It’s as daunting a task to play a icon in a film as it is to write and direct that film. But what about doing all three at once? In Miles Ahead Don Cheadle not only plays Miles Davis in a rare narrative about Davis’ life, he also co-wrote the script and stepped into the director’s chair.

While Cheadle’s directed various episodes of television in the past and has 30 years of experience as an actor, his responsibility to both family and fans of the troubled jazz musician was unshakable, and not an easy weight to carry on a first feature. Yet Cheadle couldn’t have been a better fit for the role. He’s crafted a colorful, energetic free-form biopic—not a traditional one, mind you, but one that holds true to Davis’ spirit and style.

Like many first-time directors, Cheadle is quick to give credit to his crew on the film. In fact, the filmmaker was so influenced by Davis, he says, that he (whether consciously or not) ran his set in a fashion similar to how Davis worked with his band. Before our conversation, Cheadle recalled a Herbie Hancock anecdote about playing with Davis onstage early in Hancock’s career. Davis starts to play, but Hancock freezes at the keyboard, asking, “What do you want me to play?” According to Cheadle, “Miles was like, ‘Piano, motherfucker! I hired you ’cause you’re Herbie Hancock. You may not know you’re Herbie Hancock yet, but I know you’re Herbie Hancock.’” (Hancock lent Cheadle his help on a various fronts for Miles Ahead, even as a supporting actor.) In the end, a successful film is the product of harmonious collaboration.

I talked to Cheadle at the 2016 South by Southwest Film Festival about taking on his first feature as a director, portraying a legend, and what he’s learned working with other filmmakers.

Andy Young, MovieMaker Magazine (MM): This is your first feature as a director. What was it about the story of Miles Davis that made you feel like, “I have to be the one to tell it?”

Don Cheadle (DC): This was something that was sort of announced by Miles’ nephew [Vince Wilburn, Jr.] when Miles was inducted into the Rock and Roll Hall of Fame—that they were going to do a movie about his life, and that I was going to play him.

Don Cheadle as Miles Davis in Miles Ahead

Don Cheadle as Miles Davis in Miles Ahead

MM: And were you a part of this conversation?

DC: Only after! [Laughs] I mean, prior to that, writers Chris Wilkinson and Steve Rivele started early on with this project. Chris in particular wanted to do something around Miles’ life and he said, “I’m gonna be meeting with the family; I’m gonna mention you and I think you should do it.” And I didn’t know that I really wanted to do that at that time. I had done several biopics before that and I was kind of over it, to be honest.

MM: What about doing biopics made you kind of sick of it?

DC: I just wanted to play someone modern; I wanted to play somebody from the year that I actually lived in, you know? But as I said, Vince announced this at the Rock and Roll Hall of Fame induction ceremony, and then I started getting calls saying, “When are you doing the movie?” And I was like, “What are you talking about?” So I met with the team. They pitched some ideas to me that I wasn’t too keen on—that felt like kind of biopic-y ideas.

MM: Like crib-to-grave kind of stuff?

DC: Yeah, yeah. And I said, “If I do this movie, I want it to feel like Miles feels to me. I want it to be gangster. I want it to be dynamic and improvisational and unexpected and, you know, I want to feel crazy because that’s what I think this guy’s brought to the gang. If anybody’s doing anything like that, give me a call.” [Laughs]. But it soon became apparent to all of us that the best chance of that happening would be if I actually did it. So I kind of backed into that role.

MM: I love talking to actors that turn into directors because in my opinion, you’ve have the best film school. You’ve worked with so many great filmmakers over the last 30 years. Did you pick up anything from them while you’re on set, learning what makes a great director “great” and a bad director “bad?”

DC: Oh yeah! Tons of stuff. I think one common denominator with all the really good ones is an ability to be malleable, flexible and collaborative with the people that they’ve hired. And, conversely, with the bad ones, it’s just the opposite, you know? You see people who cannot let go of the stick. It’s always been strange to me—when you hire these talents around you that you believed in when you said “yes”—to then somehow micromanage all their decisions and not let them do their work. When I hired all of my department heads I told them, “I want to hire you the same way Miles hired his bandmates.” Like, I told my editor, “I want you to cut with your id. I want you to allow this material to affect you and you respond to it. You don’t have to justify all of the moves to me.” It’s very Miles Davis in that way. I wanted to do everything the way that Miles did it. I wanted to be as meta as I could.

Script Supervisor Belle Francisco and Director/Actor Don Cheadle Photo by Brian Douglas

Script supervisor Belle Francisco and Cheadle on the set of Miles Ahead

MM: I want to ask you, if you don’t mind, about Paul Thomas Anderson, because Boogie Nights is probably my favorite performance of yours. Was there anything in specific you learned from Paul Thomas Anderson as a filmmaker?

DC: A lot of things. Paul is a singular talent and very innovative, smart and creative, and has always been a real big supporter of me. What I’ve learned a lot from most good directors is temperament. Never really becoming unhinged, no matter how bad it gets. You can’t stomp off and sit in your trailer and pout because things aren’t coming together. You’ve got to always be looking for solutions and constantly be a team player and marshal the troops and giving support. You know, treating them in the same way you would want to be treated. And I think a lot of times people allow their vision to cloud that.

MM: Going off that trust, when you’re playing the lead role in the film and directing, one of the most important keys would be the director of photography; you have to put a lot of confidence in this person when you’re not able to be behind the camera. What was your relationship like with them? How did you guys plan out the visual and tone of the film?

DC: Roberto Schaefer and I got along great, to the degree that we could storyboard this whole movie out. Clearly a lot of responsibility rests on Roberto being able to interpret what I’m attempting to do. But once we’re on set, we’ve already spent 12 weeks together talking about all of the different shots and color palettes and ways we wanted to move the camera. And then, we’re dealing with the real realities of shooting on the budget that we’re shooting, in the place that we’re shooting. We didn’t have a Steadicam operator until the second week. But we were very locked into things from the beginning. It’s tricky.

MM: Did you have influences from other films?

DC: For Steven Baigelman, who co-wrote the script, and myself, Toto the Hero was a film that we looked at a lot. It’s a movie that takes place in three or four different storylines. But the transitions between the storylines all feel like they’re gaining momentum and moving forward. It doesn’t ever feel like the movie stops to go back and refer to something. It feels like every moment that’s a “flashback” isn’t really a flashback—it’s more information to move the story forward. It doesn’t come back to the same moment that it left. It’s always tumbling forward to its conclusion and everything sort of comes together at the end. Other movies were All That Jazz and Little Big Man, actually.

MM: What’s the dynamic like with the performers when you’re on set? Is it tough to remove the “I’m directing this” idea in your head while you’re in the middle of a scene with an actor as Miles Davis, or are you able to 100 percent immerse yourself in the scene, and then once you cut, go back to thinking about what everyone did?

DC: Well, I think the trickiest aspect of that is you tend to short yourself more because you don’t want to be, you know, “OK, I’m going to do nine takes!” [Laughs.] “I’m going to give you two, and then we’re going to move on.”

Emayatzy Corinealdi as Frances Taylor in Miles Ahead

Emayatzy Corinealdi as Frances Taylor in Miles Ahead

MM: But to be fair, you are the star of the film, and if you don’t nail this part it’s entirely on you.

DC: And everybody understands that. That’s the thing, you know? There was a clear understanding of what we were all doing and the difficulty of what we were doing. I empowered them as well; If we’d be in a scene, and they’d go, “Argh. I don’t know, I think we should try it like this,” I wanted them to be a part of that process and not be intimidated or concerned about the fact that I was the chief. We’re all in this together collaboratively, and I wanted their eyes and perspective in order to do this, to get the best result.

MM: Going into the editing process, is it a challenge to remove yourself from the fact that you’re editing your own performance?

DC: It’s impossible. The first assembly, I almost threw up; I couldn’t watch it. I left the bay and didn’t come back for probably a week and a half. And it wasn’t because [the editor] had done it badly, it’s just hard watching every cut of a film. We were just in Berlin, and I went in the theater to make sure that the levels were right, and I thought, “Oh! I’m actually going to watch the movie. Because it’s in a beautiful theater, and the acoustics are amazing. It’s built to actually be a music venue.” But I went in and I watched a couple minutes and something, some reaction that I thought the crowd would have, they didn’t have, and I started getting a knot in my stomach and I walked out. So it’s going to be a long time, I imagine, before I have any sort of objective perspective.

MM: I think it’s like that for most filmmakers, though. I’ve talked to filmmakers who made what we consider all-time great films, and they’re just like, “Ugh! I can’t even talk about that film anymore.” But I’m like, “It’s a classic!”

DC: But then, imagine being the lead in that film as well. [Laughs.]

MM: Exactly, and that’s such a responsibility. And another huge responsibility you have with this movie, obviously, is the music. How did you go about hiring everyone to do that, because that’s such a crucial part of the film?

DC: Well, you hire people that are smarter than you about that. Herbie Hancock was really our godfather for this. He wasn’t able to be our composer, given his schedule, but Vince Wilburn, Miles’ nephew, introduced me to Robert Glasper, whom I’ve known from R&B stuff but I didn’t know that he was a jazz musician. I called Herbie and asked, “Hey, what about Rob Glasper? Do you know Rob?” And he’s like, “Oh, I really want to work with Rob!” And I went, “OK. That’s good enough for me.” When we wrote the script, we had music in mind as we were creating each scene, even a lot of the cues, even a lot of the breaks between the scenes. I wrote with Miles’ music on all the time. So I had clear ideas about what I wanted to do with that, and I gave that to Robert, but again with that caveat that I wanted him to also come with it and bring his own ideas.

Ewan McGregor plays Dave Braden in Miles Ahead

Ewan McGregor plays reporter Dave Braden in Miles Ahead

MM: Speaking of collaboration, you’re working alongside Miles’ family and I’ve seen documentaries about Miles Davis but if there’s been another narrative about him it escapes me. Working with the family, was there ever a moment where they didn’t agree with a vision you had and, if so, as a director, do you have to listen to what they have to say?

DC: Oh, you have to listen. [Laughs.]

MM: Of course you have to listen, but what about staying true to your vision rather than compromising?

DC: Well, there were a couple “come-to-Jesus” moments that I had to have with the family. Because whatever the movie is, it’s not a love letter to Miles Davis. I thought that would actually be the worst way to tell this story—to somehow make him less than human. As much as he is revered we always have to remember that we’re telling a story about a person. The more we understand his misgivings and shortcomings and dreams and all of that, the more we identify with him. It’s hard to identify to an icon.

MM: Right, especially when icons still have blemishes. In other cases I’ve seen family members not want to tell that part of the story.

DC: Of course, and, you know, if someone said, “I’m gonna tell a story about your dad, and this is all the things we’re going to say,” I know I might have some problems with that too. So like I said, we had a couple of “come-to-Jesus” moments but, at the end of the day  I would say, “Do you think Miles would want us to make a movie that felt like a bunch of things you’ve probably seen before, and gloss over all of these things that he himself didn’t gloss over?” He made his autobiography [Miles: the Autobiography, 1989]—he’s very open about everything and he says, “I’m not hiding anything. Some things I don’t feel that great about, but other things? I’m not ashamed of that.” So, I said, “We can do what he did, or we can do some other version of some of what other people might do with this story.” And ultimately, the family was all like, “We want to see a movie that Miles Davis would have wanted to star in.” You know, my take on this was Don Cheadle is Miles Davis as Miles Davis in Miles Davis.

MM: You should put that on the poster! Was this a one-time thing, for you to direct, just because you really wanted to tell this story? Or is this something you want to keep doing in the future, if there are other stories you want to tell as a filmmaker?

DC: Well, again, I didn’t have any designs on directing this one, originally, or even being in it. I’ve directed a lot of TV; I’ve directed commercials; I had never directed a feature. When I was doing Bulworth, Warren Beatty was always hammering on me to direct something. Like, “You’ve got to direct. You’re a director. You’ve got to direct.” And I’d say, “I’m not ready, you know I don’t think I’m ready.” And he’s like, “You’re never ready. I wasn’t ready. I just did it. You just do it, and you get ready.”

MM: So what advice would you give to another first-time moviemaker?

DC: Make sure that you’ve put the pieces around you that you believe in. Hire the right people. That’s where you really have to fight the hardest, I think, in the casting of your movie—not just the actors and actresses, but the people behind the camera, the people that are going to keep that thing moving forward when you want to just pull your hair out. And you have to trust them, and let them do their work, give people the opportunity to surprise you with how much they understand your vision. You have communicate that vision very clearly, but once that’s been done I think you have to let those bright minds around you do what they’ve been hired to do, and bring you things. Don’t be afraid to let other voices in. MM

Miles Ahead opens in theaters April 1, 2016, courtesy of Sony Pictures Classics. Photographs by Brian Douglas.