ULTRA MEGA SUPER POST INBOUND:

Ornette Coleman - Free Jazz, The Shape of Jazz to Come

Kurt Rosenwinkel - Our Secret Place, Star of Jupiter

Miles Davis - 'Round About Midnight, Kind of Blue, Bitches Brew, Live-Evil, Sketches of Spain

Moondog - S/T

Thelonious Monk - Monk's Dream, Thelonious Monk and Sonny Rollins

Fire! Orchestra - Enter, Exit

Colin Stetson - New History Warfare Vol. 2: Judges

Moon Hooch - This is Cave Music

Jacques Coursil - Clameurs

Zs - Xe

Eric Dolphy - Out to Lunch

Hiromi - Alive

John Coltrane - Ascension, A Love Supreme, Giant Steps (although Giant Steps is super entry level)

Captain Beefheart & His Magic Band - Trout Mask Replica (more blues-rock than jazz, but there are jazz elements)

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If you can't decide where to start, start with one of the Miles Davis albums or Ornette Coleman's Free Jazz. Free Jazz is really cool because it's a double quartet with each quartet assigned to an audio channel (one quartet per ear). Essentially, it's like listening to two albums at the same time, except that the albums interact with each other. Plus, it's FREE JAZZ.