‘Interstellar’ (2014)
Christopher Nolan has maintained such secrecy around his films that he was actually able to hide the fact that Damon was in Interstellar until it was released. While a few rumours had pointed to his involvement, the actor showed up to give a brilliant performance as Dr Mann, the duplicitous astronaut who attempts to sabotage Matthew McConaughey’s Cooper by stealing his ship.
It’s a powerful examination of the frailty of human nature, showing that even respected pioneers could become cowards if they were forced to choose between selfish desires and the collective good of society. Moreover, it was instrumental in kicking off Damon’s relationship with Nolan, which continued when he played a key role in Oppenheimer, and one of the most exciting aspects of The Odyssey is the enthusiasm with which he has discussed working with Nolan on what may be one of the most anticipated performances of all time.
‘Field of Dreams’ (1989)
One of the most famous urban legends about Damon and Affleck is that they served as extras in the Kevin Costner baseball classic Field of Dreams, which they would later cite as the movie that made them want to get into filmmaking in the first place. It would take an eagle-eyed viewer to pick out exactly where Damon and Affleck are in the crowd at Fenway Park, but the notion that they showed up to support the Red Sox is more than believable.
That Damon and Affleck started out working as extras, one of the lowest-ranked jobs in the business, makes their rise to success and eventual fame feel all the more inspiring. It also doesn’t hurt that Field of Dreams is the best of Costner’s baseball films and a timeless love letter to America’s favourite pastime, which ends on such a powerful note that it is bound to make anyone cry.
‘Jay and Silent Bob Strike Back’ (2001)
Clerks kicked off a cinematic universe for Kevin Smith, in which he tied in multiple characters for recurring appearances throughout subsequent films like Mallrats and Chasing Amy, and Jay and Silent Bob Strike Back took the titular stoner characters, played by Jason Mewes and Smith himself, respectively, and set them on an adventure throughout Hollywood.
Few films have been packed with as many cameos, but Damon appears in one of the film’s funniest moments when Jay and Silent Bob run through various studio lots in a parody of the ending of Pee-Wee’s Big Adventure. Damon and Affleck appear as themselves, making the completely unnecessary sequel Good Will Hunting 2: Hunting Season, which transforms the heartfelt drama into an action film. It’s a great gag because the duo and Gus Van Sant are all in on the joke, and the damning portrayal of Hollywood cynicism has aged surprisingly well.
‘Jay and Silent Bob Reboot’ (2019)
Coming in only slightly below its predecessor is Jay and Silent Bob Reboot, the long-delayed sequel that Smith made after suffering a near-fatal heart attack that inspired him to go back to his cinematic roots. Although the titular duo spend most of the film as the mentors to a younger generation of stoner heroes, Reboot features cameos from many of Smith’s other projects, including everyone from Val Kilmer to Justin Long.
It’s to the credit of Damon that he doesn’t return to play himself, but rather reprises his role as the fallen angel Loki from Dogma, which is perhaps Smith’s most underrated film. It was significant because Dogma had, for many years, been made completely unavailable for release on streaming because the rights still belonged to the Weinstein Company, and had not been transferred after it folded.
‘No Sudden Move’ (2021)
Although it may not exist as a standalone service for much longer, HBO Max was used by its parent company, Warner Bros, to distribute many films without a theatrical window. The company would receive criticism for sending big films like Dune and Godzilla vs Kong to stream the same day they were in theatres, but Steven Soderbergh’s crime caper No Sudden Move never even got a courtesy cinema release.
Damon has a memorably creepy scenery-chewing role as a crime lord who doesn’t appear until the third act, allowing the film to end on a climactic showdown with Don Cheadle’s character. It’s not a particularly distracting appearance, given that nearly every major character in No Sudden Move is played by a recognisable actor, with other bit parts going to David Harbour, Noah Jupe, Ray Liotta, Brendan Fraser, Kieran Culkin, and Jon Hamm.
‘Youth Without Youth’ (2007)
Francis Ford Coppola cast Damon for one of his first lead roles in The Rainmaker, so it was fitting that they would reunite for one of the director’s strangest films ever. While Youth Without Youth may have initially seemed like a straightforward World War II thriller, it evolves into an unusual, dreamlike fantasy odyssey in which Tim Roth plays an academic who escaped the persecution of the Nazis.
Damon plays a reporter who is tasked with interviewing Roth’s character, and actually provides a necessary perspective given how lacking in clarity the film is. While inserting a famous actor for a cameo is usually a distraction, it’s not even remotely one of the weirdest things that happens in Youth Without You; if anything, Damon’s appearance offered audience members a sense of familiarity by reminding them that they were watching a real film, and not an absurdist avant-garde experiment.
Deadpool somehow became one of the most popular superheroes in the world thanks to the sheer dedication of Ryan Reynolds, who was born to play the smug, fourth-wall-breaking anti-hero, for better or worse. The films work much better as comedies than they do as satires about the state of superhero cinema, and Damon has an amusing cameo in the second film where he appears as a redneck trucker who is brutally murdered by the time-travelling mutant Cable, played by Josh Brolin.
What’s striking about Damon’s role in Deadpool 2 is how much lazier the cameos in the third film, Deadpool & Wolverine, feel in comparison; while the latter simply inserted familiar faces for the sake of eliciting cheers from the audience, Deadpool 2 gave Damon the chance to wear makeup and do an actual comedy bit before being dismembered in a fairly memorable way.
‘Finding Forrester’ (2000)
Gus Van Sant is the director to whom Damon owes the most, as it was the brilliant directing of Good Will Hunting that elevated the screenplay into an instant classic, especially agreeing to it after many other filmmakers had passed, so it’s understandable why the actor would feel obliged to make a cameo in the director’s new film, which happened to be another academic drama.
Damon’s role is that of a stern lawyer who represents the privileged, crusty elitism that Finding Forrester points to as a societal ill; that someone as inherently likable as him was able to play a character devoid of any charisma is a true achievement, but it also showed that he had begun to drop the ‘boyish’ qualities that has been associated with him in late ‘90s films like Saving Private Ryan and The Talented Mr Ripley.
Kevin Smith had the rare distinction of knowing Affleck and Damon before either of them was famous, as Chasing Amy was in-production before they broke out with Good Will Hunting and won an Oscar. Damon has a small part in the film as a television executive who attempts to take the comic book written by Affleck’s character, Holden, and turn it into a television series.
While it was obviously a jab at cynical Hollywood executives who would try to corrupt the integrity of an artist, something Smith was well aware of, Damon plays it as a real part, and doesn’t give as many winks and nods as one might expect. It ends up being one of his best cameos because he was not yet a celebrity, and thus could not fall back on his star persona in place of giving an actual performance.
‘Thor: Ragnarok’ (2017)
Taika Waititi briefly felt like the director who could save the MCU because Thor: Ragnarok dropped the overtly serious, monotonous worldbuilding of its two predecessors to make a rip-roaring space opera in the vein of Flash Gordon. Given that Waititi was first and foremost a comedy veteran, he included a self-aware scene in which the events of the first two films are recreated by actors in the realm of Asgard.
Damon appears as an actor who has been cast in the role of Loki, Thor’s half-brother and occasional ally, with the joke of the scene being that Loki has secretly possessed the body of their father Odin, played by Anthony Hopkins, and is using the play as a source of propaganda to make sure that Asgard knows he is really a hero. Damon essentially has to be in an intergalactic soap opera, and he pulls it off with aplomb.
Jersey Girl is one of the most underrated films directed by Kevin Smith, who took a break from his crass comedies to make a more sincere dramedy that starred Affleck as a struggling father trying to improve the life of his daughter. Although the film notably featured a role for George Carlin in one of his few major acting roles, Damon gets to cameo as a slimy member of the film industry who blocks Affleck’s character from making progress with his idea.
Smith’s dialogue is well-suited for someone like Damon, who can commit to ridiculous line deliveries and wacky physical comedy. What’s most interesting is that it offered a taste of what he could do playing a completely unlikable character two full years before The Departed, in which he played a traitorous member of the Boston police who is secretly an undercover mole for gangsters.
‘Confessions of a Dangerous Mind’ (2002)
George Clooney and Damon have been friends ever since they appeared in Ocean’s Eleven together, and so it made sense that he would appear in Clooney’s directorial debut, Confessions of a Dangerous Mind, which starred Sam Rockwell as a game show producer who claims to have been a member of the CIA, and a brief glimpse of the in-film The Dating Show features appearances by both Damon and another Ocean’s Eleven star, Brad Pitt.
The friendliness between the three actors makes for a fun scene, even if it’s Pitt who ends up getting most of the best lines. As with pretty much every film that Clooney has directed, Confessions of a Dangerous Mind is handsomely made and features great performances, but you can’t help but feel as if it would have worked better in the hands of a filmmaker with a little more style.
Unsane is another unusual experiment from Steven Soderbergh because it was the first film he shot entirely on an iPhone. While this has now become a more common technique used on films as big as 28 Years Later and for several of Sean Baker’s projects, it was considered to be quite a big swing when Unsane was first released.
On one hand, the film is about a woman, played by Claire Foy, struggling to determine what her reality is, which is made all the more distressing as a result of the voyeuristic visuals. To include a recognisable face like Damon’s would theoretically work as part of the meta commentary, but his cameo ultimately represents the failures of the film; it’s a far more interesting idea in concept that becomes utterly flimsy when stretched out over the course of a feature-length presentation.
Damon’s appearance in the cult comedy EuroTrip was the result of a few strange coincidences. He had been college friends with the screenwriters Alec Berg, Jeff Schaffer, and Dave Mandell, who happened to be shooting Terry Gilliam’s fantasy film The Brothers Grimm with Heath Ledger nearby. Damon proceeded to pop up for a memorable, yet overstayed cameo in the film as a ridiculous suburban punk character.
It’s certainly one of the most memorable cameos he has ever given, but the sight gag of seeing him in a completely different form doesn’t have much staying power, especially when considering that he would take on more ambitious physical transformations later on in his career. The film itself is also a complete disaster that has aged worse than nearly any other comedy of the early 21st century, and even a few funny lines from Damon aren’t enough to make it worth revisiting.
‘The Third Wheel’ (2002)
Damon and Ben Affleck are an inextricable screen duo who have been great partners ever since they both appeared in the underrated coming-of-age drama School Ties. However, 2002 marked a time in which they had both gone their separate ways; Damon was coming off a key supporting role in Ocean’s Eleven and was fronting The Bourne Identity, whereas Affleck was attempting to make more commercial projects.
The Third Wheel is a rather forgettable romantic comedy, and Damon’s cameo adds nothing; it didn’t feel like a grand reunion with Affleck, as they had just recently appeared in Dogma together two years prior and suggested that the latter was not a strong enough star to generate attention on his own, an assumption that was proven correct in subsequent years when Damon-less star vehicles like Daredevil, Gigli, and Paycheck all ended in thunderous disappointment.
‘Che: Part Two’ (2008)
Damon has done a number of smaller roles in the films of Steven Soderbergh, who always has an affinity for getting A-listers to do smaller parts. The two-part biopic Che is one of Soderbergh’s most underseen films and features a tremendous performance by Benicio del Toro as the famous revolutionary.
Del Toro has frequently discussed his affinity for Soderbergh, as he had just come off winning an Academy Award for his work in the director’s previous film, Traffic, but that said, incorporating well-known Hollywood actors for a serious drama about liberation felt like an odd choice that wasn’t consistent with the rest of the tone. Damon isn’t necessarily bad in the film, but his appearance is distracting because it would have been far more effective to simply cast a character actor who could have disappeared into the part.
‘Thor: Love and Thunder’ (2022)
Damon has never played a Marvel superhero, which is somewhat surprising given how dominant the franchise is, and although he perhaps wanted to avoid the mistakes that Ben Affleck made while doing Daredevil, Damon popped up briefly in each of the last two Thor films that were directed by Taika Waititi.
Thor: Love and Thunder is one of the worst films in the MCU, and was clearly a case where Waititi was high on his own supply; the idiosyncratic quirks that had made Thor: Ragnarok so much fun had been beaten into the grown, as the director awkwardly balanced his goofy humour with a more serious storyline involving Natalie Portman’s Jane and her illness. Damon’s cameo was funny the first time around, but he overstays his welcome by playing another narcissistic actor who had found a permanent position performing in plays in Asgard.