How Chris Messina Forced Matt Damon to Up His Game in ‘Air’

Chris Messina has a hard time admitting that he’s funny.

Even after his hilarious turn as a silver-tongued sports agent in “Air” and six seasons as a drolly charming doctor on the sitcom “The Mindy Project,” he is surprisingly self-critical when it comes to his comic abilities.

“Comedy is so hard,” he said in a recent video call from his home in Los Angeles, adding an expletive for emphasis. “It’s hard to land a joke. So I still struggle with that. I’m best when I either don’t know it’s a comedy or don’t play it as a comedy — then you might find me funny.”

This is difficult to believe if you’ve seen “Air.” As Michael Jordan’s outrageous, surly representative David Falk in the story of the creation of the Air Jordan sneaker, Messina is uproarious, screaming and swearing his way through fever-pitch negotiations with voluble panache. In the most memorable exchange, Messina calls the Nike scout and marketer Sonny Vaccaro (Matt Damon) to lambaste him for secretly visiting the Jordan family. Messina goes utterly ballistic, hurtling around his office as he barks threats and insults involving various bits of bodily anatomy. The Ringer described him as the film’s “foul-mouthed” M.V.P.

“Phone calls are usually just a bore,” Messina said thoughtfully, displaying an open and eager friendliness, pleased to be discussing the details of a craft he clearly loves. “There’s no one on the other line — sometimes there’s a script supervisor reading the lines off-camera.”

But for “Air,” the director Ben Affleck had the idea to shoot both sides of the conversation simultaneously. He set up Damon and Messina in offices down the hall from each other, and had two sets of cameras rolling at the same time. “It felt more alive,” Messina said. “Matt and I could talk over each other, then we could improvise, then we could come together and say, ‘How about we change this to this?’ And then go back to our offices and keep going.”

As Affleck told me in a recent phone interview, “All of the great lines in that scene are Chris’s improvisation.” And those improvisations, he said, had a particularly strong impact on Damon. “Matt could not keep a straight face. I had to use Matt laughing because there wasn’t a take of him playing it straight. He tried to play it straight, and he just couldn’t.”

Damon explained that “it was already really funny on the page.” But when Messina came up with threats, “it dictated how I had to play the scene,” Damon said. “I had to start ad-libbing. I started talking to the background artists next to me, going, ‘It’s David Falk on the phone, sorry,’ and I just started laughing.”

“Air” is Messina’s third appearance in an Affleck-directed film, after the Oscar-winning drama “Argo” and the period crime tale “Live by Night.” Affleck said, “I always look for work for Chris because he’s always so good. Every time he’s had the opportunity, he’s always done more than I envisioned or imagined.”

Though “Live by Night” was not a commercial success, Affleck said he was “particularly proud” of Messina’s performance, for which he gained 40 pounds. “I said he could wear a body suit. He said no, it wouldn’t be the same,” Affleck said. “I can’t say enough good things about him.”

Damon echoed the sentiment, describing his co-star as an actor’s actor, the kind “all the other actors always talk about. Did you see him in this? Or, he’s in that, that’ll be good.”

Messina’s career started on the stage. A “tried and true New York theater actor” from Long Island, as he put it, he plied his trade “mostly Off Broadway, and Off Off Broadway, and sometimes Off Off Off Broadway, in the Bronx and in Queens and on the Lower East Side.” He speaks of those scrappy early days with a nostalgic air, reminiscing about plays “where the actors outnumbered the audience, or where, when it rained, it would leak on the stage,” he said. In short, he loved it.

For a long time, Messina yearned to find glory the romantic way. “I really thought, stupidly, that Mike Nichols would discover me in a play and put me in ‘The Graduate 2,’ you know? I had read about Dustin Hoffman. But that never happened.”

Instead, Messina transitioned to the screen. After a couple of small, forgettable parts in films like “Rounders” (with Damon) and “The Siege,” he landed his breakout role, on the final season of the funeral-home drama “Six Feet Under,” playing the amiable, strait-laced lawyer Ted Fairwell, the love interest of Lauren Ambrose’s Claire. On the strength of his work on that HBO drama, he began landing high-profile films, including Sam Mendes’s “Away We Go” and Woody Allen’s “Vicky Cristina Barcelona,” as well as recurring parts on the cable dramas “Damages” and “The Newsroom.”

Most viewers, though, probably know Messina best for his work on “The Mindy Project,” starring as the sometimes ill-tempered, sometimes charismatic Danny Castellano opposite the series creator, Mindy Kaling. When casting began in 2011, Kaling was specifically seeking actors she “hadn’t seen do a lot of comedy” or, if they were experienced, “weren’t the usual suspects they always send you,” she said in a recent interview.

She knew he was perfect straight away. Describing him as one of the most comical actors she’s worked with, she said Messina was “so rooted in the truth of his character that he can’t help but be funny.”

She attributes that expressly to the fact that he is not a traditional comedian. “Your average sitcom actor wants to hit their moments, make the day, and go home. Chris isn’t like that,” she said. “It’s almost exhausting, the level of honesty and truth he brings to every scene. He was really listening to my character and reacting if the character did something funny or absurd. He made me a better actor. I was listening better when I was with Chris, because he set the bar so high.”

Although Messina proved well suited for the role, he originally didn’t even want to do it, turning down the part multiple times before relenting. (“Mindy wouldn’t take no for an answer,” he explained.) He was, he said, “very worried about every aspect of it,” including the commitment to a network comedy with 20-plus episodes per season, potentially for many years — perhaps making it more difficult for him to do the kind of serious work he dreamed of as a performer.

“I wanted to do ‘Dog Day Afternoon.’ I wanted to do ‘Midnight Cowboy,’” he said. Though he liked the role and Kaling, “I was afraid of it running forever.” And, of course, he was afraid of something else: the genre. “I was afraid of not being able to keep up with them comedically,” he said. “I am afraid of jokes.”

On the other hand, being afraid is what Messina wants. “Being scared of a role, of an opportunity, being challenged, that’s what I’m looking for. Maybe it’s corny or too actorly, but I do like finding closed doors inside of me.”