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The allure of the entrepreneur movie, from Air to Tetris to BlackBerry

Scammers are over. It’s time to make some deals.

Ben Affleck, in a shirt and tie, sits with his bare feet propped up on a desk
Ben Affleck as Nike founder Phil Knight in Air.
Prime Video
Alissa Wilkinson covers film and culture for Vox. Alissa is a member of the New York Film Critics Circle and the National Society of Film Critics.

Only Hollywood could make me cheer for a sneaker. Or a pocket-size email terminal. Or the legal rights to a video game landing in the hands of a slightly hapless, doggedly determined, bespectacled and genial guy. I rarely think about these things and barely care, but the job of a movie is to make me care, and for whatever reason, this spring they’re trying remarkably hard.

And sometimes it even works.

There’s a crop of movies about enterprising businessmen out this spring, all at once, which is both a coincidence — studios don’t tend to collude — and probably not a coincidence at all. Like last year’s crop of scammer and scammer-adjacent docuseries, these are all about real-life wheeling and dealing, the things that happen in conference rooms and panicky stairwells while the rest of us are just walking around living our lives. And, importantly, they’re ripped from the headlines, some more recent than others.

It is not actually easy to make a lot of yelling about terms and agreements and capitalization and other businessy things very fun to watch, which I suspect is why the con artist form took off first. There’s an inherent dramatic irony to the con artist story, since its existence is predicated on at least a vague knowledge among the audience that this person is in the act of hoodwinking. We know. They don’t. That’s where the fun, and the drama, comes from.

Harder, then, when the movie is — as in the case of Air — about some guys managing to get Michael Jordan to sign a licensing deal with Nike. Like, writing that sentence almost put me to sleep. Can I just watch The Last Dance again?

But lo, a miracle: Air is great. Pitch-perfect, deeply entertaining, in the vein of Moneyball but with the addition of Viola Davis as Jordan’s mother Deloris, who injects a sense of the stakes beyond profits. Ben Affleck, who might be a better director than actor (though he’s very good at both), figured out — with the help of debut screenwriter Alex Convery — where the drama is located in a story where we already totally know the ending. We have, after all, been living in an Air Jordan world for decades.

Matt Damon sits at his desk, feet up, phone pressed to his ear.
Matt Damon in Air.
Ana Carballosa/Prime Video

And where is that drama? In a carefully crafted cocktail of ingredients, each as important as the last. The base element is the lead, Matt Damon, playing a paunchy, middle-aged Sonny Vaccaro, whose job at the upstart athletic shoe brand Nike is to connect with fresh talent in an attempt to get the swoop onto the feet, and thus the courts, of the NBA. What’s important about Vaccaro is that he’s an underdog, clearly on the downward trajectory of his career, struggling to stay in the good graces of CEO Phil Knight (Affleck) and marketing head Rob Strasser (Jason Bateman), yelling on the phone at agent David Falk (an absolutely glorious, foul-mouthed Chris Messina). What he’s got is a feeling, and a willingness to risk it all on some 18-year-old kid from North Carolina. And if he fails, his career ends, and maybe the whole company with it.

You need that element in an entrepreneur story, because it gives you somebody to root for. It shows up again in, for instance, Tetris, centering on the very plucky Taron Egerton playing Henk Rogers, a man in a desperate race to secure the rights to the video game Tetris. The movie is bafflingly limp and weirdly paced, but the risk-it-all underdog is what holds it together. You might want the movie to be over, but you still want this guy to win. Or take BlackBerry, sort of a Canadian Social Network (down to, at times, the camerawork), which sticks two plucky long-shots in the main position. Jay Baruchel is Mike Lazaridis, the nerd who has the idea and starts the company; Glenn Howerton is Jim Balsillie, who spots an opportunity and swoops in, entering on the ground floor as co-CEO.

BlackBerry also exemplifies an important ingredient in the corporate entrepreneur movie, which is that you can’t just have the charismatic deal-striker. You need your nerds, the guys who actually make the product and make it better than anyone else. Lazaridis is the nerd, but so is his buddy Doug (played by BlackBerry writer and director Matt Johnson), who manages the engineers. They’ve figured out how to make a tiny email terminal you can throw in your pocket, and we get the pleasure of seeing “email on your phone” doubted by others, then the pair triumphant for having solved a puzzle others couldn’t. There’s a nerd in Air — Peter Moore (Matthew Maher), designer of the Air Jordan shoe — and one in Tetris, Alexey Pajitnov (Nikita Efremov), who made Tetris. The nerd gives us a second underdog to love. He’s secondary to the plot, but he reminds us that real competence is involved here, not just smooth talk. These aren’t con artists; they’ve got the real thing.

And there’s another element, one that differs from the con artist genre, which seems to deal with very recent stories — Inventing Anna, Tiger King, Bad Vegan, LuLaRich, I could go on. Maybe that’s because cons are so common that we’ve forgotten the big ones from a decade ago, let alone the 1980s.

A man with silvery hair and glasses stands in a room looking at a small device, with a group of cheering engineers behind him.
Jay Baruchel in BlackBerry.
IFC Films

But the entrepreneur movie deals with the guys who won, and who imprinted themselves onto the world we’re still living in. Gen Z may never know the satisfying tap of typing on a BlackBerry, but at one point in my career I had two, and I’m just one generation older. After my Air screening, I spotted six people of varying ages on the subway platform wearing their Air Jordans. (Most of them, I presume, had gone to see the movie.) And when I got on the subway, I absolutely whipped out my phone — my iPhone, sorry to the BlackBerry guys — and played Tetris.

Yet the corporate entrepreneur genre presents the perfect opportunity to indulge in some fun period design, a little cherry on top of the whole concoction. Tetris is set in the 1980s, on the verge of the end of the Soviet Union, and we get lots of Soviet-era interior design (if you can call it that) and ill-fitting suits. BlackBerry starts in 1996 — though it’s shot with the sensibility of a 1970 paranoid thriller — and reminds us of a time when it was still shocking to encounter a room full of people typing away on their devices. And Air’s main, almost comical interest, is in ’80s hair, with Affleck in some kind of curly Roman-emperor ’do and Bateman in a truly glorious mop.

And, of course, you need all the things a movie always needs: a good script, stakes, music, solid pacing, maybe a few jokes. It’s got to be fun to watch these guys yell and think and decide in a split second to try something that might fail utterly; you generate dramatic tension not through wondering what will happen — we know the ending already — but through letting us into their thought processes, letting us watch them convince rooms of skeptics that they’re right.

Interestingly, these movies don’t bother doing what they might have done, had they been made in the era in which they’re set: insist on some romance subplot, or spend the whole movie trying to convince us our main characters are doing this because they’re estranged fathers. (There are whiffs of that here and there — Tetris’s Rogers is married and has kids, Bateman talks about spending time with his daughter on the weekend — but it’s never the main plot.) Instead, the stakes are all about the deal, and the movie makes you care. Its closest cousin is the sports movie, underdog against Goliath. Nobody’s truly a villain; “winning” means your company gets what it wants, which is less like saving the human race and more like being able to buy a really nice car. We’re rooting for them to make a lot of money.

Which, admittedly, makes me feel a little weird. Tetris and Air operate essentially as extended commercials for their brands; BlackBerry doesn’t, but only because it can’t since the BlackBerry functionally doesn’t exist anymore. (Of the three, it’s the only rise-and-fall narrative, which feels a little more traditional.) But why am I sitting here just rooting for some guys to make cash?

A man with a moustache looks intense; Tetris blocks are seen falling behind him.
Taron Egerton in Tetris.
Apple TV+

In a sense, I guess, it’s a product of the American bootstrap narrative, tapping into the broader cultural sense that millionaires and billionaires are to be admired and respected. But even if you side-eye that sentiment, these movies suggest that if they could pull it off — guys down on their luck, risking their last dollar on a huge bet — then maybe we can, too. Never mind that for every one of these stories there are probably hundreds where the main player ended up declaring bankruptcy. History is projected onto the big screen by the winners.

There’s also just something deeply wholesome-feeling about these stories. If the con artist movie is a way to admire cunning operators in spite of our better judgment, then these are guys we can admire, fair and square. They didn’t hurt anybody. They just made a good product and figured out how to sell it.

I get all that but am still uneasy over the fact that the highest good being sold in these movies is the acquisition of cash, and the highest character quality to praise is being willing to take a wild risk. Maybe it’s just that we’ve run out of admirable figures from history to emulate, leaders of movements and humanitarians and scientists and artists who go unrecognized in their lifetimes. But it’s a little deflating to think that we’re now manufacturing heroes out of guys who basically just managed to combine good business sense with luck.

But let’s be real: It’s absurd to imagine Hollywood would do otherwise. Hollywood is a land of wheeling and dealing, of taking huge risks on uncertainties and sinking millions of dollars into what’s never a sure thing. And as Hollywood has grown exponentially more risk-averse over the past 15 years, their product has suffered, leaning on the familiar and the safe instead of the original and the untested. Hollywood is about capitalism, and the essential gambling nature of it all, which means not everybody gets to win.

And so, maybe, is Air. (Affleck’s choice to end the movie with “Born in the USA,” particularly after a character tells the story of actually listening to the lyrics of it, seems telling.) Watching Air, I found myself thinking that maybe what Hollywood needs is a movie like this: fresh, fun, full of movie stars doing their movie star thing without the aid of capes or pre-chewed IP, opening only in theaters. A story about risk-taking that could prove the reward was worth it.

A weird, wild sneaker of a movie, if you will.

Tetris is streaming on Apple TV+. Air is streaming on Prime Video. BlackBerry is playing in theaters.

Update, May 10, 1 pm: This story, originally published April 7, has been updated with current viewing information.

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