Have you had this conversation?

You: Like jazz? Other Human: No, not really, but I love Kind of Blue.

I’ve had it so many times that I’ll venture Miles Davis’ 1959 album is the one jazz record you know if you know no others. And for those who do know others, it’s the singularity just before the Big Bang—the universe of modern jazz begins here.

How to explain such a thing: the once in a lifetime confluence of opportunity, execution and dissemination that changes all that comes after. Bill Evans, who famously played piano on four of the five cuts and wrote the liner notes, likened it to Zen painting, where a lifetime of thought and discipline is channeled into a few moments of spontaneous perfection.

Miles brought sketches he made hours before the session, and used the first complete take on all tracks but one. They made no others. The vibe is meditative, with bursts of saxophone fire from John Coltrane and Julian (Cannonball) Adderley. Paul Chambers played bass, Wynton Kelly played piano on one tune (“Freddie Freeloader”), and Jimmy Cobb was the drummer.

Cobb, who is now 80, is the only one of these remarkable musicians still with us, and to commemorate the half-century since, is now touring with a group he calls the “So What? Band.” They perform the Kind of Blue tunes and others from (and inspired by) that era.

Miles was the least nostalgic of musicians, and didn’t try to sustain the feel of the session on the road, quickly taking those tunes to new places. Mr. Cobb stays true to Miles’ aesthetic with an inter-generational approach. He brings together the one who was there (himself), the ones who were impressionable teens at the time and are now distinguished veterans (Larry Willis, piano; Buster Williams, bass, who also recorded later with Miles), and those born after the fact, who are willing and able carriers of the message (Wallace Roney, Miles’ only trumpet student; Javon Jackson, tenor sax; Vincent Herring, alto sax).

Some of these choices (like Wallace Roney) are obvious if the goal is to evoke the sound. Some are not so clear. (Larry Willis isn’t the first to come to mind when thinking of Wynton Kelly or Bill Evans.) And who can climb to the apex of sax perfection that the album embodies? But one can be evocative without being reiterative, and that’s a much more likely scenario.

Jimmy Cobb can’t commandeer a time machine, but he can recreate the dynamic—six extraordinary musicians bringing six lifetimes of thought and discipline to the moment of spontaneous performance. Like Zen painters.

Jeff Presslaff is a Winnipeg jazz performer and composer.