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Matt Damon vs. Ben Affleck: Who wins, then and now?

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Ben Affleck Matt Damon
Timothy A. Clary/Getty Images

Ever since they wrote Good Will Hunting 18 years ago, Matt Damon and Ben Affleck have been one of Hollywood’s most well-known bromances. But no bromance is complete without some healthy competition, which is why we’ve gone back through the years since their first Oscar win and looked at their careers.

With Samantha Highfill representing Matt Damon in one corner, and Joshua Rivera representing Ben Affleck in the other, here’s how the fight breaks down:

1997

Damon: Good Will Hunting

Sure, both Damon and Affleck won an Oscar for Best Original Screenplay, but only one of them was nominated for an Oscar for Best Actor, and his name does not sound anything like those Aflac commercials. I feel like this argument’s over, no?

Affleck: Good Will Hunting

Ben Affleck doesn’t have to get nominated for an acting Oscar to have both the movie’s funniest scene and its most affecting one (non-Robin Williams division). But hey, they’re both pretty adorable during that Oscar win.

Damon rebuttal: Tell that to the Academy.

Affleck rebuttal: Remember when the Academy voted for Crash?

1998

Damon: Saving Private Ryan

Damon might not have had a lot of screen time, but he was good enough to earn the titular role of Private Ryan in Saving Private Ryan, so what else is there to say?

Affleck: Armageddon and Shakespeare in Love

Ben Affleck, meanwhile, got loads of screen time in Armageddon, which is great, but Shakespeare in Love is Affleck’s ace in the hole this year. In a hilarious turn as Ned Alleyn, Affleck is a total scene stealer, playing what he describes as an Elizabethan Tom Cruise. It’s hard to top that one.

Damon rebuttal: Just for the record, Affleck’s “ace in the hole” is what’s widely considered one of the Academy Award’s greatest mistakes.

Affleck rebuttal: If an Academy Award is good enough for one year, it’s good enough for all of them.

1999

Damon: The Talented Mr. Ripley

Again, Damon took on the titular role in this Anthony Minghella film, which earned him yet another Golden Globe nomination, this time for Best Performance by an Actor in a Motion Picture.

Affleck: Dogma

Golden Globe, Schmolden Schlobe. As the fallen angel Bartleby, Affleck really gets to cut loose in Dogma, having the time of his life in a villainous role.

Damon rebuttal: Damon was also in Dogma, and only losers say “Schmolden Schlobe.”

Affleck rebuttal: ’99 was a weird time for all of us

2000

Damon: Finding Forrester

While Affleck made the hit film, Bounce, Damon teamed up with Gus Van Sant and Sean Connery for Finding Forrester, before starring in the Golden Globe-nominated All the Pretty Horses, which paired Damon up with Penelope Cruz and director Billy Bob Thornton. You might not remember it, but all the awards do.

Affleck: Bounce and Reindeer Games

While Damon was busy trying very hard to be a romantic lead, Affleck spent the Willennium just having a blast—which is a million times better than Finding Forrester, because man, was that movie a drag.

Damon rebuttal: If only there were an award for “having a blast.”

Affleck rebuttal: There is! It’s called ‘”not being boring.”

2001

Damon: Ocean’s Eleven

Both Damon and Affleck showed their lighter side on Jay and Silent Bob Strike Back, but in terms of drama, let’s just say that Affleck spent his time on Pearl Harbor while Damon helped launched a hit trilogy with Ocean’s Eleven. Also, this is approximately the time when Brad Pitt and George Clooney began campaigning for Damon to win People’s Sexiest Man Alive. And yes, cool friends do make someone cooler. This is Hollywood, after all.

Affleck: Pearl Harbor

It’s easy to knock Pearl Harbor now, but come on, really think back. There wasn’t a single person not thinking about Pearl Harbor, which turned Affleck into a bona fide, all-ages heartthrob. No one watched Ocean’s Eleven for the Matt Damon parts. Also, Ben met Jennifer Garner on this film, which will be important later.

Damon rebuttal: I’ve never ever seen Pearl Harbor, so I was actively not thinking about it, and for those who were, they were thinking about Josh Hartnett.

Affleck rebuttal: The people who would pick the Sexiest Man Alive next year totally were thinking about Ben.

2002

Damon: Will & Grace, The Bourne Identity

In 2002, Matt Damon made one of the most unexpected and amazing decisions of his career: He took a guest starring role on Will & Grace that will always remain one of the most memorable, and not just because he sang. And just in case you forgot, he started yet another hit trilogy with The Bourne Identity. Finally, he started Project Greenlight, but Affleck was a part of that too so good for them, I guess?

Affleck: Named People’s Sexiest Man Alive

Suck it, Damon.

Damon rebuttal: More impressively, Damon wins the same title after seven more years of aging.

Affleck rebuttal: They probably just got tired of giving it to Clooney.

2003

Damon: Stuck on You

Sure, you can focus on Damon’s slight misstep with Stuck On You, or you can realize that not only did he meet his wife on that film, but he was also filming The Bourne Supremacy that year. Make fun of Jason Bourne and see what happens.

Affleck: Daredevil and ‘Jenny from the Block’

We only hate Daredevil now because we know how much better superhero movies can be. And I hear the Director’s Cut is actually much better. Affleck didn’t really do anything great this year, but for all its ridiculousness (and these are the dark ages) the music video to Jennifer Lopez’s  (or as I call her, Ben’s Yoko) “Jenny from the Block” is such a great, Taylor Swift-ian middle finger to the haters. And let me tell you, a lot of dudes wanted to be Ben Affleck in 2003.

Damon rebuttal: [Cough, Gigli, cough]

Affleck rebuttal: Could Matt Damon have had a more boring year?

2004

Damon: The Bourne Supremacy, Ocean’s Twelve

Damon’s hard work paid off when The Bourne Supremacy hit theaters, right alongside Ocean’s Twelve. And when he wasn’t busy breaking the box office, Damon remained a good friend, agreeing to take a role that was so far beneath him to help out Affleck by appearing as PR Exec #2 in Jersey Girl. But don’t worry, nobody cared about Affleck’s film, and like a phoenix, Jason Bourne would rise again.

Affleck: Jersey Girl is kind of sweet?

Like touching? Maybe? Also Ben gets to meet James Gandolfini in Surviving Christmas which is pretty dope. Remember how you just read about Matt Damon starring in Stuck on You?

Damon rebuttal: Isn’t it sad when you have to refer back to 2003 for your 2004 argument?

Affleck rebuttal: Did you know that Ben Affleck’s full name is Benjamin Géza Affleck-Boldt? How cool is that?

2005

Damon: Syriana

Damon starred in the Oscar-nominated film alongside his other bestie, George Clooney, who took home an Oscar for his work in a supporting role. Did I mention that George and Matt are super close?

Affleck: Marries Jennifer Garner

Hey, nothing wrong with taking a year off. Besides, no one saw Syriana.

Damon rebuttal: We’ll pretend Affleck “chose” to take a year off.

Affleck rebuttal: Becoming a beautiful, Damon-crushing butterfly takes time.

2006

Damon: The Departed, The Good Shepherd

Matt Damon might’ve been in the Oscar-nominated The Good Shepherd, but this year was all about The Departed. You know, the best picture of the year. Proof of Damon’s stardom: This year launched the Jimmy Kimmel-Matt Damon saga.

Affleck: Hollywoodland

The big comeback. Affleck was critically acclaimed for his role as Adventures in Superman actor George Reeves, netting him a Golden Globe nomination and the Venice Film Festival’s Volpi Cup. He also got lots of apologies from critics who wrote him off.

Damon rebuttal: But, The Departed.

Affleck rebuttal: …was totally DiCaprio’s movie.

2007

Damon: Ocean’s Thirteen, The Bourne Ultimatum

Not only did Damon bring home two trilogies with Ocean’s Thirteen and Bourne Ultimatum, but he was finally named People’s Sexiest Man Alive, not to mention that Forbes named him the most bankable star. That’s right, even banks love Matt Damon. To top it all off, Damon got a star on the Hollywood Walk of Fame. Wait, does Affleck have one of those? (Spoiler: No.)

Affleck: Gone Baby Gone

Here’s one thing Damon still can’t call himself: critically acclaimed director. Affleck’s directorial debut is masterful, morally complex, and proof that Ben has a much cooler sibling than Matt—who, by the way, is just coasting on Bourne and Ocean’s stuff at this point.

Damon rebuttal: Watch Bourne Ultimatum and then call it “coasting.”

Affleck rebuttal: Watch Gone Baby Gone and you’ll have seen a better movie.

2008

Damon: Ponyo

Damon showed his versatility by taking some time out to do a critically acclaimed children’s film in between his travels around the country campaigning for Barack Obama’s first presidential campaign. Also, Sarah Silverman sang this song about him.

Affleck: Wins poker for charity, also rocks at SNL

Not content to just do a victory lap following the success of Gone Baby Gone, Ben goes on to win a poker tournament for charity.  This is also a good time to mention his incessant charitable endeavors and activism—something Matt does too, but probably learned about form Affleck. Oh, and there’s also his fantastic appearance on Saturday Night Live (watch it here if you’re a Hulu Plus subscriber) in which he’s not only a part of the very first Stefon sketch, but stars in a hilarious segment impersonating Keith Olbermann.

Damon rebuttal: Sure, Damon, who’s two years older and attended Harvard, learned about the world from Affleck.

Affleck rebuttal: Man, Damon’s barely in Ponyo.

2009

Damon: Entourage, Invictus

Starring alongside Morgan Freeman in Clint Eastwood’s Invictus, Damon took home an Oscar nomination and a Golden Globe nomination for best supporting actor. Correction: He took home two Golden Globe nominations, also counting his work in The Informant! And when he wasn’t busy with all of the praise, he was having fun playing himself on Entourage. Also, off-screen, Damon’s H20 Africa Foundation merged with WaterPartners to create Water.org. In other words, he literally saved the world.

Affleck: State of Play and Extract

Proving that he’s still a versatile actor, Affleck stars in both the extremely well-received political thriller State of Play, and the oddball comedy Extract. Also, if you thought that song Damon sang with Sarah Silverman was great, just wait til you see the one Affleck sang with….everyone. 

Damon rebuttal: Isn’t it cute when Affleck does something Damon’s already done to try to be like his older brother?

Affleck rebuttal: The Regular season doesn’t matter, people only remember the champ

2010

Damon: True Grit, 30 Rock (through 2011)

At this point, Damon’s schedule included the Oscar-nominated Coen brothers film, True Grit, a stint on 30 Rock, and ironically enough, EW listing him as one of the best action stars of the decade. Additionally, this was the year Affleck officially accepted defeat when he presented Damon with the 24th Annual American Cinematheque Award.

Affleck: The Town

Pretty much the year we decided that showering praise on movies directed by Ben Affleck was going to be a regular thing.

Damon rebuttal: But not so much with his acting.

Affleck rebuttal: The next time he decided to act in his own movie turned out pretty well.

2011

Damon: Adjustment Bureau, Contagion, We Bought a Zoo, SNL

This year, Damon starred in the SAG-nominated Adjustment Bureau, along with the not-great-but-not-embarrassing films Contagion and We Bought a Zoo. But his shining achievement was hosting SNL.

Affleck: Victory lap part deux

While soaking in all the adulation from The Town, Affleck and Garner have their second child. But he doesn’t rest easy—this year saw Ben winning the Chairman’s award in the Palm Springs International Film Festival and really focusing on his political activism, testifying before the House Subcommittee on Africa, Global Health, and Human Rights, and speaking alongside heavy hitters like Hillary Clinton.

Damon rebuttal: Why should he rest easy—did he give birth?

Affleck rebuttal: America loves a family man.

2012

Damon: Promised Land

Damon returned to writing with partner John Krasinksi to create an environmentally conscious film directed by Gus Van Sant and starring Frances McDormand. Is there anything better than watching a man combines his many passions? No, no there is not.

Affleck: Argo

Let’s play a game. You mention something, anything Matt Damon did in 2012 and then I say “2012 Academy Award for Best Picture.” You can’t win this game.

Damon rebuttal: [Cough, Gigli, cough]

Affleck rebuttal: Matt Damon was in Gigli?

2013

Damon: Elysium, Behind the Candelabra

When he wasn’t starring in Elysium, a solid film EW gave a B+ review, Damon was earning a Golden Globe and Emmy nod for his role in Behind the Candelabra. He also kidnapped Jimmy Kimmel.

Affleck: To The Wonder

Hey, let’s talk about something else Matt Damon hasn’t done: starring in a film by acclaimed director Terrence Malick, who’s probably the closest thing we have to someone who paints with cinema.

Damon rebuttal: Loved you in Runner, Runner, Ben.

Affleck rebuttal: Ben loved Runner, Runner, and that’s all that matters.

2014

Damon: The Monuments Men

The Monuments Men might not have been the greatest film Damon ever made, but he did it alongside some A-list talent. Also, unlike Affleck, Damon got an invite to Clooney’s wedding, which is pretty much the equivalent of winning at this game we call life.

Affleck: Gone Girl

Which, unlike The Monuments Men, is a movie that you’re actually going to go see. Right now, even.

Damon rebuttal: And you might even leave there thinking, “I wish it had been Damon.”

Affleck rebuttal: Wait, are we talking about the dick thing?