Miles Smiles is an album by jazz musician Miles Davis, released in January 1967 on Columbia Records. It was recorded by Davis and his second quintet at Columbia 30th Street Studio in New York City on October 24 and October 25, 1966. It is the second of six albums recorded by Davis's second great quintet, which featured saxophonist Wayne Shorter, pianist Herbie Hancock, bassist Ron Carter, and drummer Tony Williams.

Miles Smiles showcases Davis' deeper exploration of modal performance with looser forms, tempos, and meters. Although the album did not follow the conventions of bop, neither did it follow the formlessness of free jazz.  According to musicologist Jeremy Yudkin, Miles Smiles falls under the post-bop subgenre, which he defines as "an approach that is abstract and intense in the extreme, with space created for rhythmic and coloristic independence of the drummer—an approach that incorporated modal and chordal harmonies, flexible form, structured choruses, melodic variation, and free improvisation."[2] Music theorist Keith Waters writes that the album "accentuated the quintet's connections to both the hard bop tradition and the avant-garde."

On three tracks from this album ("Orbits", "Dolores", "Ginger Bread Boy"), pianist Herbie Hancock takes the unusual step of dispensing with left-hand chords and playing only right-hand lines. 'Freedom Jazz Dance' has more conventional accompaniment from the piano, although the quintet altered Eddie Harris's composition by inserting additional bars between the melodic phrases of the piece, as well as performing the piece at a slightly faster tempo.

On ‘Footprints’: Wayne Shorter's composition "Footprints" appears on his earlier album Adam's Apple, but on Miles Smiles, the correlation between African-based 12

8 (or 6
8), and 4
4 is playfully explored. Drummer Tony Williams freely moves from swing, to the three-over-two cross rhythm—and to its 4
4 correlative. The rhythmic approach of Williams, and bassist Ron Carter, strongly suggests compound quadruple meter (12
8), rather than triple meter (3
4), because the ground of four main beats is maintained throughout the piece. The bass switches to 4
4 at 2:20. Carter’s 4
4 figure is known as ‘’tresillo’’ in Afro-Cuban music and is the duple-pulse correlative of the 12
8 figure. This may have been the first overt expression of systemic, African-based cross-rhythm used by a straight ahead jazz group. During Davis’s first trumpet solo, Williams shifts to a 4
4 jazz ride pattern while Carter continues the 12
8 bass line.