Kind of Blue is one of the monuments of the cool jazz era. Recorded in 1959, it finds Miles Davis leading a sextet of like-minded musicians including pianist Bill Evans and saxophonists John Coltrane and Cannonball Adderley. Here Davis begins exploring modal improvisation, and makes his definitive break with bebop conventions. The album’s lead track, “So What,” features a minimalist, two-chord progression and a horn line that seems to emerge out of silence; “Flamenco Sketches” is a ruminative, impressionistic tune that floats as much as it swings. Kind of Blue is classic in every sense.

– Rick Anderson

An undisputed masterwork, this 1959 opus gathers six of the best to ever do it — Davis, trumpet and concept; John Coltrane on tenor sax; the perennially underrated Cannonball Adderley on alto; Bill Evans and Wynton Kelly trading off on piano; Paul Chambers on bass; Jimmy Cobb on drums — and gives them all room to explore a series of five simple, open-ended themes, all mid-paced if not slower. It’s a simmering, late-night album, probably the most purely beautiful music Davis ever made, as stunning on your thousandth listen as your first.

– Phil Freeman