The Upper Hand is where Grantland staffers pit unsuspecting entertainers against one another to determine which one currently has a greater grip on the hearts and minds of America. It’s a long way of saying X > Y. It may seem reductive, or even unnecessarily competitive, to put our gentle creators into a squared circle, but it’s a useful exercise in seeing who is doing things right, who is doing things wrong, who is doing things differently, and, of course, who is winning. At the end, a guest judge will hand down a verdict. Today’s debaters are Chris Ryan, on the side of Ben Affleck, and Mark Lisanti, arguing the case for Matt Damon. Bill Simmons is our guest judge.

The Contestants: Matt Damon vs. Ben Affleck

Domestic Box Office
Damon: $2,722,705,329
Affleck: $1,851,165,334

Biggest Hits
Damon: Saving Private Ryan, The Bourne Ultimatum, Ocean’s Eleven
Affleck: Armageddon, Pearl Harbor, Good Will Hunting

Most Critically Acclaimed Role
Damon: The Talented Mr. Ripley
Affleck: Reindeer Games

Chris Ryan: Let’s get one thing straight off the bat, Mark. The name of this series is The Upper Hand, not Who Is More Likely to Be Playing No-Limit Hold ’Em at Morongo, at 3:30 a.m., on a Wednesday, Wearing a Thousand-Yard Stare and a Distressed Boston PD Baseball Hat. This is not a debate about who has a more annoying public persona, or who has had more spectacular professional failures. This is about who has the Upper Hand. Right now. And if you can wipe away that image of him as a goateed douche-lord, and look deep into the calming truth waters of IMDb, you will see that, especially over the last few years, Ben Affleck has the upper hand over Matt Damon.

These two have always had a very public professional schism, despite their very public personal relationship. From Oscar speeches to Project Greenlight to Brosgiving, they have been largely inseparable over the last 20-some years. But in terms of movies, they have chosen different paths.

I can’t help but think that the “Best Part of My Day” scene from Good Will Hunting is somehow the defining moment for these two.

Sure, it’s a fake moment in a fictionalized movie. But they wrote it (they really did!), so it’s natural to think that Chuckie and Will are something of an extension of their own relationship. And there’s Affleck, telling his little genius buddy to go follow Minnie Driver and get the hell out of this town, telling him that he’s better than him.

For almost 20 years, this has been the narrative on these two. On one hand, there’s Damon, marrying a bartender, working with Soderbergh, making “smart” action movies, appearing to be nothing but humble and charming in his public appearances, and having great taste in his professional relationships.

Then there’s Big Ben. Tumbling from one star-crossed, possibly fabricated relationship to another, making bomb after colossal bomb, and getting by on his good looks and unchallenging persona.

But over the last decade, the script got flipped. Damon has become Chuckie, and Affleck has become Will. He’s been the one trying things — directing his own films, starring in new franchises, taking chances in big roles — while Damon has played it safe. Damon’s not quite a movie star and not quite a character actor. He’s like a professional cameo maker, with a side business making ponderous award-bait (stop working with Eastwood, bro) and bad blockbusters (Elysium!). Ben Affleck has the upper hand now.

Make your case, Lisanti. You owe it to me.

Mark Lisanti: I’m not sure if I’m supposed to come out swinging here, ready to take one on the jaw — the Affleck move, because when you’ve got a chin like that, you lead with it — or retreat a little bit, survey the lay of the land, and formulate a more cerebral plan of attack, like Damon would. But then you say deliberately incorrect and inflammatory stuff like “not quite a movie star” and “professional cameo maker” and you make it feel like it’s time to tear off the Harvard sweater, muss up the side-part, and start flipping tables in the eating club. (Does Harvard have eating clubs? One of those Ivy places has eating clubs. Damon could tell us. Affleck would just be like, “Pff, you’re in a club to eat food now, what are you, the fancy little prince of Cambridge? That’s wicked dumb. Hold on, the nutritionist’s here with my 10 daily bags of sous vide chicken. Gotta get Bat-swole on clean protein or the Internet’s gonna be mean to me again.”)

At the same time, I want to pause and tip my hat to how you open with the move where you remind me how The Upper Hand is about where we are now, not the past — and it is, thank you for the helpful clarification; this is still a new series and the rules can get foggy — so as to strike Gigli, Daredevil, Paycheck, Jersey Girl, and Surviving Christmas from the conversation, as well as the entirety of Affleck’s acting work from the years 2003 to 2010. So I’m not going to bring any of that up. They’re as irrelevant to the matter at hand as a hundred-foot-tall collage of People and Us Weekly Bennifer covers that might serve as the backdrop of this fight if we were digging into ancient history, which we’re not. We’ve moved on, the world has moved on, and, most importantly, Ben Affleck has moved on.¹

Which brings us to the more recent section of Affleck’s IMDb page, and it would be disingenuous, no matter how heated the battle gets, to not nod respectfully in its direction. The Town was a big hit, even if it suffered from the slight misguided vanity of a director who cashed in his first fistful of post-movie-jail currency to cast himself in the lead role against a scene-stealing killer like Jeremy Renner. Argo won Best Picture (though not Best Director, because Ang Lee made a movie about a tiger on a boat), even if it suffered from the not-so-slight misguided vanity of a director cashing in his next fistful of Hollywood currency to miscast himself in the lead role of a 1970s period drama, and then write in a gratuitous scene in which he takes off his shirt, because everyone knows that Tony Mendez’s abs smuggled those hostages out of Iran. Then we’re at Gone Girl, which has the best performance Affleck’s ever given, by a mile, because David Fincher realized how to harness that vanity properly. Eventually we will get to Batman v Superman, the logical move for a guy who came thisclose to getting a Best Director Oscar and just did the best acting of his life in a big, smart hit, because when that particular superhero carrot is dangled, Affleck is going to knock the stick out of your hand and grab it, because he’ll never have to hear the word “Daredevil” again. I mean, I’m impressed. I should probably pack it in and go home, and I haven’t even really talked about Matt Damon yet.

I realize I threw around the word “vanity” a lot there, because I’m a board-licensed armchair psychologist, and it’s something completely absent from Damon’s choices. While Chuckie’s kicking up his feet on the desk of his career and rambling on about retainers (is there a bigger retainer than being Batman?), Will’s quietly back at the blackboard, figuring things out. You say Damon’s playing it safe, and maybe he is, if your definition of “safe” includes always seeking out the best and most interesting directors. He’s worked with Spielberg, Anthony Minghella, the Coen brothers, Soderbergh, Scorsese, Eastwood, Cameron Crowe, Kenneth Lonergan — shout-out to Margaret, all 15 glorious hours of it! — Terry Gilliam, George Clooney, Christopher Nolan, and Neill Blomkamp.

Ryan: Yes! Hail Monuments Men!

Lisanti: Maybe he didn’t pick the right projects with all of them, but he took the chances — Elysium didn’t come together, but were you going to bet against the guy who did District 9 bolting an exoskeleton to Jason Bourne and seeing what happened? We all invested in that one on the Fandango futures market, even if we took a bath.

But this is why Damon’s one of our best movie stars — he tries things. He looks for challenges. He’ll fatten himself up and flop-sweat through an Informant!, then he’ll drop back into the Green Zone with buddy Paul Greengrass, then he’ll make a (really underrated!) movie about magical hats, then he’ll glue on a nose and play Liberace’s lover. The superhero carrot’s been there for him, and he didn’t grab it — he slapped it aside and redefined what a superhero is with the Bourne franchise, returning to a multiplex near you in 2016, right after he wraps up The Martian with Ridley Scott. He makes bank (check out the numbers at the top of this story) and he takes risks. He is America’s Aspirational Best Friend.

And he will never be your Chuckie.

https://www.youtube.com/watch?v=2xcY0-dscn0

Chris Ryan: Oh well, god forbid a movie star has vanity. We wouldn’t want that! I feel like we’re having a conversation about alternative music in the 1990s. Does Damon boycott Ticketmaster too?

I think people — you, me (yes, me!) — like Damon because he gives off the slight air that all of show business is basically bullshit, which is something we all think. The way he’s gone about his career is admirable and dignified. If you asked most people what kind of life they would want, if they were to be a movie star, they would probably pick Matt Damon. You never hear anything bad about him. I wish he would join my nonexistent softball team, and I’m sure if there was a self-deprecating viral video to be made out of it, he would.

You say Damon tries things, and you’re right. He does. But he doesn’t take risks. Doing low-octane Soderbergh movies — fake belly or face aside — is not exactly exploring the rings of Saturn, acting wise. Damon was at the height of his powers when he was gambling with his likability (The Talented Mr. Ripley, The Departed), or leveraging that likability in blockbuster fare (Bourne movies). In the last few years, he’s pretty much tapped out of being important. We can mock Affleck, the movie star, for getting too many close-ups in movies by Affleck, the director. But at least Affleck has the balls to direct movies in the first place! Damon didn’t even direct the movie he was supposed to helm. Then again, after watching Promised Land, I don’t blame him.

This is why I give Affleck the upper hand. Damon may have better taste, and better survival instincts, but Affleck takes more chances, and is willing to fail more spectacularly to make something more spectacular. Like, maybe Damon never would have starred in something as ridiculous as Armageddon. But has Damon ever made anything as ridiculously entertaining as Armageddon, either?

Mark Lisanti: I guess one man’s “ridiculously entertaining” is another man’s “second-best Yo, That Massive Asteroid Is About to Wipe Out All Life on Earth movie of 1998,” but we can agree to disagree about whether we’d want to spent our final minutes as a species listening to President Morgan Freeman calmly explain how it’s all going to go down or Michael Bay shouting, “Eat those goddamn animal crackers out of Liv’s belly button like you’re a starving bear, Ben, a giant rock’s about to fall on your head!” through a megaphone. But I digress. If we’re talking about the pure entertainment value of Damon vehicles, I could clear this room by throwing any of the Bournes out there, or The Departed, or the Ocean’s movies. And I’d probably take Damon’s “secret” 10 minutes in that space flick we all just saw over the entirety of Argo, but again, that’s just me. You’re trying to make it sound like Affleck’s out there tapping Hollywood’s kegs while Damon’s grinding out fracking docudramas. Matt Damon knows how to have fun! There’s a whole song about how fun it is to fuck him! (Affleck did a sequel, but no one cares to remember that.)

I’ll tell you what’s not so fun, though: being Zack Snyder’s Batman. Did you see what that guy did to Superman? He turned a happy-go-lucky dude in red and blue pajamas into a bummed-out, murderous lumberjack Messiah. Where’s Snyder going to go with the “dark” superhero? Is his Batman going to eat Superman’s dog while the Man of Steel is restrained by Kryptonite nipple clamps? Affleck signed up for like 10 of these, and it’s his deal with the comic-book devil. It might turn him into the biggest movie star in the world if it all breaks right, a giant bat-finger raised to the people who doubted him before he directed himself back to relevance in The Town. (You know what’s better than The Town? Gone Baby Gone.) He’s going to be too busy to do much else for the next five or six years — maybe he’ll sneak in a Live by Night here and The Accountant there, but he’s going to be defined by what happens in that mask. He’s leading with that chin again. It could work for him. It’s a pretty good chin. God help me, I like him and his big ol’ chin.

Still, I’m going to bet on Damon right now. No, he’s not directing, but he’s the better and more versatile actor. He’s taking another big swing with The Martian. And he’s hedging that bet with the money-minting guarantee of another Bourne movie. Get a little crazy and also get paid, Will Hunting. Chuckie’s gonna be busy pimping out the Batmobile for a while. RE-TAIN-ER!

https://www.youtube.com/watch?v=-JBvfZTx-vs?t=14s

The Verdict

Guest Judge Bill Simmons: This could have gone for another 10,000 words. By my calculations, the Damon-Affleck rivalry flipped six times starting in 1992 (Damon getting the bigger School Ties part), then 1993 (Affleck getting Dazed and Confused right after Damon lost Scent of a Woman to Chris O’Donnell), then 1996 (Damon in Courage Under Fire), then 1997 (Affleck in Chasing Amy), then 1997 once again (Damon getting the bigger Good Will Hunting part and everything after that), then Damon held serve for 13 astonishing years until 2010 (Affleck’s The Town). And for the past four years, Affleck has clearly been sitting in the driver’s seat.

Lisanti — you knew this. That’s why you tried to steer your case away from the present tense. Yeah, Damon jumped back into the lucrative Bourne franchise, and yeah, The Martian will probably be huge, and yeah, he’s probably making Rounders 2. But what if the next Bourne movie ends up being a cross between Rambo 4 and Jordan on the Wizards? What if The Martian sucks? What if they screw up Rounders 2? (And by the way — Koppelman and Levien, if you screw up Rounders 2, I’m never forgiving you.) YOU CANNOT PREDICT THE FUTURE, MARK LISANTI.

Also, you keep effusively praising Damon for taking so many chances these past few years; what’s a bigger gamble than Affleck sitting on a GIGANTIC pile of post-Argo career poker chips, then saying, “Fuck it, I’m going for it, I’m driving everyone off this table” and grabbing the Batman lead? That was the single ballsiest move by an actor in years. That Batman franchise is ludicrously sacred for comic-book nerds. If Affleck’s Batman movie fails, only one person is getting blamed. And Affleck knows it. And he doesn’t care. He risked an astonishing amount of career momentum right as his buddy Damon was safely parachuting back into his sure thing of a Bourne franchise. That’s not a big enough swing for you, Mark Lisanti???? You’re just holding a grudge because you’re a Yankees fan and you still can’t believe that a Red Sox fan bagged Jenny from the Bronx. We see right through you.

Ben Affleck, you have the Upper Hand.

1. People now likes to run pictures of his Starbucks runs with J-Garn and the kids. It is adorable.