Ben Affleck vs. Matt Damon: Who’s Had the Better Career?

It’s been almost twenty years since Matt Damon and Ben Affleck exploded onto the Hollywood A-list – becoming the youngest writers in history to win a Best Original Screenplay Oscar for a movie about a super-intelligent janitor, calculus, apples and the Sawx – and you still can’t talk about one without the other.

Boston’s favourite sons both went on to become legitimate movie stars, headlining summer blockbusters and trading People’s “Sexiest Man Alive” titles. But for a while there, comparing Damon and Affleck’s actual careers was like comparing apples to sad, tabloid-hounded oranges. Damon was the one launching franchises and working with Spielberg and Scorsese. Affleck? He was the fuck-up little brother whose movies tanked and dating life made him a late-night punchline.

But then Affleck made an improbable comeback, rebuilding himself as an award-winning writer/director and getting a do-over on the superhero movie front. Now, he’s got a new thriller out, The Accountant, where Affleck plays a forensic accountant/super-soldier who also happens to be autistic. (If that sounds like some kind of bizarre mash-up of Jason Bourne and Good Will Hunting… yeah, that’s probably not unintentional.)

So forget this year’s disappointing AF Batman v. Superman. We’re pitting Affleck against a much more challenging opponent, his childhood BFF Damon, to determine who’s the real pride of Boston, some 20 years after their big break.

B.G.W.H. (Before Good Will Hunting): 1981-1997


Key Credits
Affleck: Dazed and Confused, Mallrats, Chasing Amy, this amazing after-school special
Damon: Courage Under Fire, School Ties

While Damon was busy dropping out of Hahvahd, the former child actor Affleck – shout-out to all The Voyage of the Mimi fans out there – was making a name for himself playing frat-boy assholes in slacker comedies, parts he played well enough (maybe a little too well?) to earn a shot as a leading man. Not to mention, the chance to sport one of the most gloriously douchey goatees in cinema history. Damon? He had… a single line in Mystic Pizza and a supporting role in the 10th-best Denzel movie.

Advantage: Affleck


The “Good” Old Days: 1997-2000


Key Credits
Affleck: Armageddon, Shakespeare in Love, Reindeer Games, Phantoms
Damon: Saving Private Ryan, Rounders, The Talented Mr. Ripley

Life can be pretty good when Hollywood decides you’re the “Next Big Thing.” And for those first few post-Good Will Hunting years, things were looking great for Matt and Ben. Affleck was dating a pre-Goop Gwyneth and blowing up asteroids with Bruce Willis. Meanwhile, Damon was flexing his acting muscles for Spielberg and playing against type in The Talented Mr. Ripley, and, well, The Legend of Bagger Vance probably seemed like a good idea at the time. Still, these were the halcyon days for two Boston kids made good.

Advantage: Damon


The “Bennifer” Years: 2001-2004


Key Credits
Affleck: Pearl Harbor, Daredevil, Gigli, Jersey Girl
Damon: Ocean’s Eleven and Twelve, The Bourne Identity and Bourne Supremacy

Then “Bennifer” happened, and it all went to shit for Affleck. He went to rehab (when Charlie Sheen drives you to rehab, it’s… not great), dated Jenny from the Block, practically cratered his career with the one-two nut-punch of Daredevil and Gigli and became yet another overexposed, Hollywood cautionary tale. All while Damon was rubbing elbows with Clooney and Pitt and Casey Affleck (Et tu, Casey?) and playing action hero in the Bourne movies, giving him not one, but two massive Hollywood franchises.

Advantage: Matt Damon! And it’s not even close.


The Pivot: 2005-2011


Key Credits
Affleck: Hollywoodland, Gone Baby Gone, The Town
Damon: The Departed, Ocean’s Thirteen, The Bourne Ultimatum, True Grit

If you were looking for a State of the Union on Matt and Ben’s public image circa 2005, this Family Guy joke pretty much says it all. Most of us just assumed Affleck was the guy riding Damon’s humanitarian ambassador, “serious” leading man coattails. The Johnny Drama to his Vinnie Chase. (Hey, it was 2005, remember? Don’t judge us.) But then Affleck took the year off, got married to his Daredevil love interest Jennifer Garner, and when he came back, he started quietly choosing better movies – admittedly, it would’ve been tough to choose worse movies – earning begrudgingly good reviews from critics. Call it regression to the mean if you want, but by the time Affleck made his directorial debut with the sneaky-good missing kid drama Gone Baby Gone, we all started to realize maybe there was another gear to this guy after all.

Advantage: Still Damon. But Affleck started closing the gap.


The Modern Era: 2012-Present


Key Credits
Affleck: Argo, Gone Girl, Batman v Superman: Dawn of Justice
Damon: Elysium, The Monuments Men, The Martian, Jason Bourne

By the time Argo brought Affleck back to the Oscar stage in 2012, it became impossible to dismiss his directing career as a one-hit wonder. Yes, Damon’s worked with more big-name filmmakers – Scorsese, Ridley Scott, Eastwood, the Coen Brothers, we could keep going… – but Affleck’s become a big-name filmmaker in his own right. Imagine an athlete winning Rookie of the Year, playing out of position for a full decade and never quite living up to those first big contracts, before finally rediscovering his form and winning MVP. That’s the type of storybook comeback we’re talking about here.

Affleck even managed to re-establish himself as a leading man, mining his past as a tabloid target for Gone Girl. Now, he’s Batman. Batman. So what if Dawn of Justice sucked. Damon hasn’t exactly been bomb-proof either lately. (Elysium, anyone?) We’ll spot Matt his Martian Oscar nomination, but Boston loves an underdog. And this last round’s all Affleck.

Advantage: Martha! Affleck. By an Oscar count of 1-0.


Final Tally


Affleck started and finished strong, but Damon still narrowly edges him out 3-2. Check back in another five years though, because Affleck’s catching up. Long live the Ben-aissance.