Toward the end of his career, the great silent film star Buster Keaton was struggling. A life of hard drinking and grueling physical comedy had taken its toll. He couldn’t pull off his most outlandish stunts anymore, and Hollywood wasn’t begging to see him star in anything. But he still loved to work, so he took to cameos. He played a train conductor in the Oscar-winning Around the World in 80 Days, and showed up in a series of “beach musicals” with Frankie Avalon and Annette Funicello. Most famously, he lent credibility to Billy Wilder’s classic Hollywood satire Sunset Boulevard as an uncredited poker player.
After Keaton retired, the cameo reverted to being a reliable tool for filmmakers looking to give their audience a jolt of energy. Some films seemed to be built around cameos, like The Muppet Movie or The Wiz. This was especially true of Hollywood satires like This Is the End or The Player, which almost certainly holds the record for most cameos per minute. But the idea of a cameo artist—that is, a film star who specializes in cameos, and understands how to make an impact in one minute or less—was lost until a young man from Boston took up Keaton’s torch, and carried it farther than anyone else had.
Matt Damon has more cameos than most actors have credits. He started doing them before he was famous—he has a nonspeaking role in the Ben Affleck–starring Glory Daze, released two years before Good Will Hunting. Unlike the odd movie star who pops into a major blockbuster just to remind us of their power, Damon takes his cameos seriously. He’s there to act, not just to be seen.
The cameo, typically understood as a one-scene appearance by a recognizable actor who doesn’t appear in the film’s marketing, is a skill in short supply these days. Like nearly every other corner of our cinematic landscape, the cameo has been transformed by the comic book film. I bet when most moviegoers hear the word “cameo,” they think of Stan Lee, who appeared in every Marvel film until his death in 2018 (perhaps more seasoned moviegoers will cite director Alfred Hitchcock, who appeared in nonspeaking roles in a majority of his work). But Marvel has also degraded the cameo through its post-credits stingers, which often feature characters from upcoming Marvel properties. It is well-understood that characters have usurped movie stars as the viewer’s primary draw; the Spider-Man suit is more important than who’s under it. That same thing has happened to the cameo.
Damon has avoided comic book movies, except for the occasional cameo, like in this year’s Thor: Love and Thunder, but even in those films, he’s working hard to assimilate into the film’s overall tone, rather than stand out from it. He’s the last of a dying breed, a true cameo artist—and as a ranking of his work as a Hollywood day player will reveal, he’s the best who has ever done it.
16. Jay and Silent Bob Reboot
You can learn a lot about an actor from their cameos. For example: Matt Damon values loyalty. He has been married to the same person since 2005. He has stuck with his buddy Ben through good times and bad. And he just keeps working with Kevin Smith, no matter how trivial the role or inconsequential the film. In the latest Smith Family Circle Jerk, Damon returns to the role of Loki, his earthbound angel from Dogma, and rattles off a few flat jokes about the Marvel Cinematic Universe (“I was Loki in the ’90s before it was cool, and I did it without the fake British accent”) and some awful puns about The Bourne Identity. Even in Smith’s world, where callbacks routinely substitute for story, the blatant attempt to capitalize on Damon’s celebrity feels shockingly cynical—his little monologue adds nothing and was clearly added simply because Damon made himself available for a couple hours. Still, there may be no greater testament to man’s capacity for loyalty.
15. The Third Wheel
And a theme emerges: Loyalty can backfire. The Third Wheel stars and was written by Jay Lacopo, who was also in Affleck’s 1993 short film I Killed My Lesbian Wife, Hung Her on a Meat Hook, and Now I Have a Three-Picture Deal at Disney. Affleck trusted Lacopo; that’s why he took a part in The Third Wheel. Damon trusts Affleck; that’s why he agreed to a cameo. Unfortunately, it’s a profoundly misguided comedy about a date between coworkers played by Luke Wilson and Denise Richards (imagine the sizzling chemistry!) that gets repeatedly interrupted by a houseless person (Lacopo) that Wilson hits with his car. As a vile ex-boyfriend, Damon channels the slithery energy he brought to his bigoted preppie in School Ties. That he’s even less likable here is an accomplishment, but it’s an insignificant moment in an utterly forgettable movie.
14. Chasing Amy
Ah, the rare cameo-in-retrospect. When Chasing Amy came out in March 1997, just nine months before Good Will Hunting, Damon wasn’t yet a movie star, so his scene as a TV exec who threatens to corrupt the idealistic Holden McNeil (Ben Affleck) by turning his comic book into a shitty animated series wouldn’t qualify as a cameo. He wasn’t famous enough yet. But Chasing Amy made only $12 million at the U.S. box office before finding its audience on DVD, and by then the grinning mugs of Affleck and Damon were plastered on every magazine cover in America. Which is to say, the categorization of this particular cameo is more notable than the cameo itself, which is unremarkable in just about every way. If you ever wanted to hear Damon say, “Snootchie bootchies,” however, this is probably your one and only chance.
13. Che: Part Two
Steven Soderbergh’s bifurcated epic about the Cuban revolutionary is, for better and for worse, driven by Guevara’s collectivist ideals. It’s the rare biopic in which no one stands out—not the charismatic leader at the center of its plot or the enormous movie star who appears in a single scene. Damon pops up about halfway through the second film as a German priest in Bolivia who negotiates with the rebels to provide safety for his town. In keeping with the film’s modest ethos, Damon first appears with his back to the camera and is then viewed entirely in a long shot. It’d be easy to miss him altogether, making this a rarely anonymous cameo (though not a particularly useful one).
12. Finding Forrester
I have a theory about Finding Forrester. On the surface, it’s a blatant cash grab by director Gus Van Sant, capitalizing on the success of Good Will Hunting by directing an inferior script about another young genius from the wrong side of the tracks who gets mentored by a bearded white guy. How could an indie stalwart like Van Sant make something so cheap and hollow? I think the guy who directed a shot-for-shot remake of Psycho two years earlier saw Forrester as another art project, in which he demonstrates how badly the studio system can corrupt a good idea by corrupting a good idea himself. Damon’s late-breaking cameo as a bland estate lawyer is the punchline of the joke. He delivers an impish grin, then a solemn face, followed by a few lines of exposition, offering nothing to the film except a poignant reminder of the better one that preceded it. Either it’s on purpose or it’s just one of the worst things Damon and Van Sant have ever been a part of.
11. Confessions of a Dangerous Mind
For George Clooney’s directorial debut, the probably fictional story about a game show producer who claimed to have led a double life as a CIA agent, he called in favors from two of his Ocean’s Eleven costars. In a scene depicting the filming of an episode of The Dating Game, the camera pans over the first two contestants—played by Damon and Brad Pitt—before landing on the comparatively ordinary third contestant, who wins the date over his hunky competitors. Good for Damon for being in on the joke, but it’s hard to give Damon too much credit for this one, since all he had to do was sit there and look good.
10. Youth Without Youth
Movie stars are the quintessential American export, so if you’re going to have a minor character who represents the American experience in your European-set film, you need a movie star to play him. Youth Without Youth is a late-period classic by Francis Ford Coppola, who directed Damon in 1997’s The Rainmaker. Here, Damon shows up as a reporter from Life magazine who tracks down Dominic Matei (Tim Roth), an aging academic who was transformed after being struck by lightning and is in hiding from the Nazis, who suspect they can harness his mutation to win the war. It could have been a first-rate thriller, but Coppola is after something more dreamlike. Anyway, Damon cuts through the clutter in his brief appearance. After encountering Matei in a casino, he aggressively courts him for a story, even offering him government protection if he acquiesces. It’s impossible to tell if he’s an earnest patriot hoping to draw Matei toward the right side of history or a bloodthirsty leech angling for a Pulitzer. Damon’s blend of effortless charm and subtle force paints an ambiguous, compelling portrait in just a few swift strokes.
9. Jersey Girl
In Kevin Smith’s underloved dad-com, Damon pops up as a film industry PR hack, a gatekeeper for Ollie Trinke (Ben Affleck), who, after quitting the biz to raise a child, is trying to get back into the game. It’s a variation on the part Damon played in Chasing Amy: a frat bro in a suit representing the sleazy side of the entertainment world. And Damon doesn’t half-ass it. He gives it his full ass. He does not wink to the camera as if to say, “Look, it’s me, movie star Matt Damon.” Instead, he approaches each cameo like an actor. Here, his gleeful delivery of, “You went apeshit. You trashed your client back to the stone age!” is pitch-perfect. It’s the kind of thing that would get a day player noticed, but for Damon, it’s just another day at work.
8. Thor: Ragnarok
The best cameos come with an element of surprise, and there was nothing more unexpected than Damon popping up in Thor: Ragnarok. He had never been in a superhero movie, let alone the Marvel Cinematic Universe, but there he was in the first act as an actor playing Loki (opposite Luke Hemsworth, Chris’s brother, playing Thor) in an Asgardian play put on for the real Loki’s benefit. Damon delivers his lines with aplomb (“I’m a trickster!”), and his early appearance in the film sets the stage for its devil-may-care attitude. Ultimately, though, the real delight here is simply spotting Damon in a place he never belonged, right up until he did.
7. Thor: Love and Thunder
Can you have a cameo franchise? Damon may be the first to do it, reprising his role as “Actor Loki” in the latest MCU installment. In an early scene, he performs on a New Asgard stage with Sam Neill, Luke Hemsworth, and another star whose appearance I won’t spoil here, re-creating a scene that played out in Thor: Ragnarok. Damon hams it up good and proper, but the real surprise comes later, when he shows up again as the same actor, this time out of character, pitching an idea for a new play based on more recent events to a distracted Valkyrie. Damon basically plays himself here—a dedicated actor, passionate about a project—but his expanded cameo brings us what we rarely see in the MCU: a glimpse outside the main story into the lives of its ancillary characters. It’s enough to make you dream of the Robert Altmanesque MCU ensemble piece that could be.
Appearing in flashback in Soderbergh’s thriller about a woman who is involuntarily committed to a mental hospital where—oops—her stalker happens to work as an orderly, Damon plays a Boston police officer who advises Sawyer (Claire Foy) on the changes she must make to her routine to protect herself from this potentially violent creep. Outside of the Boston connection, there’s nothing here to attract Damon—and, strangely, he doesn’t even do the accent—but he nails the scene anyway, matter-of-factly laying out the many ways Sawyer’s life is about to change without considering the new, awful reality he’s revealing to her. A lesser actor would have made the detective a more caring and empathetic figure, but Damon’s dispassionate portrayal perfectly fits the film. He’s just another man who is blatantly insensitive to Sawyer’s needs.
How many movie stars would be willing to play a coward like Dr. Mann? An unbilled coward, no less? In Christopher Nolan’s sci-fi epic, Damon plays an astronaut who, we are told, was sent to investigate a planet to determine its viability for human colonies. He knew it was a potential one-way ticket, but after finding nothing worth writing home about, he gets lonely, falsifies his data, and sends for another team, wasting their time and risking the end of humanity just to save his hide. That this weak excuse for a man is played by Damon is a delightful reveal, providing a burst of astral energy just when the film needs it, and his heel turn is even more jolting because he’s the last actor you’d ever expect it from.
4. Jay and Silent Bob Strike Back
In talk show appearances, red carpet interviews, and magazine profiles, Damon comes across as down-to-earth and self-deprecating, but he never had the opportunity to really flex those muscles on screen until Jay and Silent Bob Strike Back (and then later in The Martian). The film tracks the title characters as they road trip from Jersey to Hollywood, but it’s really just an excuse for a series of juvenile antics and meta-commentary, none more delightful than the vignette occurring on the set of Good Will Hunting 2: Hunting Season. In a lively few minutes, Affleck defends himself against accusations of killing sex workers, Gus Van Sant counts an enormous stack of money, and Matt Damon acts like a jaded, cynical prick. The characterization is succinct—“Get ya fucking hands off me,” he says to an assistant director who tries to bond with him and his costar, followed by a suggestion to Affleck to “just think about the paycheck” as they gear up for a particularly embarrassing scene—but in just a few well-sculpted minutes, Damon gets the biggest laughs in the movie by cheekily subverting his natural likability.
3. Deadpool 2
“Toilet paper is a plenty fine appetizer. But then Huggie’s Natural Care Wet Wipes. That’s your main course.”
When Damon’s career is over, what will we remember? His raw, star-making turn in Good Will Hunting? His transformation into a sensitive serial killer in The Talented Mr. Ripley? Or will his legacy be Redneck no. 2, who pioneered a novel approach to wiping one’s ass in Deadpool 2? Name another actor who would strap on a prosthetic gut, a trucker’s hat, and a ratty beard to jaw in a thinly veiled Matthew McConaughey drawl with Alan Tudyk about pooping before getting incapacitated by Josh Brolin and being played off by “Escape (The Piña Colada Song)”? You can’t. There is only one: Matt Damon, King of the Cameo.
2. No Sudden Move
I suppose they could have gotten a veteran character actor to play Mike Lowen, former auto industry executive turned evil overlord who appears at the end of the neo-noir No Sudden Move. Or Steven Soderbergh could have hired a major star to simply phone in his performance; it still would have worked as the kind of late-breaking cameo that skirts by on the casting alone. In Damon, the film gets the best of all worlds, a character actor with the presence of a star. When Lowen casually opines on the American caste system and his place atop it, we instinctively buy it. But Lowen is not content with his riches, and Damon infuses him with anger and a sick desperation, surely borne from the actor’s own views on income inequality and the super-rich. It’s a one-scene performance that speaks to the contradictions within the actor himself, and his ceaselessly thoughtful approach to even the smallest roles.
Eurotrip, a spiritual sequel to the didn’t-deserve-a-sequel 2000 comedy Road Trip, was written by three guys Damon went to college with: Alec Berg, Jeff Schaffer, and David Mandel. The trio have talent to spare, and have been intimately involved in creating some of the best comedy series of the last 30 years, including Seinfeld, Veep, Curb Your Enthusiasm, The League, and Barry. Eurotrip, on the other hand, has aged much worse—except for the three minutes in which Damon blows the doors off the place. After Scott “Scotty” Thompson (Scott Mechlowicz) is dumped by his girlfriend Fiona (Kristin Kreuk) at his high school graduation, he arrives at a party where he learns that she was cheating on him in the most embarrassing way possible. The singer of a pop-punk band, played with wide-eyed zeal by Damon, launches into the absolute banger, “Scotty Doesn’t Know,” that chronicles his affair with “sex puppet” Fiona through lyrics like “I can’t believe he’s so trusting / while I’m right behind you thrusting” and the final dagger in Scotty’s heart: “I did her on his birthday.”
The song, written by Boston-based rock band Lustra, is a solid earworm, but it’s Damon who turns it into high comedy. The actor fully commits to the bit, shaving his head, popping on a bunch of piercings, and lip-syncing his heart out. After Damon exits the stage, there’s no real reason left to watch Eurotrip, which makes him both the film’s savior and its destroyer. It’s a live-wire act that subverts his typical approach. Damon doesn’t try to blend in. He gets up on stage and dominates it, leaving the rest of the performers struggling (and failing) to keep up.
Noah Gittell is a film critic and journalist based in Connecticut.