The Best Movie Ever | Best Matt Damon Movies List

In the Film department here at Crave we try to avoid “celebrity” talk as much as possible, and focus on the films people make more than what the people that make them wear, who they’re sleeping with and what dumb things they may have said in the past week. But Matt Damon isn’t making it easy for us. After the astonishingly dumb and offensive comments about Hollywood diversity and homosexuality he’s made recently (whether or not he actually “meant” well), many audience members are turning their back on the acclaimed actor, who otherwise seemed to be on the verge of one of the biggest hits of his career in this weekend’s acclaimed sci-fi thriller The Martian.

So this week’s planned installment of Best Movie Ever has taken a somewhat depressing tone this week. Our critics William Bibbiani, Witney Seibold and Brian Formo were asked to pick just one of Matt Damon’s movies to hold up as his best work, but praising the actor this week is an iffy prospect at best. 

Suffice it to say that whether Matt Damon is being justly pilloried or merely in the middle of a temporary, albeit disastrous P.R. nightmare, he’s still made some excellent movies over the past 20+ years, and in the long run, decades down the line, his best films are what people will probably remember him for. So what IS his best film? Let’s find out what our critics had to say in this week’s installment of Crave’s highly debatable ongoing series…

Best Matt Damon Movies List

Witney Seibold’s Pick: The Talented Mr. Ripley (1999)

Paramount/Miramax

The joke I heard about Matt Damon – made by comedian Andy Richter back in 1999– was that his best films are the ones where he plays a guy who’s really good at something. Looking over Damon’s career, we see a stretch of films wherein Damon is a fresh-eyed and hard-working expert. He’s played pickpockets, geniuses, undercover criminals, soldiers, liars, lawyers, psychics, and spies, each of them the most talented guy in the room. Damon has been blessed with handsome, boyish features, and seems to project an affable, intelligent confidence in all his roles, even if he plays scumbags or backstabbers. He’s so appealing a screen presence, it’s easy to see why certain people find him grating; like George Clooney or Justin Timberlake, he might be a little too perfect.

Matt Damon’s best film also features his best performance, and its his very affability that pushes it over the top. Anthony Minghella’s 1999 thriller/tragedy The Talented Mr. Ripley subverts what we naturally receive from Damon, turning his alluring charm into a form of social awkwardness, and his intelligence into something outright sinister. Based on a character created by Patricia Highsmith, Tom Ripley is a complex, pathetic, tragic, awesome villain who might be called a noodly version of Iago from Othello. In the first of his misadventures (he was featured in a whole novel series), Ripley is a college student who is enlisted by a rich man to travel to Europe to retrieve his prodigal son Dickey (Jude Law). Once there, he is seduced and allured by Dickey’s charm and rich lifestyle; Ripley has never been popular or even acknowledged by his peers. This sad, social outcast ends up falling in romantic love with Dickey, which leads to a rather shocking event involving a rowboat paddle.

Ripley’s talent, we learn, is subterfuge, lying, and sinning. He is best, most confident, most on-his-game when he is tricking people and manipulating people. But, as Damon plays him, he rarely comes across as someone hateful or sadistic. He is just following his natural urges, and gradually discovers that he is an evil bastard. Just by personality. I haven’t seen other movie characters like that, and Damon creates an angry nerd who is just now realizing that he long ago shed any sort of relevant moral code. This is a twisted and glorious movie that punches one in the gut, but keeps one rapt. And Damon is the one holding it all together. I’m going to go watch it again right now. It’s so good.

William Bibbiani’s Pick: The Talented Mr. Ripley (1999)

Paramount/Miramax

There is a very decent chance that we are watching Matt Damon implode at the moment. With a series of ill-advised remarks about diversity in the entertainment industry and the need for gay actors to stay in the closet (yes, really), he could very well be harpooning his career right before the release of The Martian, which is one of his best movies in years. It’s Tom Cruise on Oprah’s couch all over again.

I hope Damon recovers, and that he doesn’t turn out to be a total schmuck, because he’s one damn fine actor. The actor’s showcase Good Will Hunting was a weepy melodrama without shame, but it was a good one and it would have completely tanked if Damon hadn’t given a bravura performance. In the years he starred in some great movies (RoundersThe Departed) and not a lot of bad ones, and helped redefine the action genre altogether with his naturalistic turn in The Bourne Identity.

But he’s never been better than he was in Anthony Minghella’s The Talented Mr. Ripley. My associate Witney went into the thick of why it’s such a fantastic performance already, but right now I wonder if it isn’t also an important achievement. Tom Ripley isn’t a bad man, but he does bad things. He can’t help how he feels or what he says or what he has to do to convince people he’s decent. He’s constantly forced to perform, to present a lovable persona, for fear of being judged. 

We’ve all felt that way. Matt Damon probably feels that way a LOT right now. It’s the kind of role that doesn’t get played very often but probably needs to, and with the sort of understanding and depth that Damon provided in Minghella’s film. It’s the best Matt Damon movie ever. In fact, I’d also call it one of the best performances of the 1990s.

Brian Formo’s Pick: The Martian (2015)

20th Century Fox

Confession: Matt Damon has always seemed a little false to me. The whole narrative surrounding Good Will Hunting being an out of nowhere success story for two struggling actors is stuff of fluff legends. In Hunting, he played a janitor who was actually a math genius and needed some hugs from Robin Williams to let the genius come out of him. In the same year that movie is getting made, Damon is acting opposite Denzel Washington and Meg Ryan in one film and being directed by Francis Ford Coppola and Steven Spielberg in two others. Hunting had the studio-fashioned fake narrative of launching an underdog actor when it was actually a calculated release to happen all at the same time. How do you like them apples?

That’s all fine, stars aren’t made overnight. Still, Damon’s best performances are when he’s playing a character who’s trying to pretend to be someone else—as a sociopath who steals the identity of an upper crust socialite in The Talented Mr. Ripley and as a lover of Liberace who allows himself to be surgically transformed to his lover’s specific desires in Behind the Candelabra—and in his biggest franchise, the Bourne films, he doesn’t even know who he is. When I like Damon, I don’t trust his identity.

In the past few weeks, we’ve been getting to know more of who Damon is. And to be honest, he seems like an ass who talks out of his ass. With Project Greenlight he said diversity in film only matters in front of the camera not by those who shape the stories, or work on set. In an interview with The Guardian he blamed out actors for any career downturn with a “what do you expect?” shrug. Now I really don’t trust him.

So for the best Matt Damon movie ever I’m choosing The Martian. It’s really fun. I came away wanting to make sure loads of my tax dollars went to scientific innovations. When’s the last time a movie made you fist pump and grin ear to ear for its portrayal of all-caps SCIENCE? But here’s something else about The Martian—when it really kicks into gear and becomes a hugely entertaining film it’s when we spend less time with Damon and more with the team that’s trying to bring him back from Mars safely. That’s mostly how I like my Matt Damon right now: absent.

Let us know what you consider the best Matt Damon movie ever in the comment section below!

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