Miles Davis’s album Kind of Blue turns sixty years old this month. Believed to be the best-selling jazz album ever, it’s a landmark in the history of jazz. In fact, it represented just one phase in the career of an artist who constantly sought new musical territory and who, along the way, sometimes produced works of astonishing beauty.

Davis was a troubled man—violent, angry, and drug addicted. Yet none of these qualities could be detected in his early work, particularly the famous albums released in the decade before Kind of Blue. Known as the Prestige albums for the record company that sold them, they featured the first of what became Davis’s two legendary quintets. Members included Red Garland on piano and a little-known saxophonist named John Coltrane, who had not yet developed the radical non-melodic style that would make him world famous.

Eager to get out of his contract with Prestige, Davis held two marathon recording sessions in 1956 to produce four entire albums—Cookin’, Relaxin’, Workin’, and Steamin’—considered classics today. Their raw quality—including banter between Davis and the recording engineers and even one startling missed note by Coltrane in “If I Were a Bell”—highlights the music’s lively and spontaneous quality. It’s been said that jazz is the music of nonchalance, and that certainly describes such breezy and upbeat tunes as “I Could Write a Book” and “Blues by Five.” Such cheerfulness would disappear from Davis’s later work—during the period in the late 1960s when he came to be called “The Prince of Darkness.” But in the years that climaxed with Kind of Blue, he was focusing on the melodic and laid-back qualities that music historians later saw as a transition between the “bebop” and “cool” styles of jazz.

The most effective songs on these albums were the slow, romantic ballads, such as “When I Fall in Love” on Steamin’—probably the most beautiful thing Davis ever recorded. It perfectly captures a sense of subdued yearning—an atmosphere of midnight intimacies as ephemeral and striking as moonlight on an empty Manhattan street—which became forever associated with Davis’s art. Even after he stopped playing them in the 1970s, these love songs would prove among his most popular—and the sweet, melancholy style in which they were played among his most lasting musical achievements.

Davis, however, was constantly changing his music. After leaving Prestige, he signed with Columbia Records and began recording a series of albums with large orchestras, including Porgy and Bess, Milestones, and Sketches of Spain. These records traded the intimacy of the first quintet for a bolder, more upscale sound, and their classical influences gave Davis credibility with upper-class audiences. But the music lacked the individualism of the jazz Davis played both before and after—even as they introduced a level of sophistication that he would exploit on Kind of Blue.

To record that album, he brought in new personnel, including pianist Bill Evans, and Julian “Cannonball” Adderley on alto saxophone to supplement Coltrane on tenor sax. And he took a new direction in the music’s structure as well.

Kind of Blue would be composed in a style known as “modal” jazz, which in some ways was the opposite of the bebop style of the Prestige albums. Bebop had been innovative in its day, but Davis saw that it was based on musical structures that limited what soloists could do while improvising. If a soloist played certain notes, or failed to end phrases at specific times, the result would sound wrong. Seeking ways around these confines, Davis, like the Romantics who had rebelled against classicism a century and a half earlier, sought a new kind of music that would liberate soloists. Modal jazz used sparse chords in the background and put more emphasis on melody, which made the solos more important and resulted in music with a freer, more individualistic quality. It managed to be more abstract without becoming alienating or unmusical, and it was adaptable to melancholy (as in “Flamenco Sketches”), casualness (as in “Freddie Freeloader”), or suspense (in “All Blues”).

The album, which Davis began recording on March 2, 1959, has a smooth refinement like the finest gems, despite the fact that the band held no rehearsals—Davis thought they destroyed spontaneity—and was released without edits of any kind. Kind of Blue was an experiment six decades ago. But whereas many things that were cutting-edge then have become clichés today, it remains as fresh as it was when new.

Davis went on to form a second quintet and to change his style repeatedly in the years that followed. Along the way, he produced some finely honed masterpieces and some duds—but nothing that rivaled the creativity and beauty of his greatest jazz masterpiece.

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