Milestones, the predecessor to Miles Davis’ galvanic musical breakthrough Kind Of Blue, only underscores what a leap the latter represented in both style and presentation. The personnel on the two albums is substantially the same—Davis on trumpet, John Coltrane on tenor sax, Cannonball Adderly on alto sax, and Paul Chambers on bass, with Red Garland on piano and Jersey Joe Jones on drums here, replaced by Bill Evans and Jimmy Cobb on Kind Of Blue—but the vibe is markedly different.
While Milestones pointed toward the future in the title track’s exploration of modal jazz, the bulk of this album remains within the hard bop realm that Davis was finding increasingly confining. And while I may be projecting a bit, to my ear Miles’ frustration with feeling trapped inside a musical box is apparent. For this listener, the most striking thing about Milestones is the ferocity with which Davis attacks most of these tunes. Milestones offers all the virtuosity of Kind Of Blue while only hinting at the latter’s elegant swing and otherworldly grace.
Leadoff cut “Dr. Jekyll” (a.k.a. “Dr. Jackle” after its composer Jackie McLean) opens up all flash with Davis and Coltrane driving at breakneck speed before Miles solos exuberantly, repeating and then playing off of a series of little riffs. In response, Coltrane and Adderly fire off runs so fast that you lose track of individual notes as everything blends into a blizzard of sound. Chambers employs both fingers and bow on his bass solo and they leave space for a little drum break early in the sixth minute before the horns return, delivering an avalanche of notes up to the point where the players seem to collapse in a heap at 5:46.
“Sid’s Ahead,” a Davis composition, adopts a more measured tempo with Coltrane laying down some typically creative and evocative solos that also suggest why Davis and Coltrane were a dynamite pairing that couldn’t last. There just wasn’t room for two creative talents that big in a single sextet, especially when the marquee name was the famously controlling Davis, who ended up playing what little piano is heard on this track himself after 
Garland walked out of the session. That said, Davis shines in a great solo trumpet bit in the fifth minute with Jones swishing away on the cymbals underneath. Next up, the high-energy “Two Bass Hit,” a Dizzy Gillespie number, comes on strong with all six players trading bits and especially athletic solos from Adderly and Coltrane.
Up to this point it’s been mostly hard bop with a hint of blues—and then they move into Davis’s landmark composition “Milestones” and the fireworks start going off in this listener’s ears: “Oh yeah! This is the stuff!” It’s modal jazz, and after reading dozens of paragraphs about that particular subgenre I still don’t have a clue what that combination of words actually signifies, but I know this: it’s my favorite style of jazz. There’s a snap and elegance and charm and melodiousness to it that just works for me. The tempo is quick but not frenetic and the soloing—see Davis’s in the third and fourth minutes, followed by Coltrane—has an easy sophistication to it that just draws you in. When they return to the main theme at 4:45, with Davis and Coltrane playing little juking notes in unison, it’s finger-snapping, toe-tapping magic in the first degree, leaving you wanting more when they fade out a minute later.
Batting fifth, “Billy Boy” offers a showcase for Garland and the rhythm section, a hornless number that opens with his piano establishing the melody before soloing exuberantly, right hand running wild while his left plays a percussive series of chords. Around 2:45 they hand off to a bowed bass solo from Chambers and a series of tumultuous drum breaks from Jones, before in the fifth minute Garland and Jones begin trading licks like a pair of gunfighters firing off volleys. In the final minute Garland asserts supremacy again and restates the core melody
The album closes with the entire band jamming hard on the Thelonious Monk number “Straight, No Chaser,” with Adderly offering a swerving, squealing opening solo before giving way to Davis. When Coltrane’s moment arrives around four minutes in, he unleashes another minor blizzard of hopscotching notes, sprinting runs whose pure athleticism is more impressive than melodic. Garland and Chambers take extended solos before the horns circle back to reprise the opening at the 10:43 close.
In the end, Milestones—other than its beguiling title track—is one of those albums I respect more than enjoy; it can be dazzling in its virtuosity, but often lacks the warmth of Kind Of Blue. That said, Milestones is widely acknowledged as a critical turning point in jazz, the moment that pointed Davis directly to the unearthly magnificence of Kind Of Blue. It’s the sound of a mercurial genius trying to fight his way out of a musical box, with the clear highlight coming in that moment of discovery.