You’ve probably seen the posters. Don Cheadle in a wig, holding a trumpet, looking intensely cool and intensely troubled. Or maybe you’ve scrolled past that Netflix thumbnail for the big documentary with the gravelly voiceover.
The thing is, every film about Miles Davis struggles with the same impossible problem: how do you capture a man who changed the sound of the world four or five different times? You can’t just put him in a box. Miles was a ghost, a boxer, a painter, and a genius who happened to play the trumpet.
Most people come to these movies looking for a straightforward story. They want to see the birth of Kind of Blue or the drama of the 1950s. Instead, they often get something much weirder.
The Cheadle Experiment: Why Miles Ahead Isn't a Biopic
Let’s talk about the 2015 movie Miles Ahead. If you went into that expecting a standard "walk to the microphone and play the hits" story, you were probably confused. Don Cheadle, who directed and starred in it, basically made a heist movie.
It’s set in the late 1970s. Miles is in his "silent period." He’s holed up in his Upper West Side house, dealing with a crumbling hip, a heavy drug habit, and a massive creative block. He hasn't released music in years.
Cheadle decided that a regular biography would be too boring for a guy like Miles. So, he invented a plot involving Ewan McGregor as a shady journalist and a stolen session tape. There are car chases. There are gunfights. Honestly, it’s a bit ridiculous.
But here’s the kicker: it actually feels like Miles.
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The movie uses a non-linear structure that mirrors the way Miles approached jazz. It’s not about the dates or the facts. It’s about the vibe. Cheadle nails the raspy whisper and the menacing stillness. He shows the dark side too—the way Miles treated his first wife, Frances Taylor, was often brutal and indefensible. The film doesn't look away from the domestic violence, which is a hard but necessary truth.
Birth of the Cool: The Facts Behind the Legend
If you want the real history, you go to Stanley Nelson’s 2019 documentary, Miles Davis: Birth of the Cool. This is the definitive film about Miles Davis if you’re a purist.
Nelson got access to the estate. He found photos and footage most of us had never seen. You see Miles as a young, clean-cut Juilliard student. You see him in Paris, falling in love with Juliette Gréco and realizing that in Europe, he was treated like a human being rather than a second-class citizen.
One of the most striking things the documentary highlights is Miles’s background.
- He wasn't a "street" kid.
- His father was a wealthy dentist who owned a massive ranch.
- Miles grew up with money, which gave him a specific kind of confidence—or arrogance, depending on who you ask.
The doc also dives deep into his 1959 arrest. Miles was standing outside Birdland, a club where he was headlining, just taking a break. A white cop told him to move. Miles refused. The cop beat him over the head with a billy club. That moment changed him forever. It solidified a bitterness toward the American system that stayed in his music until the day he died.
The Voice That Isn't Miles
In Birth of the Cool, you hear a raspy voice narrating Miles's thoughts. It sounds exactly like him. But it’s actually actor Carl Lumbly. He’s reading from Miles’s autobiography (which, if you haven’t read it, is one of the most profane and honest books ever written).
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Lumbly’s performance is so good it tricks your brain. It makes the documentary feel intimate, like Miles is talking to you from beyond the grave, explaining why he turned his back on the audience or why he started playing electric fusion when the jazz critics wanted him to stay in 1955.
The Secret Masterpiece: Elevator to the Gallows
Most people forget that Miles actually was in the movies long before he was the subject of them. In 1957, he was in Paris and agreed to score Louis Malle's film Ascenseur pour l'échafaud (Elevator to the Gallows).
This wasn't a normal scoring session. Miles didn't write out a single note of sheet music beforehand. He sat in a dark studio with his band, watched the movie on a screen, and improvised the entire soundtrack in real-time.
It’s one of the greatest pieces of film music ever recorded. The way the trumpet captures the loneliness of the rainy Paris streets is haunting. It changed how directors thought about film scores. It wasn't just background noise; it was a character.
What Most People Get Wrong
There is a common misconception that Miles was always a drug-addicted "dark prince." While he struggled with heroin in the early 50s and cocaine later on, he was also a fitness fanatic at various points. He boxed. He didn't drink. He was disciplined.
The films often lean into the "tortured artist" trope because it makes for good drama. But the reality was more complex. Miles was a businessman. He knew how to market his image. He changed his clothes and his hair as often as his musical style because he knew staying the same was the quickest way to become a museum piece.
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Actionable Insights for the Miles Curious
If you want to understand the man through the screen, don't just watch one thing.
- Watch Birth of the Cool first. It gives you the timeline and the context. You need to know who Charlie Parker and John Coltrane were before you can understand why Miles was so important.
- Listen to the soundtrack of Elevator to the Gallows. Don't even watch the movie first. Just close your eyes and listen to the improvisation.
- Watch Miles Ahead as a "mood piece." Don't worry about what's true or false. Just watch Cheadle's body language. That’s the closest we’ll ever get to seeing Miles live in his later years.
- Check out Dingo (1991). This is a rare film where Miles actually acts. He plays a fictional jazz legend named Billy Cross. It was his last major film project before he passed away, and it's surprisingly touching.
Understanding a film about Miles Davis requires accepting that the man was a walking contradiction. He was shy but loud. He was violent but capable of incredible tenderness in his playing. He was a black man in America who refused to be told what to do, and that defiance is what you’re really seeing on screen, whether it’s a documentary or a fictionalized heist.
The best way to experience him is to let the movies be the introduction, but let the records be the final word. Start with Kind of Blue, then jump straight to Bitches Brew. The shock you feel between those two albums? That’s Miles Davis.
Next Steps
If you're looking for where to start, hunt down the Birth of the Cool documentary on your favorite streaming service. Once you’ve finished it, pull up a playlist of his 1960s "Second Great Quintet" recordings. You'll see exactly how the visual stories you just watched translate into the revolutionary sounds he pulled out of thin air.