Milestones is an album that needs no introduction. Often overshadowed by its younger sibling Kind of Blue in the rankings of greatest jazz records, it nonetheless holds a pivotal place in the history of modern jazz. Critics and devoted listeners alike recognize its importance: an early – and outstanding – example of modal jazz, recorded by Miles Davis’ so-called “first great quintet” (actually sextet, this time), featuring legends like John Coltrane, Red Garland, Paul Chambers, Philly Joe Jones, plus Julian "Cannonball" Adderley. So, how did this extraordinary lineup come together?

It began in the summer of 1955, after Davis’ performance at the Newport Jazz Festival. Columbia Records executive George Avakian approached him with a contract offer—on the condition he form a steady band. Wasting no time, Davis recruited Garland, Chambers, and Jones. The first gigs in July 1955 featured Sonny Rollins on tenor sax, but due to struggles with heroin addiction, he soon stepped away, making room for the emerging Coltrane. From October 1955, over the course of about 11 months, the quintet began recording sessions for 'Round About Midnight – Davis’ first album for Columbia. Its release was delayed until early 1957 due to his ongoing contract with Prestige Records. To listeners, the quintet might have seemed short-lived, especially as Davis' next Columbia release, Miles Ahead, was a large-ensemble suite arranged by Gil Evans. But by February 1957, the quintet – now expanded with Adderley – was already deep into the sessions that would become Milestones.

If Davis’ earlier work straddled the line between hard bop and modal jazz, Milestones crosses decisively into new territory. The off-kilter intro of “Dr. Jekyll” is a wild, neurotic riff that channels the urgency of early '50s jazz while gesturing toward a more spacious, conceptual future (shouldn’t it have been called “Mr. Hyde?”). Coltrane dives into virtuosic spirals, while Garland and Chambers pull things back into a lush, languid groove. From Davis' first solo onward, everything changes. Even when the opening riff returns, it feels transformed – nothing sounds like the first time you heard it. “Sid’s Ahead” is the only track penned by Davis on the album, yet it echoes (perhaps unintentionally) the blues-infused language Coltrane would later explore in his solo work. Fittingly, it's Coltrane’s solo that steals the spotlight. It’s on the title track, “Milestones”, that hard bop finally gives way to modal clarity. Davis delivers one of the finest solos of his career – measured, unhurried, and precise, where every note points purposefully to the next. No flash, no filler. Coltrane responds with restraint, avoiding his more mystical detours.

A foundational document of early modal jazz, Milestones may have been eclipsed by more famous works, but it remains a fan favourite – an essential piece in the evolution of jazz, and a testament to a group of musicians reshaping the form in real time.