By the end of 1986, with Miles’ career in resurgence, he was approached by the producers of a major Hollywood film, Siesta, based on the book by Patrice Chaplin and starring Ellen Barkin, Gabriel Byrne and Martin Sheen. The story takes place in Spain, and the director had already used tracks from Sketches of Spain as placeholders, hoping for jazz music with an Iberian flavor and a mournful edge. That the narrative unfolded with a mysterious, dream-like quality suggested Miles as well. Miles agreed to create the music for the movie and immediately asked Marcus Miller to help compose and produce. 

Miles was no stranger to the world of film. In 1958, he had created the impromptu modal jams that became the soundtrack for Louis Malle’s first feature—L’Ascenseur pour l’echafaud . His 1970 album Jack Johnson had originally been conceived as a score to a boxing documentary, and as recently as October 1986 had played on tracks for the film Street Smart.

As had taken place with Tutu, Miles looked to Miller—working with keyboardist/programmer Jason Miles—to compose and construct the various tracks, over which he blew his trumpet parts. Matching the music to the mood and tempo of the film’s scenes lay on Miller’s shoulders. The soundtrack came together in early 1987 in Los Angeles, Miller and Jason Miles working in North Hollywood, and Miles driving in from Malibu to play his parts. As on Tutu, Miller brought in a number of players to add solos and texture: guitarists John Scofield and Earl Klugh; flautist James Walker, and drummer Omar Hakim. 

Siesta hit screens in November to scathing reviews bemoaning its self-conscious hipness and scrambled structure. The soundtrack however had been released a few months earlier, to positive reception; The Observer lauded it for being “elegiac, Miles Davis being use for his remarkable ability to make the trumpet sound like the most wisely sad of all instruments.”