The dynamic duo of Matt Damon and Ben Affleck is a classic Cinderella story in Hollywood. At one time, they were two young Boston boys who broke into show business together, playing extras in Field of Dreams in 1989. Within less than ten years, they would go on to win the Academy Award as a pair. Though they have had their share of ups and downs throughout their careers, there is no doubt that when Damon and Affleck share the screen in a movie, the natural brotherhood shines through.
With Netflix’s The Rip marking the duo’s latest effort as on-screen partners, we rank seven of the most meaningful movies featuring Damon and Affleck together, including some humble beginnings and era-defining masterpieces. Left off the list are the aforementioned Field of Dreams, as well as any film roles with either star appearing in the background or a throwaway cameo. The movies highlighted here are the ones that defined the legacy of the Boston-born talents.
7
‘School Ties’
School Ties was more than just a career launch pad for Damon and Affleck. Featuring up-and-coming stars such as Brendan Fraser, Chris O’Donnell, and Cole Hauser, the Robert Mandel teen drama was inspired by future Law & Order creator Dick Wolf’s formative years as a young Jewish boy in the ‘50s struggling to conceal his heritage from an otherwise Anglo student body. Damon embodies the jealous perfectionist student, Charlie Dillon, who grows to detest Fraser’s alienated football star while desperate for attention to please his parents back home.
The film was an early standout for Damon, in contrast to Affleck being relegated to the lesser role of fellow athlete Chesty Smith. Limited to roughly six lines, Affleck is simply just another face in a gang of antisemite prep students making life for Fraser a living hell. Yet, he and Damon lean so well into their antagonist roles that the suspension of disbelief they display would prove vital in future collaborations.
6
‘Jersey Girl’
Despite getting hurt at the box office due to the public backlash towards Affleck and then-girlfriend Jennifer Lopez, Jersey Girl was a sharp departure for director Kevin Smith. The geek-loving creative mind of Clerks and Mallrats aims for a melodramatic comedy in which Affleck’s successful entertainment publicist sees his world flipped upside down when a family tragedy results in shifting responsibilities to him as a single dad to his daughter (Raquel Castro).
Clearly a star vehicle for Affleck, Jersey Girl features several A-list cameos, including Damon as a PR executive opposite Smith regular Jason Lee. The scene is brief with Affleck’s Ollie Trinké in an interview seeking to get back into the game, only to realize he’s there for Damon and Lee’s amusement over a past embarrassing incident. It is by no means a wasted moment, as Damon’s cameo adds to the emotional baggage Affleck carries, making Jersey Girl just one of many films where the two stars naturally bounce off each other.
5
‘Jay and Silent Bob Strike Back’
Jay and Silent Bob Strike Back was for Smith’s View Askewniverse what Avengers: Endgame was to the Marvel Cinematic Universe. Frequent collaborator Affleck pulls triple duty on the 2001 comedy by reprising his comic book creator role from Chasing Amy, playing the voice of a movie studio guard over the radio, and himself. In what ends up being one of the movie’s biggest gags, Affleck and Damon not only poke fun at their newfound Hollywood fame but also take part in a sequel parody to their Oscar-winning hit called Good Will Hunting 2: Hunting Season.
As absurd as any Smith movie, Jay and Silent Bob Strike Back is a celebration of how far the View Askewniverse has come. Damon and Affleck were clearly box office draws by this point in their careers. But they are so in on the joke that being self-deprecating about selling out for the big bucks is a refreshing sight to behold.
4
‘The Last Duel’
The Ridley Scott medieval drama was not only the most ambitious effort to feature Damon and Affleck, but it was also their second produced screenplay alongside co-writer Nicole Holofcener. Taking place in late 1300s France, The Last Duel stars Damon as Sir Jean de Carrouges, who seeks revenge against ex-friend Jacques le Gris (Adam Driver) after the squire is accused of raping the knight’s wife (Jodie Comer). Affleck appears as Count Pierre d’Alençon, the overlord of Sir Jean.
What makes The Last Duel so different from the other films on this list is the contrast. Damon plays to Sir Jean’s misplaced honor, while Affleck leans into the Count’s smarmy wealth and performative charm. Despite the film’s failure at the box office, Affleck told Entertainment Weekly that he still thinks highly of the effort.
3
‘Air’
If The Last Duel fell short of expectations, 2023’s Air soared above them. Serving as star and director, Affleck plays the flamboyant Nike CEO Phil Knight, with Damon as basketball talent scout Sonny Vaccaro. Their mission is to find the right spokesman for the struggling shoe division. The company’s answer comes in the form of a rookie from North Carolina taking part in the 1984 NBA Draft named Michael Jordan.
Air was the perfect representation of Damon and Affleck’s maturity in the entertainment industry. Gone is the tough Boston street banter. Now the two stars breathe life into a professional atmosphere that showcases both Affleck’s confidence as a filmmaker and Damon delivering a tour de force performance, which reaches its peak when Sonny makes a passionate sales pitch to the future Chicago Bulls icon. As the only film where Affleck directed his best pal, Damon told the crowd at the SXSW screening of Air that the film was the culmination of years as collaborations.
“Honestly, it was kind of a natural progression. We’ve written a bunch of movies and produced and acted together for so many years and decades, so it didn’t feel any different, working this way.”
2
‘Dogma’
Controversial at the time of its release for its spiritual themes, Smith’s Dogma had every reason to outrage the religious community. Damon and Affleck’s natural chemistry from Good Will Hunting would be the basis for their roles as Dogma’s main villains, Loki and Bartleby. Together, the fallen angels seek re-entry into Heaven by undoing all of creation through disproving the existence of God. This raunchy, fantasy road comedy featuring Jay and Silent Bob as the leads opposite Linda Fiorentino stretches cross-country from Wisconsin to Smith’s hometown of Red Bank, NJ, marking the View Askewinverse creator’s most ambitious film to date.
Damon and Affleck’s commitment to Smith’s outrageous material is the main aspect of Dogma that keeps it from being mean-spirited compared to most late ‘90s comedies. They play against type with the usually focused Damon being the hysterical personality in contrast to the normally laid back Affleck, exerting a vindictive force of religious conviction. When the pair blow off some steam by gunning down passengers on a bus before Damon’s Loki breaks into a Run-DMC rap, they make the shocking tonal shift work while retaining Smith’s brand of low-brow humor.
1
‘Good Will Hunting’
Gus Van Sant’s Good Will Hunting will forever be the defining moment of Damon and Affleck’s careers. The title character, played by Damon, is a blue-collar MIT maintenance worker from South Boston who would rather get drunk and cause trouble with his pal Chuckie Sullivan (Affleck) than harness his gifted abilities with mathematics. Few can make a breakthrough into Will’s personal defenses until he begins psychotherapy sessions with fellow Southie, Dr. Sean Maguire (Robin Williams).
Damon and Affleck translate their real-life friendship into the character in their Oscar-winning screenplay. Each of their scenes together feels earnest and real without being overbearing. The one instance in which Affleck’s Chuckie reveals how he wants to live a day without his best friend answering the door when he knocks is one of the purest depictions of true friendship ever captured on film. It exemplifies the way in which Damon and Affleck have supported each other’s ambitions then and remain true to this day.
- Release Date
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December 5, 1997
- Runtime
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126 minutes
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