Is "Air" Worthy of a Ben Affleck and Matt Damon Reunion?

There’s plenty retro about Air, Ben Affleck’s new behind-the-scenes drama about the negotiations resulting in Michael Jordan’s partnership with Nike, cemented in 1984. It has plenty of ’80s-era outfits and hairdos, albeit mostly filtered through the sensibilities of relatively buttoned-up, middle-aged shoe-company execs. It opens with a montage of broad pop-culture talking points for older viewers to orient themselves in time, and transitions between scenes with a hit parade of extremely obvious needle-drops. It’s also a general throwback, as most Affleck-directed pictures are, to a time when dramas made by and for middle-aged adult audiences were multiplex fixtures, rather than occasional indulgences. Its sneakiest and most interesting retro accessory, however, is its reunion between Affleck and Matt Damon.

Affleck and Damon are the rare A-list actors who became famous more or less as a package deal even as their careers remained largely separate. Real-life friends, they’d appeared in some of the same films — they’re both in the 1992 drama School Ties — before writing Good Will Hunting together, with Damon starring as the title character and Affleck playing his on-screen bestie. The movie was a hit, the duo won a screenwriting Oscar, and both went on to star in a plethora of films, mostly apart. Since Good Will Hunting cast Damon as the rough-edged golden boy and Affleck as the good-hearted lunk, they’ve appeared together primarily in Kevin Smith movies: First as a genuine double act in Dogma (which features one of Affleck’s best performances), and then periodically in movies where one or both of them performed cameo-favors to their old friend.

This changed with 2021’s The Last Duel, the historical drama they wrote together (in conjunction with Nicole Holofcener) and appeared in, though Affleck had more of a scene-stealing supporting role to Damon’s lead. That’s the dynamic again in Air. Damon plays Sonny Vaccaro, who spearheaded the company’s courtship of Jordan; Affleck has a smaller part as Nike founder and then-CEO Phil Knight, who hems and haws and drags his feet as Sonny advocates to spend their entire endorsement budget on this promising NBA freshman (who, less promisingly, absolutely loves Adidas track suits).

This isn’t so different from the Damon and Affleck audiences may remember from Good Will Hunting, which also favored Damon’s point of view; Dogma is an outlier in terms of giving the two actors equal weight. At times, Air resembles, well, not exactly a Good Will Hunting sequel (the idea of which was memorably parodied by both actors, again courtesy of Kevin Smith, in Jay and Silent Bob Strike Back), but a kind of middle-aged, corporate companion — Will Hunting reshaped as a talented white-collar brand loyalist. Damon still plays a prodigy of sorts, only here it involves scouting basketball players to hire to wear Nike sneakers, hoping to restore the company — lagging in its basketball-shoe division, flourishing among joggers — to its former cultural glory. Vaccaro reads, like a lot of later-period Damon protagonists, as kind of a schlub; the movie makes a low-key gag out of his decidedly unhealthy eating habits and aversion to exercise. Affleck, meanwhile, again gets to needle a guy he’s known for years, only from his perch as an irritable (and, in the movie’s telling, increasingly risk-averse) boss. They’re no longer playing best friends — but do any of these real-life characters have best friends? Mostly, they seem to have co-workers.

That’s both the fantasy and the unacknowledged limitation of Air. The movie’s chatty scenes of planning, negotiating and occasional shoe-designing are like Aaron Sorkin rewritten to eliminate both the sharpest banter and, thankfully, the self-satisfied preening. The screenplay, not by Damon or Affleck, especially avoids the classic Sorkin tactic of feeding the bad guy a stupid mistake for the hero to righteously and verbosely correct; when Sonny and Phil bicker over whether to bet it all on Jordan, writer Alex Convert mostly keeps the certainty of hindsight at bay. Yes, we know that Sonny will be proven right about Jordan, and that his insights about the real target of Nike’s pitch — Jordan’s mom Deloris (Viola Davis), who guides family decisions — will pay off. What keeps the movie from evangelical fervor are the moments of mundane office-world teamwork, bringing in Sonny’s buddy Rob Strasser (Jason Bateman) and designer Peter Moore (Matthew Maher). It’s neat to see these guys wheel, deal and craft an iconic piece of footwear on the fly, even if the Air Jordan’s utility as a marketable product is the true function following its eye-catching form.

The movie does indulge in a different sort of faith, however: in the power of the elder-statesman auteur. Air’s director does some hands-on ribbing of Phil Knight over his quasi-philosophizing and frequently shoeless feet, and honors the group effort to lure Jordan away from Adidas and Converse. Yet there’s still a kind of incurious acceptance of Nike’s slogan-packed corporate culture, of men being men, which in this context means working around the clock on securing an endorsement deal. (It’s the kind of movie that brings out one worker’s post-divorce custody sob story for late-breaking human-interest sympathy, without even attempting to ask why, exactly, he’s only allowed to see his child once a week.) Affleck and Damon long resisted working together, attempting to define their careers’ respective independence, and they seem to have been reunited by a desire to pool their resources as established non-superhero stars who want to do things the old way. The adult-drama, human-story, limited-visual-effects way. The Clooney way. The Costner way.

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Broadly, this is valuable. Twenty-six years ago, it wasn’t a complete shock that Good Will Hunting wound up one of the 10 biggest movies of the year — not nearly as much as it would be if Air managed that feat in 2023, despite a quarter-century’s worth of accumulated star power and, uh, good will. (Damon’s last art-of-business dad movie, Ford v Ferrari, did well, but not that well.) Maybe nagging at Air for lacking real substance is as pointless as it sounds. Affleck and Damon are fighting the good fight. But what specifically is Air fighting for? Good Will Hunting and Dogma lets the two friends bicker over life choices and philosophies, with an unpretentious, joshing sense of humor. The Last Duel, less lighthearted, placed them in a conflict over toxic masculinity and rape culture. Air sets them at odds over annual earnings, budgets and — this is supposed to be part of the stakes, I think — Sonny’s future doing a player-scouting job he admits he can’t exactly quantify. The human story on par with Good Will Hunting feels like it’s happening off to the side, wherever Viola Davis is; she has a Jordan-like ability to outplay everyone else on the court, in just a handful of substantial scenes.

There’s nothing wrong with Affleck and Damon paying attention to more workaday characters rather than a once-in-a-generation basketball superstar, of course; Affleck the director wisely opts not to let an actor impersonate Jordan, keeping him as a quiet physical presence rather than a character, lest the movie be pulled into the gravitational field of a biopic. There’s an appealing modesty in watching a bunch of guys try to excel at their jobs — and, in the final stretch, an underestimated woman taking charge of the opportunity presented to her family. At the same time, there’s something unchallenging and backwards-looking about Air, an unearned wistfulness about the mere fact of its 1984 setting. It’s like a bunch of Hollywood guys got together and agreed that the best sports stories focus mainly or perhaps even exclusively on the coaches, rather than the players. George Clooney has fallen into this trap as a filmmaker, too, with some late-period movies that feel like throwbacks in subject matter more than actual craft. Damon and Affleck reuniting for Air, with the prospect of more collaborations to come, feels personal. The movie itself, less so. Its makers never fully reckon with their nostalgia for the way things were.