7 greatest Matt Damon and Ben Affleck collaborations you can’t miss

If Hollywood bromances had a Hall of Fame, Matt Damon and Ben Affleck would be its co-presidents. Childhood friends from Boston, these two have not only survived the brutal currents of Tinseltown - they've surfed them, often on the same board. Whether they're writing screenplays in cramped apartments, playing poker-faced heroes with layered backstories, or poking fun at themselves in bizarre comedies, Matt Damon and Ben Affleck have a habit of sprinkling a little magic dust on every project they touch together.

But don’t expect a perfect track record. Their careers have had all the elements of a good screenplay - highs, lows, and a few "what were they thinking?" moments. What makes their collaborations tick isn't just talent - it’s timing, trust, and that undeniable Bostonian shorthand that can turn a heated argument into a creative breakthrough.

Over the years, they've worn many hats: actors, writers, producers, and even action stars. They’ve taken creative risks that paid off big time, and others that...well, let’s just say the fans were supportive. Here are seven Damon-Affleck team-ups that show just how varied, weird, and wonderful their joint resume is. So buckle up for a wild ride with everything from Southie to sci-fi.

7 greatest Matt Damon and Ben Affleck collaborations

1) Good Will Hunting (1997)

Before Good Will Hunting, Matt Damon and Ben Affleck were just two struggling actors in L.A. sharing a beat-up car and dreaming big. Then came the script that changed everything. Written by the duo, the film tells the story of Will Hunting, a genius janitor from South Boston who’d rather fight than feel. Directed by Gus Van Sant and buoyed by a stirring performance from Robin Williams, the film was a critical darling. And yes, they won the Academy Award for Best Original Screenplay, sparking the ultimate “we made it” moment. Talk about a great success story!

2) Dogma (1999)

If Good Will Hunting was their Oscar-winning debutante ball, Dogma was the chaotic afterparty in a church basement. Directed by Kevin Smith, this religious satire casts Matt Damon and Ben Affleck as fallen angels Loki and Bartleby, wandering Earth in existential crisis and naturally, attempting to sneak back into Heaven through a theological loophole. It’s loud, sacrilegious, and wildly entertaining. The duo plays off each other like two brothers fighting over the remote, except the stakes are cosmically higher. Bonus: Alanis Morissette plays God. Because why not? It was the '90s! Irreverent and oddly touching, this is the cult classic you didn’t know you needed.

3) Jay and Silent Bob Strike Back (2001)

Speaking of chaos, this Kevin Smith-directed carnival of cameos featured Matt Damon and Ben Affleck poking serious fun at themselves. Playing themselves, and also their Good Will Hunting characters - they blur the lines between satire and self-own. At one point, Ben yells, “Who cares about the script? Let’s just shoot it!” while Matt Damon mutters about not wanting to do another sequel. It’s fourth-wall-breaking nonsense at its best. The film didn’t win awards, but it did win over legions of Gen X-ers who appreciated a good inside joke and a pair of actors who didn’t take themselves too seriously.

4) The Last Duel (2021)

After decades of separate successes, Matt Damon and Ben Affleck reunited for this historical epic based on true events in 14th-century France. Written by the duo, The Last Duel is surprisingly cerebral for a film featuring swords, chainmail, and gallons of mud. Damon plays the gruff knight, Affleck the bleach-blond hedonist nobleman, and Adam Driver rounds out the cast. The film tackles sexual assault and justice from three perspectives, Rashomon-style. While it didn’t exactly crush the box office, it got solid reviews and reminded us these guys still have storytelling chops.

5) Project Greenlight (2001-2015)

Okay, this one's not a movie, it’s a reality show - but Project Greenlight might be their most underrated collaboration. The premise? Matt Damon and Ben Affleck gave first-time filmmakers a shot at directing a feature. It was part mentorship, part chaos, and all passion project. Behind-the-scenes drama? Absolutely. Useful lessons about the film industry? Plenty. Some films flopped, others gained cult followings, but the series itself became a fascinating glimpse into the indie filmmaking process. It was the duo’s way of paying it forward, minus the sugarcoating. Because nothing says “we believe in you” like Ben throwing a budget spreadsheet across a room.

6) Air (2023)

In Air, Ben Affleck directs while Damon plays Sonny Vaccaro, the Nike exec who saw magic in a young Michael Jordan’s sneakers before anyone else did. This is not a sports movie - it’s a corporate chess game with 1980s flair, and it works shockingly well. Affleck steals scenes as eccentric Nike co-founder Phil Knight, while Damon delivers a heartfelt, determined performance. Viola Davis shows up and steals the spotlight, because of course she does. Critics praised the script, pacing, and, perhaps most importantly, the Affleck-Damon synergy that gave the film its pulse. It's business storytelling with soul!

7) Stillwater cameo & beyond (Easter eggs & small bits)

Sometimes, it’s not the full roles but the cameos that show how tight this duo is. Take Ben’s rumored behind-the-scenes involvement in Stillwater or the way they always seem to name-drop or reference each other in press junkets. They’ve even worked together on skits and commercials for their production company, Artists Equity. They pop up in unexpected places, like cinematic Easter eggs, often uncredited but unmistakable. It’s like spotting the friend you didn’t know you needed at a party. These moments don’t demand Oscars, they just remind us that Matt Damon and Ben Affleck are more than collaborators. They’re lifelong co-conspirators!

In a business where friendships are often as fleeting as box office trends, Matt Damon and Ben Affleck have proven that loyalty can be a long game. From scribbling dialogue on napkins to forming their own production company, their partnership has matured without losing its spark. Sure, they’ve had solo hits and flops - but their best work still seems to come when they're bouncing off each other. Whether it's dueling on medieval battlefields, riffing through absurd comedies, or championing the next wave of indie filmmakers, they bring something out in each other that's rare in Hollywood: trust, humor, and a shared refusal to phone it in!