From Devil in a Blue Dress to the MCU, and beyond.

It's been a long time since the prolific Don Cheadle was out of sight.

And that's more true than ever in July 2021. The actor, 56, reunited with Out of Sight and Ocean's Eleven director Steven Soderbergh for HBO Max's No Sudden Move (now streaming), his Wall Street comedy Black Monday is currently earning laughs with season 3 airing Sundays on Showtime, and next up he's going one-on-one with LeBron James as a rogue A.I. in Space Jam: A New Legacy.

"Don Cheadle is amazing," New Legacy director Malcolm D. Lee tells EW. "He's such a chameleon, he's such a great character actor. To play a cartoony villain but still have some emotional resonance and pathos, it wasn't an easy character to find on the page. It took us a while to figure that out, but Don is so patient and inventive and looking at the long game, and because he's a writer and a director and a great actor, we found that definition of who Al G Rhythm was."

That busy lineup for Cheadle is as good an excuse as any to have the MCU staple and now 11-time Emmy nominee look back on his most iconic roles.

Devil in a Blue Dress, 1995

Cheadle says "everybody but me" was up for the scene-stealing role of Mouse, a loose cannon aiding Easy Rawlins (Denzel Washington) in director Carl Franklin's neo-noir thriller. Cheadle felt like Franklin still thought of him as the 19-year-old who'd starred in his student film — until a chance encounter between the two. "My agent was beside herself, and I was like, 'He knows me, if he wants to see me, he'll call me,'" recalls Cheadle, who at the time was starring on the CBS drama Picket Fences. "This search was going on for months all across the nation, and I was in an ear, nose, and throat doctor's office and the waiting room was packed; I was sitting behind the door, the door opens, slams into my leg, and it's Carl Franklin! Literally the moment that happened, the receptionist comes out and goes, 'This room is too crowded, you two go in that room.' And the two of us go off and just chopped it up. My agent called me that night and said I had an audition."

But that audition still wasn't enough to sell Franklin — which didn't bother Cheadle, who initially "didn't see myself in the role." The director told him to come back in costume to fully get into character. It is then when Washington — already an Oscar winner — was brought in to read opposite Cheadle. "Denzel and I hit it off immediately," Cheadle says. "Denzel looks at Carl and goes, 'This is Mouse, what are you guys doing? Cast him.'"

Don Cheadle Role Call
Don Cheadle and Denzel Washington in 'Devil in a Blue Dress'
| Credit: Everett Collection

Boogie Nights, 1997

Franklin later connected Cheadle with a young filmmaker named Paul Thomas Anderson, who wanted him to star as a cowboy porn star named Buck Swope. "I was like, 'My parents are alive, I can't do that,'" Cheadle says with a laugh. "Paul was super-confident and telling me that this was going to be a classic and you're going to beat yourself up if you aren't in it. Carl asked what I thought and I said, 'This dude's a banana bird.'"

Cheadle eventually signed on to star opposite Mark Wahlberg, Julianne Moore, Philip Seymour Hoffman, and Burt Reynolds. "It was nuts," Cheadle recalls of filming. "But Paul was firmly in control of his movie. He knew exactly what he wanted and how to get it."

Don Cheadle Role Call
Don Cheadle in 'Boogie Nights'
| Credit: G. Lefkowitz/New Line

Anderson earned an Oscar nomination for the Boogie Nights script and has since become one of the most revered directors in Hollywood — and a "dear friend" to Cheadle. "I go to his house and he shows me the early screenings of all of his movies," he brags of the Phantom Thread filmmaker.

Out of Sight, 1999

Cheadle's longtime relationship with another auteur started with a simple request: Help with a reading of Steven Soderbergh's Out of Sight at producer Danny DeVito's house. "I was walking out the door and they stopped me and said, 'Do you want to be in it?" Cheadle says of the "very underrated" Elmore Leonard adaptation.

The role of Detroit boxer-turned-criminal Maurice Miller pitted Cheadle against George Clooney and Jennifer Lopez, but it was the dynamic with Soderbergh that's still paying dividends. "He was a bit of a cipher at first," Cheadle admits. "Steven, you walk on his set, and he doesn't go, 'You stand here, this is where the camera is.' He goes, 'Okay, guys, show me,' and he'd figure out a way to work it around you. You always feel like you were part of the process."

Don Cheadle Role Call
A scene from 'Out of Sight'
| Credit: Everett Collection

Cheadle and Soderbergh have now worked together six times, most recently on No Sudden Move. But even Cheadle is still amazed at how productive Soderbergh can be. "Steven sent me two scripts that he wrote during COVID," he says. "He's like, 'Hey, man, don't give me downtime.' I was like, 'This is pretty dope,' and he said, 'Give me a week,' and he sent me another script!"

Cheadle adds of No Sudden Move: "He literally had a cut by the time we wrapped. He was like, 'You want to see it?' And I was like, 'You're done?!'"

Rush Hour 2, 2001

When pitched the cameo role of Kenny, the owner of a Chinese restaurant in South L.A., by "he who will not be named," a.k.a. disgraced director Brett Ratner, Cheadle was told he'd be getting his "ass kicked by Jackie Chan." His counter: "I will fight Jackie Chan to a draw."

"We went to Jackie's place, and Jackie speaks very little English, and he's like, 'Okay, let's go. We fight fast,'" Cheadle recalls of training for his one scene in the Rush Hour sequel. "And he started going so hard. I was like, 'Yo, this is a movie, bro.' I'm glad I didn't get my jaw broken."

Don Cheadle Role Call
Jackie Chan, Don Cheadle, and Chris Tucker in 'Rush Hour 2'
| Credit: Everett Collection

Cheadle couldn't have predicted the character's longevity, which is largely thanks to rapper Kendrick Lamar, who adopted the alter ego Kung Fu Kenny. "Kendrick was performing at Coachella and said he had a surprise for me," Cheadle says. "He has this film at the beginning where he's doing martial arts. The show was over and I said great show, and he kind of had this look on his face. We then ate and hung out all night, and then the next morning I woke up and was like, 'Wait a minute — Kung Fu Kenny?!'"

Ocean's Eleven, 2001

Cheadle can't help but laugh when thinking about how his star-studded trilogy with Soderbergh, Clooney, Matt Damon, and Brad Pitt began. "[Producer] Jerry Weintraub was calling Matt and going, 'Hey, I got Clooney, I got Pitt,' and then calling me and going, 'Look, Damon and Pitt are in it,' and calling Brad and going, 'Cheadle and Damon are in this,' and none of us had said yes."

But once they were all on set — and joined by the likes of Casey Affleck, Bernie Mac, and Carl Reiner — the Rat Pack-inspired heist film wasn't as glamorous for Cheadle as expected; he instantly regretted agreeing to do a Cockney accent for explosives expert Basher. "They're out playing basketball and poker; I'm sitting in the trailer with the speech dude," he recalls. "We should have just changed it!"

Don Cheadle Role Call
A scene from 'Ocean's Eleven'
| Credit: Bob Marshak/Warner Bros.

The 2008 death of Mac ended talk of a fourth film (Reiner passed away in 2020) — until Soderbergh recently floated the possibility to Cheadle. "We were talking about it, and then Bernie passed, and very quickly we were like, 'No, we don't want to do it,'" Cheadle says. "But I just did a movie with Steven and he said, 'I think there may be a way to do it again. I'm thinking about it.' And it didn't go much further than that. But I don't know; I don't know who all would be in it. I imagine the main group of us would be in. It would be interesting to see."

Hotel Rwanda, 2004

The role of hotelier Paul Rusesbagina, who sheltered thousands of refugees during the Rwandan genocide, "literally changed my life," says Cheadle. But not because of the Oscar nomination it earned him, rather that "it brought me into a whole other aspect of activism and being out there attempting to garner support and raise awareness."

That's why the only thing Cheadle can think of when asked to reflect on Hotel Rwanda is the man he portrayed. "Paul is in prison under very questionable circumstances," he says. "Trying to marshal attention and get him out on humanitarian considerations has been very difficult. Hopefully very shortly the powers that be [can] step in and do something, but there's no guarantee. It's just really sad to have it come to this."

Don Cheadle Role Call
Don Cheadle in 'Hotel Rwanda'
| Credit: Frank Connor/Lionsgate

Crash, 2005

In addition to casting Cheadle as Det. Graham Waters, writer-director Paul Haggis brought him on board as a producer of the crime drama, which explores race in Los Angeles. "We heard 100 nos," Cheadle recalls of seeking financing. Not only would they eventually get a yes, but Crash went on to became a controversial Best Picture winner at the Academy Awards. (Cheadle wasn't present for the ceremony, having not qualified for the producing Oscar.)

"It was polarizing to begin with," Cheadle says of the film, which beat frontrunner Brokeback Mountain. "People were like, 'This is a very hokey, ham-handed way to talk about racism,' and I understand looking through a certain lens that, yeah, you could say that. I think the movie was always a fable and more an allegory than supposed to be taken specifically. It's trying to raise these ideas and talk about them in a way that maybe people didn't think was nuanced enough. The first job of a movie is entertain people, and if it can move the needle forward on some conversation or get people more engaged, that's a great byproduct. But that's not really what I look for movies to do for me. If you want to really dig into issues, it's probably better to go somewhere else than a movie that in 90 minutes has to wrap everything up in a bow."

Don Cheadle Role Call
Don Cheadle in 'Crash'
| Credit: Everett Collection

Iron Man 2, 2010

While playing laser tag at his daughter's birthday party, Cheadle was given an hour to decide whether to join the superhero sequel as Iron Man sidekick James Rhodes, a.k.a. War Machine, which had been originated in the first film by his Crash costar Terrence Howard.

"It's been a whirlwind," says Cheadle, who just earned an Emmy nomination for his two-minute (!!) The Falcon and the Winter Soldier guest spot. "They said, 'You have an hour to make a decision.' And I said, 'I'm at my daughter's birthday party playing laser tag right now.' They're like, 'Okay, take two hours.' Oh, that is so generous of you, take two hours to decide on the next 11 years of my life, and on a role you guys haven't even cracked yet! [Laughs] But my wife and I kind of hunkered down with these fake guns, and she's like, 'I guess you kind of have to take a flier, say yes, and figure it out?'"

Don Cheadle Role Call
Robert Downey Jr. and Don Cheadle in 'Iron Man 2'
| Credit: Industrial Light & Magic/Marvel

Neither of them could have predicted that 11 years and seven movies later he'd be one of the longest-tenured MCU characters. "What's amazing is that what's to come is a whole other level," he teases of Armor Wars, the upcoming Disney+ series centering on Rhodes. "This will be an opportunity for the first time to really see who he is and what makes him tick."

House of Lies, 2012-2016

Shortly after debuting as Rhodes in Iron Man 2, Cheadle decided to make a return to where his career started: TV. He signed on to lead Showtime's comedy series House of Lies as driven and immoral management consultant Marty Kaan, for which he'd win a Golden Globe.

"I'm material-driven, and it was smart, funny, interesting, dark, and risky," he says. "I couldn't anticipate what was going to happen on the next page, and that's not always what the case is. We've always been platform-agnostic, and just go where the good thing is. It was a no-brainer."

Don Cheadle Role Call
Kristen Bell, Ben Schwartz, Josh Lawson, and Don Cheadle in 'House of Lies'
| Credit: Jordin Althaus/SHOWTIME

Black Monday, 2019-present

Cheadle wrapped his House of Lies run in 2016 after five seasons, but he quickly found himself back fronting another Showtime comedy. He's now on his third season of starring on Black Monday as Wall Street maverick Maurice Monroe, the leader of a group of wacky outsiders who took on the establishment and ended up causing the titular financial disaster.

"We're always trying to crack each other up, trying to push everything, and still have these characters have a center and talk about things that are happening today through the prism of the '80s and '90s, and show how much hasn't changed," says Cheadle, who costars opposite Regina Hall, Andrew Rannells, and Paul Scheer. "This season has been even more supercharged. We blew up season 2 and everyone is kind of an island, but now we're coming back together, to more antics and high jinks."

Don Cheadle Role Call
Don Cheadle in 'Black Monday'
| Credit: Nicole Wilder/SHOWTIME

Space Jam: A New Legacy, 2021

Director Malcolm D. Lee's long-awaited follow-up to the semi-animated 1996 box office smash finds NBA superstar LeBron James sucked into the Looney Tunes universe of Bugs, Daffy, and Zendaya's Lola Bunny by Al-G Rhythm, Cheadle's "misunderstood" rogue A.I. The kid-friendly film is a change-up from Cheadle's more serious dramatic roles, but he says he wanted not only to work with James but also to try something a bit… different.

"It was a big job, and you roll the dice because you don't know what these things are going to be, but I think people are going to have a lot of fun," says Cheadle, who wishes he was surprised by internet conversations about things like Lola's updated look. "That's really important, you won't be able to enjoy the movie unless you're attracted to this animated bunny!"

Don Cheadle Role Call
Don Cheadle in 'Space Jam: A New Legacy'
| Credit: Warner Bros.

Space Jam: New Legacy arrives Friday in theaters and on HBO Max.

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