From the day he left St. Louis for New York as a teenager to the day he died, Miles Dewey Davis III was the coolest motherfucker on the planet. I don't say "motherfucker" to be vulgar; it was Miles's favorite word. In his 400-page autobiography, it appears 312 times. Miles used "motherfucker" the same way people from Philly use "jawn." It had no inherent definition to Miles, and its meaning changed according to the context in which he used it. It's impossible to summarize Miles's eccentric life and unparalleled career as a musician, painter, and fashion icon with one word, phrase, or sentence, but this seems fitting: Miles Davis was a real motherfucker.
In his own words, Miles changed music "five or six times." That might even be undercutting it. At just 18, he played an integral role in the bebop revolution in the late 1940s, becoming the regular sideman for the art's brightest star, Charlie Parker. He was the band leader for the nonet that produced the first cool jazz recordings in 1949, a series of 78s that were later compiled as Birth of the Cool (1957). His great quintets—which made stars of now-legendary musicians John Coltrane, Cannonball Adderley, Wayne Shorter, Herbie Hancock, Chick Corea, and Tony Williams just to name a few—recorded albums that are definitive for almost every major subgenre of jazz at the time, including hard bop, post-bop, modal jazz, and fusion.
Often to the chagrin of fans and critics alike, Miles's music constantly evolved; he never made the same record twice. His long close friendship with composer Gil Evans lead to experiments in jazz orchestration that sound fresh and original even 60 years later. Some believe Miles abandoned jazz altogether with his push into fusion with albums like Bitches Brew (1970) and On the Corner (1972). After resurfacing from a five-year retirement, Miles continued to earn the scorn of jazz traditionalists by wholly embracing the modern synthesizer sounds of the 1980s, culminating in a testy public feud with a brash teenage trumpet prodigy not unlike Miles at that age, Wynton Marsalis.
Miles Davis's personal life was no less controversial than his music thanks to the boundless hubris that came with his relatively privileged upbringing. He earned the nickname "the Prince of Darkness" in the media with venomous critiques of white America and aloof and erratic stage behavior that sometimes bordered on hostility, particularly in front of white audiences. His showy fashion sense and taste for expensive cars made him a target of racial profiling from white police, leading to a number of high-profile run-ins with the NYPD. He was rarely faithful to the seemingly hundreds of women he saw, and he admitted to multiple instances of domestic abuse. There was hardly a person in his life whom Miles didn't berate at one time or another in his distinctive raspy voice.
But there was noise that came out of Miles Davis other than insults: the sound of his trumpet. His sandpaper voice and his brilliant trumpet sound perfectly symbolize Miles's duality. Like Kanye West, he was as hard a person to love as he was a genius, and that's saying something, because his genius was a motherfucker.
So you want to get into: Miles Davis the Bebopper?
Miles Davis moved to New York City in 1944 ostensibly to attend the prestigious music school Juilliard, but the 18-year-old prodigy had an ulterior motive: find Bird. Charlie "Bird" Parker was leading the bebop revolution in clubs along 52nd Street and in Harlem. Miles had been transfixed by the art since hearing Bird and Dizzy Gillespie play in St. Louis a few years prior, and like Bob Dylan moving to NYC to find Woodie Guthrie, Miles was dead set on joining them. Bird took an immediate shine to Miles, and soon the budding duo was playing together regularly. Miles's laid back solos were the perfect complement to Parker's furious fits of notes, but, more importantly, Miles organized and booked gigs and recording dates for their group. Bird was so hopelessly addicted to heroin that getting him to even show up was a challenge in itself, and Miles served as both sideman and caretaker to the troubled genius.
This playlist is presented in chronological order so you can hear young Miles progress over time and find his identity next to Bird. Bird is clearly the highlight of these early recordings, and critics initially panned Miles as a cheap imitation of Dizzy Gillespie. But Miles's contributions to the bebop movement both onstage and off were invaluable to spreading the art outside of New York City, where white audiences often treated it with the same fear and disdain that gangster rap was treated in the 1980s.
Playlist: "Now's the Time, Pt. 4" / "Yardbird Suite" / "Donna Lee" / Milestones" / "Half Nelson" / Dewey Square" / "Scrapple From The Apple" / "Klaunstance" / "Marmaduke"
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So you want to get into: Miles Davis and Gil Evans?
Miles Davis met Gil Evans in 1947 when the latter wanted to do an arrangement of "Donna Lee"—the first Miles Davis composition to ever be recorded—for the Claude Thornhill Orchestra. Miles regularly referred to Evans as his best friend and used him as an example that "not all white people are evil." Evans was a composer of great depth and vision, and Miles with his pristine trumpet sound was the perfect muse for him. Having attended Juilliard, Miles was able to grasp the more complicated musical concepts Evans wanted to introduce into jazz orchestra, although Miles eventually dropped out of Juilliard because "the shit they was talking about was too white for me."
Birth of the Cool, recorded in 1949 but released under that title in 1957, was their first collaboration, and it took jazz in a sharply different direction than bebop. As the title suggests, the original 78s of this session were the birth of "cool jazz," although Miles ceeded the genre and much of the credit for creating it to Chet Baker and Gerry Mulligan because he spent the four years after its recording addicted to heroin. After Miles quit heroin cold turkey, he and Evans reunited on Miles Ahead in 1957, a sophisticated take on big band jazz, and Porgy and Bess in 1959, an adaptation of George Gershwin's opera. But their most daring and controversial project was Sketches of Spain in 1960, which borrows heavily from Spanish classical music of the early 20th century and sparked what may have been history's first "is this jazz?" debate.
Playlist: "New Rhumba" / "Boplicity" / "Will O the Wisp" / "Gone" / "Venus De Milo" / "The Duke" / "Saeta" / "Deception" / "There's a Boat That's Leaving Soon for New York"
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So you want to get into: The Great Miles Davis Quintets?
While Miles Davis played "Round Midnight" with a quintet at the 1955 Newport Jazz Festival, Aram Avakian turned to his brother George, an executive at Columbia Records, and told him to sign Miles immediately, but George resisted because Miles was still considered a junkie. "Don't be a fool," Aram snapped. "Did you hear what he played? Best thing in the whole festival!" Months later, Miles was exclusive with Columbia. He produced quintet masterpieces for label for the next 15 years.
Miles's quintets set the standard for jazz improvisation for generations to come, in addition to pushing the boundaries of music theory. The First Great Quintet—Miles, John Coltrane, Philly Joe Jones, Paul Chambers, Red Garland, and sometimes Julian "Cannonball" Adderley to make it a sextet—recorded what many consider to be the best jazz albums of all time, including 'Round About Midnight (1957), a nod to the performance that landed him at Columbia, Milestones (1958), and the immortal Kind of Blue (1959), the highest selling jazz album ever.
Miles desperately wanted to keep this group together, but Coltrane's star was burning too bright for him to stay a sideman. In the early 1960s, Miles, by then approaching 40 years old, put together another group of completely unknown teenagers—Herbie Hancock, Tony Williams, Ron Carter, and Wayne Shorter—and the prodigious young talents became the tools with which Miles crafted his vision. The group's experiments with unorthodox melodies, chords, and polyrhythms produced seminal works for the post-bop era that incorporated elements of free jazz without wholly submitting to it; Miles vehemently rejected free jazz as a white conspiracy to destroy black music. Miles Smiles (1967) is the high point of the Second Great Quintet, but Sorcerer (1967), Nefertiti (1968), Miles in the Sky (1968), and Filles de Kilimanjaro (1969) are fascinating pivot points for Miles going electric.
Playlist: "Dr Jackle" / "Conception" / "Freedom Jazz Dance (Evolution of the Groove)" / "So What" / "Milestones" / "Footprints" / "Black Comedy" / "Nefertiti" / "Ah-Leu-Cha" / "'Round Midnight - Live (1955 Version)"
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So you want to get into: Jazz Fusion Miles Davis?
Miles Davis's father was a dentist and a prominent member of the black community in St. Louis. Miles didn't live the life of poverty that most in his race endured, and he was always vexed by it. In the late 1960s, it reached a breaking point. John Coltrane's death in 1967 stopped jazz dead in its tracks, and Miles saw his audience had become mostly older white people. He was desperate to find a way to reconnect with young black audiences that had drifted to rock and funk. Through his young pianist Herbie Hancock and bassist Ron Carter, Miles was introduced to the electronic sounds of those instruments, and by the early 1970s Miles was more a rock star than a jazz musician.
His foray into electronics began with the Second Great Quintet, as Miles in the Sky (1968) marks the first time he uses electronic instruments. But a year later he blew up the quintet with In A Silent Way (1969) by using two electric piano players (Herbie Hancock and Chick Corea), an electric guitar (John McLaughlin), and an organ (Joe Zawinal). Critics at the time accused Miles of chasing popular trends with his fusion albums. That may be true to some degree, but he undoubtedly produced two of jazz fusion's greatest records in Bitches Brew (1970) and On the Corner (1972).
Although it is now heralded as one of his best albums, On the Corner was a total flop, which played a role in Miles retiring in the mid-1970s, a period during which he succumbed to heavy drinking, cocaine use, and womanizing. When he returned in the early 1980s, he continued to incorporate modern electronic sounds. However, because synth sounds in the 80s were a little hokey, his post-retirement work sounds quite dated; Tutu (1986) is the highlight of this Miles era. In one of the great "what if albums" of Miles' career, he and Jimi Hendrix were planning to do an album together before Hendrix died suddenly in 1970.
Playlist: "Stuff" / "John McLaughlin" / "Black Satin" / "In A Silent Way/It's About That Time" / "Frelon Brun (Brown Hornet)" / "Right Off" / "Tutu" / "Jo-Jo"
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So you want to get into: Miles Davis for Lovers?
Miles Davis hated being asked about old records; he wanted you to listen to the new stuff. This is encapsulated in a famous Miles quote: "You know why I quit playing ballads? Because I love playing ballads." While his forward-thinking approach to music lead to innovations that you can still hear in music today, one of the most painful sacrifices of this approach for fans is that he stopped writing ballads. Miles's crystal clear open trumpet sound and the buzz of his harmon mute, played over cascading piano chords, can melt even the most frigid hearts. It should be noted again that Miles's relationship with women was at times revolting, and this dark side of his character deserves to be heavily criticized. But separating the art from the artist, Miles's ballads are undoubtedly some of the most beautiful music of the 20th century, and, in the 21st, the perfect soundtrack for snuggle time with bae.
The bulk of Miles's ballads were recorded in the mid-1950s when he was recording with Prestige. After signing with Columbia, the volume of ballads slowed, but as is the case with much of Miles's discography, this period yielded the best of his baby-making music. "Someday My Prince Will Come" from the album of the same name in 1961 is a timeless rendition of the Snow White song; it's also one of the last times Miles played with Coltrane. The two ballads on Kind of Blue—"Flamenco Sketches" and "Blue in Green"—will bring you to tears, even on the thousandth listen.
Playlist: "Someday My Prince Will Come" / "It Never Entered My Mind" / "Flamenco Sketches" / "In Your Own Sweet Way" / "My Old Flame" / "Stella By Starlight" / "When I Fall In Love" / "I Fall In Love Too Easily" / "I See Your Face Before Me" / "Blue in Green"
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Jeff Andrews is a writer based in New York City. Follow him on Twitter.