Seven musical artists who turned in exquisite five-album runs

These five-album runs are not to be missed.
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Milestones (1958)
Porgy and Bess (1958)
Kind of Blue (1959)
Workin’ (1960)
Sketches of Spain (1960)

Of all the artists on this list – indeed, of all the artists in the canon of post-war western music, no one put out as much outstanding music in as compressed a timeline as Miles Davis. You could easily jump ahead a decade to the vital rock and blues fusion music from the late ‘60s and find an even more incendiary run of albums. But I don’t go back and listen to Bitches Brew these days.

I do listen to these albums, centered around the groundbreaking Kind of Blue, which many critics have identified as the most important jazz album ever released. This particular run features an astonishing array of musical styles and performers. Because recording dates and release dates don’t always coincide on Davis’s albums, these albums also show off the transition from his original quintet with John Coltrane on tenor sax to the modified sextet with the addition of Cannonball Adderly’s alto sax. You can hear that new energy from the very first track of Milestones, “Dr. Jekyll”

From there, he shifted direction with his adaptation of Gershwin. His frequent collaborator Gil Evans arranged the American classic for Davis’s sextet, supplemented by other horns and woodwinds for a sound that was both orchestral and free-flowing.

On the other side of Kind of Blue, we get a throwback to the original quintet with top-tier compositions by Coltrane and Dave Brubeck, before closing the run with the exceeding beauty of Sketches of Spain, another Gil Evans collaboration, which closes with “Solea,” one of Davis’s most towering achievements.