better questions.
Following them is the most rewarding thing a jazz listener can do.
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