Milestones, Miles Davis’ third Columbia outing, is a transitional hybrid of two bands: the First Quintet, with then-controversial tenor John Coltrane, pianist Red Garland, bassist Paul Chambers, and drummer Philly Joe Jones; and the Kind of Blue sextet, with Coltrane and Cannonball Adderley together on saxes and Chambers still on bass. Garland and Jones were out after Milestones, replaced by alternating pianists Bill Evans and Wynton Kelly and drummer Jimmy Cobb. So here in 1958 we have Davis, Coltrane, Adderley, Garland, Chambers, and Jones—an incredible band in its own right, more extroverted than the one on Kind of Blue but presaging what’s to come on a harmonically open tune like “Milestones” (not to be confused with a different “Milestones” from Davis’ famed 1947 Savoy session with Charlie Parker). “Dr. Jekyll” (“Dr. Jackle” on some printings) is edge-of-seat uptempo blues, arguably one of the greatest leadoff tracks in jazz. Thelonious Monk’s “Straight, No Chaser” closes out with blues as well, not as fast but still bright and plenty exploratory. The John Lewis-Dizzy Gillespie big-band bebop staple “Two Bass Hit” is a shot in the arm, as is the Red Garland trio feature on “Billy Boy” (closely following Ahmad Jamal’s arrangement).

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