Batman and Robin. Frodo and Sam. Snoopy and Woodstock. Ben Affleck and Matt Damon.
Affleck and Damon have been one of the most fascinating and exciting Hollywood duos for decades, a pair of actors and filmmakers who went from being childhood friends to co-Oscar winners. The two have shared the screen together since essentially the starts of their respective careers, with both getting early uncredited roles in 1989’s “Field of Dreams.”
Since then, Affleck and Damon have built a healthy filmography of co-starring projects, ramping up with a steadier stream the past few years. Friday, Netflix released “The Rip,” their new collaboration which features the duo as a pair of cops who get in too deep when they discover a house stashed with millions in cartel money.
In honor of “The Rip,” here’s a ranking of seven of Ben Affleck and Matt Damon’s biggest collaborations.
7. “The Rip”
I take no pleasure in reporting that Affleck and Damon’s latest collaboration, “The Rip,” is probably their weakest. I wouldn’t go as far as to call it bad. Writer/director Joe Carnahan excels at ratcheting tension as the walls close in on a group of characters sitting on millions in cartel money. The largely single-setting movie gives Affleck and Damon (as well as co-stars Steven Yeun, Teyana Taylor, Sasha Calle and Catalina Sandino Moreno) a wealth of screen time together, allowing their natural chemistry to elevate a sometimes rocky script.
But there’s a bit too much Netflix in this Netflix movie for it to get a high rank in the duo’s largely stellar filmography. The visuals are often lacking, the action can be spatially incoherent and the dialogue feels written toward second-screeners. “The Rip” is a good way to pass a night on Netflix, and the Affleck/Damon duo certainly elevates the film, but it doesn’t stand among their best.
6. “School Ties”
“School Ties” is definitely the most lopsided in the Damon/Affleck alchemy (hence the photo), lending to its low ranking on the list. Robert Mandel’s 1992 coming-of-age drama, written by Dick Wolf and Darryl Ponicsan, takes place at a prep school in 1955. Brendan Fraser stars as David Greene, a young man who starts attending the school in his senior year as their new quarterback — and chooses to hide the fact that he’s Jewish from his antisemitic peers.
Damon gets second billing in the film as Charlie Dillon, an affluent and popular football player who becomes David’s friend-turned-bully (in a bit of serendipity, Charlie is longtime roommates with a fellow student named “Rip”). The young Damon excels at the part, playing, as David describes him in the film’s closing line, “a prick.” Affleck, meanwhile, gets a much smaller role, playing fellow senior Chesty Smith.
Despite the Damon/Affleck duo not really being focused on in “School Ties” (Fraser’s performance is both the focus and the highlight of the film), it’s a delight to see both actors at the very start of their careers. Even with little screen time together, the pair’s dynamic peeks through in small moments, like when Affleck wraps his legs around Damon as the pair pretend they’re monkeys. It would be a stretch to call “School Ties” an Affleck/Damon collaboration (it falls more into the same camp as projects like “Chasing Amy” and “Jersey Girl” that aren’t featured on this list), but there is something joyful about seeing them together at their beginning.
5. “Dogma”
One of the best on-screen Affleck/Damon dynamics comes in Kevin Smith’s “Dogma.” The film sees the duo play fallen angels Bartleby and Loki, trekking from Wisconsin to New Jersey in an attempt to secure re-entry into heaven through a loophole involving an overzealous cardinal and his “Buddy Jesus.” Unfortunately for the rest of us, Bartleby and Loki’s success would prove God wrong, thus jeopardizing the rest of existence. Heady stuff!
Smith, Affleck and Damon have a great energy together, with their scenes being highlights of “Dogma.” If you just want to see the vibes of these two actors together, this is definitely one worth the watch.
4. “Jay and Silent Bob Strike Back”
There are a few Kevin Smith films with Affleck and Damon that do not appear on this list, cases in which the screen time from one or both of them is relatively brief. That being said, I would be remiss to not mention “Jay and Silent Bob Strike Back” if only for one key scene.
In case you don’t know, the film, starring Jason Mewes and Smith as Jay and Silent Bob, features a moment where the iconic duo end up on the set of a fictional sequel to “Good Will Hunting” titled “Good Will Hunting 2: Hunting Season.” Damon and Affleck appear in the scene as themselves, as do Scott William Winters and Gus Van Sant (seen counting his money).
Every single moment of “Good Will Hunting 2: Hunting Season” exists perfectly crystalized in my brain — Will getting way too angry at Clark for regurgitating Gordon Wood, Winters over-emphasizing his dialogue, a guy standing behind Winters getting weirdly excited when he says, “You’re just no longer that good, Will Hunting.” I cannot count the number of times I’ve watched the scene, an over-the-top parody of hyper-repetitive sequels.
This might genuinely be my favorite performance Affleck’s ever given. In two minutes, he has about four line deliveries that have permanently altered the way I think and speak.
We’ll talk a little bit later about my favorite moment these two have ever shared on-screen, but a close second has to be Affleck’s utterance of “I don’t like the sound of them apples, Will! What are we gonna do?!” As Affleck looks at Damon during this line, a smile creeps onto the edge of his mouth. He seemingly struggles to keep himself from breaking. These are two best friends who hit the jackpot and are living the dream. Should we all be so lucky.
3. “Air”
After a string of heavier films, Affleck lined up a fun one for his first time directing Damon. “Air,” written by Alex Convery, follows Damon as Sonny Vaccaro, a Nike employee who wanted to strike up a deal with Michael Jordan to create the Air Jordan. Affleck co-stars as Nike co-founder Phil Knight.
This could easily come across the finish line as a two-hour advertisement (and sure, some of that is there). Yet “Air” is a handsomely directed, well-written, and strongly acted examination of American symbols and myth-making. Affleck and Convery use the world of commerce and advertising as an asset rather than a liability in a zippy bio-drama with plenty on its mind.
2. “The Last Duel”
The 2020s saw the resurgence of the Affleck/Damon on-screen duo, starting with 2021’s “The Last Duel.” Ridley Scott directed the film based on a screenplay written by Affleck, Damon and Nicole Holofcener.
“The Last Duel” tells the story of Marguerite de Carrouges (Jodie Comer), married to knight Jean de Carrouges (Damon). When Marguerite accuses Squire Jacques le Gris (Adam Driver) of rape, Jean challenges Jacques to a duel as a means of trial. Affleck, Damon, Holofcener and Scott approach the story in a “Rashomon”-like fashion, with three distinct chapters showing events from Jean, Jacques and Marguerites’ perspectives (the latter of which is the film’s strongest and most sobering). Affleck co-stars as the dopey Count Pierre d’Alençon in a memorable performance.
“The Last Duel” is a sharp and compelling drama, with easily the best screenplay for a film starring the duo since their Oscar win. Damon and Affleck both deliver solid performances, but Comer’s haunting turn (particularly during the titular duel) is the reason to watch. How she didn’t get her Oscar flowers is beyond me.
1. “Good Will Hunting”
If you can’t tell from the photos I’ve selected, Affleck and Damon collaborations follow a trend — when the pair take a project together, Damon tends to be the star. There are a few exceptions to this rule (Kevin Smith’s films, as mentioned before, tend to favor Ben, though I wouldn’t really call these Affleck/Damon collabs). But when the two unite for true “Ben and Matt” movies, Damon generally takes the lead and Affleck takes supporting.
This is certainly true of “Good Will Hunting,” a movie that brought the two friends a Best Original Screenplay Oscar and really skyrocketed their careers. While Damon takes on the titular role of Will Hunting, Affleck, as Will’s best friend Chuckie, gets far less screen time in comparison. I feel like some people write his performance off a bit as a result. After all, Damon got nominated for Best Actor, while Robin Williams eclipsed Affleck with a (fully deserved) Best Supporting Actor nomination and win.
But there’s a scene in “Good Will Hunting” (a favorite film of mine that I’ve watched more than I can remember) that I think of more than most. As Will and Chuckie work another day on a construction site, Will begins to share his dream — to keep living next door to Chuckie for the rest of his life, continuing to avoid the opportunities that have come his way. In a moment of sobering honesty, Chuckie reveals the best part of his day: the 10 seconds before he knocks on Will’s door, when he gets to hope that his best friend has gone after the life within his reach. It’s a perfect scene, one that shows how well suited both men were for their roles — and what a feast Affleck can make out of a handful of moments.
Affleck and Damon weren’t unknowns when “Good Will Hunting” came out, and it’s easy to imagine that parts would still have come their way without it. But they didn’t know when they cast “Good Will Hunting” that one would go on to be Batman and direct a Best Picture winner, or that the other would become Jason Bourne and get three acting Oscar nominations. They didn’t know they’d both get to be successful movie stars.
Yet in the movie that would guarantee their careers, the duo crafted a beautiful moment that encapsulates what it means to be a friend: to want the best for someone even when the best doesn’t include you.
“Good Will Hunting” is a perfect movie, filled with many such incredible scenes. But this will always be a favorite — and a key text of Affleck/Damon cinema.
