At a time when Hollywood can’t get enough of cinematic universes and whatever the hell you want to call the Warner Bros. IP orgy that was Space Jam: A New Legacy, movie stars—the type of actors who can sell a film just by slapping their name and face on a poster—are becoming an increasingly rare breed. But no matter the scope of the project or the genre, the ones who have endured remain magnetic on-screen presences—few more so than Matt Damon, who has stealthily made some of the most fascinating creative choices among Hollywood’s biggest A-listers.
While Leonardo DiCaprio and Tom Cruise have made headlines for eating raw bison liver and executing death-defying stunts, respectively, Damon has carved out a niche by elevating his movies—and his résumé—with unpredictable makeovers. To understand what I mean, look no further than the actor’s 2021 film slate, in which he goes from playing a guy who looks like he’s crushing the Cracker Barrel loyalty rewards program to sporting the world’s greatest (first?) historical mullet in The Last Duel. These days, if you see Matt Damon’s name attached to a new project, there’s a significant chance he’ll be Doing a Thing.
Why has Matt Damon embraced such varied makeovers over the years? Perhaps he has a mild and recurring case of Justin Theroux Syndrome: He’s a character actor trapped inside the body of a conventionally attractive leading man. But whatever the reason, Damon’s experimental looks have kept us on our toes for decades, and honestly, a celebration of that dedication is long overdue. These are the Matt Damon Makeover Awards.
Preppiest Boy at the Country Club: Mystic Pizza Matt Damon
In his first film role, in the 1988 romantic comedy Mystic Pizza, Matt Damon plays Steamer Windsor, the younger brother to rich boy Charles Gordon Windsor Jr., who briefly dates Julia Roberts’s Daisy Araújo. While Damon has a minuscule part in the film—uttering a single line of dialogue over dinner about not wanting to eat “green stuff”—the actor still pulls off a memorable look. The Windsor family is supposed to be snobby; suffice it to say, Damon’s wavy hair and polo shirt do a lot of heavy lifting to emphasize that point:
With just a few minutes of screen time, you get the feeling that Damon’s character would be an insufferable hang—the fact that he goes by “Steamer” is just the icing on the cake. Mystic Pizza isn’t going to make the actor’s highlight reel, but the film was an early and subtle indication of Damon’s transformative powers. Steamer has such a different vibe than someone like Will Hunting, and it’s all in the hair.
Deadliest Twink: The Talented Mr. Ripley Matt Damon
As far as surface-level impressions go, Damon’s Tom Ripley is attractive and stylish, but in a manner that’s rather unassuming compared to Jude Law’s flamboyant Dickie Greenleaf. But Damon’s appearance as Ripley belies something sinister: a sociopathic scammer who isn’t afraid to rack up a body count to enjoy life’s glorious, addictive excess. Still, we have to give credit where it’s due: This burgeoning serial killer looks like the kind of person you’d bring home to your parents without a second thought.
Aside from being one of his best performances, full stop, The Talented Mr. Ripley is Matt Damon’s finest contribution to Glasses Cinema. Would cop.
Worst Person to Find Out Your Girlfriend Is Cheating on You With: EuroTrip Matt Damon
If you’ve watched one raunchy aughts teen comedy, you’ve seen them all, but EuroTrip has endured because of three unforgettable words: Scotty doesn’t know. At the start of the film, Scotty Thomas (Scott Mechlowicz) discovers that his high school ex was cheating on him, and that the details of the affair have been immortalized in a punk rock anthem headlined by, of all people, Matt Damon. Worse, it immediately becomes apparent that this frontman is the guy who Scotty’s ex was cheating with. (The lyrics “I can’t believe he’s so trusting / While I’m right behind you thrusting” kind of give it away.) The novelty of “Scotty Doesn’t Know” is that it’s being sung by a famous actor with a shaved head and a ton of piercings; Damon looks as if the Warped Tour were a person here. But just as importantly, the song is really catchy:
“Scotty Doesn’t Know” has no right to be as good as it is, and Damon milks every moment of his incredible cameo. As EuroTrip cowriter David Mandel said in an oral history of the song: “With any hope, when Matt Damon dies—and hopefully not for a long time—but when he dies, [‘Scotty Doesn’t Know’] is what they lead with.”
Most Suburban Dad Energy: The Informant! Matt Damon
The year is 2009. Matt Damon is approaching 40, which is another way of saying that he’s ready to dive headfirst into substantive dad roles. (Roles in which he plays a dad, but just as crucially, roles that also appeal to dads.) As the whistleblower Mark Whitacre in Steven Soderbergh’s The Informant!, Damon brings some of his best on-screen dad energy to date. This is the look of a person who could talk to you for hours about Ken Burns documentaries:
Despite the movie being about a real-world price-fixing scandal for an animal feed additive, it wouldn’t take much to trick someone into thinking The Informant! is about one brave dad infiltrating PTA meetings of a rival school board. Damon undergoes a similar transformation in 2017’s Suburbicon, but The Informant! deserves a shout-out because it tapped into the actor’s suburban dad potential first. (It’s also a way better movie.)
Most Likely to Host the Country Music Awards: True Grit Matt Damon
Another in the long line of Coen brothers doofuses, Damon hams it up as LaBoeuf (pronounced, iconically, “le beef”), a feckless Texas Ranger tracking down the outlaw Tom Chaney (Josh Brolin). Damon is clearly having a blast in the role—I’ll never get over how proud LaBoeuf looks flashing his credentials to Hailee Steinfeld’s Mattie Ross—and has a spectacular appearance to go along with it. If you look up the word “beige” in the dictionary, this is what ought to pop up:
LaBoeuf might be an idiot who spends part of the film with a swollen mouth that prevents him from speaking normally, but I love him and Damon’s performance all the more for it. It also helps that LaBoeuf carries himself like someone who thinks this is what all cool Rangers look like.
Best CrossFit Trainer From the Future: Elysium Matt Damon
Perhaps the most striking part of the dystopian sci-fi epic Elysium is Damon’s physique, as the actor got admirably shredded to play futuristic blue-collar worker Max Da Costa. It’s impressive enough that Damon looks imposing even without the robot exoskeleton strapped onto his back, but with it on, he’s definitely channeling Sigourney Weaver fighting the xenomorph queen in Aliens:
The transformative power in this role mostly lies in how ripped Damon is, but don’t discount the shaved head and copious tattoos, either, which underlines that his character is Going Through Some Shit. (It’s also kind of fun to pretend that this Bald Damon is the same Bald Damon from EuroTrip.) And while Max Da Costa taking on 1-percenters in the year 2154 would make Bernie Sanders proud, my guy and his exoskeleton are definitely needed in the year 3050 to stop Skeletrex and his bone brigade from adding humans to his army of bone soldiers. FRIGGIN’ BONIES!!!!
Most Shocking “Wait, Matt Damon Is in This Movie?!” Moment: Interstellar Matt Damon
Before certain moviegoers lost their minds over Captain America wielding Thor’s hammer, there was the collective disbelief when Matt Damon emerged, without warning, midway through Christopher Nolan’s masterpiece—yeah, I said it—Interstellar. The film builds up Damon’s character, Dr. Mann, as heroism personified; he has agreed to survey a potentially habitable world without any guarantee he’ll be rescued, and coaxed 11 other scientists to join him to explore other planets. It’s almost too perfect that the great Dr. Mann is played by none other than Jason Bourne:
It’s a normal Damon look, to be sure, but Interstellar has to be lauded for the sheer WTF-ery of his appearance, and what it leads to. It’s hard to think of a more contemptible villain than Dr. Mann, someone so scared of dying on a desolate planet that he risks the extinction of the human race to buy himself more time. If nothing else, Interstellar is a terrific endorsement for a different type of Matt Damon makeover: breaking bad. (Also, paired with The Martian, it seems that Hollywood can’t get enough of stranding this dude in outer space.)
Best Sales Pitch for the Ponytail As a Sex Symbol: The Great Wall Matt Damon
When it comes to trying to make a cross-cultural blockbuster, The Great Wall has to be deemed a failure—commercially, the film bombed in both the United States and China. Instead, the movie’s greatest contribution to society was, without question, Matt Damon’s ponytail. It’s not easy to one-up someone as effortlessly suave as Pedro Pascal, but the Damon-tail conquers all:
While Damon didn’t grow out the ponytail himself—they were hair extensions—it didn’t matter on a level of thirst. As recounted to the actor on The Graham Norton Show, the ponytail caused quite a stir on Twitter, most of which is too NSFW to repeat in this blog. (Come for horny Matt Damon ponytail tweets, stay for Jessica Chastain’s pained reactions to them.)
The Great Wall may have fallen, but Damon’s ponytail is, and always will be, a treasured piece of art.
Most Deserving of an Asgardian Tony Award: Thor: Ragnarok Matt Damon
The Marvel Cinematic Universe is no stranger to A-listers, so the fact that Damon’s cameo in Thor: Ragnarok became an instant franchise highlight shows just how great it was. When Thor returns to Asgard, he discovers a statue erected in Loki’s honor before stumbling upon a play celebrating his supposedly deceased brother’s heroics. As Loki-disguised-as-Odin oversees the narcissistic festivities, the man playing Loki in the drama looks quite familiar:
The best part might just be how much Damon oversells Loki’s emotional parting words to Theatre Thor, who just so happens to be played by the God of Thunder’s IRL brother, Luke Hemsworth. But having Damon in the full superhero getup with Loki’s flowing hair also underscores the inherent silliness of these movies—one of the reasons Ragnarok is one of the best Marvel entries is that it refuses to take itself seriously. With any luck, the rumors of Damon reprising his role-within-a-role for Thor: Love and Thunder carry some weight.
Most Likely to Join Jeff Bezos on His Penis Rocket: No Sudden Move Matt Damon
Yet another entry in the “Wait, Matt Damon is in this?!” canon, No Sudden Move sees the actor reunite with Steven Soderbergh for his latest heist movie. But while his name doesn’t appear in the film’s opening credits, Damon’s appearance is more than just a flashy cameo. As low-level criminals Curt Goynes (Don Cheadle) and Ronald Russo (Benicio del Toro) follow a money trail related to Detroit’s booming auto industry in the 1950s, the man at the top of the conspiracy is Mr. Big (Damon), an executive working on behalf of the city’s top manufacturers. Mr. Big may seem unassuming, but there’s an understated menace behind Damon’s bespectacled appearance:
Loosely based on a real antitrust case, No Sudden Move is less about pulling off a heist and more about Detroit’s ugly history of corporate greed and systemic racism—and Damon is tasked with being the evil (and extremely punchable) face of this web of collusion. Obviously, Damon’s look is totally appropriate for the movie’s period setting, but as an avatar of capitalism’s inherent failures, you could totally see a present-day version of Mr. Big trying to go to space (and generally avoiding paying taxes).
Most Likely to Have Strong Opinions About Kneeling During the Anthem: Stillwater Matt Damon
Stillwater’s biggest selling point is supposed to be that it’s inspired by the infamous Amanda Knox murder case, and while there is a world where that could be true, it’s impossible in the film’s current incarnation. That’s because the young woman who gets arrested for murder, played by Abigail Breslin, is completely overshadowed by her dedicated father, Bill Baker (Damon). As Bill, Damon undergoes a transformation that I can only describe as a Clint Eastwood wet dream:
Bill is an oil rigger, which is about the least surprising information in the world. I also know, without a shadow of a doubt, that Bill’s favorite show is Duck Dynasty and that ordering the Tex-Mex Shrimp Bowl at Applebee’s is his idea of experiencing other cultures. (Which, to be fair, makes the whole “traveling to France to get his daughter out of prison” all the more compelling.) Matt Damon might be done with Stillwater, but I’ll be thinking about Bill Baker for the rest of my time on this Earth.
Best Imagining of Morgan Wallen During the Middle Ages: The Last Duel Matt Damon
Ridley Scott returns to the fruitful well of historical dramas with The Last Duel. The titular duel is between the knight Jean de Carrouges (Damon) and his squire Jacques Le Gris (Adam Driver), who supposedly raped his wife Marguerite (Jodie Comer). Make no mistake: The movie, slated for an October 2021 release, looks promising, but the characters’ hairstyles are distracting across the board—none more than Damon’s mullet. I’m not sure how Damon pulled it off, but even though electricity won’t be invented for hundreds of years, Jean de Carrouges has the vibe of someone who listens to Joe Rogan every day:
That haircut is the most frightening creation of Scott’s filmography since the xenomorph. And in what is either a bizarre coincidence or shameless self-plagiarism, Damon’s look most closely resembles a character in Raised by Wolves, the HBO Max sci-fi series executive produced by Scott, who also directed the first two episodes. The Last Duel takes place in the 14th century, while Raised by Wolves is largely set on a faraway planet in the 22nd century. Clearly, the most important takeaway here is that the mullet is timeless, especially when it’s on Matt Damon’s capable scalp.
