When the great Miles Davis was assembling his quintet in 1955 and chose a troubled young saxophonist named John Coltrane over more established and experienced players, many assumed the partnership wouldn’t last. While Davis was a reserved, dapper aesthete born to achievement, Coltrane was cut from coarser cloth but no less of a musical genius for that. Surely two such outsized talents were bound to clash, especially with the specter of Coltrane’s drug use looming overhead.

There were no pyrotechnics apart from the musical variety however, note Farah Jasmine Griffin and Salim Washington, authors of an illuminating book due out next week, Clawing at the Limits of Cool: Miles Davis, John Coltrane and the Greatest Jazz Collaboration Ever—because “Coltrane was too humble, and Miles was simply too cool.” And thank god for it, or they might never have gotten around to laying down Kind of Blue.

While suit-makers look increasingly towards the accountants and ad men of the 50s and 60s, it’s amazing to think they’re overlooking one of the best subcultures of the era. Forget the twenties: the fifties and sixties were the real jazz age.

Miles Davis speaks for himself, but a whole generation of icons stood along with him, ditching the porkpie hats and traditional chord structures in favor of a new kind of music and a new kind of style. Taschen did us a favor rounding up 500 pages worth of album covers for their appropriately named Jazz Covers. We can’t think of a better window into the age…other than the albums, that is.

See the covers»

Speaking of American classics, another one is coming up on its 50th anniversary. We’re talking about Kind of Blue, Miles Davis’ masterwork and the odds-on favorite for the greatest jazz album of all time. The album saw Davis working with arguably the best band of his career—including Bill Evans, Cannonball Adderly, and John Coltrane, for a start—exploring modal sketches to work out a new kind of downbeat jazz.

We’ve gushed about Miles Davis before, but fifty years down the line, it’s interesting to consider the album as a document of 1959. It was a bestseller on release, even though it cut against the grain of Eisenhower-era culture. The world of the gray flannel suit wasn’t available to Davis and his bandmates, and the new freedoms they were opening up were entirely musical, but they still looked more attractive than life in Connecticut. As mainstream America got less and less happy with the suburban dream, this was the sound of the underground.