Don Cheadle won the role of Miles Davis before he even knew he was being considered. In 2006, when Davis was posthumously being inducted into the Rock and Roll Hall of Fame, Davis’s nephew, Vince Wilburn, told reporters that Cheadle was the guy to play the jazz genius. ​”I had not been reaching out for this role in any way, shape or form,” says Cheadle. “There was a pronouncement made, I guess — a proclamation — that I was going to play his uncle in a movie.”

Ten years later, Miles Ahead is ready to open in theaters, and Cheadle not only stars as the raspy-voiced trumpet master, he also made his directorial debut. The film premiered at the 2015 New York Film Festival and will open in theaters on April 1. Rather than a conventional cradle-to-grave music biopic, Cheadle built the narrative around Davis in 1979, a period of artistic paralysis. Ewan McGregor plays a persistent journalist who intrudes on Davis’s privacy, but becomes his reluctant partner in crime when they have to retrieve a missing tape of valuable session music. Like Davis’s music, their adventure knows no boundaries, and the film flirts with the surreal. In flashbacks, Davis courts and obsesses over dancer Frances Taylor (Emayatzy Corinealdi), and their romance has a major impact on his music.

In the exclusive trailer, Davis is a loose cannon: fighting, shooting guns, and behaving like a less than perfect husband. But this isn’t Walk the Line. As Davis says in the clip, “If you’re going to tell the story, come with some attitude, man.” This is a Miles Davis joint.

ENTERTAINMENT WEEKLY: When did you discover Miles Davis?

DON CHEADLE: He was someone that my parents listened to. The music was in the house since I can remember, but I think at 10, when I started actually playing music, playing sax, is probably when I started paying more close attention to the kind of music and the construction of the music and the composition and all of those aspects of it.

What was he doing differently than anyone else?

It was more what he wasn’t doing. It was more about the space that he created. It was more about the way he allowed things to finish in the listener’s head, as opposed to trying to define every moment. Miles was a lot about space, and that’s something that was unique. People usually wanted to show everything that they know, and Miles seemed to intimate and insinuate and let you finish things off in your head.

For a directorial debut, this is pretty tall order. Did you always see this story as one you wanted to direct?

No, and when it first came to me, it was just something for me to act in. When I met with [Miles’] family, I told them I wanted to do something that wasn’t like I had seen before, and I had a take on the movie, that if I was going to play him, that it had to be as creative and different, that if it wasn’t as aspirational as he was, then I wasn’t really that interested. And before I got to my house after that meeting, it kind of came to me that that would be hard for anyone else possibly to see it the same way that I was seeing it, so if I was going to do it, I’d probably have to direct it. And as I was calling them, they were kind of calling me to say the same thing.

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Miles had this huge life, this huge career, this huge personality. How did you decide to frame his life and focus on what you did? Because so many music biopics fall victim to familiar tropes.

I had seen other films that have done it — because I’ve been a part of several of them, by the way. Biopics, where I guess you could say tropes; I would say they’re also just signposts you have to hit along the way. When you set out to make a biopic, the purpose, whether stated or not, is usually to hit the highlights or lowlights of someone’s life in order to crescendo at the end. It is trope, I guess that’s the word. But I thought, especially with someone like Miles Davis, whose life seemed to very antithetical to that, and whose art was so mercurial and spontaneous and not dedicated to any sort of form that he had done before. He went on to the next thing and he kind of never looked back. I thought it would really be totally anathema to him to do something that felt standard, so to speak.

The film jumps around, but the main thread of the plot is set around 1979. Why did you chose to focus on that time period?

Just the fact that he wasn’t playing. The fact that he hadn’t played for five years, up to that point, and in a way, was either chomping at the bit to figure out what to say again, if to say again, or he was going down towards death very quickly. He was standing on that knife’s edge at that point, and I don’t think he even know which way it was gonna go. So for us, when we got to the period in all the research about how Miles didn’t play for five years, we were like, “What?” [Laughs] That was the part that was the most interesting from a human being standpoint to me. Musically and what he did with his art form was amazing to me all the time, for the most part. But for me, as a human and an artist and someone who’s a creative person, what happens when you just stop for five years? That’s why we picked that moment to sort of be the departure point: him on the verge of talking again, basically.


There’s a great line in the movie where Miles says, “It takes a long time to be able to play like yourself?” I imagine that’s not a foreign sentiment for any actor, no matter how accomplished. Looking back at your career, was there a moment where you figured out who you were? Because I imagine when you started out, you’re just acting as an actor. But at some point, does something click?

I can’t say that I think I’ve ever arrived at a moment where I feel like, “Now, this is it.” And I don’t know many actors that actually feel like that. Some bad ones, probably. [Laughs] But I think most actors and most people who are still curious and trying to get better and figure stuff out don’t feel like they really ever have it.

So is that an element of fear?

Well, I don’t know about fear. You’re out there in front of everybody while you’re trying to figure it out. You’re not doing it in your garage. You’re doing it in front of people, so I guess there’s a vulnerability, definitely. But I think that’s when you’re supposed to know, or recognize, “Oh, that’s what I’m supposed to be.” Because I’m not in my comfort zone. I’m reaching for something, and when you reach for something, you stumble. You don’t actually get to get there cleanly, which is another thing I loved about Miles. The story goes that if he heard you rehearsing something, if you were guys doing a date and you were in your hotel, and he heard you rehearsing your solo or whatever, and you came down on stage and performed that same solo, you were out, you were done with the band. Because, as Herbie [Hancock] said, “Miles paid us to rehearse in front of people.” That, to me, is like the most respectful thing you can do. It’s like, I’m going to show you all of the bumps and bruises along the way, and how we get to something. I’m not going to come out here and make sure that we’re totally polished and everything’s slick and perfect. That’s not what he wanted to do. I feel like, when it’s the best, that’s how you’re supposed to feel. Like, you’re reaching, that you’re always trying to figure it out. And if you’re always reaching, then yeah, you’re always going to feel vulnerable. I don’t know, fear may be another way to say it, but you’re always going to feel you’re exposed.

Is that something you tried to channel when you were playing Miles. You obviously weren’t winging it, because that’s not how this works, but were you acting a form of jazz on screen?

I was trying to do both things at the same time, which is have a form and allow yourself to be somewhat formless inside the form. If it’s just totally formless, then it’s just kind of, to me, bullshit. But you have to, inside of the form, be able to at some point, have stuff just be where you don’t know, and be out there. That’s the feeling, of having all the conditions set and then not knowing what’s going to happen. You have to know what the chords are, but then anything inside those chords is allowed.

The conversation around this year’s Oscars has been more about the films that weren’t nominated instead of the films that were, in part because no minority actors were honored. Will you be attending this year’s ceremony?

Oh, I don’t go to the Oscars unless I’m nominated usually. I might want to be there this year just to watch Chris Rock, but I have yet to make plans.

The first 15 minutes of the show are going to be electric.

Oh, it’s got to be. This could be a career-defining moment for him. I hope he just goes in and gets everybody. [Laughs]

Miles Ahead
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