Ben Affleck & Matt Damon’s Collaborations, Ranked — Will ‘The Rip’ Rip Up the List?

This fantasy sports drama comes in last place on the ranking not because it’s a bad film — to the contrary — but because Affleck and Damon were Fenway Park extras who aren’t even visible in the final cut. Kevin Costner does remember meeting the then-teenagers, though. “They were sitting in the stands, like college guys. And they would both lean in at the same time, lean back at the same time, look at each other at the same time,” he said on Jimmy Kimmel Live. “We talked, and they had this big enthusiasm. They were on fire.”

A deep cut from Affleck and Damon’s résumés is this coming-of-age comedy about Santa Cruz roommates contemplating their post-college future. Affleck is the top-billed star; Damon is peripheral as a character with a long name — that’d be Edgar Pudwhacker — and short screen time. Glory Daze didn’t have glory days at the box office. Amid negative reviews from critics, it earned a little over $15,000 from moviegoers.

Perhaps Affleck and Damon are relieved Miramax shelved this poorly-reviewed rom-com, which they executive-produced and had small parts in. Luke Wilson plays Stanley, a man who finally gets a date with workplace crush Diana (Denise Richards), but their night out together is derailed by a meddling homeless man (Jay Lacopo). Affleck played a friend of Stanley’s, and Damon played an ex of Diana’s, but despite the star power, The Third Wheel never rolled into U.S. theaters.

Not only is Jersey Girl one of director Kevin Smith’s worst-received films, both critically and commercially, but Damon again only has a cameo. In the comedy-drama, Affleck’s publicist character has to navigate a new chapter in his life after becoming a widower and a single father, with Jennifer Lopez playing his late wife during the era of Bennifer 1.0. Damon, on the other hand, has a brief appearance as a PR exec who denies him a job.

Affleck joined Smith’s View Askewverse in Mallrats, and he brought Damon on board for this next film in the series. In the story, Holden (Affleck) meets and falls for Alyssa (Joey Lauren Adams), a lesbian fellow comic book creator. The film got a warm reception, but queer viewers are still debating the storyline’s productive-versus-problematic ratio. And yet again, Damon is barely onscreen, playing a TV executive hoping to make a cartoon out of Holden’s comic.

Here, at last, it’s Damon who has a larger role than Affleck. As Brendan Fraser plays a Jewish football player struggling to fit in at a Protestant prep school, Damon plays a bully who leads the harassment against him, while Affleck plays another brute of a student (whose name is Chesty, we kid you not). School Ties was a decent movie and a springboard for Affleck and Damon, but it was a breakout job for Fraser.

Affleck returned as his Chasing Amy character in this buddy action comedy in Smith’s View Askewverse. As the title characters realize Holden’s comic, which they inspired, is being turned into a movie without their profit participation, they seek justice. That leads them on a rampage throughout Hollywood, where one of the films in production is Good Will Hunting 2: Hunting Season, bringing Damon into the mix and giving Affleck yet another character in the film.

Not only did the Jay and Silent Bob sequel prove a worthy successor to the original for fans of the stoner duo — nearly two decades later, no less — Smith’s follow-up comedy also offered a coda to Holden and Alyssa’s Chasing Amy storyline and a meta monologue by Damon. He appears as Loki, his Dogma character, and says his “re-Bourne identity” was Jason Bourne

Affleck and Damon shared top billing for the first time in this Smith film, playing fallen angels determined to get back into heaven, even if doing so proves God is fallible and undoes all earthly existence. Some Catholic activists decried the film as blasphemous — and Miramax pawned off Dogma to another distributor amid the controversy — but Dogma actually straddles the line between satire and sincere exploration of faith.

Alongside Nicole Holofcener (Enough Said), Affleck and Damon adapted Eric Jager’s book of the same name into a historical epic drama. Never mind Affleck’s bleached-blond hair and goatee and Damon’s mullet in the film — under Ridley Scott’s direction, the two men join Jodie Comer and Adam Driver in an interesting, perspective-shifting, he-said-she-said story ending, of course, in a duel to the death.

Who knew a sneaker could have its own big-screen origin story? Affleck and Damon co-headlined this biopic, with the former playing real-life former Nike CEO Phil Knight and the latter playing marketing exec Sonny Vaccaro as the two men work to create the Air Jordan. Under Affleck’s direction, both actors turn in solid performances, even if they get upstaged by Viola Davis in the role of Michael Jordan’s mom.

Affleck and Damon’s best collaboration is, undoubtedly, the film for which they both won the Academy Award for Best Original Screenplay — and got Robin Williams a Supporting Actor Oscar, too. Damon plays the titular parolee with mathematical genius, Affleck plays the blue-collar friend who wants a better life for Will, and Williams plays the psychiatrist who helps Will get there. It’s a heartfelt story with moving performances from all three.