Every Ben Affleck & Matt Damon Movie, Ranked From Worst To Best

Over the years, Hollywood has delivered an abundance of memorable on-screen partnerships — Bob Hope and Bing Crosby, Jack Lemmon and Walter Matthau, Paul Newman and Robert Redford, Katherine Hepburn and Spencer Tracy, and Tom Hanks and Meg Ryan, among many others. Over 30 years after their first collaboration, it's probably safe to add Matt Damon and Ben Affleck to the list. 

Together, the dynamic duo have produced memorable entertainment aplenty, putting their remarkable chemistry to good use in everything from Kevin Smith's "Dogma" to Affleck's "Air." These guys have teamed up on nearly a dozen projects, even for a brief cameo or minor supporting role. Recently, their partnership has intensified with the aforementioned "Air" and Ridley Scott's "The Last Duel," it's a shame they haven't found more films to work on together over the years, because these boys are wicked smaht.

To celebrate this long-running partnership, we decided to rank the films in which Damon and Affleck appear together from worst to best. How do you like them apples!  

Yes, Affleck and Damon are apparently in Phil Alden Robinson's classic baseball drama "Field of Dreams." Good luck finding them, however, as they don't actually appear on screen. Instead, they served as extras during the Fenway Park bit where Kevin Costner's Ray Kinsella, seated alongside the late, great James Earl Jones, receives another essential message from a mysterious voice. According to Damon, in an interview with Dan Patrick, he and Affleck just wanted to go to Fenway. Remarkably, the pair struck up a five-minute conversation with Costner, picking his brain about the movie business. Even crazier, Costner remembers meeting them, as recounted in an interview with Jimmy Kimmel.   

That said, considering their lack of a prominent appearance in the popular film, we decided to list "Field of Dreams" as an honorable mention. Had they enjoyed screen time, this entry would've made it close to the top. "Field of Dreams" is an absolute classic, brimming with cinematic magic, and one of the all-time great endings. So, next time you watch, remember that this fabulous film played a part in creating Affleck and Damon's massive careers.

Also, as a side note, Affleck went on to work with Robinson on "The Sum of All Fears." 

A wannabe "Reality Bites," 1995's "Glory Daze" is probably best remembered for its stunning ensemble of rising superstars, chief among them being Affleck and Damon (the latter in a brief, non-speaking role), along with Sam Rockwell, French Stewart, Alyssa Milano, Matthew McConaughey, Brendan Frasier, and Leah Remini — hopefully, the casting director received some sort of compensation somewhere down the line.

Otherwise, this throwaway comedy from Rich Wilkes, of "Airheads" and "xXx" fame, lacks the punch of similar Gen X flicks. The plot revolves around a group of college kids staring down the cold reality of life on the eve of graduation. None, specifically Jack Freeman (Affleck), is ready to move on, while others rush to fulfill unrequited love or create new memories before their time at school expires.

It's not a terrible film, but it has nothing new to say, and it doesn't make the most of its large ensemble. Still, there's enough here to warrant a look, provided you keep expectations in check. "Good Will Hunting" this ain't, folks, though we'll recommend it to anyone yearning to see their favorite stars yucking it up '90s style. 

Damon and Affleck spent a good deal of their early careers drifting in and out of Kevin Smith's filmography, eventually culminating in 1999's "Dogma." Both would feel a particular dedication to the man who helped shape their careers and occasionally toss him a bone or two. Unfortunately, what started as a beautiful partnership devolved into 2019's "Jay and Silent Bob Reboot," a "satisfying but clumsy" comedy that tried a little too hard to rekindle the magic of Smith's early films but lacks the ingenuity necessary to pull off the feat.

In an act of overt fan service, which, let's be honest, is basically "Reboot" in a nutshell, Affleck and Damon reprise their roles from "Chasing Amy" and "Dogma," respectively, and they each explain what they've been up to in the years since. Affleck's Holden McNeil decided to have a child with ex-girlfriend Alyssa Jones and has fully embraced fatherhood. In perhaps the film's best scene, the actor delivers a heartwarming monologue — at Comic-Con, no less — about being a father that resonates deeply. Damon, on the other hand, reveals that Loki, the fallen angel, survived the events of "Dogma" and returned as both Matt Damon and, humorously, Jason Bourne. It's all for the sake of nostalgia and harmless fun for fans of the View Askewniverse, but it's a far cry from Smith, Damon and Affleck's best work together.   

Better than "Reboot" by a longshot, "Jay and Silent Bob Strikes Back" sees Kevin Smith and Jason Mewes' foul-mouthed protagonists set off on a quest to prevent a comic book film based on their likeness from destroying their image. Along the way, they bump into past View Askewniverse characters, including Affleck's Holden McNeil and, in a terrific cameo, Damon as Will Hunting, currently shooting "Good Will Hunting 2: Hunting Season," which also includes Affleck reprising his role. The pair recreate the famous bar scene from their Oscar-winning drama — "Do it for the paycheck," Damon tells his friend before the cameras roll — except this time, rather than participate in a verbal joust with Clark (Scott William Winters), they blow the poor guy away with a shotgun. Yeah, it's that kind of film.

Again, like most of Smith's work, you're either in on the joke or not. Luckily, "Jay and Silent Bob Strikes Back" is pretty damn funny, with notable appearances from Jason Lee, Will Ferrell, Carrie Fisher, Chris Rock, and Mark Hamill.

1992's " School Ties " is heavy-handed with its messaging to a fault, but it's no doubt compelling. It sees David Greene (Brendan Frasier), a young Jewish boy, incur bigotry during his senior year at a Massachusetts prep school. In a meaty co-starring role, Damon plays the main antagonist, Charlie Dillon, while Affleck appears in a minor part as Chesty Smith, another in a long line of cruel young men who make David's life a living Hell. Will our young victim rise against his attackers or flounder against adversity?

"School Ties" could have been done with a little more nuance. Director Robert Mandel lays it on thick, hits a couple of emotional high notes and gleans the most from its impressive ensemble, even if it took three tries to nail the ending. Damon, in particular, plays a terrific villain, displaying the exact wormy, self-serving nature that he would use to significant effect in Martin Scorsese's "The Departed" nearly 15 years later. 

Co-starring Chris O'Donnell and Cole Hauser, "School Ties" delivers solid, albeit predictable, drama that became a breeding ground for Hollywood superstars.

The highest-grossing film in the View Askewniverse, "Dogma," offers an irreverent takedown of Catholicism through a story about a pair of fallen angels attempting to work their way back to heaven. What follows is a surprisingly thoughtful, albeit hilarious, story about faith, redemption, and the importance of free will, crafted by Kevin Smith's righteous hand.

Affleck and Damon star as Bartleby and Loki, two angels exiled from Heaven after failing to fulfill their chosen duties. Luckily, they discover a loophole that allows them to return home, but it requires going against the very fundamentals of God and would lead to the destruction of mankind. Naturally, only Jay and Silent Bob, a disillusioned Catholic named Bethany (Linda Fiorentino), an apostle (Chris Rock), and a muse (Salma Hayek) can save the day.

"Dogma" affords Affleck and Damon the chance to show off their superstar charismas, and the duo delivers the goods with well-honed performances that capture the essence (and humor) of their character's plight. At the very least, they look like they're having an absolute blast, as is Smith, who creates perhaps the most comic book movie of his career. Co-starring Jason Lee, Alan Rickman, and Alanis Morissette, "Dogma" is a blasphemous good time.

If you missed out on its release 25 years ago, fret not for Smith has big plans for "Dogma" in the coming years, now that it's finally in his control. 

Our final entry in Damon and Affleck's collaboration with Kevin Smith is the director's best work. This thoughtful dramedy stars Affleck as Holden McNeil, a comic book artist who falls for a writer named Alyssa (Joey Lauren Adams). Problems arise when Holden discovers that Alyssa is a lesbian, resulting in a complicated relationship that shakes the very fabric of his life, notably his friendship with his best friend Banky (Jason Lee). As is typical, Smith tackles complex issues with his trademark bluntness but reveals a softer side not typically seen in his features.

As for Affleck, Holden remains perhaps his trickiest role, playing a flawed protagonist whose decisions hurt everyone around him. Yet, we empathize with him as he struggles with self-doubt and root for the man to succeed despite his immaturity. As for Damon, the young actor only appears in a minor cameo as an executive working to turn Holden and Banky's comic book into a multimedia franchise. It's a short but pivotal scene that adds an extra layer of drama to the proceedings — does Holden sell out or continue serving as a true artist? 

The most unique film on this list, Ridley Scott's "The Last Duel," looks at a heinous crime from three perspectives. Set in medieval France, the film stars Matt Damon as Jean de Carrouges, a seemingly virtuous knight who accuses his former friend, Jacques Le Gris (Adam Driver) of raping his wife, Marguerite (Jodie Comer). At first, we see this story play out from Jean's point of view and witness a man struggling to maintain his virtue in an unjust world. Later, however, we see the same narrative from Jacques' perspective and finally from Marguerite and learn that this particular scenario is far more complicated than initially presented.

Affleck co-stars as the hedonistic Count Pierre d'Alencon, a morally ambiguous overlord whose actions exacerbate the situation. This leads to a violent trial by combat in which Jean and Jacques battle each other to the death. Though difficult to watch given its subject matter, "The Last Duel" nonetheless is a powerful exploration of truth, honor, and justice, and it's "prestige period filmmaking" told with panache by a master filmmaker.

If you're looking for a fun cinematic exercise, watch "Good Will Hunting" and immediately follow it up with a viewing of 2023's "Air," just to see how Damon and Affleck have changed as actors. That's not a critique of their work in their Oscar-winning 1997 drama, but seeing how they've evolved over the years is fascinating. Modern-day Damon is far more nuanced and can convey much with a simple expression. Affleck can quickly morph from a charismatic buddy to a world-weary man harboring painful inner demons. Life does that to a guy.

As for the film, "Air" is a terrific true-life tale brought to vivid life by Alex Convery's sharp script, Affleck's energetic direction, and fine performances from the impressive ensemble — namely, Damon, Affleck, Jason Bateman, Marlon Wayans, Chris Messina, Chris Tucker, and Viola Davis. The story revolves around Nike's courtship of Michael Jordan to endorse their new basketball shoe line, a marriage culminating in millions for the company and its crass executives. Damon takes the lead as Sonny Vaccaro, who is responsible for securing the deal, while Affleck plays Nike co-founder and CEO Phil Knight. 

Together, the two stars create a thoroughly captivating, though under appreciated, business drama that effectively celebrates the Nike brand.    

The obvious choice for No. 1 on this list, "Good Will Hunting," wracked up a slew of Academy Awards, including Best Screenplay for Damon and Affleck, earned a killing at the box office, and instantly catapulted Damon and Affleck to superstardom. At the time, each had already caught the eye of the moviegoing public thanks to prominent roles in films such as the aforementioned "School Ties," as well as "Courage Under Fire" and "The Rainmaker." But "Good Will Hunting" changed everything, transforming them into bonafide superstars that Hollywood took full advantage of.

Following Gus Van Sant's picture, Damon earned gigs in Steven Spielberg's "Saving Private Ryan" (though he was actually cast before his newfound fame) and eventually scored "The Bourne Identity" and "Ocean's Eleven" franchises. He has since worked with iconic directors like Martin Scorsese and Christopher Nolan. Affleck starred in the blockbuster "Armageddon," and became a critically acclaimed director, earning an Academy Award for Best Picture on "Argo."

Damon stars as Will Hunting, a troubled teen who happens to be a secret mathematical genius. After attacking a police officer, Will is forced to see a shrink (Robin Williams), forming an unlikely friendship that places him on a better path. Co-starring Affleck, Stellan Skarsgård, Minnie Driver, and Cole Hauser, this uplifting drama celebrates the power of self-discovery and second chances. And don't even get us started on that ending. It's one for the ages.