Ben Affleck and his all-star Air cast give a play-by-play of making their Michael Jordan movie

The cast of Air photographed by Alex G. Harper for Entertainment Weekly
The cast of Air photographed by Alex G. Harper for Entertainment Weekly
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Alex G. Harper for EW

Dream teams don't come much dreamier than the cast of Air.

Directed by Ben Affleck, this '80s-set movie based on real events stars Matt Damon as Sonny Vaccaro, a Nike marketing executive convinced the company should take the unprecedented step of giving a basketball prodigy, Chicago Bulls third overall draft pick Michael Jordan, his own line of shoes. The problem? Most of Vaccaro's colleagues think he deserves to be benched for coming up with such a ridiculous idea. Undeterred, Vaccaro sets out to persuade his colleagues — played by Jason Bateman and Chris Tucker — and Nike founder Phil Knight (portrayed by Affleck) that his is a baller plan.

But those three won't be enough. He must also convince Jordan's parents Deloris and James, brought to the screen by real-life couple Viola Davis and Julius Tennon, that their son should sign with Nike, known for its running shoes, and not the corporation's cool-with-the-kids competition, Adidas. Along the way, Vaccaro seeks advice from basketball coach George Raveling (Marlon Wayans) and tangles with Jordan's hard-nosed agent David Falk (Chris Messina).

The cast of Air photographed by Alex G. Harper for Entertainment Weekly
The cast of Air photographed by Alex G. Harper for Entertainment Weekly

Alex G. Harper for EW (Clockwise from top left) 'Air' stars Chris Tucker, Matt Damon, Viola Davis, Julius Tennon, Chris Messina, Marlon Wayans, Ben Affleck, and Jason Bateman

It's no spoiler to say that Vaccaro ultimately succeeds in his quest, securing a buzzer-beating deal that would launch the Air Jordan and open the door to young athletes properly participating in the profits of sports merchandise.

"One of the things that was really interesting to me was highlighting the difference between a salary versus an actual ownership," says Affleck, flanked by his lineup of actors for one of EW's starriest Around the Table chats ever (full video below). "Oftentimes, whether it's the entertainment business or the sports business, you've seen young people coming in and signing contracts and paid far less than the wealth they generate for other people. I would argue that's still the case with college athletics, where athletes are not paid, inexplicably. It just baffles me how you could have a billion-dollar television contract and the people who actually play the games receive nothing. So that's something that's important to me."

Affleck and Damon are, of course, longtime friends and collaborators who won the Best Original Screenplay Oscar for 1997's Good Will Hunting and serve as producers on Air through their recently founded Artists Equity company. Over time, Affleck has acquired a heavyweight reputation as a filmmaker with movies like 2010's The Town and 2012's Best Picture Oscar-winning Argo — but Air is the first time he has directed his pal. Isn't it?

"First time that you're aware of," says Damon.

"I like to think I've been directing him my whole life," Affleck quips.

"We did high school theater together," adds Damon, good-naturedly. "He's been in my ear for fortysomething years."

Matt Damon and director Ben Affleck on the set of 'Air'
Matt Damon and director Ben Affleck on the set of 'Air'

Ana Carballosa/Prime Matt Damon and Ben Affleck on the set of 'Air'

After getting involved with the Alex Convery-written movie — which Prime Video will release in theaters April 5 — Affleck met with Jordan, who had very specific thoughts about who should portray his mother, Deloris.

"Michael Jordan was very adamant that the only person who was fit to play his mother was the best actor in the world — Viola Davis," recalls Affleck, who adds that the early version of the role wasn't worthy of the EGOT winner. "I was like, 'Well, okay... Mike, there's two lines in the script right now that the character has, so probably Viola's not going to respond to that.' But, really, what was so beautiful about that gift was that it inspired us to go, 'This is the central character, the protagonist, the hub of this wheel. We're going to build this story around this person.'"

Davis reveals she didn't know she was Jordan's choice for the role until very recently, and is "probably" glad she was unaware of the basketball star's enthusiasm for her prior to filming.

"It's just not my style to react to compliments," says Davis. "I wish it were — I would have saved a lot of money in therapy."

"It's a good thing your agent didn't know about it," chips in Bateman, who plays the late Nike marketing executive Rob Strasser, eliciting laughter.

Davis admits she was a little apprehensive ahead of the Air shoot, given she would essentially be the only woman in the cast of a sports-themed movie.

"It's going to be just hyper-masculine energy," the actress, an Oscar winner for 2016's Fences, recalls thinking. "You always imagine men with their face painted and dressed as mascots, screaming. I was surprised at the heart in the movie. Because a lot of times, you talk about just winning. That's what I see when I watch sports. I'm like, oh, they talk about winning. 'We just won a game, man!'"

"And then, when they cry, she makes a joke out of it," adds Tennon, laughing. "I always go, 'Viola, you can't do that!'"

"I don't do that," Davis quickly interjects.

"We cry when we lose games! That's what we do!" says Tennon, once again prompting laughter around the table. "As athletes!"

"Oh my God, Julius!" Davis responds, bringing it back to her original point. "No, but I love the heart in the movie."

Viola Davis as Deloris Jordan in 'Air'
Viola Davis as Deloris Jordan in 'Air'

ANA CARBALLOSA/Prime Viola Davis as Deloris Jordan in 'Air'

Davis may love the heart of the movie, but her Deloris is a woman not given to wearing her heart on her sleeve — an acting challenge her director feels she nailed.

"It's easy to [act] opaque — I'm not going to show you anything," explains Affleck. "It's extremely difficult to be opaque and have the sense that there's an enormous amount of feeling inside, you just don't know what it is. It makes you want to lean in even closer, and that is as good as acting gets."

"That's masterful acting," adds Damon. "That's what Brando did, right? It's not doing nothing, it's the opposite of doing nothing. You present it as if you're doing nothing, but everything in the world is happening right underneath, and it's awesome."

"It's a mask that a lot of African Americans wear as they move through life, especially Deloris' generation, [because] of constantly being told that they're not good enough, or people talking over you," says Davis of her character's stoic demeanor. "You put the mask on. It's from a famous poem: 'We wear the mask that grins and lies…' And that's what I felt with Deloris."

Messina's character, however, is anything but stoic — a shrewd agent whose work is his life. The actor previously worked with Affleck on both Argo and 2016's Live by Night, so the chance to work with him again, plus the quality of the cast, made his decision to sign an easy one.

"When Ben calls you up and asks you to do something, and you get the cast list, you're like, 'I don't have to read it,'" says the actor, who admits he also relished in getting to play against type as the fiery Falk. "This is the A-team in front of the camera and behind the camera. It was kind of like a family affair. It felt like you were just hanging out with friends, having fun, making a movie."

That sense of fraternity, and conviviality, lives on during the cast's EW sitdown. When Tennon recalls how enjoyable it was playing off his castteammates, including Messina, Bateman pretends to act surprised.

"You got something off of him?" the Ozark star asks Tennon of the Mindy Project actor.

"A little bit," deadpans Messina, replying to Bateman. "I didn't really give you much."

Tucker, on the other hand, got a lot from Howard H. White, whom he portrays in Air, his first film since 2016's Billy Lynn's Long Halftime Walk. The Rush Hour star had a home-court advantage of sorts: He's friendly with White, Nike's primary liaison with NBA stars including Jordan and Charles Barkley.

"It was like kismet to me," Tucker says of taking on the role. "Howard is somebody that I knew I could channel, who he was about, what he's about, who he is. He had me talking to people [from] when he was 5 years old, these people he was hopscotching with in the street, and the coaches and teachers, up to Charles Barkley saying, 'Yo, yeah, he's my mentor. That guy like Confucius!' I was like, whoa, this is great, I got a lot of stuff, I'm going to throw a lot of stuff at Ben, I hope he can handle it. And Ben was like, 'Come on.' So it was great. And working with Matt — I'm glad I forgot who Matt was, all the movies he's done, him and Ben. I was real comfortable around these guys."

Tucker fondly recalls Affleck's dedication to getting the best from his cast while the actor was filming a scene in which White calls Damon's Vaccaro from a phone booth. With such sequences, directors often shoot the two sides of the conversation separately, but Affleck arranged to film the two actors at the same time, with Damon situated elsewhere on the set.

"That's what you want as an actor, you want everything to be as real as possible," says Tucker. "So you can really go in and channel what you're trying to say, the filling of the scene. I was like, okay! Alright! Matt got on the phone and it was like we had a real conversation."

"I was watching both scenes, and you did something that really surprised me," Affleck tells Tucker. "You brought out this feeling of humanity and love that was so vulnerable. I thought it was an important thing, a side of masculinity to show, and it really moved me. It moved me to tears when I saw it. [When Matt] came in, he saw me, he was like, 'What? What is it?' I was like, 'I wasn't really watching you — Chris was amazing!'"

"He was like, 'Chris is going off!" adds Damon, pretending he was disappointed at being outshone in the scene. "And I was like, 'Oh, great. Well, we play [the scene] on him then…'"

Wayans, whose own writing credits include the 2000 blockbuster Scary Movie, is similarly complimentary about Affleck's filmmaking chops and the freedom he granted his actors.

"I mean, it's hard. I rarely stick to my own lines," says the actor. "Like, seriously, there has been a time when I had a movie [and was] rewriting everything I wrote. So it felt good that that was welcome."

Wayans often works with members of his family — including his brothers Shawn and Keenen Ivory — and bonded over that experience with Damon, who feels his near-familial bond with Affleck makes things easier and saves time on set.

"When you grow up with somebody, I think there's an understood baseline of deep and abiding respect that kind of allows you to dispense with all of the diplomacy that sometimes you get on a set," says The Martian star. "People talk around solving the problem because they don't want to hurt anybody's feelings. 'I'm wondering if you might be a little…'"

"Quicker!" barks Affleck, impersonating his direction of Damon.

"He's just like, 'That was terrible, man! And you've got to say it faster!'" explains Damon. "We do that when we write, too. He said one of the most profound things that anybody's ever said to me: When we started writing Good Will Hunting he said, 'Hey, judge me for how good my good ideas are, not how bad my bad ideas are.' That, to me, is the most important thing when you embark on a collaborative process with somebody. You've got to get the window open to throw every idea in there and not be afraid to have s---ty ideas, because we all have s---ty ideas. Sometimes you need the s---ty idea, and then you iterate on that, and then it builds into a good idea. But you have to feel free to express it."

Alas, there is no more time for the Air crew to express themselves further. Although Bateman seems to be under the impression that this has all just been practice for the real deal.

"Great rehearsal, guys," he declares. "We're going to have lunch and then we'll shoot!"

Watch the Air cast's full Around the Table video below:

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