Miles Davis: where to start in his back catalogue

The album to start with

Kind of Blue (1959)

Kind of Blue isn’t just the best introduction to Miles Davis, it’s the best introduction to jazz as a whole, an album that typifies the genre’s musical freedom, haunting gospel tone and restless adventure. An instant classic on release in 1959, Kind of Blue marks the moment that Davis definitively broke with the predominant hard bop style in favour of modality, moving from the chord sequences of 40s and 50s jazz to a looser melodic approach based around scales and improvisation.

Davis’s revolutionary shift on Kind of Blue has incited vast swathes of critical thinking and influenced records from John Coltrane’s A Love Supreme to Pink Floyd’s The Dark Side of the Moon. But you don’t need to be a musical scholar to appreciate Kind of Blue: the record’s exquisite melodies connect on a very human level. Davis said that the album was inspired by the gospel music he used to hear walking home from church and you can hear the melancholy pull of nostalgia in the impassioned blues lines that Davis coaxes from his trumpet.

Inspiration tumbles from songs such as So What and Blue in Green, but Kind of Blue never rushes or fumbles: instruments are given space to stretch their legs, as Davis’s sublime sextet (including John Coltrane on tenor saxophone) bend time around them, allowing Kind of Blue to whip past in a flash and linger for an eternity.

The three to hear next

Bitches Brew (1970)

Miles Davis went into the recording of Bitches Brew in a typically combative mood. “I wasn’t prepared to be a memory yet,” he wrote in his autobiography. “I had seen the way to the future with my music and I was going for it like I had always done.”

Recorded in 1969, Bitches Brew was a response to the progressive rock music that many people believed would consign jazz to history, and after Davis’s second wife, Betty Mabry, introduced him to the work of James Brown, Sly Stone and Jimi Hendrix. Bitches Brew follows the rock tradition in bringing the band’s rhythm section to the fore, employing two bassists, three drummers, three electric piano players and a percussionist in a simmering saturnalia of percussion, while favouring rock’s straighter rhythmical pulse over the typical jazz swing.

Yet Bitches Brew took music farther off into the ether than even the most experimental rock band could venture, as Davis pulled at the fabric of musical norms. In rehearsals for the album, Davis presented his group with a series of musical sketches and told them to follow their instincts, with the idea being to get away from any “prearranged shit”. The resulting recordings soar with immaculate musical freedom: from the nervous collapse of the title track, Davis’s trumpet bouncing over the mix like search lights through the New York skyline, to the rubbery Latin funk of Miles Runs the Voodoo Down, it feels as if all musical life is here.

In a Silent Way (1969)

Released a year before Bitches Brew, In a Silent Way prefigures that album’s use of electric instruments and tape slice editing, with producer Teo Macero arranging the highlights of a three-hour studio session into two distinct works, Shhh / Peaceful and In a Silent Way, for the album release. Yet in mood, the two records could hardly be more different. While Bitches Brew throbs with frantic, funky energy, In a Silent Way is brooding and pensive, an eternal meditative masterpiece that marries the late-night introspection of Kind of Blue with the post-genre pulse of Davis’s more experimental records, all drones, drift and space. In 1969, Lester Bangs called In a Silent Way “the kind of album that gives you faith in the future of music”; 51 years on, it is hard to disagree.

Sketches of Spain (1960)

Released just a year after Kind of Blue, Sketches of Spain shares that album’s rich, easily digestible musicality and airy lightness. However, its sound, inspired by the Spanish folk tradition, demonstrates the kind of bold thematic leap that Davis would make throughout his career.

Sketches of Spain came about after Davis’s first wife, Frances Taylor Davis, insisted he accompany her to a performance by the flamenco dancer Roberto Iglesias. The following day, Miles called composer and arranger Gil Evans and they set about interpreting the flamenco sound for a US jazz audience. The duo took source material that dug deep into the heart of Iberia, including Joaquín Rodrigo’s Concierto de Aranjuez, Manuel de Falla’s Will o’ the Wisp and Galician folk song The Pan Piper, giving Davis a strong, distinctive melodic base to weave his spell around.

That magic can be heard in the elegant scurrying of castanets that opens Concierto de Aranjuez (Adagio) and drives Will o’ the Wisp, to which Davis and Evans add jazz and classical instrumentation, creating an album that hangs tantalisingly between the Spanish sierra, the New York concert hall and the jazz club dive, a wonderfully transportive work of musical inspiration.

One for the heads

On the Corner (1972)

Depending on who you talk to, On the Corner is either the inspirational motherlode, an album that birthed musical genres from trip-hop to drum’n’bass, or a sprawling mess. In truth, this fascinating 1972 release is a little bit of both; the unlikely collision between Miles’ interests in Indian music, Karlheinz Stockhausen and Ornette Coleman.

In his autobiography, Davis said that Stockhausen’s influence enabled him to understand music in a new way, abandoning the circular structures of modern music in favour of subtly shifting soundscapes. On the Corner, then, is less a work of song or melody and more a constantly evolving musical monolith, with Michael Henderson’s rock-solid electric bass underpinning hulking layers of keyboard, electric trumpet and percussion.

In a Jazz Journal review, Jon Brown wrote: “It sounds merely as if the band had selected a chord and decided to worry hell out of it for three-quarters of an hour.” That description nails why On the Corner was so hated by contemporary listeners and why it is so loved by adventurous music fans today, with the album’s preference for groove and texture prefacing the tactile sprawl of modern electronic music.

Related: 'It sounded like the future': behind Miles Davis's greatest album

The primer playlist

Further reading

Miles: The Autobiography
In his autobiography, Miles Davis (in the company of veteran journalist Quincy Troupe) writes exactly as you would expect Miles Davis to write, his intense prose peppered with wonderful turns of phrase, raw passion and an avalanche of “motherfuckers”. For all that, The Autobiography is a difficult read, full of rank misogyny, score settling and unbridled egotism, but it remains the definitive story of one of the 20th century’s most enduring cultural icons.

Miles Davis: Birth of the Cool documentary
Stanley Nelson’s 2019 documentary Miles Davis: Birth of the Cool offers an intoxicating, if limited, overview of Davis’s life. At times it comes too close to hagiography – there is little serious attempt to hold Davis to account for his violence towards Frances Taylor Davis, for example – but as an introduction to his life it may inspire further digging.

Miles Style, by Quincy Troupe
Troupe is also behind Spin magazine’s epic 1985 interview piece, which explores everything from systemic racism to what makes Davis’s trumpet playing unique. (“He plays sideways,” according to Lester Bowie, another great American trumpet player.) It’s a fascinating read, alternately dark and hilarious, that gets close to capturing Davis’s unsettling genius.