Damon and Affleck: RANKED
- 1 day ago
- 8 min read
Ben Affleck and Matt Damon are one of those rare Hollywood stories that actually lives up to the mythology. Childhood friends. Two kids from Cambridge, Massachusetts. Two guys who grew up two blocks apart, obsessed with movies, obsessed with acting, obsessed with the idea that somehow, against all odds, they were going to break into this impossible business together. And somehow, they did. Not just together, but by betting on each other when nobody else really would.
They met when they were kids because their mothers knew each other, which already feels like the opening scene of a movie. One was eight, one was ten, and they bonded over the same things: movies, baseball, acting, pop culture, the idea of escape.
They went to the same high school, Cambridge Rindge and Latin, which had a strong drama department, and they were already hustling early. These guys weren’t just dreaming, they were planning. They had “business lunches” in the cafeteria.
They opened a joint checking account to pay for auditions in New York. They literally shared money to chase the same goal. The password to that account was “RiverP,” named after River Phoenix, who was one of their heroes. That detail alone tells you everything you need to know about who they were and what kind of actors they wanted to be.
They even showed up together as uncredited extras in Field of Dreams, which is one of those great pieces of trivia that feels poetic in retrospect. Two future movie stars standing in the background of a movie about faith, dreams, and belief.
Kevin Costner remembers them leaning in and out at the same time, finishing each other’s thoughts, already acting like a unit. They were kids, but they were already locked in.
The real turning point, obviously, is Good Will Hunting. Damon starts it as a class assignment at Harvard. Affleck helps him shape it. They expand it together while living in Los Angeles. And instead of letting the system chew them up, they fight to keep control of the script, insisting that they star in it themselves.
That gamble pays off in one of the most satisfying underdog stories in modern Hollywood history. They win the Academy Award for Best Original Screenplay, they become instant stars, and suddenly these two guys from Cambridge are the faces of a new kind of smart, emotionally open, actor-writer-driven Hollywood movie.
What’s fascinating about Affleck and Damon is that their collaboration has never been limited to just acting together. They’ve written together. They’ve produced together. They’ve built companies together.
Pearl Street Films, named after the street they used to walk down to visit each other as kids, was a decade-long experiment in trying to make smart, adult movies inside the studio system.
And when that ran its course, they pivoted again, creating Artists Equity, an independent company built around the idea that filmmakers and crews should share in the success of the work.
They also produced and were the faces of the HBO documentary series, Project Greenlight, which was a television series that focused on first-time filmmakers being given the chance to direct a feature film. The guys put their money where their mouths were, and helped young filmmakers get their movies made.
That’s not just branding. That’s two guys who remember what it felt like to be on the outside trying to get in.
And on screen, their chemistry is undeniable. Whether they’re playing tortured geniuses, arrogant jerks, best friends, parody versions of themselves, or aging men looking back on missed chances, there’s always an ease between them.
They know how to play off each other. They know when to push and when to step back. You can feel decades of shared history in even the smallest scenes.
They’ve also never been afraid to poke fun at themselves. Their appearances in Kevin Smith’s movies, especially Jay and Silent Bob Strike Back, where they parody Good Will Hunting and their own personas, show a level of self-awareness that a lot of movie stars never develop.
What I really admire about their partnership is that it’s evolved. They’re not just replaying the same beats from their twenties. As they’ve gotten older, their collaborations have shifted toward producing, directing, and supporting other filmmakers, while still occasionally stepping in front of the camera together.
Movies like Air feel like the work of guys who’ve been around the block, learned some hard lessons, and now want to tell stories about systems, power, creativity, and compromise.
And through it all, the friendship has stayed intact. That’s the part that’s almost unheard of in this business. Decades of success, failure, tabloid nonsense, personal struggles, reinventions, and they still show up for each other.
Affleck has said flat-out that he wouldn’t be where he is without Damon’s support. Damon has openly wondered why they didn’t work together more and made it clear that, at this stage in their lives, that time feels more precious than ever.
So this list isn’t just about movies where Ben Affleck and Matt Damon happen to share the screen. It’s about a partnership. A shared history. A long, strange, fascinating journey through Hollywood that includes massive hits, cult favorites, misfires, self-parody, reinvention, and genuine artistic growth.
I’ve taken the twelve movies in which they appear together (sometimes only briefly, sometimes in just wordless cameos) and ranked them in order of my personal preference.
These rankings are based on the quality of the movies themselves, not on how entertaining, or cool Damon and Affleck's onscreen moments or scenes are (although, sometimes that does factor into the evaluation).
These reviews/rankings are about how good the movie is on its own, even if, as in some cases, Damon and Affleck are barely in it.
I am having some fun with this list, because that’s what I do, and because their shared filmography tells a really interesting story when you line it all up.
So here we go. These are the twelve movies starring Ben Affleck and Matt Damon together, ranked by me, in order of preference.
DAMON AND AFFLECK: RANKED (in order of my preference):
This is still Kevin Smith’s best movie and, by extension, the best Affleck/Damon-related project they both appear in, even though Damon’s role is small. It’s smart, messy, emotionally honest, genuinely funny, and actually about something real. It's about relationships, identity, insecurity, and how badly people screw things up when they don’t know how to communicate.
Affleck gives one of his best performances ever here, raw and vulnerable in a way he rarely allows himself to be, and the movie hasn’t aged nearly as badly as some of Smith’s other work. It’s imperfect, but it’s brave, personal, and heartfelt, which puts it at the top for me.
This movie surprised the hell out of me. It’s slick, smart, entertaining, and incredibly well-paced, taking something that could have been dull corporate boardroom nonsense and turning it into a genuinely engaging character-driven story.
Affleck directs the hell out of it, Damon is terrific as Sonny Vaccaro, and the whole thing has a confident, old-school studio-movie feel that we just don’t get anymore. It’s fun, energetic, well-acted, and proof that these guys know how to tell a story when they’re locked in. One of the best sports-business movies ever made.
This movie is ridiculous, juvenile, self-indulgent, and completely stupid, and I love it. It’s Kevin Smith at his most shameless, throwing everything at the wall, breaking the fourth wall, mocking Hollywood, mocking himself, and having an absolute blast.
Damon and Affleck showing up to parody Good Will Hunting is inspired and still hilarious. It’s not a “good” movie in the traditional sense, but it’s funny, quotable, and endlessly rewatchable if you’re in the right mood.
This is Kevin Smith swinging big, and while it doesn’t always land, I admire the ambition. It’s smart, profane, thoughtful, and genuinely interested in faith, belief, and organized religion in a way most comedies wouldn’t dare touch.
Affleck and Damon are both solid, the cast is stacked, and the movie has some truly great ideas mixed with uneven execution. When it works, it really works, and when it doesn’t, it’s still interesting. It’s messy, but it’s gutsy.
This one hasn’t fully landed yet in the cultural conversation, but it’s a solid, gritty crime thriller that plays to both guys’ strengths. There’s a grounded, no-frills toughness to it that I appreciate, and it feels like a conscious attempt to get away from glossy spectacle and back to character-driven tension.
It’s not a masterpiece, but it’s effective, lean, and engaging, and it shows that Affleck and Damon still know how to pick projects that suit them as they get older.
This is one of those mid-’90s indie ensemble movies that exists in a very specific time capsule, and I like it for that. Besides Affleck and Damon, you get: Sam Rockwell, Matthew McConaughey, Mary Woronov, Alyssa Milano, French Stewart, Brendan Fraser, Leah Remini, even Spaulding Gray shows up!
It's uneven, scrappy, and clearly made by people figuring things out, but there’s an earnestness to it that’s hard to dislike. It’s not great, but it’s likable, and it captures a certain slacker-post-college malaise that was everywhere in the ’90s.
Yes, it’s important. Yes, it launched careers. Yes, it won Oscars. And yes, I still think it’s overrated. It’s a good movie, not a great one, and it leans hard into sentimentality and wish-fulfillment.
That said, there’s no denying the performances, and the script does have moments of genuine insight. Damon is very good, Affleck is solid, and the movie absolutely mattered, I just don’t love it the way a lot of people do.
This is nostalgia overload, pure and simple. It’s funny in spots, exhausting in others, and way too long, but there’s an undeniable warmth to it.
It’s Kevin Smith processing his own career, aging, legacy, and fandom, and while it doesn’t always work comedically, it works emotionally more often than you’d expect. Damon and Affleck popping in is part of the fun, but this one is more about reflection than laughs.
A perfectly fine early-’90s drama that feels more important than it actually is. The themes are strong, the performances are earnest, and you can see future stars finding their footing, but the movie itself is stiff and a bit preachy.
It’s interesting historically more than cinematically, and while it has its moments, it never fully comes alive for me.
This one gets a bad rap, but I think it’s mostly just… fine. It’s uneven, sentimental, and definitely mis-marketed, but there’s a sweetness to it that I don’t completely reject.
Affleck is trying something different here, and while it doesn’t always work, it’s not the disaster people make it out to be. It’s flawed, but not hateful.
This one I actively dislike. It’s painfully unfunny, awkward in all the wrong ways, and built around a premise that never sustains a feature-length runtime.
Damon’s involvement feels like a favor rather than a passion project, and the movie itself just grates. There’s nothing charming or insightful here... it’s just annoying.
This is directed by Ridley Scott, which means I don't like it... I don't like it at all. It’s bloated, self-serious, relentlessly grim, and emotionally exhausting without being rewarding.
The Rashomon-style structure is interesting on paper but repetitive and hollow in execution, and the movie mistakes heaviness for importance. This is a slog, and one of the few Affleck/Damon collaborations I have no desire to revisit. Thanks Ridley.
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