Miles Davis: The Blueprint for Living Fly

Miles Davis reinvented himself five times, dressed better than anyone in any room, and never once explained himself. Here is why he remains the definitive blueprint for the fly ass life.

THE CULTURE

Will

7/19/20263 min read

person playing trumpet during night time
person playing trumpet during night time

The Culture | FlyAssLife

Most artists spend their careers perfecting one thing. Miles Davis spent his becoming a different artist entirely, repeatedly, across five decades, each transformation arriving at the moment when the previous version had become comfortable enough to coast on.

He could have coasted. The evidence is staggering: Birth of the Cool in 1957, Kind of Blue in 1959 — the best-selling jazz album in history, the record that defined a genre, the one that still moves units in the streaming era. A lesser man finishes there, plays those songs for forty years, dies celebrated. Miles Davis released Bitches Brew eleven years after Kind of Blue and invented fusion, alienating half his audience in the process and creating the other half of the next decade's music.

He was not interested in your nostalgia for who he used to be.

The Sound Was Never the Whole Story

Miles Davis grew up in East St. Louis, the son of a successful dental surgeon and landowner. He arrived at Juilliard in 1944 not because he needed the formal training — he was already operating at a level the school's curriculum couldn't contain — but because New York was where Charlie Parker was, and Charlie Parker was what Miles Davis had come to study.

The apprenticeship under Bird was everything and then it was over, because Miles Davis understood something that lesser musicians didn't: that learning from someone and becoming that person are two different outcomes, and only one of them has any future. He absorbed bebop at its source and then walked away from it, toward something cooler, more spacious, more interested in what wasn't being played than what was.

The space in Miles Davis's playing — the deliberate silence between notes, the phrases that ended before the obvious resolution — was not restraint. It was confidence. Only a musician who understood completely what to play could choose, on purpose, not to play it. The silence said: I know exactly where this goes. I'm choosing not to take you there. Follow me somewhere else.

The Wardrobe Was a Statement

In a musical culture where Black performers were expected to wear tuxedos and address their audiences with a deference that had nothing to do with the music and everything to do with the racial architecture of mid-century American entertainment, Miles Davis turned his back to the audience, wore what he wanted, and said nothing that wasn't communicated through the horn.

By the 1970s he was wearing Ferrante & Sons custom suits, Issey Miyake, clothes that hadn't been designed for jazz musicians because jazz musicians weren't supposed to look like this. He drove Ferraris and Lamborghinis through Manhattan. He trained as a boxer with Sugar Ray Robinson. He designed his own apartments. He painted.

None of it was affectation. It was the external expression of a man who had decided, at a very early stage, that his life was going to be lived entirely on his own terms and that every element of it was subject to the same standard he applied to the music: it had to be exactly right, or it had to change.

The Five Reinventions

Cool jazz. Hard bop. Modal jazz. Fusion. Electric funk. Each transition arrived when the previous idiom had been exhausted — not by the audience, but by Davis himself. He followed his ear and his curiosity regardless of where critical consensus said he was supposed to be, and in doing so he made critics irrelevant while making music that critics spent the following decades trying to catch up to.

Wynton Marsalis, who represents a certain reverent approach to jazz tradition, once suggested that Miles Davis's electric period was a betrayal of the music. Davis's response to this line of thinking, delivered throughout his career in various forms, was essentially: I am not a museum.

He was not wrong.

What He Leaves Behind

Miles Davis died in 1991 with a body of work that covers more creative ground than most musical movements, a personal aesthetic that influenced fashion and design as much as music, and a biography that reads like a manual for the kind of life FlyAssLife is trying to articulate.

Know your craft completely. Dress like it matters because it does. Drive something worth driving. Refuse to repeat yourself when you've already said a thing perfectly. Hold your standard above the market's opinion of what your standard should be.

Turn your back to the audience if the music requires it. The audience will catch up.

The Culture is FlyAssLife's lens on the art, music, and creators who define what fly actually looks like.