Milestones

Milestones was made by his first quintet with Cannonball Adderley added on alto saxophone, and it came out in September 1958. John Coltrane had returned to the group that year, and the album belongs to the modal phase that led to Kind of Blue. AllMusic's Thom Jurek said the title track introduced modalism to jazz. Davis plays piano as well as trumpet on Sid's Ahead, a blues reminiscent of Walkin', and moves to the keyboard to accompany the saxophonists and Paul Chambers's bass solo in the absence of Red Garland.

The Penguin Guide put it in its Core Collection as one of the very great modern-jazz albums. Davis wrote in his autobiography that he loved the way the band sounded and felt they had something special. The record was first issued in mono and in electronically re-channeled stereo, and was remixed in true stereo for the 2001 Columbia/Legacy reissue.