It’s a hot summer night in 1955 in Newport, Rhode Island and Miles Davis is about to take the stage. Things haven’t gone well for the great Jazz trumpeter over the course of the last few years. His addiction to heroin (which he’d finally kicked the year before after locking himself in his father’s room, experiencing horrible withdrawals) had completely ground the joy out of his once great career. He’d blown a promising relationship with French actress and singer Juliette Greco sending him into a spiraling depression. The public had all but disregarded him as a loon after an incident at Detroit’s Blue Bird club in which he stumbled into the dive drenched from the evening rain, interrupted the standing band with a rendition of “My Funny Valentine,” and then stumbled back out into the night. Just like that night, on this summer evening his trumpet was the only true friend he had. As he and his band of acquaintances began the subtle crooning signaling the introduction to the 1944 Jazz standard “‘Round Midnight” he began to play. His career would never be the same.

Even today, Davis’ performance of ‘Round Midnight on that August evening is the stuff of legend. It signaled the return of the greatest Jazz performer who ever lived, setting him up for a series of studio classics including ’59’s Kind of Blue, which is widely (and correctly) heralded as the greatest Jazz album ever recorded. But the ongoing Bootleg Series of Davis’ recordings capture him at his most pure, as the endlessly creative, exploratory and chaotic face of Jazz for decades.

Amazingly, even though the performances included on this box set took place over a span of 20 years, everything flows together seamlessly. So seamless, in fact, that I didn’t even notice that my Spotify playlist was on shuffle until several songs in. Even so, Davis’ range as a performer is on full display from screeching solos to quick tempo breakdowns to soft crooning. And when he makes the transition from classical instrumentation to bringing in electric guitars armed with Hendrix levels of fuzz and distortion, prepare to have your head explode.