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To make his passion project and debut as a feature film director, Don Cheadle did not want to make the type of conventional biopic that one would expect about jazz legend Miles Davis.

“I didn’t want to do it the same as films I’ve seen about historical figures, musicians especially,” shares Cheadle. “We wanted to have a movie that felt like composition, as opposed to something that was didactic, clicking off all the highlights and the lowlights.”

That is certainly the type of film that audiences have seen many times before, Ray and Walk the Line being the most prominent examples, but in making Miles Ahead, Cheadle abandoned the conventional structure where a musician struggles, gets famous, battles addictions and then conquers his demons. This could have been the film that Cheadle made about Miles Davis, but he chose something more unconventional. He selected some of the major events of a period of Davis’ life in the late ‘70s and compressed them into what was essentially a single day.

“It’s all true!,” Cheadle says. “How much of it is facts? A lot of it. If you want to do the facts/true distinction, it’s interesting if you take his autobiography and a biography of Davis, and read those side by side and see how both are so different. There are events that did happen. Miles was shot in a drive-by – absolutely true. Clearly, we took poetic license to support the narrative, to create the momentum.”

Cheadle even considered opening the movie with Davis stating that most of it was true, until David O. Russell used the same conceit for another kinetic 1970s caper, American Hustle.

Cheadle’s work on Miles Ahead is a culmination of over 10 years of work, from when he first conceived of the project and its multiple incarnations – including a possible production by HBO – to its eventual feature release today. Cheadle at first considered the life of Miles Davis to be so rich that he would do multiple films about the musician instead of taking the entire span of his life.

“The first title of our movie was Kill the Trumpet Player, Vol. 1 because we always thought it would be great to do five Miles Davis movies. They’d all be different and interesting and valuable, but we chose this period of time because it felt very meta,” he reveals. “One of Miles’ biggest dictums was ‘play what’s not there,’ and it felt like this was kind of a down note before the up.”

For Cheadle, despite directing episodes of his Showtime comedy “House of Lies” and a long career as a producer that includes the Best Picture winner Crash, he felt a particular pressure taking on the roles of actor, writer, producer and director at once.

“There was no part of it where fear wasn’t in the sidecar. Taking on any one of the roles was fear inducing. I tried to give this away several years ago and hire a director so that I wouldn’t have the responsibility, but everyone I met insisted that this should be my vision. If it hadn’t worked out, I would have bitched a bit about it, but there would have been relief.”

While Cheadle did successfully pull off the work in the end, it is doubtful that he will ever attempt the experience again.

“My wife came down to see me halfway through shooting, and she said, ‘You can never do this again.’ I had lost weight, I was stressing out, and I wasn’t sleeping.”

Even watching the dailies could be a miserable experience.

“You feel very exposed and vulnerable, and I don’t want to have to watch this. It’s like when you call to hear your messages on your voicemail and hear your voice. Imagine that feeling, only 25-feet wide and 20-feet tall.”

Fortunately, Cheadle found himself in good company among other acting heavyweights who have stepped behind the camera. He spoke with Denzel Washington, who told him a story about when he directed The Great Debaters.

“His Assistant Director had to come into the trailer, and Denzel said that he couldn’t move. The AD told him to stand up, take a step, now take another step. He had to baby-walk him all the way to the set. I completely understand that. You’re taking on something that is so important to you, and it’s like being handed a newborn baby.”

For Cheadle, playing a figure as iconic as Miles Davis was not more daunting than playing other real-life figures, as he has done in the past.

“It’s something that’s in the eye of the beholder, the comparison between someone who’s known and someone who is not known as much, where you can get away with things. In both exercises, I try to get as close as I could to them,” he says. “With Miles, it’s a little bit different. There are certain masks that you have to have with you so that the host body doesn’t reject the organ.”

There may be extensive footage of Miles Davis on which Cheadle had to base his performance, but playing a non-celebrity like Paul Rusesabagina, the basis for Cheadle’s leading role in Hotel Rwanda, might have different challenges. Davis died nearly 25 years ago, but Cheadle played Rusesabagina when the courageous hotel manager was not only alive, but on set for filming. Between takes, Cheadle looked over to Rusesabagina to see if he thought he was playing him accurately, to which Rusesabagina replied, “You know, it’s a movie.”

Miles Ahead is now in theaters.

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