Miles Davis led two different quintets that are usually mentioned in the same breath, a decade apart, and each one reset what a small jazz group could sound like. The first — with John Coltrane, Red Garland, Paul Chambers and Philly Joe Jones — took the standard hard bop lineup and played it tighter, faster and meaner than anyone else was doing it. The second — with Wayne Shorter, Herbie Hancock, Ron Carter and Tony Williams — kept the same five chairs but treated the rhythm section as something to improvise, not just something to keep time with. Same bandleader, same instrumentation, two completely different ideas about what a band could do.

The First Great Quintet (1955–1957)

Davis put this band together in 1955, right after signing with Columbia while he still owed Prestige a stack of albums under his old contract. The quintet knocked out enough material in a handful of marathon single-day sessions to fill four Prestige LPs — Cookin', Relaxin', Workin' and Steamin' — none of which sound rushed. Coltrane was still finding his own voice here, rougher and more searching than he'd be within a few years. Garland's block chords and Chambers' bowed-bass solos gave the band a sound that felt relaxed on the surface and merciless underneath, and Philly Joe Jones drove it all — few drummers in jazz have ever swung harder at a medium tempo. The one true studio album Davis released under his own name during this run, 'Round About Midnight, is still the clearest single record of what this band actually sounded like.

The Second Great Quintet (1964–1968)

Davis rebuilt the band almost from scratch in 1963, after Coltrane, Chambers and the rest of the first group had all moved on to lead their own bands. He found a seventeen-year-old drummer in Tony Williams, a bassist in Ron Carter who could imply four different chords with a single note, and — after a long run of auditions — a twenty-three-year-old pianist named Herbie Hancock. Wayne Shorter joined on tenor in 1964, completing the group. What made this quintet different wasn't the notes so much as what the rhythm section refused to do with them: Williams and Carter stopped keeping time in any fixed way and started reacting to whatever Davis or Shorter played, so the ground under a soloist could speed up, stall or drop out mid-phrase. Musicians who played with this band later described the approach as a kind of controlled freedom — the harmony was still there to hang onto, but nothing about the rhythm section was predictable anymore. E.S.P., their first studio record together, sounds like a band inventing its own vocabulary while the tape was rolling.

What actually changed

The First Quintet was a hard bop band playing at the outer edge of what hard bop could do — precise, swinging hard, still built on chord changes a listener could follow bar by bar. The Second Quintet used the exact same structure, head–solos–head, but treated the rhythm underneath as something to improvise too. Both bands were built on the same idea: surround Davis's trumpet with musicians who don't sound like anyone else, and let the friction between them carry the record. In the first band, that friction came from swing pushed to its absolute limit. In the second, it came from removing the assumption that a rhythm section has to swing predictably at all.

The records

Start with one from each band, then decide which sound you want more of.

01
'Round About Midnight — Miles Davis (1957)
The First Great Quintet's only true studio album
Coltrane's tenor is still rough-edged here, closer to his early Prestige work than the sound he'd have by 1960, and that roughness is part of what makes the record work — it sits against Davis's cool, muted trumpet like sandpaper against silk. Philly Joe Jones' drumming on the title track is one of the great entrances in jazz: a single cymbal crash that snaps the whole band into motion.
02
E.S.P. — Miles Davis (1965)
The Second Great Quintet's first studio record
No standards, no old material — every track is an original, mostly written by Shorter and Carter. The band sounds like it's still deciding what its rules are, which is exactly why it's worth hearing first: you can hear the group figuring out, in real time, how far the rhythm section can bend before something breaks.
03
Miles Smiles — Miles Davis (1966)
Where the Second Quintet's approach fully clicked
Williams plays almost no straight time on this record — the pulse is implied more than stated, and Hancock often lays out entirely, leaving Davis and Shorter to solo over just bass and drums. It's the most purely rhythmic record either quintet made, and the one most often pointed to as the moment this band became something new.
04
Nefertiti — Miles Davis (1968)
The rhythm section takes over the composing
The title track has no solos at all — Davis and Shorter simply repeat the melody while Williams, Carter and Hancock improvise underneath it, inverting the usual roles of a jazz band entirely. By this point Hancock, Carter and Williams were writing most of the group's material, and the record sounds like a quintet quietly handing the wheel to its rhythm section.

Both quintets broke up the same way bands like this usually do — the players outgrew the format. Coltrane left to lead his own group and never looked back. Shorter, Hancock, Carter and Williams all went on to shape jazz through the 1970s and beyond, mostly by taking pieces of what they'd learned in this band and building something else with them. Davis, both times, went and found four new people and started over.