Actor & Director Don Cheadle

The award-winning actor joins us to discuss his directorial debut and starring role in the Miles Davis biopic Miles Ahead and the return of Showtime’s House of Lies.

Don Cheadle has built a solid acting reputation with diverse roles in such films as Hotel Rwanda—for which he received an Oscar nod—Iron Man 2 and 3 and The Guard, which he exec-produced. He makes his directorial debut with a biopic about Miles Davis entitled Miles Ahead which Cheadle writes, produces and stars in as the jazz legend himself. He has also worked in numerous TV series, winning a Golden Globe for his lead turn in Showtime's House of Lies, which returned this spring for its fifth seasonPassionate about the people of Rwanda and Darfur, Cheadle co-wrote Not on Our Watch, which he calls an "activist handbook," and is a U.N. Goodwill Ambassador.


Tavis Smiley: Good evening from Los Angeles. I’m Tavis Smiley.

Tonight a conversation with actor-director, Don Cheadle. He joins us to talk about his directorial debut and starring role in the new biopic, “Miles Ahead”, along with his return as Marty Kaan in Showtime’s “House of Lies”.

We’re glad you’ve joined us. A conversation with actor and now director, Don Cheadle, coming up right now.

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Tavis: Always pleased to welcome Don Cheadle back to this program. The Oscar-nominated actor makes his directorial debut and stars as Miles Davis in the new film, “Miles Ahead”, opening select theaters this weekend.

He also returns on April 10–and I can’t wait–Marty Kaan in season five of Showtime’s “House of Lies”. Don knows how much I love that show. Before we start our conversation tonight, though, about the new film, a look at a clip from “Miles Ahead”.


Tavis: I was just telling you that was one of my favorite scenes in the movie and you were saying you’ve been hearing that from other people as well.

Don Cheadle: Yeah. You know, it was one of the scenes where in the script it just says, “Miles works on “Gone”. There was no dialog, there was no–we didn’t write the scene really. It’s the last day of shooting and I said, “I just need musicians. I just need people that can really play, and we’re just gonna work through the music. Just give us the charts and we’ll just figure it out.”

Tavis: I loved it because you feel in that part of the film–I mean, you feel this way throughout the film, but in that part in a unique way you feel a part of his world. You go inside the studio and see how he worked, how he got it. It’s kind of like watching Michael Jackson on “This Is It”. You know, you got to see the way he did what he did, but I love that scene because it takes you inside his world.

Cheadle: And it’s great because we’re not really acting. You know what I mean? It’s like we’re really trying to work out the music.

Tavis: Speaking of not acting, everybody who I’ve talked to who’ve seen this, including myself, is amazed at your playing [laugh]. You actually picked it up and started working on it.

Cheadle: Yeah. Well, you see a lot of movies with actors playing musicians and often they don’t have a facility with their acts and I didn’t want to go in, especially a movie about Miles Davis, and not have a real relationship with that trumpet.

Tavis: How difficult or, conversely, how fun was it for you?

Cheadle: No, it’s the first word [laugh]. It was definitely difficult and unforgiving, you know. It’s an instrument that you can’t just put down and come back to and be the same a week later. Like if you didn’t shoot baskets for five or six days, you wouldn’t start throwing the basketball over the back of the back board.

But if you don’t play trumpet every day, you know, in two or three days, it’s like you feel like you didn’t know ever how to play.

Tavis: So what is the deeper, greater level of appreciation you have now for trumpet players?

Cheadle: Well, you know, I grew up playing in bands my whole life and I always had that brass section sitting right behind me. I played sax, but they were always right there. Every once in a while, I’d try to, you know, figure it out.

My best friend played trumpet growing up, but, yeah, actually the demands of keeping it up is what’s the most interesting part of it. It was never a moment I could put the sax down and I could come back to it relatively quickly and I’m there again. But with trumpet, you really feel like you’re on fawn legs when you start.

Tavis: What makes it so unforgiving, to use your word?

Cheadle: Because I think that the setup is just not natural. There’s nothing that’s natural about the way you have to create your embouchure to play. And then everything you do during the day, eating, chewing, drinking, talking, works to like break that structure back down. So you got to find it again and you’re trying to make a lot of noise through a very small aperture.

Tavis: Yeah. I was pleasantly surprised, but again, taking aback when I actually saw the film because it is, as I said to you when you showed up today, the word I used, an unorthodox–try it again, Tavis–an unorthodox telling of his story. Tell the audience what the story is and why you chose that as your way in to a guy who you…

Cheadle: Who’s unorthodox.

Tavis: Exactly.

Cheadle: Well, I always thought that the telling of the movie should be befitting the subject matter and we wanted to create a story that felt like a Miles Davis experience, you know, that you would experience with his music and a lot of the apocryphal things that I’ve heard about him.

And having him standing right there has been great, you know, to really let us see things that not a lot of people have seen and tell stories that other people haven’t necessarily heard.

But I wanted the film to, like I said, to feel like it’s an experience. So when you go through the research and bump into this five-year period where one of the most prolific figures in art, not just music, but in every aspect of the 20th century, goes quiet and doesn’t play for five  years, as a storyteller, you look at that and go, okay, well, that’s my point of departure.

That’s a place where I want to figure out what happened, how did it happen, what’s in there, how does he get out of there, does he get out of there, what does he say once he’s out of there, you know? What’s going on in that moment? And use that as the place to start trying to have things all churn up to like push him out of his own way and get back to playing again.

Tavis: Well, I just realized something here after 13 years of doing this show. I am not an artist [laugh]. You just told me I’m not an artist because, when I read that that was going to be your way in, I’m like now why would Don pick the five years when the Negro wasn’t playing as the way to tell the story about a guy who we loved because of what he played?

Cheadle: That’s right, yeah.

Tavis: But when I saw it, I understood why.

Cheadle: Yeah, and it’s kind of famously very meta in the way for Miles. You know, it’s like “Play what’s not there” is one of the biggest things that he said and then you kind of feel like, well, here’s the down note. Here’s a what’s not there moment to try to craft a story around this artist and use all of the music.

I didn’t want to be locked in to specific dates with the specific time periods that we were depicting. It’s like if I want to be in 1958 and use something from 1982, I want to do that and vice versa. So we, the co-writer, Steven Baigelman, and myself, just wanted to create a story that felt like a Miles Davis experience. My goal was to do Don Cheadle is Miles Davis as Miles Davis in “Miles Ahead”, you know.

Tavis: I get that. So how much creative license, as they say in this town, was taken in the project?

Cheadle: A lot, but no more than other “biopics” that we’ve seen. And there are tons of facts in there. You know, it is wall to wall facts without me getting a book and going, okay, check that off fact, check that off fact, check that off fact. We sort of took the puzzle and pushed the pieces up in there and then reformed it in the way that we wanted to to tell the story that we wanted to tell.

But, you know, those recordings, that’s real, all of that, the secret recordings, the Dave Braden character, the reporter that’s trying to get this story, an amalgam of many people at that period in Miles’ life that were trying to get in to either write the obituary or the comeback. They didn’t know which one it would be. Frances, obviously, is absolutely real and that whole “B” story is real.

Tavis: And a great actress.

Cheadle: Emayatzy Corinealdi, yeah.

Tavis: And cast beautifully.

Cheadle: Yeah.

Tavis: Having done this now–and we’ll come to your directing in a second, but I’m just talking about the acting piece. Having done this now, is Miles Davis more complicated or more simplified for you now as a person?

Cheadle: That’s a good question, and I don’t know that it’s binary. I think sometimes it’s both.

Tavis: Okay.

Cheadle: You know, I think when I look at the consistency of his journey, it is always someone who is searching for the next thing and trying to hear the next sound. You know, right before he passed, he was making music with Prince, so he was never finished and he never wanted to go back.

He always wanted to figure out what the next thing was and that’s something, when you look at his life and is work throughout his life, is totally consistent. But he was a complex figure and he was someone who always put the music before anything.

So when you’re in a relationship with a person like that, be it as a friend and a lover, a wife, a husband, a coworker, whatever, you are often that which is left in the wake to a greater or lesser degree.

But I also think that you understand that that’s the contract, you know, and the people in Miles’ life were the beneficiaries often of his creative genius and what he was able to produce, but also sometimes got their wings, you know, burned when they fly that close to the sun.

Tavis: I wondered whether or not it was his confidence that led to his curiosity or his curiosity that built and fueled his confidence. And what I’m getting at here is, I mean, he knew he was good. I mean, obviously, there’s some confidence here.

And yet he was such a curious person, as you said earlier. He would try so many different things, not always knowing whether those things were going to work or not. What’s the relationship between his confidence and his curiosity?

Cheadle: Well, I think that the confidence, what belies that sort of façade to me, the cool, you know, you hear things like Miles used think is it cooler to tap my whole foot to keep time or just tap my foot inside my shoe? That doesn’t sound like the most confidence person in the world in that way. That’s like, oh, that’s something that reveals a vulnerability to me, that you’re thinking about how you’re perceived.

It looks like Miles could care less and just did whatever he wanted to do and if you got whatever. But there’s someone who’s very thoughtful there and a lot of people that knew Miles very well said that he was incredibly sensitive. When you listen to the music, of course, he was.

A monster is not producing that beautiful music. And a lot of what he put on was to protect this softer part of him, this part from which he created, which can be fragile and people were at him a lot.

This sort of like tough guy image, this stay at arm’s length image, a lot of times is protection. A lot of times, it was other things too, but that was a part of it that was interesting to understand, the vulnerabilities that this super cool dude had.

Tavis: I was about to say–and this is my take on it. Others will have their own opinion when they see it, but I think they’ll agree with me on this, that you did a really, really good job, particularly for a directorial debut, a really job of finding and balancing that confidence and that vulnerability.

There were scenes in here where–I mean, I took away a number of lessons about his vulnerability, but how he managed them as well. There are some scenes in there that really I’m like Miles did have some vulnerabilities. Because to your point, he seems onstage like the most confident–any cat that gets onstage and turns his back to you [laugh] and play, he’s a cat who’s got some confidence, man, yeah.

Cheadle: Yeah. You know, whether it’s true or not, and I understand it, Miles would say, “Does a conductor face the audience when they conduct? I’m dealing with my band. We’re trying to work on stuff and find things.” He would walk around the stage to see acoustically what pocket sounded better where he was playing.

And some of it was attitude, but the thing that I liked about Miles and about the way he worked is that it was all about process. It as all about process, you know. He didn’t introduce songs because he’s like I’m not gonna get up and do the sort of entertainment thing. I’m actually doing something that’s a lot more ingratiating to you in a way which is going, “Come look at how we work on stuff.”

Come see the journey, because that’s really what they were about, you know. Herbie said Miles paid them to practice in front of people, you know, not come down and do your polished perfect work, but let’s all be out here and try to figure some stuff out together.

Tavis: Speaking of Herbie, how cool was it–I’ll fast forward to the end of the film when you’re onstage with Herbie and Wayne Shorter and Esperanza Spalding and you’re playing with them.

Cheadle: Gary Clark, Jr.

Tavis: And Gary Clark, Jr.

Cheadle: Antonio Sanchez and Rob Glasper. No, I was like…

Tavis: How cool is that [laugh]?

Cheadle: That was enough of an excuse to do the movie right there. I mean, I had no idea that we would be able to do that.

Tavis: To pull that off, yeah.

Cheadle: But, yeah, I was someone who, you know, came up sort of surrounded with musicians and in that sweet spot of that creativity and that creation. It was great to be there with these masters who just do it all the time.

Tavis: Speaking of masters, Carlos Santana was sitting in that chair just a few weeks as a guest on this program. Always pleased to have him. I’ve gotten so much mail from people, you know, literally snail mail, email, from folk who saw that conversation.

Because Carlos, at one point, seemed to suggest that he was advanced, enhanced, by the drugs that he took as opposed to suffering artistically from being drugged up.

I raise that because, in the movie, you don’t shy away from Miles’ cocaine use. You know, Miles isn’t here to answer this, but what’s your sense of whether or not that aided and abetted him artistically or whether it got in the way of what could have been even a greater iconic repertoire?

Cheadle: Well, I think often it’s not, but it’s and, you know. Again, if we were going to parse it, I mean, if we had him on the couch, maybe a therapist was here, they could talk him through it and we could find the moments where like now that’s probably the coke didn’t help you [laugh]. I imagine the heroine at that point wasn’t really additive.

But we also do know that drugs do open up different centers and they do make different connections that you would make when you were not high. It is a slippery slope and one is not necessarily benefiting the other. I know that it was really hard for Charlie Parker because it didn’t stop his playing. It didn’t have a negative effect until everything caught up.

But he could get high and play unbelievably to the rafters and do things that no one could imagine they could ever hear coming out of a sax. And that, in many ways, led to his undoing. If he had lost all of his facility, I don’t know. He was hooked.

Maybe he would have been able to be more in a position to quit, but probably not. I mean, we’ve seen many, many great–this isn’t a new story, unfortunately, the presence of drugs with this kind of genius that seems to be boundless.

Tavis: The relationship that we see in the film, the acidic relationship that we see in the film that Miles had with the record company at that time, was that typical of the way he tended to get along or not get along with record executives?

Cheadle: Well, you know, again, some of that is dramatized. I think specifically his relationship with George Butler ultimately was very good, you know. George sent him a piano. George was at him to come back, but not in a way that was necessarily combative.

And I don’t think we portray him that way in the film, but he was saying, hey, man, come back, you know. We’d love to hear your voice again and get you back in the studio and get you working.

He did, during this period of time, record this session that was never released and, you know, people haven’t heard. I’ve heard it. I think you can find it online if you dig around. But he was often–there’s famous notes that he sent to the studio [laugh] just was a like a number and a date, and he’d send it. Where’s it at? Let’s go, you know.

Tavis: Let me shift from the acting now to the directing. Is it cool for you to hear that term “directorial debut”?

Cheadle: Sure, when you say it [laugh]. It rolls off really nice.

Tavis: So what’s your takeaway from this maiden voyage?

Cheadle: Oh, man, it was a tricky way to do it, you know.

Tavis: And a tricky subject. I’m gonna high-five you on that, as a matter of fact.

Cheadle: Appreciate it.

Tavis: I was like, if I would be making my directorial debut, this is not the subject that I would have chosen. That’s a real…

Cheadle: Well, I didn’t set out to do that. That really was not the goal. I was not saying, well, let me find the hardest thing… [laugh].

Tavis: Exactly. That’s what I’m saying, I would have found me something easy to do [laugh].

Cheadle: And the hardest way to do it. No, I wasn’t–and when this all came to pass, it was because Vincent Wilburn saw me in “Devil in a Blue Dress” and he’s like, oh, if we ever do a movie, it’s gonna be Miles…

Tavis: I love Vincent.

Cheadle: Yeah, he’s great.

Tavis: Hey, Vince! What’s up, Vince? Yeah.

Cheadle: It had been sort of swirling around, but he kind of made a declaration when Miles was being inducted in the Rock and Roll Hall of Fame in 2006 that they were going to do a movie and I was going to star in it. So I said okay.

So I met with the family and I just pitched them this idea about how I kind of felt we should approach his life and the material and what the movie should feel like. It was a departure from the things that had been pitched to them before, so they were kind of excited about it. I said, okay, well, somebody writes that, let me know and I’d love to do it.

But it became apparent pretty quickly that, if that was how it was going to be done, it was probably going to take me to do it. And it’s something that I tried to give away a few years ago. I tried to find another director for the part so that I could just focus on the acting and I didn’t want that responsibility.

But everybody that I pitched it to were both doing their own thing and were also saying, “But this is your movie. This is your vision. This is your whole thing, so why wouldn’t you do it?” I’m like, “Cause I don’t want to die.” [laugh] I didn’t want to be hospitalized at the end of it. But, ultimately, it fell to me to do it because that’s the only way it was going to get done.

Tavis: I thought that the estate, the family, was very generous in the story that they allowed you to tell because I think you intimated this earlier in this conversation that some of that stuff–I mean, we see these stories that get sanitized and sterilized and deodorized…

Cheadle: All of it.

Tavis: And then it flops because everybody know it ain’t real.

Cheadle: Exactly, and you got to do the PG version of it. It’s like, “Really? James Brown, PG?”, but whatever. If it had not been Miles, and I think if they did not understand really what his quest had been his entire life, it would have been much more difficult.

Had they not been themselves artists and understand creativity, they would not necessarily have been down for something that was more in line with what he would have done, they believe, and something that he would have wanted to see done about him.

And he’s famously kind of gone in on movies that were about historical figures, musicians that felt like sort of cookie cutter things that he’d seen before. He’s like I don’t want that. So whenever we would discuss the film and how we wanted to go about it–because I wanted them onboard the whole way and was totally deferential to what they wanted out there.

I said, “Do you think that he would want something like what we have seen before in these kinds of movies that feel like cliff notes of the person’s life, or do you think he’d want something that’s wild and gangster and feels like it’s chasing itself down a hole and comes out the other end and just feels like it’s got some drive in it?”

They’d be like, well, let’s do that. And Miles wasn’t shy about his behavior ever, you know. He wasn’t trying to hide his drug use, his relationship with women.

He was like, yeah, I did all that stuff, and he very much regrets his relationship with Frances and how that all came to pass. They were friends afterwards, so it’s a very complicated relationship in that regard. He has been on record being really open with all of it.

Tavis: So now that you have survived, you didn’t die, it didn’t kill you…

Cheadle: Right.

Tavis: They say what doesn’t kill you makes you stronger?

Cheadle: I don’t think that’s been proven medically [laugh]. I think what they said is that stress actually kills you. I mean, isn’t that what we’ve learned?

Tavis: Yeah, yeah, yeah. So I guess the question is, did you enjoy it enough to want to do it again?

Cheadle: Nope. Not like that.

Tavis: Okay, but you do want to direct again, though.

Cheadle: Yeah. I would direct again.

Tavis: Okay.

Cheadle: Yeah. I think that was too many things to freight it with. But I felt like I went to school and got my “comprodirectorate” [laugh]. Comprodirectorate, that’s what I got on that movie.

Tavis: I got you [laugh]. And I thought you were going to say, “You know, I’ll direct again, but I don’t nothing to do with that Cheadle guy again, man. I don’t want to direct that Cheadle guy again.”

Cheadle: Yeah, he was a drag.

Tavis: I got a minute to go and I can’t end this without asking about my man, Marty Kaan. April 10?

Cheadle: We’ll be back.

Tavis: You’re back on Showtime?

Cheadle: That’s right.

Tavis: You shot in Cuba?

Cheadle: Yes, we did.

Tavis: How cool was that?

Cheadle: It was very interesting. I mean, have you been?

Tavis: Oh, yeah, a couple times.

Cheadle: So you know that that country needs something and that, you know, you go over there potentially with this exoticism of like, oh, the people and the music. It’s gonna be–and then you get over there and it’s like there is that, but there’s also like a lot of depression here and there’s a lot of sadness and poverty.

We hope that there will be some sort of an exchange, not just culturally, but there will be an ability to have the trickle down–which then does that ever work–but I hope it will when this infusion of capitalism happens that the people can get uplifted.

You know, when the guy in the hotel who’s bringing your towels is a surgeon and he’s got to work in the hotel to make chips or your waitress is a physicist, this is what you do? They’re like, yeah, I trained in school for 20 years. It’s like, wow. You know, they need something.

Tavis: From your mouth to God’s ears.

Cheadle: There we go.

Tavis: “Miles Ahead” is the film that Don Cheadle stars in and directs this weekend. I highly recommend it, if that means anything to you. I enjoyed it, and Marty Kaan is back on “House of Lies” on Showtime on April 10. Mr. Cheadle, you’re welcome here any time you want, sir.

Cheadle: I’ll be back.

Tavis: Good to see you, my friend.

Cheadle: Thank you.

Tavis: That’s our show for tonight. Thanks for watching. Goodnight from Los Angeles and, as always, keep the faith.

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Last modified: April 1, 2016 at 3:20 pm