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What Is Ben Affleck’s Best Role?

There is a Ben for all people, and ahead of ‘The Way Back,’ Ringer staffers select their favorites

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Over the course of his career, Ben Affleck has been a lot of different people. He’s been a dangerous man, a loyal man, a Batman. He’s coasted through movies on the power of his own screen presence, elevated others in unexpected ways, and perhaps more than any other actor in Hollywood, he’s often used his characters to work through his own personal life—as he’s doing in The Way Back, Gavin O’Connor’s soon-to-be-released film about a down-and-out high school basketball coach. There is a Ben Affleck for all seasons, for all people. Below, Ringer staffers select their favorites.

Chuckie, Good Will Hunting

Playing the tracksuited, square-shouldered Southie heavy-with-a-heart-of-gold Chuckie in 1997’s Good Will Hunting, Ben Affleck is at the center of both the movie’s funniest scene and its most emotional one. In the former, his suit is too small and his hair is real slicked and he’s wearing gym socks and boat shoes as he leans back all cocky-like in his chair, play-acting as his genius friend Will and shouting “RETAAAAINER!” at bewildered hotshot think tank recruiters. This was a version of Affleck that, at the time, I was familiar with; his performance felt related to his previous dickish, caddish turns as a paddle-wielding senior in Dazed and Confused and a skeezy VW Bug–haunting “Fashionable Male” in Mallrats.

But then there was the other side of Chuckie: the townie who will break your heart with his soul, the guy who can squint into the sun as he tells his brilliant best friend that he hopes to never see him again. “You don’t owe it to yourself,” Chuckie tells Will, imploring him to transcend the place where he’s from. “You owe it to me.” Affleck and Damon were in their early 20s when they wrote the Oscar-winning screenplay for Good Will Hunting, and were inspired to write this scene by having worked construction for a few summers. (Luckily, director Gus Van Sant’s idea to “crush Chuckie like a bug” in a construction accident did not gain traction.) Affleck had agonized over the “best part of my day” exchange for so long that he was shocked when he nailed the take right away.

“It was just kinda like, ‘Is it over?’” he told Boston Magazine. “It’s just hard to almost internalize the fact that, OK, we’re going to wait four years, and it’s gonna be over in five seconds. Kind of like losing my virginity.” Now that’s the Chuckie, and the Ben, that we know and love. —Katie Baker

O’Bannion, Dazed and Confused

To be clear: Ben Affleck was not cast as the biggest, dumbest asshole who you went to high school with because he was a real-life prick. He just happened to be someone who could play that guy really well. “Ben was smart and full of life,” director Richard Linklater once said. “You don’t cast the unappealing person; you cast the appealing person.”

In limited screen time, the angry goon Fred O’Bannion—he failed to graduate and has to repeat his senior year; of course he’s a jerk—terrorizes incoming freshmen by beating them with a wooden paddle that says FAH Q in big letters. He is an aggressively unfunny person, but to the audience, he’s hilarious—a credit to Affleck. Naturally, O’Bannion gets his comeuppance when the teens he’s violently hazed douse him with a bucket of paint as Black Oak Arkansas’s “Lord Have Mercy on My Soul” plays in the background. Before we see a whitewashed O’Bannion get into his Plymouth Duster for the final time, Affleck puts a perfectly petulant flourish on his performance. “Fuck all of you!” he yells, before jumping up and screaming, “Fuck you!” once more. Then he smashes his precious paddle to pieces. —Alan Siegel

Doug MacRay, The Town

This movie is basically a bizzaro Good Will Hunting, and Affleck’s Doug MacCray is the gifted one. Except instead of math or apples or whatever Will was great at, Doug’s skill is masterminding heists. He and his Charlestown crew—made up of Boston rapper Slaine, Owen Burke, and Jeremy Renner, who redefined what a Masshole could be—have knocked over two banks and six armored trucks using semi-automatic assault rifles and Skeletor and nun masks. Along the way, Doug falls in love with a witness (Rebecca Hall), with whom he hopes to run away to Florida. But first, Dougie and the boys have to pull off one more heist—of Fenway fucking Park.

There was a time in the 2000s when the Greater Boston area seemed to be at the center of the cinematic universe: Mystic River, The Departed, The Fighter, Fever Pitch, Gone Baby Gone—hell, even Ted—brought the region’s provincialism and dropped R’s to the big screen during that strange decade. But none nailed the Bostonness of it all quite like 2010’s The Town, which is partially a love letter to the city. That’s a testament to Affleck’s directing and acting. In the wrong hands, Doug MacCray would’ve felt like a caricature: a macho, washed-up hockey player turned small-time crook with repressed trauma hanging out in bars named Sully’s. Affleck, who grew up in Cambridge, embraces clichés while still playing the character with pathos, and it manages to make Doug’s experience nearly universal. So when he barks, “I’m putting this whole town in my rearview mirror” to Renner’s Jem, you understand that, whether you’ve been over the bridge or not. —Justin Sayles

Baseball Fan at Fenway Park, Field of Dreams

They say the best actors disappear into their roles, and Affleck has never disappeared more skillfully than he did during Field of Dreams, the 1989 prequel to The Town in which he plays a 16-year-old Douglas “Doug” MacRay casing the joint he would one day rob (in my headcanon, anyway). Affleck and Matt Damon served as extras in the film’s Fenway Park crowd scene in the summer of ’88, and when Affleck later teamed up with Field of Dreams director Phil Alden Robinson on The Sum of All Fears, he supposedly said, “Nice working with you again.”

We’ll have to take Affleck’s word for his Field of Dreams appearance; the background is too blurry to make him out, though that hasn’t stopped some YouTube commenters from speculating that the blue-shirt-wearing figure behind James Earl Jones is the 16-year-old Affleck.

This is what the young Affleck actually looked like:

So no, I don’t think it’s possible to pick him out of the crowd. But the fact that we can’t see him only makes his performance more powerful: In contrast to his scenery-chewing uncredited cameos as “Man at Store” in Curb Your Enthusiasm or “Basketball Player #10” in Buffy the Vampire Slayer, Affleck’s low-profile appearance as a guy at a game proves he can convincingly blend into a faceless ensemble. The diehard Red Sox supporter—who later refused to wear a Yankees cap in Gone Girl, advised New York fans to “pound salt up their ass,” and narrated a DVD called Red Sox Baby that was designed to indoctrinate toddlers into rooting for the Red Sox—has never been more believable than he was in this early, true-to-life role. “Baseball Fan at Fenway Park” is the part he was born to play. —Ben Lindbergh

Jack Ryan, The Sum of All Fears

Most film or TV incarnations of Jack Ryan work under the assumption that because he’s the most famous fictional employee of the CIA, he’s the American version of James Bond. This could not be further from the truth. He’s a finance bro, an academic, even a diplomat and politician, but he’s most decidedly not an action hero. Occasionally he’s called on to kick some ass, but the drama of such plot turns comes from the knowledge that deep down, Ryan is just some dork who’s not comfortable with a gun in his hands.

Two Jack Ryan actors have understood this: Alec Baldwin in The Hunt for Red October (the greatest American film of the past 40 years) and Ben Affleck in The Sum of All Fears. Affleck, a gigantic man who exudes jock energy, has played asskickers, but his Jack Ryan is the perfect mix of impetuousness, earnestness, and fish-out-of-water discomfort. In Affleck’s hands, Ryan rises to the moment not out of ambition or arrogance, but because if he doesn’t, no one else will. —Michael Baumann

Tom “Redfly” Davis, Triple Frontier

Triple Frontier is not Ben Affleck’s best movie. It is, however, his most Ben Affleck movie. Think about it. Five bros, the Colombian woodlands, high action, an inexplicable plotline, and a metric ton of cash, earned by physically tearing down a drug lord’s compound. “The house is the safe,” Affleck says in the same inflection as Batman, only months removed from his tenure as the superhero. Then he and his boys pull $250 million out of the walls. This happens in the first half of the film. Things only escalate from there.

In a cast that includes heartthrobs like Oscar Isaac, Charlie Hunnam, Garrett Hedlund, and Pedro Pascal, it’s Affleck, playing the Honorary Roger Murtaugh Character, who fills the movie’s emotional center. He’s too old for this shit, he tells his former crewmates. Alas, it’s an action movie, and the geezer comes back for one last score. Redfly works by a set of rigid guidelines, but as he sees the money pile up, he breaks them, leaving himself and his team in danger. Of all the characters Affleck has played in the second half of his career, none seem more likely to have secretly gotten an enormous, gaudy back tattoo, and for that, I could not possibly love him more. Long live Redfly, Ben Affleck’s most Ben Affleck-y role. —Shaker Samman

Nick Dunne, Gone Girl

“This is something that Ben is extraordinarily good at, when he has to cook up a phone conversation, when he has to hear somebody on the other end of the phone,” David Fincher says in Gone Girl’s DVD commentary. “If I was his wife, I think I would be very suspicious, always, of whoever just called.” While the director wasn’t intentionally taking shots at Affleck’s soon-crumbling personal life, the way Fincher discusses his performance in the film straddles the line between complimenting his star and owning him for seeming so suspicious all the time. But it’s that quality that makes Affleck a perfect casting for Nick Dunne, and why it’s so hard to get a read on the character’s behavior.

If you went into Gone Girl not knowing the big twist—as I did—Affleck does an incredible job of making Nick an enigmatic figure. You’re unsure whether the dude whose wife mysteriously disappeared is weirdly indifferent, having a hard time expressing his emotions, or is just a straight-up killer. (What’s up with this smile?!) In turn, it’s hard to know whether Nick deserves our loathing or sympathy. The brilliance of Affleck’s performance in Gone Girl is that he credibly makes you feel a bit of both: the middle-aged equivalent of a fuccboi trapped with a punishment that doesn’t fit the crime. I’m not sure what it says about Affleck that it seems like the most authentic role of his career. —Miles Surrey

A.J. Frost, Armageddon

It’s hard to explain what charisma is, but when I’m forced to try, I usually just say “Ben Affleck in Armageddon.” With that fresh face of his and those super white, adult teeth that Michael Bay made him get, he’s unbelievably watchable as A.J., the driller-turned-astronaut who is also having sex with his boss’s daughter. He’s a pain in the ass, he’s endlessly charming, he tucks animal crackers into Liv Tyler’s underwear—he’s everything that made Affleck a megastar in the late ’90s.

But truly, Affleck’s best performance is not in Armageddon, but as a commentator of Armageddon. His DVD commentary of the movie is the stuff of legend. “You ever notice how everyone in these movies, they always have to be the best?” Affleck asks no one in particular, on his way to savaging a movie that he is one of the stars of. “Bruce Willis is the best deep-core driller? I didn’t know they rated deep-core drillers. You know what I mean? Like, if you went around and asked somebody, ‘Who’s the best deep-core driller?’ How do you know? Who keeps track of these things?” Moments later, he says, “I asked Michael why it was easier to train oil drillers to become astronauts than it was to train astronauts to become oil drillers and he told me to shut the fuck up.”

It’s a stunning, hilarious, honest performance. It is the past, present, and future of Ben Affleck. —Andrew Gruttadaro