Don Cheadle: ‘I never felt fully comfortable as a director’

Boogie Nights, Ocean’s Eleven, Hotel Rwanda, The Guard – over his two-decade career, Don Cheadle has set himself apart as a character actor to be reckoned with. His talents don’t end there; with recent film Miles Ahead – an unconventional biopic focused on legendary jazz trumpeter Miles Davis – the actor turned writer-director.

We spoke with Cheadle about his filmmaking struggles, whether he’ll return as War Machine in future Marvel outings and how Rush Hour 2 led to him playing one of the most celebrated musicians of our time.

Would you describe Miles Ahead as a passion project?

It went through a lot of different stages and a ten-year journey to bring it to the screen but I guess ultimately what drove it more than that was just the sense of responsibility to the [Davis] family – and to myself – to complete it and not just walk away. Because it seemed at times it was going to be impossible to finish. The film’s gone through every single kind of emotion – torture, joy, pain – so maybe passion is all of those things.

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What was the key obstacle that you faced in getting the film made?

Oh, there was every obstacle – the financing, casting, the timing. We had a home at HBO who had a relationship with Picturehouse and was going to release it theatrically there. Then the world broke and everybody’s money dried up and we were back to square one. We were out beating the bushes trying to find independent money and that was a grind. Right up until post production on the movie, we were still dealing with issues; it never stopped.

Was it true the Miles Davis family wanted you and nobody else for the role?

Yeah, Miles was inducted into the Hall of Fame in 2006 and they were interviewing his nephew Vince Wilburn and they said: "Are you ever going to do a movie about his life?" and he said, "Yeah, and Don Cheadle’s going to play him." So that was when I became fully aware [laughs]. I didn’t know I was going to direct or write, that was not in my mind – Vince just knew I was going to play his uncle. He said he saw Devil in a Blue Dress (1995) and he also saw me in, of all things, Rush Hour 2 (2001).

When did your decision to direct arise?

The decision to direct came out of when I met the family and they pitched me some ideas in ways they would tell the story and, to me, they all felt kind of biopic-y and standard. I said, "If I do the movie, I want to do something that feels like Miles – like a gangster movie, a heist movie. I just want the music to be pumping through the whole film. I don’t want to do a CliffNotes of his life." We wanted to make the movie feel like a music composition as much as a film.

Was it a relief when you made that decision?

No, I never felt fully comfortable in that seat because I was always doing three other things at the same time and could never really totally give myself over and focus on just that. There was no other way to make the movie, though, so that became the way it had to happen. But I was never relaxed.I never chilled; I was always stressing about one thing or the other, dealing with that.

Do you have plans to direct in the future?

Yes, I’m going to be uncomfortable again on some other things. But I’m not planning to be in them which will help a lot – having to wear all those hats simultaneously led to the stress.

You have such an extensive list of credits. Do you have a personal defining career moment?

I hope to look back in years from now and be able to answer that questions better. Miles Ahead was a defining moment for me in many ways; a maturation, a graduation – learning that I could put something together and muscle it through was a big step for me. But yeah, I’ve been a very fortunate dude, worked on really great films with some really good filmmakers and even though our business seems to really be suffering from un-imagination right now, you hope that the studios will become courageous again. I don't see how it’s gonna happen – I think the studios are done with it, they’re just too bottom line right now.

The studio that seems to be taking over Hollywood is Marvel – and you’re a part of that Cinematic Universe [Cheadle replaced Terence Howard as Lt. Colonel James Rhodes in 2010’s Iron Man 2] – but producers seem to be increasingly employing a diverse range of talent to oversee the films

Yeah, it’s cool to have movies that get that broad appeal that people keep coming to. We also know that they’ve got to change because you can’t continue to do the same thing over and over and accept that people are going to come to it with the same enthusiasm or that it’s going to work, quote unquote. So I’m excited to see the changes that are going to come; Black Panther could be a completely different movie to anything that’s come before.

Do you plan to be a part of those films for a while longer?

I don’t think you ever know what you’re going to be a part of. They just call you up and go "Hey, you’re in this one." I wasn’t supposed to be in Captain America: Civil War – I was never contracted.

That was quite a big one for your character. Were you worried you were being killed off?

Yeah, I didn’t know. I saw the script and they were like "Oh yeah, something happens..." Then you got to get through 500 pages and you’re like: “Am I gonna make it?”

If you could choose any other Marvel character’s film to be in that you haven’t been in already, who’d you pick?

I think a War Machine movie would be the best to star in [laughs] I don’t know, let’s start a whisper campaign that it’s already happening and then maybe they’ll have to do it.

Are you going to be in the next Avengers film, Infinity War?

I... don’t know. They’ve got to figure out what happens with that dude’s legs. We’ve got to sort them out. But no, I haven’t seen anything yet.

Would you star in another TV series? [Cheadle’s series House of Lies was cancelled after five seasons]

If it was the right situation, an interesting project and something that felt like another fun thing to get into, yeah I’d do TV again; it’s really where the most interesting writing is now. It’s where you get some of the best creative minds because people can’t do it in movies anymore. It’s hard to find the space to say the things you want to say and create these complicated characters – everything has to be binary in movies these days.

You’ve worked with an impressive range of directors – do you recall being given any advice that has stayed with you to this very day?

When I was on the set of films, I would always hang out on set – I didn’t often run back to the trailer, I’d go and sit next to the DoP [Director of Photography] or shadow the director because I wanted to know all aspects of filmmaking and how everybody did everything. I tried to siphon from everyone. Paul Thomas Anderson, [Steven] Soderbergh, Carl Franklin – these are people who I still to this day talk to about film and about story. It’s been cool to continue those relationships.

Miles Ahead is out now on digital platforms, and on Blu-ray and DVD from 22 August, courtesy of Icon Film Distribution