Ben Affleck & Matt Damon’s Best Movies Together, Ranked
Time to drop your “r”s and ask yourself if you like them apples, because Matt Damon and Ben Affleck are returning to screens in Joe Carnahan’s The Rip.
Everyone’s favourite Massachusetts duo are set to rekindle their on-screen bromance as Dane Dumar and JD Byrne in the film, two Miami policemen who discover a pile of cash and have to deal with the fallout. The movie’s impressive cast also features Kyle Chandler, Teyanna Taylor and Steven Yuen—so expect a few classy moments among all that action and suspense.
Lifelong ‘Damfleck’ fans will not need reminding, but this is not their first shared rodeo. The lifelong friends—whose production company, Artist Equity, is behind Carnahan’s film—have appeared in a remarkably wide range of movies over the years, even co-writing a few of them.
I’ve kept the list below—which is arranged in ascending order—exclusively for films in which Damon and Affleck have directly shared the screen. This means no room for Glory Daze, The Third Wheel, Jersey Girl or Chasing Amy—all movies in which Affleck starred and Damon only briefly appeared—but that still leaves a whopping eight times in which the duo have treated us to their unique chemistry.
Read on to discover more and use the guide below to find out where to stream them on AppleTV, Netflix, Prime Video and elsewhere.
Back in 1989, when both of them were still teenagers, Damon and Affleck appeared in Kevin Costner’s Field of Dreams. Granted, neither managed to get their name in the credits or even really appear on screen in the movie, but their appearance together as fans in Fenway Park—home of the Boston Red Sox—offers at least a spiritual glimpse of what we’d come to know them for in later years.
The movie itself is a distinctly American phenomenon, but if you’re open to a little Costner schmalz (ala Dances With Wolves) and baseball romance (ala Moneyball), it’s definitely worth a swing.
Affleck and Damon’s first credited roles together came in 1992’s School Ties, a movie in which Brendan Fraser stars as a Jewish kid who wins a scholarship to a preppy boarding school. Damon and Affleck get to share some scenes as two of the bullies who terrorise Fraser’s working-class character, David Greene.
As that synopsis might suggest, Robert Mandel’s movie doesn’t exactly allow the actors to stretch their comedy muscles or use their leading man charms, but if you’re a fan of stories set in that kind of world (think The Holdovers, Dead Poets Society), the film is worth seeking out.
Perhaps the most endearing thing about Affleck and Damon, certainly when compared to some of their peers, is how easily they seem to be able to laugh at themselves. It’s true, no matter how lofty or serious their roles become, they’ve always been good sports when it comes to subverting their own stardom with self-depricating humour.
Case in point is 2001’s Jay and Silent Bob Strike Back, in which the duo—who basically got their foot in the door in Hollywood thanks to the movie’s director, Kevin Smith—play themselves, appearing in a scene where they’re found shooting a cash-grab sequel to Good Will Hunting. If you’re not familiar with the movie, you probably know Jay and Silent Bob for their appearances in Clerks and Mallrats—or pretty much any film in Smith’s ‘View Eskewniverse’.
On any other list or Affleck or Damon’S work, Ridley Scott’s excellent The Last Duel—a Rashomon-style tale of varying perspectives set in 14th century France—would rank higher, but seeing as we’re here to talk about the duo’s chemistry, it would be a stretch to claim that they get to do a whole lot together in this one.
They do, however, represent the story’s Yin and Yang: Damon as the staunch, hubristic, Jean de Carrouges—a knight determined to fight for his wife’s honor (even if she’d rather he didn’t); and Affleck (who helped write the script) as Count Pierre II of Alençon, an indulgent partyboy with an outrageously Dalston-coded haircut. If you like Scott in his period-set pomp (movies like Gladiator or Kingdom of Heaven), you’re gonna love it.
It’s safe to say, if you’re a fan of Affleck and Damon’s work, especially in action-forward movies like The Accountant 2 and Elysium, and are partial to some humid, Florida-set crime—think Miami Vice or Bad Boys—The Rip should be right up your alley.
What’s more, director Joe Carnahan is the mind behind movies like The Grey and Boss Level—so if you like your action delivered with B-movie swagger, make sure to add his latest to the watch list.
Given how consistent Affleck’s work as a writer-director has been—Gone Baby Gone and The Town showcased his talent for directing genre movies; Argo won the Oscar for Best Picture—it’s strange that it took five films before he managed to land Damon in a role. Whatever the case, the wait was probably worth it, as 2023’s Air was perfectly suited to both their talents.
Inspired by Nike founder Phil Knight’s Shoe Dog, a ripper of a memoir, Affleck decided to make a movie about how the company managed to sign Michael Jordan at the height of his fame. The deal led to the development of the iconic Nike Air Jordan, thus establishing the then relatively second-rung company as one of the biggest sports brands in the world. If you’re a fan of movies like The Social Network and The Big Short, this one’s a low-key slam dunk.
A year after winning best Original Screenplay at the Oscars (more on that in a moment), Affleck and Damon confirmed their positions as the go-to leading men of the slacker generation with Dogma—a movie that was Kevin Smith’s first mainstream hit after the indie success of Chasing Amy and the theatrical disappointment of Mallrats.
Like several films from that era (think Devil’s Advocate, Angel Heart), Dogma draws some inspiration from John Milton’s Paradise Lost—but, as you might expect for a Kevin Smith feature, it does so with tongue planted firmly in cheek. Dogma is especially notable on this list as it’s basically the only film pre-The Rip in which Damon and Affleck are undoubtedly co-leads.
The duo play Loki and Bartleby, two fallen angels adrift on earth who attempt to scam their way back into heaven. Alan Rickman plays the villain. Alanis Morissette plays god. Need I say more?
As the best friend of Damon’s genius MIT janitor, Affleck doesn’t get a huge amount of screentime in Good Will Hunting, but his scenes—including a wonderful monologue and a touching sequence near the end—are some of the most moving. This one will always take the top spot on any list of Damon and Affleck’s shared career as the duo not only stars in the movie but also wrote the screenplay.
Both Damon and Affleck have claimed that they wrote Hunting as a way to give themselves the kind of meaty roles they couldn’t land at the time, but of course, it went on to earn them more acclaim than they could have possibly imagined. Alongside Robin Williams’ win for his iconic performance as Sean Maguire, the duo won a shared Oscar for Best Original Screenplay in 1998, beating tough competition from the likes of Paul Thomas Anderson (Boogie Nights) and James L. Brooks (As Good as it Gets). At the time, the 25-year-old Affleck was the youngest person to ever win the award, and that record still stands.
