Image via Complex Original
In the first advertisement for his show Any Given Wednesday, Bill Simmons makes a lot of bold statements. Aside from using the F-word for the first time on HBO, he also utters, "I believe that every DiCaprio movie would be a little bit better as a Matt Damon movie." Now, this opinion is lodged next to things like "Soup is a good food" and "God made the Red Sox win," so clearly the statement should be taken with a grain of salt.
Or, it could be taken with extreme offense. It could lead an entire group of people to react like Ben Affleck after a handful of Rum and Cokes. It could make this group of people write an entire blog post arguing the exact opposite just to prove a point. So that's what you're about to read: the exact opposite of Bill Simmons. On the same day Damon's new Jason Bourne movie drops, we're going to argue that ACTUALLY, every Matt Damon movie would be better if it were a DiCaprio movie, and talk about a few Damon roles that DiCaprio would have totally slayed. Because Leo doesn't deserve that slander, Bill.
The Jason Bourne Movies (2002-2016)
Throughout Leo’s career, we’ve seen him tackle a wide number of roles: he’s played the mentally disabled younger brother who loves to climb in What’s Eating Gilbert Grape, a drug addict–turnt–writer in The Basketball Diaries, and a Casanova who becomes a human popsicle (spoiler alert) in Titanic. He’s played in Westerns, period pieces, and in total mindfucks like Inception. What makes you think he couldn’t take on the role of Jason Bourne, a supreme assassin that’s all amnesia-fied, trying to uncover whatever secret CIA organizations turned him into a killer while getting rid of his identity?
Sure, Leo might not have the close quarters combat skills that Damon exhibits throughout the Bourne series, but Leo’s also driven himself to the ends of earth in multiple films—word is that he really bit into bison liver and damn near froze that Oscar-winning face off while shooting The Revenant. Do you think he’d miss an opportunity to learn Krav Maga or whatever Matt Damon was using to beat all of the ass throughout the Bourne series?
Plus, it’s easy to admit that Leo > Damon in most categories, right? Sure, Matt Damon’s career in the mainstream could be defined by his battles with Blackbriar, but imagine the life (and humor) that Leo could’ve brought to this role. It’s wack to be like “this role would be beneath Leo,” but with the decades of leading man experience Leo’s got resting behind those baby blues, Bourne would be both a cakewalk and a chance for Leo to, at the very least, get his beach body ready for all of those blonde bombshells that seem to fall in his lap. —khal
The Talented Mr. Ripley (1999)
Let’s make this clear right off the bat: The Talented Mr. Ripley is a supremely underrated film that more than holds up. An adaptation of the Patricia Highsmith novel (homegirl was a lowkey horror creep in her own right), it follows Tom Ripley, (Damon) a ~poor~ youth who lucks into being mistaken as the Princeton classmate of a wealthy bro named Dickie (Jude Law), whose father pays Tom to go abroad to get him to come back to the States. After pretending to be Dickie on his way over, he ends up integrating himself into Dickie’s life, to um, murderous results. Damon’s great in this—very innocent boy next door who is suddenly monstrous—but imagining young Leo in this role, goddamn. It’s easy to imagine that his Tom, instead of being instantaneously trusted because of his boy next door sheen, would do so by force of sheer fucking charisma (please look to Catch Me If You Can for reference), seducing Dickie, GOOP, Carol (Gov Name: Cate Blanchett)—hell, everyone in his path. But underneath that endless charisma would always lurk a bit of DiCreepio (hayyyyyy)—not something that he’s shown much of in film (maybe in Django Unchained) but more so when he’s looking for models at the club. It’d be a bit sinister and would totally blow up by the film’s conclusion. I mean, Leo was originally supposed to play Patrick Bateman after all. —Kerensa Cadenas
The Legend of Bagger Vance (2000)
So yeah, this is a pretty questionable movie about a magical black man who helps a white man attain ultimate whitehood through the mastery of the game of golf. Matt Damon’s okay in it as said white man, Rannulph Junuh, who has a drinking problem and the proclivity to tuck his tie into his dress shirt. But let’s be real, the Academy gets fooled into voting for this privileged garbage if Leo is playing Damon’s character. A 26-year-old DiCaps would’ve killed the scenes where Junuh is a scary drunk, and he probably would’ve slipped some subtle wariness into the character, a necessary addition anytime Will Smith is teaching someone how to hit a chip shot. No, I’ve never seen Leonardo DiCaprio engage in an athletic activity, but who cares? —Andrew Gruttadaro
30 Rock (2010-2011)
Yeah, yeah, yeah—I know Leo would NEVER do this. But who would have expected Mr. Jason Bourne himself, A-list mega star Matt Damon to end up on 30 Rock? Damon played Carol Burnett, Liz’s pilot boyfriend, a total Straight Man to Liz. Carol was instantly appealing because a) he thought her job was cool, b) he was a pilot, so he was never around, and c) they were basically the same person. Like I previously mentioned, Damon plays Carol pretty straight, so it’s funny but also a bit jarring when he eventually gets super emotional on Liz. Also, Carol, generally, is a bit boring (no disrespect to Liz). So imagine if Leo played Carol—homeboy has long had underrated comedic chops—we see glimpses of that in Catch Me If You Can and even a tiny bit in Romeo + Juliet. Leo’s Carol would have a bit more charisma off the bat than Damon’s Carol—like the IRL equivalent of what I imagine the collective narrators of “Brandy, You’re a Fine Girl” to be like. Utterly charming, maybe a tad stick in the mud, but certainly not boring. Plus, we’ve all seen Leo’s cry face—envision THAT in Carol’s emotional breakdown about the difficulties of pilot relationships. —Kerensa Cadenas
Good Will Hunting (1997)
Every Masshole just puked in their mouth and I love it. Leo is so far and away better than Matt Damon that he’d even eat Damon’s lunch doing the guy’s most famous role, a role he wrote himself. You may be saying to yourself, “YEAH BUT MATT DAMON’S FROM BOSTON. NO ONE COULD SAY ‘DO YOU LIKE APPLES’ LIKE HIM!” But just picture Leo during the “It’s not your fault” scene. Picture Leo during the scene where Will's yelling about getting cigarettes put out on him as a kid. Damon does well during those, but Leo could take those moments and turn them from emotional to so-fraught-it’s-scary. And we know Leo can do the Boston thing—we’ve all seen him play a more damaged version of Will Hunting in The Departed. (Speaking of, what would happen if Damon and DiCaprio switched roles in that movie?) —Andrew Gruttadaro