Keeping to his standard procedure at Columbia to date of alternating small group records and big band studio projects with Gil Evans, Davis followed up Sketches of Spain with an album by his working quintet. In 1960, however, the jazz world had been in flux. Although Davis had garnered acclaim for Kind of Blue, the entrance of Ornette Coleman and free jazz via his fall 1959 residency at the Five Spot Café and his albums for Atlantic Records had created controversy, and turned attention away from Davis.
Similarly, Davis' touring band had been in flux. In 1959, Cannonball Adderley left to form his own group with his brother, reducing the sextet to a quintet. Drummer Jimmy Cobb and pianist Wynton Kelly had been hired in 1958, but most difficult for Davis was the departure of John Coltrane, who stayed on for a spring tour of Europe but left to form his own quartet in the summer of 1960. In 1960, Davis went through saxophonists Jimmy Heath and Sonny Stitt before settling on Hank Mobley in December, the band re-stabilizing for the next two years.
Unlike Kind of Blue, which featured nothing but group originals, this album paired equal numbers of Miles Davis tunes with pop standards, including the title song resurrected from the 1937 Disney film Snow White and the Seven Dwarfs. The titles to all three Davis originals refer to specific individuals: "Pfrancing" to his wife Frances, featured on the album cover; "Teo" to his producer Teo Macero; and "Drad Dog" to Columbia Records president Goddard Lieberson. While the cover credits the Miles Davis Sextet, only the title track featured six players, Coltrane making two cameo appearances on the album, taking solos on the title track and "Teo," the latter with Mobley laying out. On March 21, ex-Davis drummer Philly Joe Jones made his final contribution to a Davis session, replacing Cobb for the original "Blues No. 2" which was not used on the album.