Hey, before we start, two things:

Two things bring me tremendous joy: putting words on paper and editing the slop while Miles Davis's horn blasts through my AirPods Max, and the fact he spent 50 years pissing off his fans.

Late in his career, while seated at a White House dinner, some politician's wife asked Miles what he'd done to get invited. "Well," he famously replied, "I've changed music five or six times — what have you done?" Classic Miles: defiant, arrogant, and brutally honest. A giant of 20th century music, Miles wasn't just a cultural icon but an obsessive innovator whose commitment to reinvention shaped the evolution of not just jazz, but also electronic music and hip-hop.

His career was not a steady ascent but a series of deliberate, often shocking breaks with his own success, his critics, and his fanbase. Miles's legacy extends beyond his musical contributions. It includes a playbook — a set of mind-fucking moves that repeatedly shattered the status quo.

Here is that playbook.

In 1944, an 18-year-old Miles moved to New York City with a scholarship to the prestigious Juilliard School. His real education, however, started when he dropped out and began playing in the jazz clubs of 52nd Street alongside his idol and bebop pioneer, Charlie Parker. Here, Miles faced an immediate and serious challenge: he couldn’t keep up.

Bebop is a style of jazz defined by fast tempos, complex chord progressions, intricate melodies, rhythmic changes, and virtuosic improvisation. Miles just didn’t have that explosive style in him. He was known for cracking notes and cracking under pressure. He later admitted, "I used to quit every night... the tempo was so up. The challenge was so great."

For most, this skill gap would've ended their creative ambitions. For Miles, it became the catalyst for a brilliant strategic pivot. Instead of competing on terms set by others, Miles created a new language, a unique voice built on what he could do. Bebop's blazing clichés made him nauseous, so he began exploring a more calculated, lyrical approach. His new work prioritized melody and emotional nuance. He learned to convey more by playing less, a principle he would later distill into a simple mantra: "I always listen for what I can leave out."

Miles began using a Harmon mute, held close to the microphone, to create a soft, breathy, and intimate sound that became his signature. This move was the antithesis of the brash trumpet that had dominated jazz. By turning a potential weakness into his greatest strength, he didn't just find his voice; he invented an entirely new aesthetic, effectively "birthing the cool" and creating one of the most influential styles in music history.

His 1957 album, Birth of the Cool, though not an immediate commercial success, inaugurated a new movement in jazz. Critics thought it too cerebral, polished, and restrained, saying it lacked the raw expressiveness and swinging energy that characterized earlier forms of jazz. Little did they know Miles's cool jazz period would become essential in expanding jazz's vocabulary and would lay the groundwork for even more groundbreaking innovations.

After a period of personal struggle with heroin addiction in the early 1950s, Miles re-emerged with a heroic focus. His comeback marked a strategic pivot away from the cerebral, highly arranged coolness of his earlier work towards a more raw and powerful expression.

The aggressive, prideful, and blues-rooted sound he now embraced — hard bop — was a direct manifestation of his hard-won battle with addiction and renewed purpose. It was a visceral, muscular assertion of life after a period of self-destruction, an aesthetic that would not only restore his career but also establish the dominant mainstream jazz aesthetic for the next decade.

But by the late 1950s, Miles was itching for something new. He felt bebop and hard bop's complexity was becoming a creative straitjacket. So he stripped it all away.

The result was Kind of Blue, the best-selling jazz album ever, and the birth of modal jazz. The concept was simple: instead of improvising over a rapid-fire sequence of chords, musicians would improvise over simple scales, or "modes," that remained static for long passages. In one of music history's most brilliant counterintuitive moves, Miles departed from fifty years of harmonic tradition. Through radical simplification, he discovered that severe limitations could unlock unprecedented creative freedom. The recording sessions themselves were legendary for their spontaneity. Miles brought together John Coltrane, Cannonball Adderley, Bill Evans, Wynton Kelly, Paul Chambers and Jimmy Cobb, and with minimal rehearsal, he gave them brief sketches of scales and modes just before the tape rolled, forcing them to react in the moment, creating a playful atmosphere of exploration and discovery.

By the late 1960s, Miles, once again, abandoned what had made him successful — modal jazz — and began experimenting with electric instruments and incorporating elements of rock, funk, and avant-garde music. The common image of this electric fusion period is one of expansive, uncut psychedelic sessions. Albums like In a Silent Way and Bitches Brew sound like the raw, unfiltered energy of a band entering a shamanic trance. The reality, however, was far more experimental.

In the studio, Miles was less a bandleader and more a director, guiding huge ensembles through long, unstructured improvisations. His longtime producer, Teo Macero, would then take hours of these tapes and become a co-composer. Through tape splicing — physically cutting and reassembling audio tape — Teo would collage the final album tracks from fragments of the jam sessions to create a seamless whole, making Miles a pioneer not only of fusion but of using the recording studio as a primary compositional tool, a method that foreshadowed the production techniques of modern electronic music and hip-hop.

Miles understood the impact his taste had on the evolution of music and culture. Naturally, he despised his most celebrated work, famously telling his musicians, "If you learn any of that old shit you're fired." He knew he couldn’t step into the future without letting go of his past.

In a 1986 interview, years after his electric and pop phases, he was asked about the groundbreaking modal jazz he created with pianist Bill Evans on Kind of Blue. His response, as you can probably imagine, was brutally (and comically) honest:

This wasn't pretentiousness. It was his philosophy of perpetual reinvention — the same philosophy that nurtured his career and fueled his rise to greatness. This relentless forward motion, this courage to abandon universal acclaim in pursuit of the unknown, this willingness to burn it all down and start anew is what separates Miles from nearly every other artist of his stature.

By the 1980s, many jazz purists felt Davis had lost his way. His covers of pop songs like "Human Nature" and "Time After Time" were seen as selling out. His final album, the posthumously released Doo-Bop, a collaboration with hip-hop producer Easy Mo Bee, was viewed by many as a desperate attempt to stay relevant.

This narrative misses the point entirely. His final act was not a betrayal of his past, but a logical conclusion. The dense, groovy funk of his 1972 album On the Corner — which critics hated at the time — was a sonic collage that sounded like "walking down a Manhattan street and hearing six languages in as many blocks." Decades later, its layered rhythms and raw textures have been credited as a blueprint for the production styles of hip-hop giants like Public Enemy's Bomb Squad and Timbaland.

His collaboration on Doo-Bop, therefore, was not a desperate wild turn but a full-circle moment. It wasn't Miles chasing a trend; it was an homage from the genre he helped create. Easy Mo Bee’s raps serve as an ode to Miles, a nod of thanks and acknowledgement of debt from the younger generation to an established master. Doo-Bop was the sound of an artist engaging with a new social sound his own music had prophesied, a final, defiant refusal to become a forgotten museum piece.

Miles’s legacy is not just in his records, but in his relentless courage to abandon success. He built empires only to walk away from the throne in search of new worlds to conquer. His entire career was a challenge to the very idea of a fixed creative identity.

In the 1970s, a fan approached him after a show, complaining, "Miles, you're my man, but that new shit you're into, I just can't get with it." Without missing a beat, Davis clapped back, "Should I wait for you?"

It's as if we are still trying to catch up.

I get paid when you click this. It’s shit I actually like, so maybe you will too.

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