In the grand scheme of Miles Davis’ immense, indelible catalog, there is not necessarily anything particularly special about My Funny Valentine. But, it was the first Miles Davis record I owned (because I found this copy for cheap ten years ago), and for a while, it was the only Davis record I owned.

But it was also recorded fifty-five years ago today, which is a happy accident.

In the time between Kind of Blue and this Lincoln Center performance, Miles had not strayed very far from the cool jazz he had pioneered in the late 50s. He had recorded the jazz-classical fusion Sketches of Spain, but most of his work was still safely under the umbrella of Blue’s restrained swing—consistent, but unremarkable in the light of history.

The live show at Lincoln Center was split into two releases: this record showcased the more relaxed tunes and Four & More contained the more upbeat tunes. And the tracklist here is fairly indicative of the work in his Cool Period. “All Blues” from Kind of Blue appears in a greatly reworked version. The rest of the tracks are culled from standards of the day, such as the title track.

But what is notable is the personnel here, and My Funny Valentine is one of the first collaborations between Davis and pianist Herbie Hancock and drummer Tony Williams, both of whom would later become major forces within Davis’ band during his Electric Period. While this show is still quite marked with Davis’ trademark restraint (what Kenneth Tynan calls “duende: the ability to transmit a profoundly felt emotion with the minimum of fuss and maximum of restraint”), some of the embellishments that Hancock and Williams bring to the table point to the wild inventiveness that was to come in the next decade. It’s also worth mentioning that this was their first performance in a large theater, and they were racked with nerves. Hancock later remarked that the group left the show thinking they had bombed—which you would never guess listening to the record.

Even though it may be little bit forgettable in the light of Davis’ other contributions to jazz, My Funny Valentine is, above all, a satisfying and rewarding listen. The solos are as perfect as you could expect from performers of this caliber, and the chemistry of this group is absolutely spellbinding, a testament to Miles’ choice in bandmates. And while Miles, Herbie, and Tony would go on to much greater heights (check back in tomorrow), this live performance showcases that their chemistry was always top-notch—even when they were playing closer to the middle of the road.