Consider Ben Affleck: the cerebral lug, the regally square-jawed scoundrel, the thinking man’s matinee idol, the matinee idol’s thinking man. He has a quarter century’s worth of experience in the Hollywood muck now, a career rife with both Oscar glory and ignominious bombs, glossy triumph and tabloid disgrace. It’s as convoluted and fascinating a collection of arcs as you could ask for in an A-lister. His 2016 campaign alone stretches from the blockbuster debacles Batman v Superman: Dawn of Justice and Suicide Squad to the shrewdly perplexing B-movie thriller The Accountant to the imminent prestige-play gangster epic Live by Night, which he also directed.
Few careers are as unpredictable and nonetheless durable, as rife with distinct phases and moods and backlashes to backlashes. As Live by Night plants flags in a few theaters now and prepares to invade the rest of the country in January, let’s try to make sense of where we’ve been, and where we’re going, and why we’ve been willing to follow him anywhere. The ride hasn’t always been fun, but it has never for one second been boring. Nor has it ever stopped. Here, now, is a somewhat thorough (and usually gentle) phase-by-phase breakdown.
The Superstar Rookie (1992-1997)
The moment you picture young Ben Affleck, pure and dapper and fresh-faced and ascendant, the line pops into your head as though it’s a memory from your own life, as though he’d asked you directly, in person. “You know what the best paht of my day is?” It might end up being the best paht of yours, today.
There he is. A movie star. Obviously. The lower half of his face very, very lightly smudged to indicate he’s a humble construction worker who’ll never make it out of Boston. Right. Unbelievable. It doesn’t matter. It’s perfectly ludicrous, and perfect. Good Will Hunting minted Affleck and Matt Damon as double threats: In the absence of a screenplay worthy of their blinding star wattage, they wrote one themselves. You likely still tear up whenever you stumble across it, or hear an Elliott Smith song, or encounter the expression “How d’ya like them apples?” It’s fine. It’s great. It’s not your fault.
Affleck’s grown-up debut came in 1992 with School Ties, playing an anti-Semitic and occasionally shirtless bully named Chesty Smith. (Damon had a bigger role.) A natural villain, brutally handsome and casually cruel. The following year he stalked through Richard Linklater’s Dazed and Confused, wielding a frat paddle with “FAH Q” scrawled on it, bringing just a tiny bit of Boston to Texas. Eventually he catches a bucketful of white paint—a rousing comeuppance, and the first hint that we might like Affleck best when he’s humiliated. Same deal with 1995’s Mallrats, his first Kevin Smith joint, playing an oily statutory rapist who works for a clothing store called Fashionable Male. His sex-tape scene (“Who’s your favorite New Kid? Call me Joey … Call me Donnie”) isn’t on YouTube, which is one of the internet’s few remaining small kindnesses.
Good Will Hunting came along in 1997 and made him, inarguably, and he makes the best of his limited screen time (nice socks). Arguably, it’s his best movie, even now. But it’s not his. The first film that Affleck truly commands is Smith’s caustic romantic comedy Chasing Amy that same year, and he owns both its pulverizing ugliness and fleeting hints of transcendence, with his white T and ratty cardigan and pornographic goatee. Joey Lauren Adams explains lesbian sex to him; he explains skee-ball to her. He’s the scruffy-yet-adorable hero, but also, unambiguously, the villain, arrogant and clueless and cruel as ever. He finds love and blows it catastrophically, and the ugliness overall is really something: It’s best for your psyche if you turn this movie off the second you hear the words “finger cuffs.” But before all that happens, this does:
Chasing Amy is a movie of long, wordy speeches that not everyone can handle. (Smith himself sure can’t.) But Affleck sells the drama no matter how overwrought it gets, imbuing a clunker like “I can’t talk to you without wanting to express my love for everything you are” with all the grace he can muster. It’s convincing. We’re convinced. He’s a movie star. Obviously. Stick around for the second half of that scene if you want—the rain machine, the impassioned screaming, the dramatic run-in kiss, the accidental glimpse of the cameraman’s reflection in the window. It’s a clunky, prickly movie, far meaner than it is sweet, far more repellent than it is charming. But it’s the earliest, and maybe still the best, indication of what Affleck could make sing.
The Conflicted Megastar (1998-2002)
“Pay attention,” he crows in 1998’s Shakespeare in Love, starring Gwyneth Paltrow, the first of his infamous triumvirate of celebrity paramours. “You will see how genius creates a legend.” He’s playing a pompous actor. You’re convinced.
He got to do some blockbusters; he made them better, or at least a little more bearable. Michael Bay’s Armageddon, also from ’98, burns through Chasing Amy’s total budget in 10 minutes or less (the prologue takes place 65 million years ago), and after you’ve guzzled six or more Bud Lights, you will convince yourself (and endeavor to convince others) that no, this is Ben Affleck’s best movie. There are, to his credit, many worthy candidates. But only one winner.
This isn’t it, but Armageddon holds up, dude. It’s absurd. It’s great. Your boy has very little to do in it, the ensemble sturdy and the disaster-flick machinations loud and relentless and blissfully distracting. He gets to sarcastically call Bruce Willis “Mr. All-Go-No-Quit-Big-Nuts” and canoodle with Liv Tyler, and that’s plenty. He also freaks out on the Russian cosmonaut while driving the badass moon tank, and it’s the most believable anyone in the movie sounds saying anything: “NO. NO. YOU KNOW WHAT? I HAVE NO IDEA WHAT I’M DOING. I HAVE NO IDEA. THIS BUTTON? I DON’T KNOW WHAT THAT DOES. OK?”
One byproduct of winning the Oscar for Best Original Screenplay before the superstar part of your acting career even begins—this speech is still pretty great—is you start carrying yourself like you’re smarter than other people’s material, or everyone just assumes that you must be even if you’re not. For Ben Affleck that’s always amounted to the same thing. A certain intellectual remove is his trademark, as an actor and a public human: a tweed professorial jacket’s arm’s length. Which may explain why he delivers the best performance in this movie, and his best performance of this era, in the running Armageddon DVD commentary, jovially inveighing on the ridiculousness of its training-drillers-to-be-astronauts plot.
Amazing. That’s delightful. You’d love to drink six more Bud Lights with that guy. This natural charm came in handy for Round 2 with Michael Bay, 2001’s Pearl Harbor, which stunk up the joint. The god Roger Ebert: “Pearl Harbor is a two-hour movie squeezed into three hours, about how on Dec. 7, 1941, the Japanese staged a surprise attack on an American love triangle.” Josh Hartnett is another point on that triangle. Don’t get involved.
Affleck, playing a Tennessee farm boy turned hotshot pilot named Rafe McCawley, has a far meatier part than last time; unfortunately, his accent is plainly ridiculous, the melodramatic strain palpable. At high-stress moments we get a glimpse of the guy’s darkest possible timeline: Nic Cage territory. “But I just wanna know whhhhyyy.” You wanna watch Ben Affleck cry, here you go. If you do end up drinking with him, don’t mention this movie.
He hooked up with Damon again for Kevin Smith’s super-talky 1999 Catholicism satire Dogma, which is mostly unavailable streaming-wise, which is frankly a relief, because Dogma is unwatchable. (Still, “Alanis Morissette screams until Ben Affleck’s head blows off” is a decent one-line summary of the 1990s.) He did two romantic comedies with, respectively, Sandra Bullock (1999’s Forces of Nature) and yes, Paltrow herself (2000’s Bounce). Changing Lanes, a 2002 brawl with Samuel L. Jackson, was a quick, modest, callous B-movie, a safe space for them both; Affleck back in his element as a harried, entitled jerk.
But his peak performance in that vein came in 2000’s financial-scam drama Boiler Room, a film so explicit in its aims that there’s a scene where the characters sit around quoting Wall Street from memory. (Affleck is wearing a Trojan shirt and a Hustler ball cap.) His big boardroom speech is a hoot. A fucking hoot. “I’m a millionaire,” he announces, amazing even himself. “It’s a weird thing to hear, right? I’ll tell ya: It’s a weird thing to say. I am a fucking millionaire.” It goes on. “They say money can’t buy happiness? Look at the fucking smile on my face. Ear to ear, baby. You want details? Fine.” He provides details. You don’t need them. You believe him. This dude is bulletproof. He’ll outlive us all. Not even God himself could sink this ship.
The Punching Bag (2003-2006)
But Jennifer Lopez might. A little light viewing for you:
Ben Affleck’s 2003 was basically America’s 2016. That’s an hour-long special on Bennifer. “Will this be America’s Big Fat Sneak Wedding?” Holy crapola. His dark years began in earnest the year before, with J.Lo’s “Jenny From the Block” video, a strained and goofy attempt at satirizing their opulent, yacht-groping lifestyle and quelling as fearsome a backlash as any celebrity couple could hope to inspire. Don’t hate them because they’re beautiful. It didn’t work.
He will forever insist, to this day, that Gigli was a victim, a martyr, an innocent bystander. The wayward but harmless romantic comedy as collateral damage. A plain old bad movie elevated to an all-universe catastrophe and schadenfreude bacchanal simply because it starred the hottest couple in Hollywood. He’s not wrong. But yeah: Gigli is awful. And for you J.Lo unenthusiasts, any attempt to pin it on her alone is undercut by the inconvenient truth that Out of Sight is better than any movie on Affleck’s résumé.
Do not watch Gigli, even as a joke. To linger on it is unkind to him and us both. Nothing makes sense or feels good. “I am the fuckin’ sultan of slick, Sadie,” his hapless, toothless gangster boasts, absurdly. “I am the rule of fuckin’ cool.” He and Lopez discuss the relative virtues of the penis and the vagina whilst she does yoga. He cuts the thumb off a cadaver with a plastic knife as an ambiguously mentally handicapped gentleman sings “Baby Got Back.” Also: “It’s turkey time,” she purrs, kicking off the big love scene, “Gobble gobble.” Christopher Walken and Al Pacino fare no better in their cameos, and their presence is another darkest-timeline glimpse: the perils of a total lack of quality control. Not even as a joke. Don’t let me catch you watching this movie.
Same deal for that year’s Daredevil, which he’s far less apt to defend, also to this day: “I hate Daredevil so much,” he allowed, just this month. He traces his decision to take on Batman all the way back here, in fact: “I wanted to do one of those movies and sort of get it right.”
What you get here instead is a hokey quasi-Matrix playground fight-cute with one Jennifer Garner, near-future mother of his children and eventual-future taker of umbrage. It’s uncomfortable. Affleck spends the movie with painful-looking blinded-by-nuclear-waste contact lenses and a lousy haircut. The best part is the montage set to Evanescence’s “Bring Me to Life”; the least-best part is not the montage set to Hoobastank, which is a terrible sign. It’s stuck exactly halfway between the Hokey Comic Book Movie Era and the Gritty Comic Book Movie Era; Affleck does a lot of stilted narration, and you know he knows he’s smarter than this, and he’s right. (“Can one man make a difference? There are days when I believe. And others when I have lost all faith.”)
Evanescence aside, the only other cool thing that happens is when Michael Clarke Duncan’s Kingpin is introduced to the delightful strains of N*E*R*D’s “Lapdance.”
Forget it. The only consolation your boy can take is by this point, he knows how to avoid being the worst part of a bad movie. Whereas Colin Farrell, as Bullseye, manifestly does not.
The third and last film Ben Affleck made in 2003 was literally called Paycheck.
A couple rough years follow that galactically horrible year. Bombs beget bombs. In 2004, the romantic comedy Surviving Christmas (which no one did) plus the Kevin Smith reunion Jersey Girl, in which J.Lo dies at the beginning and Affleck ends up with Liv Tyler instead, as if trying to shift his career from neutral into reverse. In 2006, when he wasn’t shooting pool through the quasi-Tarantino ensemble mess Smokin’ Aces, he played tragic Adventures of Superman star George Reeves in Hollywoodland, brooding up a storm while dressed as the biggest, sunniest superhero of all time. The fuckin’ sultan of slick laid low, wearing that cape and hating every minute of it. Look what you made him do.
Mr. Prestige (2007-2014)
His rehabilitation began, crucially, not on-camera but behind it. Affleck’s directorial debut, 2007’s Gone Baby Gone, starred his brother Casey instead, and stuck close to the grim, uncompromising, tough-guy Dennis Lehane novel, impressive in its utter refusal to soothe or please. It surprised and unsettled and intrigued people. The ground beneath Clint Eastwood’s mansion shuddered, just a bit; he had competition in the Sophisticated American Badass sweepstakes, a worthy adversary who’d finally found a lane worth sticking to.
It’s not that he immediately stopped pandering—2009 brought, among other frivolities, a starring role in He’s Just Not That Into You, which at least made money. But the following year he directed and starred in bank-robbing opus The Town, deepening and lightening the tough-guy palette just slightly; and brace yourself for some Truth, because The Town is Ben Affleck’s best movie as an actor or director, full stop.
For one thing he’s profoundly in his element. The Extreme Bahstoness, refining and transcending all those the-city-is-a-character clichés, is so pervasive and so perfect you can’t mock it this time even if you’re dying to. Affleck wears both Red Sox and Bruins gear within 15 minutes, among various stylish tracksuits and hoodies. He likewise wears his charisma lightly, the accent growing on you. He’s monotone and a little dead-eyed, trying harder to not look like he’s trying so hard. He limits himself to one killer monologue (“The sound woke me up”). He looks like a fucking millionaire, especially when there’s no smile on his face at all.
He lets Jeremy Renner flex instead, spectacularly; Jon Hamm, as the handsome and pissy detective, flexes slightly less spectacularly, just starting to figure out the less-is-more Zen technique Affleck’s got down cold by now. Blake Lively is a weird and discomfiting outlier, sure, but it’s hard to argue with the Fenway Park robbery/shootout finale, as tense and rousing and assured an action sequence as you’d seen your boy in since, hell, probably Armageddon. Rad movie. That’s the moment you knew Affleck would be OK.
No particular argument if you’d rather ride for 2012’s Iran-exfiltration saga Argo, which was Affleck’s biggest swing yet, the real-life-history angle (mostly) perfect, his direction at his slickest, his performance unflashy, the tension organic and exquisite, his Best Picture Oscar speech rambly and maritally unwise and close to perfect. Shazam. He wins. Rehabilitation complete.
That’s the apex of his career, topping off the latest of his many winning streaks, but what makes those winning streaks so fascinating is his next choice. Gone Girl, David Fincher's gonzo 2014 psychosexual thriller, is way more fun to talk about, even if it's way, way, way less pleasant to actually experience, because it comes immediately after his Oscar. After rehabilitation, apparently, comes total deconstruction. It’s the moment you knew “OK” wasn’t what he wanted to be anymore.
“It’s hard to believe you. I think it’s your chin. It’s quite villainous.”
“You seem pretty laid-back. Type B.”
“When you’re upset, you can seem angry. Or else you swing into your mama’s-boy charm offensive, and that can feel glib.”
“You looked like hammered shit.”
Gone Girl is two and a half hours of Ben Affleck being owned by everything and everyone, a masochism bacchanal. Your boy is reduced to a wan shrug, a slight paunch, a hangdog expression he can’t shake even in those few feeble moments where he tries to fight back. (“Everybody's examining me, projecting their shit on me.”) By the time the paparazzi’s hounding him everywhere and every move he makes backfires, you’re convinced no other human alive could’ve played this role, or would even want to. You’re likewise convinced that this is a pretty great movie you don’t ever want to see or even think about ever again. Sorry about that.
Anyway, this era is a shocking, smashing, unqualified success. Game over, right?
Ooh Look, I’m Batman (2016-???)
Sort of? Why plunge yourself into the wayward-ass D.C. Comics cinematic universe the second you’re clean? If “he earnestly wants to make amends for Daredevil” is a little too pat an explanation as to why Affleck would lash himself to the decks of Zack Snyder’s Batman v. Superman: Dawn of Justice and David Ayer’s Suicide Squad, try something even more self-serving: He thinks he’s the comic-book-flick Theo Epstein. Once his beloved Red Sox won a World Series, he sought out an even bigger challenge. These clowns are the Cubs. If he can make them bearable, he really can do anything.
“I had a lot of offers,” is the way he explained it to Bill Simmons this summer on Any Given Wednesday. “Forks in the road that are legitimate different paths. Where you think, ‘Well, boy, my life’s gonna be really different if I go down this way, or if I do Batman, or if I do this other iconic thing. Or I could just have movies where kids fart on me.’”
That would very possibly be preferable to Dawn of Justice, where the best you can say is that Batman is the least of its many, many problems. He’s fine. He’s a relief, even, neither overdoing it nor underdoing it, scrunching up his eyebrows and looking thoughtful and content to be the only adult in the room. No super-corny Batman Voice, at least. He’s not in Suicide Squad long enough for it taint him or for him to redeem it. Fine.
His best movie most fans will see this year is The Accountant, an odd and morose and pretty entertaining crime thriller in which he plays an autistic math supergenius who can also kick rich amounts of ass at a moment’s notice. His monotone and overall vibe even flatter, his charm whittled down to a few weird sparks with Anna Kendrick. It’s a confusing but not unfun movie, though when Affleck downplays his charisma too much—his jaw set too tight, his slight smile just a little too smug—he’s basically indistinguishable from John Corbett.
(Sorry about that, John Corbett.)
Next up is Live by Night, another Lehane adaptation, macho and morose. Affleck directs, produces, and stars; early word is not terribly promising, but not terrible, either. The late-December limited-release date suggests award-season aspirations; it’s possible the infinite Batman stuff is a “one for them, one for me” sop, and he’ll be looking to replicate Argo’s triumph every three to five years from here on out. Not a bad strategy, but alternately swinging from the critical to commercial extremes doesn’t yield Peak Affleck. He’s better off in the murky, disorienting grey area in between; his motives unclear, his success unassured. That’s where he truly surprises you, for good or ill.
Next year also brings Justice League and beyond that, what for now is tentatively called The Batman, coming soon if you’re lucky and even sooner if you’re unlucky. Apparently there are only 30 problems with it, see, which is fewer than last time, frankly. He might actually pull this off. No one knows better than Ben Affleck how long and arduous and bizarre a process redemption can be.