Don Cheadle Will Carry Your Crutches, and 31 Other Things We Learned From Hanging Out With Him

Don Cheadle, who plays Miles Davis in his directorial debut, ?Miles Ahead.
Photo: Williams + Hirakawa/The New York Times

When you’ve spent well more than a decade interviewing celebrities, you learn how to spot the good ones — meaning the ones who will still treat you like a person when the cameras are gone and the tape recorder is off and the article is published. There are many more of the sort out there than you might expect, which I confirmed when I spent this year’s Sundance limping through the snow with a sprained MCL (thanks, Spike Lee, Natasha Lyonne, and Nate Parker!), and then again last month when I managed to sprain my ankle just before meeting up with Don Cheadle for a story in New York Magazine.

The interview was about Miles Ahead, the “electrifying” experimental anti-biopic of Miles Davis he directed, wrote, and starred in, and Cheadle took one look at my crutches and not only helped me down stairs, but also commiserated with stories of basketball injuries. You don’t need a reporter with ligament issues to tell you this, but: Don Cheadle is one of the good ones. He’s also everywhere right now, with Miles Ahead in wide release and his regular gig, Showtime’s House of Lies, having just started its fifth season. Here are some more things we learned about him while spending three days hobbling around Austin, Texas, with the actor.

He will carry your crutches for you. First off, let’s talk about how Don Cheadle walks into a hotel lobby, like Raylan Givens casing out his surroundings in non-skinny blue jeans, white sneakers, and dark sunglasses he never takes off. It’s a thing of beauty, Don Cheadle’s walk, this combination of confident striding and mad-good posture that makes the phrase, Don Cheadle is the coolest motherfucker in this room! involuntarily flash through your head, as if it’s some kind of revelation, even though it’s just a hard truth. And what he does when he sees you struggling down the stairs of The Four Seasons in Austin, Texas, with a sprained ankle, is gently tell you to use the rail, and offer to carry those crutches for you. He knows the drill, because he played basketball and was always getting injured. And when you tell him you sprained your ankle in broad daylight, he’ll joke, “Why were you drinking so early?” Also, he will tell you to take glucosamine and chondroitin and lean heavy on the Arnica (topically and sublingually), and work on your glutes, and you will go home and follow his advice.

He’s frustrated by the media’s focus on his comments that “to get this film financed, we needed a white co-star.” Specifically Ewan McGregor, playing a (fictional) magazine reporter who helps Davis chase down goons who steal tapes of the only music Davis made during his (actual) coke-addicted “retirement” in an Upper West Side mansion, between 1975 and 1980. “I hate that people are seizing on [my comment] and decoupling it from Ewan’s performance,” said Cheadle, “because it wasn’t like we had to go cast someone and bring down the quality of the movie. That’s about appealing to a European market. The domestic market is a very small piece of the puzzle.”

He originally cast Zoe Saldana as Miles Davis’s first wife, Frances Taylor, in Miles Ahead, so he’s got mixed feelings about that Nina Simone biopic. “I understand people’s reaction and disappointment about that casting,” said Cheadle, regarding the controversy over Saldana having to darken her skin and broaden her nose to play a singer whose life’s struggle was constantly being told she was “too black.” “But I also know that had Zoe Saldana not been cast, that project may not have happened at all,” said Cheadle, “and we wouldn’t even be talking about a new audience being introduced to Nina Simone. Even if people go, That’s bullshit, this is the real Nina Simone, I think there’s a valid argument to be made that it’s still valuable, to rail against it in a way that we rediscover who this woman was.”

He also gets why producers turned to Saldana in the first place; he did. “I think she’s a dope actress,” he said. Plus, she’s good for financing: “That was a name that had market value for us,” said Cheadle. Saldana pulled out for personal reasons and Emayatzy Corinealdi stepped in, but even when she was onboard, Cheadle said, “Nobody ever jumped on. There was no slam dunk. I had to crowd-fund for this. I had to spend my own money on it. I had to find friends that would give me money. Even Ewan didn’t make it a slam dunk. But he did get us much closer to the finish line.” How much of Cheadle’s own money did he put into this? “Enough. Too much.”

He almost became a musician instead of an actor. Cheadle played saxophone through high school and had college scholarships to study vocal jazz, instrumental jazz, and theater, but, he said, “I made a weather choice and went to L.A. to study acting.” It seemed less daunting than the work it would take to sound like Miles Davis or Cannonball Adderley. “You have to know every scale,” said Cheadle. “To be deep in your game. To walk into a room and have other musicians go, ‘We’re going to play this in B-flat,’ and be able to do it. I didn’t blow music off. I was intimidated by it. I respected it too much going into it. I knew that I would be incredibly disappointed were I not able to sound like those guys, and I knew that the woodshedding involved was something that as a 17-year-old I was not prepared to do.”

He studied trumpet for eight years to play Miles Davis. It started with a crappy trumpet from eBay, then he kept upgrading until he got to a Monette, which is a serious enough horn that people whistled when he mentioned it at one SXSW Q&A. He actually played all of the solos on set, to make sure the fingering and breathing were correct, and then dubbed them over with Davis’s sound. He’d also physically transcribe the music by ear to make sure he had it internalized. “It was important to me to understand what was happening, rather than grabbing the sheet music and learning it. Something about writing it out became a part of the character for me.” He still plays everyday and takes his trumpet with him wherever he goes.

He also learned boxing because it was a passion of Miles’s. Even though there’s about half a minute of Miles boxing in the film.

Save your breath criticizing Miles’s music around him. A friend of mine said he wanted to hear Cheadle try to explain that Miles’s late ‘70s and early ‘80s albums don’t suck. “A jazz snob?” Cheadle said. “Whatever. Fuck those people.” (Also, “Twitter beef? Blog shit? Whatever.”)

He calls the financial crisis “when the world broke.” As in, he had funding for Miles Ahead through HBO’s theatrical arm, Picturehouse, and then “the world broke” and they had to start over.

The guy clearly inspires loyalty, and returns it. Two of his high-school band mates were at the SXSW premiere. His high-school acting teacher came to a screening in Chicago.

His first paying gig was in “some terrible B movie starring all the famous brothers and sisters” called Moving Violations, about a remedial drivers’-ed class taking on the police. He played a Juicy Burgers worker. “Job security,” he said, “there was never a thought about it, like,  I’m going to be able to make money doing this! But I guess it worked out.”

He owes his big break, as cutthroat gangster in 1995’s Devil in a Blue Dress, to Denzel Washington. Director Carl Franklin spent months vacillating over casting Cheadle. “Then Denzel came in and we read and hit it off,” said Cheadle, “and finally Denzel was like, ‘Carl, this is the nigger right here! What are you doing? Hire him!’ That’s literally what [Denzel] said, and [Carl] literally hired me the next day.” Fun fact: Not long after that, Cheadle quit his day job, playing a prosecutor on Picket Fences.

As a young black actor, he noticed a pattern in the roles he got offered. Cheadle said he knows there have been periods of good roles for young black actors, “But for me, I was either on the service end of the gun or the other end of the gun. I’ve played a lot of cops and I’ve played a lot of gangbangers and criminals. I wasn’t looking at a lot of doctor roles or psychiatrists.” It wasn’t that he didn’t want to play those roles; they just didn’t exist. “That’s what’s out there, you know what I mean?” he said. “You know the lay of the land from the types of auditions you’re getting. We don’t determine that. It’s the kind of movies that are made, the kinds of TV shows that dictate that. So, if there are movies where there are roles for young black men that aren’t gangbangers, then you get those calls.”

He refused to play Sammy Davis Jr. in 1998’s The Rat Pack until the script was rewritten to address the issue of race. “It wasn’t even mentioned in the script,” said Cheadle, during a Q&A with New York film critic David Edelstein. “I was like, ‘How are we going to do this movie with Sammy Davis Jr., who can’t walk through the front door of the venues that he’s playing, and not talk about the racial aspects?’ He became the butt of jokes that he said he kind of went along with. One of the famous jokes was Dean Martin used to pick him up and say, ‘I’d like to thank the NAACP for this award.’  I thought it was kind of funny! I also thought that he would have a feeling about that.”

“I think for better or worse I’ve always had a big mouth and always spoken up if I didn’t like the way something was going,” Cheadle went on. “I remember in first grade hitting one of my teachers because my teacher hit me, and my parents always told me that I could always hit anyone back who hit me. I couldn’t start a fight, but I could end a fight. They didn’t say, ‘If it’s a teacher, you can’t do that.’”

He does a great Paul Thomas Anderson impersonation. Cheadle said he agreed to a meeting about Boogie Nights with P.T. Anderson, then a first-time filmmaker, because he had serious questions about the 166-page, super-technical script: “’First of all, what is this shit? What are you talking about?’” Cheadle said, laughing. “There’s nobody like P.T.A. He’s really cocksure and super-confident. [does surfer-stoner voice] ‘The movie’s gonna be amazing, man. You’ve gotta do it because it’s fucking great. You just gotta be in it, because if you’re not in it, you’re gonna fucking lose. I’m just sayin’!’”

To prep, they went to actual porno sets, which, said Cheadle, “was titillating at first, and very exciting, and, ‘Oh man, they’re really doing it!’ And then you’re like [looks at watch] ‘They’re still doing it.’ And then it’s like, ‘What’s that piece of furniture over there?’ And, ‘Don’t eat the craft services.’”

Here’s his theory on why actors get typecast. “People tend to do casting in the rear-view mirror. They want to see people do the things they did before,” he said. “The whole venture is such a risk anyway that I think people want as close to a sure thing as they can get. So they’re looking for things that don’t stray too far from where they believe people will be able to go.”

His House of Lies character was originally a white guy. “Marty Kaan was based on a real guy, Marty Ken, who’s not black,” said Cheadle, “but David Nevins at Showtime went, ‘Wait, I think this is Don Cheadle.’” The fun of this season, Cheadle said, will be watching Marty and Kristen Bell’s character, Jeannie, dealing with co-parenting a new baby while navigating the power dynamics of Jeannie having left the company. Marty has done parenting before, with his teenage son, Roscoe, but a newborn is un-mined territory. “There’s a lot of concern about doing it right,” said Cheadle. “Even with Roscoe he was always worried, am I fucking up my kids? And now I have a new one? That I could mess up too? And Jeannie as a mom, that’s a different ball of wax. The two of them together with the baby is really scary.”

He will totally embarrass you if you accidentally turn off the lights in the middle of one of his Q&As. When a woman at one of the SXSW Q&As accidentally leaned against a light switch, Cheadle immediately shouted into his mike, “What did you do, Mom?” Then provided live commentary. “Just keep pushing buttons. I’m sure you’ll get back to the earlier light situation. No. Nope. Better. Yes!”

He wants to do more comedy. “I actually did stand-up before I was an actor, which I don’t recommend,” he told the audience at one Q&A. “If you’ve got a comedy, send it to UTA and we’ll check it out.” He seemed to mean it; when one audience member announced he had an idea for him, Cheadle told him to find him later. “I’ve got dibs on whatever that guy’s idea is!”

As busy as he is, he’s nervous that one day the phone will just stop ringing. “Because every time we wrap a movie or a TV show, I’m unemployed,” he said. “That’s it. You’re always waiting to have the last call be the last call that you get.” He’s said this line before, but it bears repeating: “There are very few people who think that they’ve made it, and two of them are wrong. At any time, this business retires you. You don’t retire from it most of the time. It’s just a situation where they’re not checking for you anymore. That’s one of the reasons I wanted to produce, really for job security, and to put out projects that I really had an interest in, as opposed to sitting and holding your hand out, waiting for something.”

As a House of Lies EP, he’s actually in the writers’ room almost daily. “I’m not shaping the story, necessarily, but I definitely have a lot of input in where the season is headed,” he said. “You could be a vanity producer and never show up. But I take it seriously. I want to have my hand in all aspects of it.”

He doesn’t take biographies as gospel. There’s a huge section in one of Miles Davis’s major biographies about his first wife, Frances Taylor, performing in Porgy & Bess, but when Cheadle asked actual Frances, who’s still alive, about it, “She was like, ‘I was never in Porgy & Bess,’” he said. “There’s a lot of stuff like that. The fact-checking revealed more that people have their own perspectives on the facts, and a lot of [biographies weren’t] necessarily factual, at the end of the day.”

He was more than a little wary of doing the Iron Man/Avengers/Captain America movies. Cheadle loves comic-book movies, but wasn’t immediately on board with taking over the role of James “War Machine” Rhodes, because he knew he might be signing away ten years of his life. “I was at my daughter’s birthday party when I got the call. They said, ‘We’re offering you this role, but we need to know pretty quickly whether you’ll do it.’ I was like, ‘What’s pretty quick?’ They were like, ‘An hour.’ I said, ‘An hour to decide for six movies where I have no idea what my role in them is?’ They said, ‘Yeah.’ I said, ‘I’m at my daughter’s birthday party right now.’ They said, ‘Okay, take two hours.’” The fears weren’t unfounded. Marvel needed him for three weeks, in London, to shoot the second Avengers at the exact moment eight years of work on Miles Ahead finally went into pre-production in Cincinnati. So he had to make do with directing via Skype. “I couldn’t say no [to The Avengers],” he said. “They were in first position on everything.”

He didn’t boycott this year’s Oscars, he just didn’t go because they’re not fun. “I never go,” he said. “I never go unless I’m nominated or I’m presenting. When you’re sitting in the audience and there’s a camera on you, that’s not a relaxed evening. I don’t know many people who think that’s a fun night. I don’t go to the Governor’s Ball afterwards. I don’t do any of that shit. I call my limo, and I’m in the car, and we’re changing clothes, and we’re headed to Commerce to play poker. I’ve never seen the end of the Oscars, even when I went.”

So, what’s his relationship to the Academy? He did get an Oscar nomination for Hotel Rwanda, after all. “You mean, do I get the screeners? Yeah,” he said. “And I have the right to buy a ticket every year. You have to pay for tickets even if you’re in the Academy.”

He would’ve nominated Michael B. Jordan for an Oscar. “Was Michael B. Jordan’s performance in Creed worthy?” he said. “Absolutely, in my opinion. If Matt [Damon]’s is, then Michael’s was. And if a movie like The Martian could be, then Creed could be.”

George Clooney was the one who advised him to fight for final cut of his movie. Cheadle’s Ocean’s Eleven buddy had done the same when he butted heads with Harvey Weinstein over the edit of Confessions of a Dangerous Mind. “George literally almost got into a fistfight with him,” said Cheadle, “and he said, ‘Look, if I’m going to get skewered, I’m going to get skewered on my decisions. I’m going to get hung up for something I decided to do, not for something you decided to do.’ You have to be really in defense of your work.”

He almost gave up on making Miles Ahead. “I tried to give the movie away, honestly, a few years ago,” Cheadle said. “I tried to find someone else to direct it, and if it had evaporated, I would’ve actually been relieved. But at some point it felt more like a monkey on my back if I weren’t able to see it through.”

He loves to tell this story about Miles Davis: “Herbie [Hancock] tells stories where Miles said, ‘I pay you to practice in front of people.’ If he heard you rehearsing some solo in your hotel room and came down onstage and played that solo, he’d fire you. He’s like, ‘I don’t pay you to come bring your polished work. I pay you to jump off a ledge and figure it out with other musicians.’”

And this one: “[Drummer] Tony Williams said that Miles used to throw up before every performance. Tony would knock on the door and go, ‘It’s time for you to throw up, Miles,’ and he’d throw up and go out and play, because he was always on the edge, he was always reaching for something and worrying about not getting there.”

And this one: Davis was such a hermit during his “retirement” that, Cheadle said, “There were weeks and months at a time where no one knew what was going on with him. [His nephew] Vince would tell me and Herbie would tell me stories about knocking on the door and Miles would open it just a crack and say, [rasps] ‘Get me some catfish.’ And they’d come back and bring him some food and he’d” — Cheadle mimes Davis snatching a bag full of catfish — “and shut the door.”

Everything that could have gone wrong during production did. They shot in Cincinnati (doubling as ‘70s NYC), a city that hosted just three film productions in 2014, including Carol. “God bless Cincinnati, but everything was not 100,” said Cheadle. “There were days when we had two cameras and one cameraman. I’d say, ‘Where’s Jim?’ ‘Oh, he went to go shoot a commercial in Dayton.’ Or, ‘Where was that woman who was in that scene yesterday?’ ‘Oh, she couldn’t get a ride today.’ ‘Fucking Uber it! What are you talking about? Who else is a size 7 who can fit into this dress?’”

Most of the snafus involved a very special special-effects guy whom, Cheadle said, “was just the guy who was like” — raises hand — “’I can do it!’” He added so much “atmosphere” to a scene in a club where Miles is playing the ballad “Blue in Green” to Frances that, said Cheadle, “the fire alarm was going off, the smoke alarm was going off, and the fire department was coming. So in that beautiful, peaceful moment, it’s REEEEEEK! REEEEEEK! REEEEEEK! ARRRRUUGGGGHAAAA!” But you can’t tell in the movie because they just dubbed Miles’s trumpet playing over the whole scene.

And then there was the time that Cheadle asked the special-effects guy to rig a lamp to explode when Miles shoots it during an argument at his record company’s office. At Cheadle’s suggestion, they did a test run before placing an actor right next to it. “So we all go to the other side of the room and 3, 2, 1. This thing explodes like Vesuvius! Blast is 20 yards, hits me in the eye,” said Cheadle. “So we do it again, 3, 2, 1. Nothing. This went on for two hours. Literally, there were seven lamps that he rigged. And you’re sweating bullets. Every minute on a movie is an hour and if you’re not going, you’re just eating money and time. The last take is the take that we used and I was like, ‘I’m sorry, my dude, if you get blinded on this one, you’re going to be blinded.’”

He’s in tentative talks to direct something else, even though he lost so much weight from stress on Miles Ahead that his wife has forbidden it. But, he said, “I hope to God it’s not like this! It almost killed me! This almost took me out.”

Things You Learn Hanging Out With Don Cheadle