Every Matt Damon and Ben Affleck movie is wildly different from the last, but they’re always endlessly entertaining. The two actors are a couple of the biggest movie stars in the world, but they also happen to be life-long best friends who owe each other’s prolific careers to what they’ve managed to accomplish together, especially in their early years. While Affleck and Damon achieved great success individually, their names will forever be synonymous with each other, considering their impeccable on-screen chemistry and the acclaimed projects they’ve also either written, directed, or produced together.
Most of the films Affleck and Damon collaborated on have been major successes, both critically and commercially, and have gone on to be some of the most iconic and recognizable films in recent history. Together, the two have won Academy Awards, and following Air, they might need to make space on their mantels for even more statuettes come award season. However, there have also been a few movies that may have flown under the radars of general audiences. Either way, every Matt Damon and Ben Affleck movie deserves more love and attention in some capacity
9 Field Of Dreams (1989)
Not many sports movies have been nominated for Best Picture at the Oscars, but Field of Dreams was more than worthy of that honor. However, it’d be easy to completely miss Affleck and Damon’s uncredited appearances, as both actors portray spectators during the baseball game at Fenway Park attended by Kevin Costner and James Earl Jones’ characters. It was a secret for years, but Damon confirmed that he and Affleck agreed to be extras in the film just for the opportunity to visit Fenway (via Dan Patrick Show). Field of Dreams is undoubtedly a classic but in terms of the “best Damon and Affleck movies,” it barely counts.
8 Jay & Silent Bob Reboot (2019)
Jay & Silent Bob Reboot is more or less the same as Jay and Silent Bob Strike Back, with the titular characters venturing out to stop a movie reboot of “Bluntman and Chronic” while running into all sorts of hilarious obstacles and celebrity guest appearances. Damon reprises his role as Loki from Dogma in a cameo, while Affleck returns to his role as Holden from Chasing Amy in another cameo. The actors don’t share any scenes, and not only is the film on the bottom end of every Matt Damon and Ben Affleck movie ranked, but Jay & Silent Bob Reboot is one of the worst View Askewniverse movies too.
7 Jay & Silent Bob Strike Back (2000)
After four movies of playing second fiddle to other characters, Jay and Silent Bob were finally given a chance to hog the spotlight for the first time in Jay & Silent Bob Strike Back, and director Kevin Smith uses it to satirize Hollywood. Affleck and Damon’s cameos are hilariously irreverent, as they play fictionalized versions of themselves alongside Damon as they film a scene for the excessively violent and non-existent Good Will Hunting sequel, Goodwill Hunting 2: Hunting Season. Playing into the satirical nature Jay & Silent Bob Strike Back also brilliantly sees Good Will Hunting director Gus Vant Sant shown counting his money.
6 Chasing Amy (1997)
Following Mallrats, where Affleck played a supporting villainous role, Kevin Smith had him cast as the lead role in his unconventional romantic dramedy, Chasing Amy, while also finding a way to work in Damon as well. In the film, Affleck plays a comic book artist who falls in love with a lesbian woman, causing a strain on his friend and creative partner. Chasing Amy contains some of the most heartfelt moments in the View Askewniverse, and Affleck’s performance is especially effective and extremely authentic. Damon only shows up for one brief scene, but his role is meant to be more of a wink to audiences than anything.
5 School Ties (1992)
Not every Matt Damon and Ben Affleck movie, sees the actors share screen time, but School Ties was the first movie that showcased how great they are together, and the 1992 movie launched both of their careers into orbit. School Ties tells the story of a Jewish prep school student in the 1950s, tackling heavy-hitting topics of antisemitism and prejudice. The film was made as a vehicle for Fraser, but Affleck and Damon are stand-out performers as two of Fraser’s antisemitic classmates. Though the sociological sports drama deals with hard-hitting themes, it’s also fun to see a group of now big-name stars in the infancy of their successes.
4 The Last Duel (2021)
Directed by Ridley Scott and based on true events, The Last Duel is widely considered one of the most overlooked films of 2021. The movie also happens to be the first screenplay that Affleck and Damon had written together since Good Will Hunting over twenty-four years prior. The Last Duel received critical praise but was a box-office bomb, failing to even make its budget back, despite being one of the best historical epics from Ridley Scott. The medieval drama is also an extremely compelling and haunting allegory for the “#MeToo” movement, and it’ll likely become a cult classic in years’ time.
3 Dogma (1999)
Almost every Matt Damon and Ben Affleck movie is directed by Kevin Smith as Dogma is another Smith-directed satire. The 1999 comedy is about a woman struggling with her Catholic faith, who is sent on a “holy crusade” to stop a pair of fallen angels from entering Heaven and negating all existence. Affleck and Damon star as the two angels, Bartleby and Loki, and their chemistry has never been more believable. The film was a subject of controversy, but it still received favorable reviews and was a modest box office success. Affleck and Damon masterfully combine their dramatic talents with their incredibly strong and often underused comedic sensibilities.
2 Air (2023)
Air was the real on-screen reunion between the two actors/best friends, as while they wrote The Last Duel, there wasn’t much fanfare when they were on screen. The 2023 movie, on the other hand, sees Affleck and Damon busting each other’s chops for the first time in years. Air is such a funny and smart biographical drama, as it follows Nike’s attempt to sign Michael Jordan in the mid-1980s. Affleck plays Phil Knight who haphazardly runs the sports brand, and Damon plays Nike’s talent scout. The movie marks the first time Affleck directed Damon, and it couldn’t have turned out better, as it led to a sure instant classic.
1 Good Will Hunting (1997)
Between the countless memorable quotes, the surprisingly hilarious scenes, and other sequences that feel like a complete emotional gut punch, Good Will Hunting is a modern classic. the legendary performance by Robin Willaims is often the noted highlight of the film, the real magic comes from the screenplay, which was written by the two actors. Both actors pull off their respective roles flawlessly when it comes to their acting, but the story they crafted is incredibly moving and their dialogue is natural and realistic. Its Oscar win for Best Original Screenplay was well-earned, and out of every Matt Damon and Ben Affleck movie, Good Will Hunting is perfect.
