Looking for Miles
For the past 10 years, Don Cheadle has dedicated himself to making Miles Ahead, a film about jazz great Miles Davis opening this month that he directed, produced, co-wrote, and starred in. It’s a passion project, for sure—just not one that Cheadle initiated.
The whole saga started back in 2006, when Davis was inducted posthumously into the Rock and Roll Hall of Fame. Around that time, music biopics such as Walk the Line and Ray were racking up awards, so it was unsurprising that reporters at the ceremony asked Davis’s nephew Vince Wilburn Jr. if there were plans to make a film about his uncle. Wilburn said that there were, and that Cheadle would play him.
Cheadle, meanwhile, had never even met Wilburn. But he was intrigued and got in touch. As it happened, Cheadle was distinctly qualified to portray the iconic trumpeter. He grew up listening to his parents’ Miles Davis records and was particularly drawn to his cinematic interpretation of the George Gershwin opera Porgy and Bess. The music served as a transporting trigger for Cheadle’s imagination. “I would see scenes and pictures and scenarios and ideas and all that stuff,” he says, sitting at a conference table in his second-floor Santa Monica office on a disconcertingly hot February day. He’s dressed in a blue-striped Henley and shorts, a large diamond gleaming from each of his ears.
As an alto saxophone player in his high school’s jazz band (“I was the kid who would run home and transcribe solos”), Cheadle used Davis as his through-line to discover other artists: Cannonball Adderley, Chick Corea, Herbie Hancock, John Coltrane, John McLaughlin. During his senior year, in 1982, he saw the We Want Miles tour at the historic Red Rocks Amphitheatre, outside of Denver, where Davis played alongside a rock guitarist, a funk bassist, and African-style percussionists. “It was like, ‘Whoa, what is he doing?’ It was just fascinating to me,” Cheadle remembers. “The spotlight just followed him wherever he went on stage. [Guitarist] Mike Stern would be soloing and Miles would be off in the wings, facing away, talking to somebody you couldn’t even see, and the spotlight would be on him.”
Just as Davis was loathe to use the term “jazz” to describe what he played—he preferred “social music”—Cheadle, now 51, is clear that Miles Ahead is not a biopic. Initially, the Davis family pitched him some more traditional ideas for the film, but he wasn’t interested. Instead, he countered with a more far-out, decidedly meta concept: “I was like, I want to make a gangster movie with Miles Davis,” Cheadle says. “I want to do a movie where Miles would want to be the star of this movie. I want to do: Don Cheadle is Miles Davis as Miles Davis in…” The film’s original title, Kill the Trumpet Player, better reflects this take. It was a wild idea, but Davis’s family got on board—and it quickly became clear that if someone was going to develop this particular vision, it would have to be Cheadle.
From a professional standpoint, Cheadle didn’t need to take on such a scrappy project, one without any major financial backing. He first made his mark way back in 1995 opposite Denzel Washington in Devil in a Blue Dress, and his star status was sealed two years later when he played a porn star searching for an image in Paul Thomas Anderson’s Boogie Nights. His portrayal of Paul Rusesabagina in Hotel Rwanda earned him a Best Actor Oscar nod in 2005, and, a year later, Crash, a film he starred in and helped produce, won the Oscar for Best Picture. More recently, Cheadle has hit a steady groove starring as the charmingly repugnant management consultant Marty Kaan in the Showtime series House of Lies (the fifth season premieres April 10) and reprising his role as Iron Man BFF James Rhodes, aka War Machine, in a slew of Marvel flicks (including this summer’s Captain America: Civil War).
But once Cheadle was in on the Davis project, he had to complete it, though the spotty financing continually threatened to disrupt production. As the director, writer, and producer—as well as a sometime collaborator on the musical score—Cheadle even resorted to raising more than $340,000 on crowdfunding site Indiegogo to see the project through to the end. “There was no second bite of the apple,” says Cheadle, on the importance of keeping the production going. “Once we would move away from sets and our locations, we’d lose them, we’d lose our actors. We just had to forge on. It was a very sweaty experience. I survived it, but it took a physical and mental and emotional and psychological toll to keep bouncing back and forth between every different job that required doing.”
Miles Ahead is mainly set in 1980, at the tail end of a lost period in the artist’s life when Davis stopped releasing music for five years and instead holed up in his New York City home, usually by himself and high on drugs. The film is largely a buddy caper, in which Davis must maintain a fractious bond with a fictional Rolling Stone journalist played by Ewan McGregor. Together, they drive around the city in a Jaguar, pull a gun in the offices of Columbia Records, score cocaine from a college student, and try to recover a stolen recording, the contents of which are unclear. Cheadle doesn’t play Davis as a sympathetic character. He’s often ornery, desperate, and paranoid. But behind the raspy voice, sour disposition, and blackout sunglasses is a man who longs for a world where his creativity can be experienced purely, free of classifications and politics.
Interspersed within this adventure are flashbacks showing what, in 1980, had already been a long and storied career. “We were interested in seeing this artist who had been so prolific and so demonstrative with his artform for so many years,” says Cheadle. “How do you go silent after that? And once silent, what’s the engine that gets you to jettison yourself out of it? That was the conceit: Let’s let this unreliable storyteller and yarn-spinner tell his own story about getting out of his own malaise or whatever he was in.”
Cheadle wrote the script for Miles Ahead with Steven Baigelman, who worked on the screenplay for the 2014 James Brown story Get on Up. Baigelman wasn’t interested in a conventional cradle-to-the-grave telling of Davis’s life, either. “We wanted to make a movie like one of Miles’s compositions,” he says. “I would never compare myself to Miles by any stretch of the imagination, but we wanted to do something that felt like jazz.”
There’s plenty of Davis’s music in the film, but for the original score, Cheadle brought on the acclaimed pianist Robert Glasper. Cheadle’s own musical prowess—besides sax, he devoted himself to the trumpet in adulthood and isn’t too shabby on bass and piano—made working with Glasper a much more collaborative experience. “Miles’s band, he trusted those guys so much when they were playing,” Glasper says. “He valued their talents and their imaginations and what they could bring to the table musically, and Don is like that as well. Even though he knows what he wants, he allowed me to be me at the same time.”
To alleviate worries about directing himself, Cheadle sought out advice from friends Ben Affleck and George Clooney. Affleck was philosophical, telling Cheadle that since he had good taste, all he needed to do was listen to it when casting actors and hiring his crew. “But George was like, ‘Do your push-ups and drink a lot of water and stay hydrated and don’t get sick,’” says Cheadle. “I was like, ‘Anything else?’ He goes, ‘No, mostly just do all that. If you’ve done everything else, it’s going to be what it’s going to be.’”
In the end, Cheadle was able to get a deeper insight into the psyche of one of American music’s towering figures. “This dude is wickedly funny, hilarious, sensitive, and also the opposite of all those things—can be a hard-ass, can be completely brutal sometimes,” says Cheadle. “What Miles Ahead paints a picture of is not dissimilar to many artists. Everything goes into the pot, and it churns and bubbles, and then they spit out Bitches Brew. Or it all goes in and it comes out ‘Blue in Green,’ the most beautiful ballad you’ve ever heard in your life.” Cheadle’s words quicken, the ideas and passion flowing out. “That person cannot just be a beast. There’s no way that dude is just super cool. That is a multifaceted, 360-degree human being.”