With his turn as the real-life humanitarian Paul Rusesabagina in 2004’s Hotel Rwanda, Don Cheadle earned an Academy Award nomination and further established his reputation as one of Hollywood’s most reliable actors. Cheadle’s filmography reads like a case study in character versatility. Since his debut in 1985’s Moving Violations, the actor’s choice of characters runs the gamut from guy who Tommy Lee Jones talked to/yelled at a lot in Volcano to kindhearted cowboy porn star Buck Swope in Boogie Nights.

Cheadle’s recent work has kept him busier than ever. He’s reprising his role as Tony Stark’s fellow robot-suited buddy War Machine in this May’s Captain America: Civil War and can be seen again in the award-winning role of inveterate asshole extraordinaire Marty Kaan on Showtime’s House Of Lies. With Miles Ahead, Cheadle didn’t just take on the task of portraying jazz legend Miles Davis; he also found himself in the director’s chair for the first time—a role that presented new challenges, rewards, and complexities.

Advertisement

The A.V. Club: Was directing, producing, writing, and taking on the title role in Miles Ahead something you planned from the beginning?

Don Cheadle: No. Not at all. [Laughs.] I was sort of prepped into service by [Davis’ nephew] Vincent Wilburn who announced after the induction of Miles Davis into the Rock And Roll Hall Of Fame in 2006 that they were going to make a movie after his life, and that I was going to play him. So that was when I was told I was going to play the part. [Laughs.] Then I came in and pitched some ideas that I had about an approach that was different than the way that they were going to go with it, and it became kind of evident that the only way that was going to come to fruition was if I took it under my control and attempted to be the arbiter of all of those things.

AVC: With a film about someone as iconic as Miles Davis, it seems like it would be incredibly difficult to keep the story from veering into the sensationalistic realm.

Advertisement

DC: I didn’t even think about it in terms like that. I only thought about it in terms of trying to get at something that felt like doing what Miles Davis did and approaching his story in the same way that he approached his art form, and telling the story about creativity that gave me the ability to use all of his music, and every type of genre that he touched, to kind of propel the narrative forward as much as the narrative did itself. For me, I wanted to focus on a character who found himself with writer’s block, for lack of a better term, and in a place that he’d never really ever been before and asking the questions that everyone was asking of him. Would he come back? What is it going to sound like? Where has he gone? Those questions of loss and ownership and all of that—that was the reason we constructed the film in that sort of way, and that was my focus. I wasn’t concerning myself too much with telling some story that was over the top, but in many ways going for something that felt big and expressive and expansive like jazz where it went everywhere.

AVC: As director, was there a challenge in terms of objectivity with the character and what you wanted the story as a whole to achieve?

DC: What I wanted to accomplish was for the story to be engaging and entertaining. I wanted people to walk away from the movie with a desire to listen to Miles’ music and investigate him themselves. The challenges I faced from a directorial standpoint were logistic in nature. We were shooting on a very truncated schedule, where I had Ewan [McGregor], Michael [Stuhlbarg], and LaKeith [Lee Stanfield] for 15 days, and then they were gone with no opportunity to get any second bites at the apple if it didn’t work. Then I had Emayatzy [Corinealdi] and everyone that we used in the ’50s and ’60s for another 15 days, so it was a very, very compressed schedule on a really small budget for the kind of scope that we were trying to accomplish. Just the logistics of that every day was very challenging. As far as having some sort of arm’s length at the performance and being objective—I never was. [Laughs.] I couldn’t be. I was completely subjective and mostly thought that I was in trouble. [Laughs.] Thankfully I had a really good team who would keep pulling me back to center and refocusing and helping me kind of stay in the lane. It was like being pulled in two different directions the entire time.

Advertisement

AVC: Now, both you and Miles have roots in Missouri, but were there other similarities you noticed while making the film?

DC: Well, his origins are in Illinois and mine are Kansas City, but we both came to Missouri at some point. I came from Missouri, and he came to Missouri. [Laughs.] We both definitely have roots there, though, and it funny because his family would often say, “You look like people in our family. You look like uncles and cousins I have,” and I did feel like there was some kind of hometown vibe happening. Like the way Miles even chewed his gum and held his mouth looked like my great-grandmother. [Laughs.] There were eerie things like that that would happen. I would play the tape of him talking before he ravaged his voice, and our voices are centered in a very similar place, so we sounded alike. Vince would come on the set and say, “Man, this is scary,” so that felt good. [Laughs.]

AVC: Did having a background in music yourself help in getting into that specific type of creative mindset?

Advertisement

DC: It definitely helped in that I had an understanding of the music. Learning to play the trumpet and learning those solos and writing the solos out and going through the actual process of that, was something that made me feel a lot closer to Miles. Because I knew that when I put the horn to mouth I would know what I was doing. I wasn’t faking it. I was playing it, and there’s a connection there that’s hard to quantify, but I feel like there’s a kind of veracity when you’re looking at those performances. It doesn’t look like I’m faking it, because I’m not. That was something that was important to me to do—to put that work in and get that. The opportunity to work with all the musicians that I worked with and to just be around that part of the creative process—it’s really the most fun I’ve ever had. More than acting, more than writing, more than directing any part of the film, was just being in fellowship with other musicians and being in that creative experience. It’s the most rewarding thing I’ve ever done in my life, really.

AVC: Just given the wide range of characters you’ve played, is there a certain kind of standard perspective you have going in initially for each?

DC: I just try to be honest on the discovery path. I’m just always trying to get as much insight as I can into what makes a person tick, and why they’re set up that certain way that they’re set up. Maybe it’s that I’m the son of a psychologist and an educator, but it’s a lot of investigation for me. Then you just have to show up and be present and be permeable in a way, and allow things to affect you and not be locked into some preconceived notion about how you have to approach things. You know who you are. Hopefully you’ve done all the homework and studied all the things you can study, and you’ve gotten as close to that person physically, spiritually, and emotionally as you can. Then you just show up and allow things to work on you. I think the best people that I’ve seen do it, do it in that way. It’s not anything that’s easy. It’s work. [Laughs.] You can’t get there, I don’t believe, without an incredible amount of work. Some people can just mercurially do it. It’s like Paul Newman used to hate James Dean because Newman said, “He just shows up and he’s there,” and Newman had to work so hard to get everything. I feel closer to the Paul Newman side. I have to work hard to get there.

Advertisement

AVC: It’s hard to imagine two more completely different characters than Marty Kaan and Miles Davis.

DC: Oh yeah. I mean, their tempo rhythms are totally different; where they come from; what they’re thinking about—all of that stuff couldn’t be more different. I don’t know that Marty thinks of music as anything other than something strategic to use to get somebody into a certain mood, so he can then come in and take advantage of them. [Laughs.]

AVC: Was there overlap between having to play both roles?

DC: Oh yeah. There was overlap. We were working on [the movie] for six years in this iteration, and my writing partner for it, Steven Baigelman, had two other things going on while we were working on this. A lot of things were overlapping. [Laughs.]

Advertisement

AVC: Was there a kind of mental reset in having to switch between such disparate characters?

DC: Not to sound pretentious, but there is a kind of decompression that you have to do and go into a figurative barometric chamber and drop all of that other energy and try to create a clean slate and come into a new perspective and stay in it. Especially on this movie it was very tricky to stay in it with all that I was doing. Thank god I had people that got the drill and were cool with being directed or instructed by me as Miles. [Laughs.] Because I didn’t want to keep going in and out and in and out with the two roles. But it’s work, and at the end of the day, if you’ve done your job, you’ll be exhausted.