Matt Damon: A Career in Cameos

After becoming famous for being such a good friend after partnering with Ben Affleck to make “Good Will Hunting” a reality, no one has done more random onscreen favors for pals than Matt Damon, who can be seen in theaters once again this week for a film that you won’t see his name on the marquee for. Throughout the years, Damon has always been game to steal a scene, often wearing crazier get-ups than he did playing Linus Caldwell in the “Ocean’s” trilogy. Here are the hows and whys behind the smallest roles played by one of the world’s biggest movie stars, including his most recent one (spoilers are blurred).

“Finding Forrester” (2000) – Appropriately enough, Gus Van Sant closed out his golden age – a double bill of this film and “Good Will Hunting,” marked less for being an artistic highpoint for the director than by their shared sepia-toned cinematography – with a last minute appearance by Damon as the executor of reclusive author William Forrester’s will.

Easily the least interesting of his cameos (but forgivable for being his first), Damon channels his “Rainmaker” days, playing the lawyer who bestows Forrester’s protégé Jamal with his apartment and belongings, in a scene more symbolic as a bookend to “Hunting” than anything else. It also doesn’t help that Damon’s cameo doesn’t have the bizarro nature of an appearance midway through the film by Joey Buttafuoco as a security guard.

“The Majestic” (2001) – By the time Frank Darabont was casting his Blacklist-era drama about a screenwriter named Peter Appleton, who is mistaken for a war hero named Luke Trimble after a car accident wipes away his memory, Damon had already played one amnesiac in “The Bourne Identity” and turned down playing another in “Paycheck.” He also turned Darabont down and left the heavy lifting to Jim Carrey. But when Darabont needed a voice to read a letter from the real Luke Trimble, he called up Damon, who obliged and wound up playing the central character in the film, anyway.

“The Third Wheel” (2002)– When the largesse of “Good Will Hunting” allowed for Damon and Ben Affleck to create their own production company, Live Planet, Damon wisely stayed out of the casting calls for the films they produced – with one exception.

Although he steered clear of being a guinea pig in one of the “Project Greenlight” films, he couldn’t avoid a last minute appearance as Denise Richards’ emotionally fragile ex-boyfriend Kevin in this ill-fated romantic comedy that went direct-to-DVD. Playing the kind of jerk he faced off with in “Hunting,” Damon makes a bad night worse for Richards’ Diana and her date, Stanley (Luke Wilson) after they hit a bum on the street and then the bum feels compelled to chaperone their date. It’s worth mentioning the plot since Damon, compared to Affleck, who gamely suffers through a full-blown supporting role, gets off relatively easy.

“Confessions of a Dangerous Mind” (2002) – Of the three men George Clooney got to play bachelors on “The Dating Game” for his directorial debut, an adaptation of game show host Chuck Barris’ autobiography, only one had not been picked as People Magazine’s sexiest man alive. That would be J. Todd Anderson, a storyboard artist for the Coen brothers who was recruited by Clooney to work behind the scenes until Clooney realized the portly Anderson would be a perfect fit to play the fussy bachelor #3 who wins the bachelorette’s heart sight unseen over the likes of bachelor #1 (Brad Pitt) and bachelor #2 (Damon). As Clooney says during the DVD commentary, “The truth was in order to ask J. Todd to play the part of the guy that would be laughed about if she ended up with him, I wanted to have two big studs in the other two roles.”

“Euro Trip” (2004) – Now a prescient precursor to Sarah Silverman’s ode to cheating on Jimmy Kimmel, Damon first showed off his singing chops as Donny, the heavily pierced and tattooed lead singer of a punk band that welcomes the film’s protagonist Scott into a party with “Scotty Doesn’t Know,” a bouncy song detailing the many times and ways he’s defiled Scott’s girlfriend, Fiona. Damon is backed up by the real-life band Lustra, comprised of some of his ex-roommates from Harvard, which is also where Damon met “Eurotrip”’s writer/directors Alec Berg, David Mandel and Jeff Schaffer before they were all bound for Hollywood. When the trio discovered that their comedy would be shooting in Prague at the same time as Damon was working nearby on “The Brothers Grimm,” they called in a favor.

“Jersey Girl” (2004) – Continuing his streak of playing #2s, Damon was one of the few players in Kevin Smith’s View Askewnverse not to appear in “Jay and Silent Bob Strike Back,” so the time had come for him to reunite with his “Dogma” director and the result was a bit of déjà vu. Shortly before he became a household name with “Good Will Hunting,” Damon took a minor role in “Chasing Amy” as “Shawn Oran – Executive #2,” an MTV producer who tries to lure Holden and Banky (Ben Affleck and Jason Lee) to adapt their comic book for TV. In “Jersey Girl,” Lee and Damon sit across from Affleck’s Ollie Trinke as PR execs #1 and #2, respectively, who interview Trinke for a job. Smith laments on the DVD commentary, “You don’t know how disheartening it is to be at a test screening and get cards back where like ‘scene liked most: Jason Lee and Matt Damon’ because you’re like dude, they were in the movie for a minute.”

“Youth Without Youth” (2007) – Damon fulfilled a lifelong dream for Francis Ford Coppola, who admits in the film’s DVD commentary that he always longed for a career where he could ask the stars of his bigger movies to show up for a smaller part in one of his personal films, à la Max von Sydow’s role as a gas station attendant in Ingmar Bergman’s “Wild Strawberries.” When Coppola needed to cast the role of an American OSS officer who attempts to recruit Tim Roth’s supernaturally gifted Dominic during World War II in the film, he asked himself who would be “quintessentially American”? Soon after, he brought his star from “The Rainmaker” to Romania for a day’s shoot. “I didn’t want to make a big deal that it was Matt Damon,” Coppola says. “But he was just so perfectly American, I couldn’t resist.”

“Che” (2008): Taking the “one for me, one for the studios” mantra to another level, Damon had a dilemma on his hands when Steven Soderbergh asked if he could come down to the south of Spain to play a German priest fluent in Spanish for “Che.” It wasn’t speaking multiple languages that was an issue for the actor, but rather finding 24 hours in his schedule to play the man of the cloth who attempts to negotiate with rebel forces in Bolivia. As he would tell Total Film, behind the scenes, Damon negotiated a clever solution, realizing that he was going to do some press for “The Bourne Ultimatum” in Europe anyway, so he’d sneak in the day-long shoot while he still was in the EU. While it was less than a minute of screen time, he booked his fourth of seven collaborations with Soderbergh and may have given Naomie Harris, who pulled a similar feat in shooting her Oscar-nominated turn in “Moonlight” while doing press in Miami for “Spectre.”

“Interstellar” (2014): Although it’s far more than a cameo, few knew before “Interstellar” was released in the fall of 2014 that a cast that already included Matthew McConaughey, Anne Hathaway, Jessica Chastain, and David Oyelowo had yet another star in it, making it nearly as many as there were in the sky. Hearkening back to Damon’s role in “Saving Private Ryan,” the actor plays Dr. Mann, an astronaut from a previous space mission that has miraculously survived on what appears to be a completely inhospitable planet, but sees an opportunity to leave when the crew, led by McConaughey’s Cooper, arrives. During a conversation with Guillermo Del Toro, director Christopher Nolan admitted in casting Damon, he was creating a parallel to the central protagonist played by McConaughey, saying, ”What I loved about what Matt did with that opportunity is here’s a man who is a crazy person, he plays him as a coward, a banal, ordinary coward who’s just chickened out, frankly and has just rationalized his own cowardice into a philosophical justification that everybody’s doomed and that to me speaks to the spirit of adventure. There’s some [Joseph] Conrad in there.”

“Thor: Ragnarok” (2017): When GQ did a profile of Chris Hemsworth in 2014, the “Thor” star thought nothing of inviting the writer David Katz over to Damon’s house to go biking together, so it probably didn’t take much convincing for Damon to be a part of “Ragnarok,” particularly when the filmmakers had such a clever cameo in mind for him. After filling the void in leadership on Asgard while Thor was on earth, Thor’s vain brother Loki (Tom Hiddleston) stages a dramatic retelling of his reign, naturally casting the universe’s best actors to play him in Damon. As director Taika Waititi recently told Entertainment Weekly, “We were looking for someone to play Loki and it felt like if Loki was going to write a play about his death he’d want the star of the Asgard theater scene to be in the play.”