I’m lucky enough to live in a world where Matt Damon and Ben Affleck have been in my life for my three decades on this Earth. On their own, Damon is the more versatile movie star, while Affleck is clearly the best director, but together, these best friends bring out the best in each other. They’ve reunited once again for “The Rip” (released January 16, 2026), an action thriller where they play Miami cops who find $20 million in a raid, sparking a standoff against the forces after the cash. In honor of their latest collaboration, here is the definitive ranking of their best work together.
At a Glance: Top Damon & Affleck Movies
• “Good Will Hunting”: The Oscar-winning breakout.
• “The Last Duel”: A gritty, Ridley Scott-directed epic.
• “Air”: The story behind the Air Jordan brand.
• “Dogma”: Kevin Smith’s religious satire.
• “School Ties”: Their first major on-screen pairing.
5. ‘School Ties’
Before Damon and Affleck became A-list stars, they played second fiddle to Brendan Fraser in “School Ties.” David Greene (Fraser) is a Jewish teenager recruited to play football at a prestigious prep school. For fear of antisemitism, David chooses to hide his religious views from the other students.
Damon portrays the antagonist, Charlie Dillon, a fellow student who harasses David and insults his Jewishness. Affleck is relegated to a minor role as Charlie’s friend and fellow antisemite. In the Matt and Ben partnership, this movie belongs to Damon, who thrives as the conniving villain and ideal foil for Fraser’s David. Although I don’t think Damon has a future as an NFL running back. Charlie Dillon walked so Tom Ripley could run.
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4. ‘Dogma’
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Affleck is Kevin Smith’s guy, having starred in numerous View Askewniverse productions, including “Mallrats” and “Chasing Amy.” In “Dogma,” Affleck brought Damon into the fold to play a pair of fallen angels in Smith’s religious satire. Because of a loophole in Catholic dogma, Bartleby (Affleck) and Loki (Damon) head to a New Jersey church to gain re-entry into heaven.
Ironically, Bethany Sloane (Linda Fiorentino), the woman tasked with stopping the duo, works as an abortion clinic counselor. With the help of two prophets, Bethany fights to save humanity by preventing Bartleby and Loki from entering the Church. Part of me wishes Affleck and Damon played despicable heels more often — they clearly have fun playing the bad guys. Plus, the duo’s chemistry flourishes in Smith’s dialogue-focused, riff-heavy script.
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3. ‘Air’
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As the Bostonians hit their 50s, Damon and Affleck are deliberately choosing to work on more projects together. For his first directorial effort since 2016’s “Live By Night,” Affleck helmed a dramatization about the recruitment of Michael Jordan to Nike in “Air.” Talent scout Sonny Vacaro (Damon) convinces CEO Phil Knight (Affleck) to go all in on Jordan, who would later go on to become an NBA legend.
Sonny quickly learns that Jordan’s mother, Deloris (Viola Davis), is the one he needs to convince to secure the generational basketball star for Nike. On paper, a movie about Jordan without basketball action shouldn’t work. Yet “Air” is such a delight thanks to a star-studded cast, Affleck’s steady direction, and an inventive script.
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2. ‘The Last Duel’
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“The Last Duel” deserved better. It was the first movie that Damon and Affleck co-wrote since “Good Will Hunting.” Nicole Holofcener (“Can You Ever Forgive Me?”) also contributed to the script. Ridley Scott, a living legend, directed the epic historical drama about the last judicial duel in France. The cast featured Damon, Affleck, Jodie Comer, and Adam Driver. Told in three unique chapters, “The Last Duel” recounts the judicial duel between Jean de Carrouges (Damon) and Jacques le Gris (Driver) following the latter’s alleged rape of Jean’s wife, Marguerite (Jodie Comer).
The ideal ingredients for a smash hit were present, but it didn’t matter, as “The Last Duel” flopped at the box office. Financial misgivings aside, “The Last Duel” is a violent medieval drama that tackles power dynamics, systemic abuse, and gender norms. It’s not for the faint of heart, but viewers will be rewarded with a showcase for talented actors operating at elite levels.
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1. ‘Good Will Hunting’
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The best Damon and Affleck collaboration is still their most famous movie, “Good Will Hunting.” It’s the movie that catapulted the duo into another stratosphere. Damon and Affleck wrote what they knew by setting the drama in their home city of Boston. The brilliant Will Hunting (Damon) works as a janitor at MIT when one of the professors (Stellan Skarsgård) discovers his mathematical genius. To avoid jail, Will agrees to attend therapeutic sessions with Dr. Sean Maguire (Robin Williams).
For a movie featuring some stereotypical Boston tough guys, “Good Will Hunting” has a lot of heart, especially during the emotionally charged conversations between Will and Sean. It’s a must-watch for anyone who feels lost or underseen in their life. Now, if you’ll excuse me, I have to go see about a girl. In this situation, the girl is in the video of Damon and Affleck thanking the entire city of Boston in their Oscars’ acceptance speech.
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