I’ve been hosting Miles on Monday on KBEM for thirty-seven years now, and I want to tell you something I’ve learned from playing these records more times than I can count: the second great quintet is the most perfectly realized ensemble in jazz history. Not the most popular—that’s the first quintet with Coltrane. Not the most influential on what came after—Weather Report and Tony Williams Lifetime had wider ripples. But the most coherent? The most disciplined in its freedom? The most complete expression of what five musicians can build together? Nothing comes close.
By 1963, Miles Davis was forty-seven years old and restless. He’d already made Kind of Blue, the best-selling jazz album of all time. He’d collaborated with Gil Evans on orchestral projects that most musicians spend their whole careers trying to match. He’d led a quintet with John Coltrane that changed what people thought was possible on the tenor saxophone. And he was done with all of it. He needed musicians who didn’t come with histories, musicians he could shape into something new.
He found them separately: Wayne Shorter, twenty-three, from Newark—the musical director of Art Blakey’s Jazz Messengers, a composer of genuine originality. Tony Williams, seventeen, from Boston—a drummer with a vocabulary nobody else had yet learned. Herbie Hancock, twenty-three, from Chicago—fresh off his Blue Note debut, technically perfect and creatively restless. Ron Carter, a Michigan bassist so harmonically sophisticated that he could function as a second chord voice in the band. When Miles assembled these four, he got lucky. When they started playing together, something happened that neither luck nor even genius fully explains.
Why Did This Band Matter More Than We Often Acknowledge?
The first great quintet succeeded because its members were individually exceptional and played hard bop with uncommon refinement. The second great quintet succeeded because it operated on an entirely different principle. These weren’t five great soloists taking turns; they were five musicians who’d developed a collective language so specific that a stranger listening to Nefertiti for the first time might not immediately identify who was doing what. The borders dissolved.
What was “time, no changes,” and why couldn’t other bands replicate it?
“Time, no changes” meant exactly what it said: improvising around a rhythmic pulse rather than over a chord progression. No changes to follow, no harmonic net to catch you if you fell. Just the feeling of forward motion and the responsibility to listen at every single moment. The harmony became implied rather than stated. If Shorter played an interval that suggested C major, Hancock might float something that suggested C minor, and instead of a clash, you got this strange, weightless space where both things existed at once.
Other bands couldn’t replicate it because it required musicians who could hear proportionally—who understood not just the notes they were playing but the weight their notes carried in the ensemble texture. Most jazz musicians are trained as soloists first, ensemble players second. These four were trained as listeners first, soloists only when the moment called for it. That’s a different kind of musician altogether.
How did the rhythm section enable the horn players to take risks?
Tony Williams played drums in a way that seemed to contradict every principle of timekeeping. He’d displace the beat, suggest a different tempo underneath the stated tempo, move the pulse so subtly that you’d feel it shift without being able to point to the exact moment it happened. Then Shorter and Miles could venture further out precisely because Carter and Hancock were building a harmonic foundation that gave them somewhere to land.
Ron Carter’s bass lines were inventions, not scaffolding. He walked when the music needed continuity, but he could also scatter his notes across registers the way a composer might scatter instruments across an orchestra. With that kind of flexibility underneath, Shorter and Miles could follow impulses that would have terrified them if the ground had been conventional. The risk was managed not through careful preparation but through deep listening.
What Do These Five Albums Actually Sound Like?
I want to walk you through the discography because each record reveals something different about how this band thought. These weren’t albums where one or two tracks mattered and the rest filled space. Every cut on every record was part of the conversation.
How did E.S.P. establish the blueprint?
E.S.P. (1965) was the debut, and it’s the most immediately accessible record in the cycle. The material was almost entirely Shorter’s—“E.S.P.,” “Eighty-One,” “Little One,” “Iris.” Shorter’s compositional voice was distinctive: melodic phrases that twisted slightly against your expectations, harmonic outlines that suggested more than they stated. Miles let Shorter’s compositions lead, and the band’s playing was still rooted in hard bop vocabulary, even if the execution was already opening toward something stranger.
Listen to “E.S.P.” itself and you hear the blueprint clearly. The theme is simple, but the way Williams plays around it—dropping bombs in unexpected places, never quite landing on a beat where you’d predict he would—changes the temperature of the thing. By the time Hancock and Shorter trade solos, the harmonic space has expanded without anything explicit having been stated. It’s a masterclass in compositional economy and ensemble flexibility.
Why is Miles Smiles the moment where the band’s voice fully emerged?
Miles Smiles (1967) is where I hear the band understanding itself completely. The title track is a minor blues—such a basic jazz form—but played with such rhythmic looseness that the blues form becomes almost suspended. Williams is the controlling force here, playing so independently that the other musicians have to track him like hunters tracking an animal through dark forest. They know roughly where he’s going, but not exactly.
The great gift of this quintet was that they understood freedom not as the absence of structure but as structure so deeply internalized that you could move within it without even thinking about it.
“Delores” is a straight-ahead waltz, but the soloing underneath has this lovely floating quality that makes you forget you’re in three. On “Hand Jive,” Miles gets playful—the first real evidence on these records that he could shift his tone as dramatically as his conceptual approach. It’s almost as if Miles himself was still discovering what these musicians made possible. That sense of discovery carries through the whole record.
How Did Each Musician Develop During These Years?
Tony Williams is the obvious answer when you ask “who changed the most,” but that obscures how all four supporting musicians grew. Let me address each one because they’re all part of the story.
What made Tony Williams such a revolutionary drummer?
Tony Williams was seventeen when Miles hired him. Seventeen. He was playing in a vocabulary that didn’t yet exist, with a confidence that most musicians take decades to acquire. He could play free and supportive simultaneously—holding the rhythm while also suggesting that the rhythm could be otherwise. Most drummers are either timekeepers or soloists, inside players or outside players. Williams was all of these things depending on what the moment required.
By the time the band broke up in 1969, Williams had essentially rewritten what a jazz drummer could be. He could make you feel the pulse without playing it, suggest a tempo underneath the stated tempo, create a rhythmic environment that was in constant motion without ever losing its foundation. When he left Miles to form Tony Williams Lifetime, he’d already accomplished something that most musicians spend their whole careers working toward. The fact that his career after this was equally significant just compounds the achievement.
How did Herbie Hancock mature as a harmonicist and band player?
Herbie Hancock came to Miles Davis as a young man who’d already mastered the technical apparatus of the piano. But mastery of technique isn’t the same as mastery of texture, and texture is what Hancock developed with Miles. On E.S.P., he’s still playing relatively full voicings, still thinking in terms of the harmonic structures he knew from Takin’ Off. By the time of Nefertiti, he’d learned to use space the way a painter uses white canvas.
Listen to what Hancock does when Miles and Shorter are stating the melody on “Nefertiti.” He’s improvising underneath them, but his role is to suggest harmonic implications rather than state them. His voicings become thinner, his touch more delicate, his sense of architecture more sophisticated. He’s not accompanying; he’s creating an environment. That’s a different skill entirely, and it’s one that served him brilliantly when he moved toward funk and electronic music in the early 1970s.
What was Ron Carter’s role beyond walking the changes?
Ron Carter might be the least celebrated member of this quintet, and that’s exactly the point. He recorded on more than two thousand sessions throughout his career, and a huge part of his influence is that he understood how to be invisible while being absolutely essential. With Miles, he became a harmonic voice as much as a rhythmic foundation.
Carter could play a bass line that suggested harmony without stating it explicitly. He could counter-melodize with Hancock. He could move across registers in ways that opened harmonic space rather than closing it. When you listen to Sorcerer or Filles de Kilimanjaro, you realize that Carter is doing something as conceptually advanced as what Williams or Shorter is doing—it’s just less immediately obvious because he’s serving the band rather than showcasing his own abilities.
When and How Did This Perfect Moment End?
The second great quintet made five studio albums between 1965 and 1968. By 1969, Miles had already begun his turn toward electric music that would result in In a Silent Way and Bitches Brew. The band didn’t disband in some dramatic split; it just became impossible to keep the band together once Miles decided he was going somewhere else.
| Album | Released | Key Compositions | Significance |
|---|---|---|---|
| E.S.P. | March 1965 | E.S.P., Eighty-One, Little One | The blueprint established; Shorter’s compositions introduce the formal approach |
| Miles Smiles | March 1967 | Miles Smiles, Delores, Hand Jive | Collective voice fully crystallized; rhythmic freedom at its peak |
| Sorcerer | May 1967 | Sorcerer, Prince of Darkness, Masqualero | Harmonic sophistication reaches its height |
| Nefertiti | June 1968 | Nefertiti, Water on the Pond, Madness | Quintet masterpiece; inverted melody-rhythm relationship |
| Filles de Kilimanjaro | September 1968 | Frelon Brun, Tout de Suite, Petite Chanson | Already moving toward electric; the band’s final statement |
The musicians went their separate ways into distinguished careers. Hancock and Shorter founded Weather Report, which had a wider commercial reach and influenced more subsequent musicians than any of the quintet recordings. Williams formed Tony Williams Lifetime, where he continued to be a revolutionary voice in drumming. Carter became a freelancer of such stature that he appeared on everything from pop records to avant-garde sessions. Miles went electric and never looked back.
None of them ever made records quite like the ones they made together. The conditions were too specific: five musicians at precise moments in their development, under a leader who understood exactly what to ask of them, documenting a conversation that had just reached its most articulate moment. Conditions like that can’t be manufactured. They arise, they burn brightly, and they vanish.
When I play these records now, after playing them for four decades, I hear something different than I did when I was twenty-six and they were fresh. I hear the discipline underneath the freedom. I hear the compositional architecture that made the improvisational freedom possible. I hear five musicians who understood that the greatest collective achievement is invisible—it looks effortless from the outside because all the work is happening in real time, in the space between the notes, in the listening.
That’s what made this quintet second to none.
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