Miles Davis's second great quintet—Shorter, Hancock, Carter, and nineteen-year-old Tony Williams—improvised through standards at the Plugged Nickel in December 1965, implying rather than stating rhythm while conversing at tempo. Columbia sat on the complete recordings until 1976 despite understanding their importance. This is intimate club music where performance dissolved into dialogue, essential listening for anyone serious about how jazz reinvented melody and time.

⚡ Quick Answer: Miles Davis's second great quintet transformed standards into explorations of harmonic space during two nights at Chicago's Plugged Nickel in December 1965. With Herbie Hancock, Wayne Shorter, Ron Carter, and nineteen-year-old Tony Williams, they improvised at conversation speed, implying rather than stating rhythm while turning familiar melodies over in light. The warm, slightly compressed live recordings captured intimate club music that Columbia delayed releasing until 1976, despite knowing its historical significance years earlier.

There are nights when the music stops being performance and starts being conversation, and this is one of those records.

Miles Davis brought his second great quintet into the Plugged Nickel in Chicago on December 22nd and 23rd, 1965, and what Columbia’s engineers captured over those two nights was something the label nearly sat on entirely. The original release — a single LP culled from hours of tape — came out in 1966. The full sessions didn’t surface until 1976, and even then the world wasn’t entirely ready to hear what had happened in that room.

The Band

The personnel here is almost unfair. Wayne Shorter on tenor saxophone, Herbie Hancock on piano, Ron Carter on bass, Tony Williams on drums. Williams was nineteen years old in 1965. Nineteen. He plays on this record like someone who had already decided what drumming was supposed to be and had moved past it.

This was a band deep in what people would later call “time, no changes” — playing inside and outside the harmonic structure simultaneously, implying rhythm without always stating it, daring each other to go further and then following. Producer Teo Macero was in the booth, but in a real sense this music was produced by the five men on the bandstand making decisions at improvisation speed.

One album, every night.

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What’s Actually Happening

The setlist that night leaned on standards — “If I Were a Bell,” “Stella by Starlight,” “My Funny Valentine,” songs Miles had played a hundred times. That’s the point. The familiarity is the canvas.

What the quintet does to these songs is not deconstruction exactly. It’s more like they’re holding the melody at arm’s length, turning it in the light, seeing what it looks like from behind. Hancock comps in places you don’t expect and disappears when you need him most. Carter anchors only what needs anchoring. Shorter plays phrases that seem to resolve somewhere you weren’t expecting to land and somehow it’s exactly right.

Miles himself sounds unhurried in a way that is actually quite frightening when you understand the tempo Williams is laying underneath him. That muted tone, the space between notes — it doesn’t sound like restraint, it sounds like confidence so complete it doesn’t need to prove anything.

The Recording

Columbia engineer Don Hunstein was the credited house photographer for many of their sessions, but the Plugged Nickel recordings were captured as live documents rather than studio productions — mixed front-of-house and fed to tape. The sound is club-warm and slightly compressed, which turns out to be exactly right. You can hear the room. You can hear the audience sitting very still.

The fact that these tapes existed in the Columbia vault for a decade before the full sessions came out is one of the more quietly maddening facts in jazz history. Teo Macero knew what he had. Sometimes the industry moves at its own pace regardless of what the music deserves.

This is not an album for background. Put it on when the house is quiet and you have forty-five minutes you’re willing to give over completely. Let “If I Were a Bell” get strange in the second chorus. Don’t skip ahead.

Ron Carter’s bass on “Stella by Starlight” alone is worth the price of the record.

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The Record
LabelColumbia
Released1966
RecordedThe Plugged Nickel, Chicago, Illinois, December 22–23, 1965
Produced byTeo Macero
Engineered byDon Hunstein
PersonnelMiles Davis (trumpet), Wayne Shorter (tenor saxophone), Herbie Hancock (piano), Ron Carter (double bass), Tony Williams (drums)
Track listing
1. If I Were a Bell2. Stella by Starlight3. All of You4. My Funny Valentine5. When I Fall in Love6. Fran-Dance7. The Theme

Where are they now
Miles Davis — continued to reinvent jazz through fusion and beyond, died September 28, 1991.Wayne Shorter — led his own quartet for decades, one of the most celebrated composers in jazz history, died March 2, 2023.Herbie Hancock — became one of the most commercially successful jazz artists alive, still performing and recording well into his eighties.Ron Carter — remains an active recording artist and educator, widely considered one of the greatest bassists in jazz history.Tony Williams — formed the Tony Williams Lifetime and pioneered jazz fusion drumming, died February 23, 1997.
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🎵 Key Takeaways

Why did Columbia Records wait so long to release the complete Plugged Nickel sessions?

The label knew what it had—producer Teo Macero was aware of the historical significance—but the industry moved at its own pace regardless of what the music deserved. The full sessions didn't surface until 1976, over a decade after the December 1965 recording.

What made Tony Williams's drumming on this record revolutionary?

At nineteen, Williams played without stating rhythm outright, instead implying it while allowing the band to move inside and outside the harmonic structure simultaneously. He had essentially moved past traditional timekeeping into something that sounded like absolute confidence in a new approach.

How did the quintet approach playing standards like 'If I Were a Bell'?

Rather than deconstructing them, the band held the melodies at arm's length, turning them in the light to see what they looked like from different angles. Hancock comped unexpectedly, Carter anchored only what needed anchoring, and Shorter resolved phrases in surprising but exactly-right places.

What does the recording quality tell us about how these sessions were captured?

The warm, slightly compressed sound came from front-of-house mixing fed directly to tape rather than studio production techniques. You can hear the room and the audience sitting very still, which turned out to be exactly right for this intimate club music.

Further Reading

More from Miles Davis

Further Reading

More from Miles Davis