Miles Davis Quintet: Miles Smiles (Columbia, 1967)

Recorded in 1966, this album featuring Miles’ second great quintet showcases not only the remarkable interplay between his stellar bandmates but also the compositional gifts of the band’s saxophonist Wayne Shorter, whose “Footprints,” “Orbits,” and “Dolores”—along with two other scintillating cuts, Eddie Harris’ “Freedom Jazz Dance” and Jimmy Heath’s “Gingerbread Boy”—would become jazz standards to be played by countless bands for the next five decades. The influential group’s distinctive open-ended quality, its continuous ebb and flow, makes Miles Smiles one of the best from their productive five-year run. LEE MERGNER

Learn more about Miles Smiles on Amazon and Apple Music.