Along with their subsequent collaborations Porgy and Bess (1959) and Sketches of Spain (1960), Miles Ahead is one of the most famous recordings of Third Stream, a fusion of jazz, European classical, and world musics.

Evans combined the ten pieces that make up the album into a suite, each flowing into the next without interruption; the only exception to this rule was on the title track since it was placed last on side A (this has been corrected on the CD versions).

Art Taylor played drums on the sessions and the then current Miles Davis Quintet member Paul Chambers was the bassist.

"[14] The Penguin Guide, on the other hand, opined that "the flugelhorn's sound isn't so very different from his trumpet soloing, though palpably softer-edged.... [S]ome of the burnish seems to be lost.

[6] Davis was reportedly unhappy about the album's original cover, which featured a photograph of a young white woman and child aboard a sailboat.