In 1963, Herbie Hancock got a new gig that would change his life—and jazz history. The great Miles Davis, impressed by Herbie’s album Takin’ Off, asked him to join a new group he was assembling. By late 1964, that group would be finalized with the addition of Wayne Shorter on saxophone. Together with bassist Ron Carter and drummer Tony Williams, they’d release a string of legendary studio and live albums that turned jazz into a kind of cubist music—you could recognize every shape, but the way they fit together was always unexpected. They’d be known forevermore as the Second Great Quintet, and their creative spirit still resonates well beyond the world of jazz.
Miles Davis was born 100 years ago, on May 26, 1926, in Alton, IL. In 2026, as music fans around the globe celebrate his centennial, Herbie himself will fete his former boss, mentor, and friend at the Hollywood Bowl on August 19. As it is with any time Herbie steps on a stage, you can expect him to travel far and wide. With the music he and Miles made together as a starting point, you can go just about anywhere.
“Miles really encouraged all his musicians to reach beyond what they know, go into unknown territory and explore,” Herbie said. And that’s exactly what the Second Great Quintet did right from the beginning. The group had gelled quickly, with the players able to anticipate one another’s changes on a nearly molecular level. That level of chemistry had its drawbacks, though. “We’'d gotten so cohesive as a band that it had become easy to play together. We had figured out a formula for making it work, but of course playing by formula was exactly the opposite of what we wanted to do,” Herbie said. “We needed to put the challenge back in, to figure out ways to take more risks.”
By the time they arrived in Chicago for a two-week stand at the Plugged Nickel for the 1965 holiday season, they had found a way. On the flight over, Williams suggested to the other sidemen that they play “anti-music,” or to play the exact opposite of what might sound “right” or expected in a given moment. Here was the trick: They’d do it without telling the boss what they were planning. The recordings made over those two weeks show them taking apart familiar standards and classics from Miles’ catalog. They forced one another into odd corners, challenging Miles to keep up and recontextualize songs he’d played hundreds of times.
If that seems cruel, they were only following Miles’ directives. Early in their stint together, Miles leaned over to Herbie during a performance and said, “Don’t play the butter notes.” Or so Herbie thought. What were the butter notes? Herbie had no idea, but decided that, because butter is fat, Miles must have been telling him to avoid excess notation. Herbie dutifully cut the root note from his chords, which opened his playing and allowed him a new level of freedom. It wasn’t until decades later, talking to another musician, that he learned Miles had told him to avoid “the bottom notes”—the very roots Herbie had snipped from his playing. In a bit of magical serendipity, he’d arrived at the right place via a very odd route, a neat encapsulation of everything jazz is supposed to be.
Even after the Second Great Quintet dissolved, Herbie and Miles continued to work together, making forward-thinking music that greatly broadened jazz’s horizons. With its starry-eyed keyboards, very gradual development, and orderly sense of possibility, In A Silent Way is considered by some to be one of the first-ever ambient records, its 1969 release preceding Brian Eno’s Ambient 1 by a full decade. The heavy jazz-rock of Jack Johnson, which was recorded as a soundtrack to a documentary about the titular boxer, followed two years later. And in 1972, On the Corner would bring together the heady pop-funk of Sly & The Family Stone with experimental methods straight from the mind of experimental composer Karlheinz Stockhausen for a knotty, hard-edged form of jazz-funk that still sounds fresh over 50 years later.
This open-ended approach, and the desire to pursue interesting sound even if it led beyond jazz’s borders, would inform the rest of Herbie’s career. In 1971, he’d form Mwandishi, one of the most out-there and experimental groups jazz had ever seen at that point, playing a form of cosmic synthesizer music that seemed beamed in from another planet. The year after On the Corner, Herbie broke up Mwandishi and started Headhunters, the supremely funky group that would make him a superstar; their debut, Head Hunters, became the best-selling jazz album of all time and Miles found himself in the odd position of opening shows for his protégé.
Working with Miles Davis would ultimately be one of the most profound experiences of Herbie Hancock’s life. “I was always frightened playing with Miles,” he told the BBC with a laugh. “It was very intimidating. I always wanted to be at my best, because I admired him so much.” But that fear pushed him to greater heights. “It was fear on one hand,” he added. “On the other hand, it was exciting. And when things were at their best, it was really inspiring. When we were all in sync, that made life worth living."