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Matt Damon's 6 Best And 6 Worst Movies

Whether his character is being rescued from behind enemy lines in "Saving Private Ryan," being rescued from Mars in "The Martian," being rescued from an even more distant planet in "Interstellar," or from any other predicament he's managed to get himself into, you can always expect Matt Damon to turn in a great performance. He's made so many classics, in fact, that we struggled to find reasons to exclude some truly excellent movies from this list.

Amazing as they are, "Saving Private Ryan" and "Interstellar" don't have quite enough Matt Damon in them to qualify as Matt Damon movies, while the likes of "Invictus" and "Contagion" came this close to being included. That being said, Damon has turned in his fair share of skippable clunkers as well, films that you might have long-since forgotten about. So what are Matt Damon's all-time best movies? And what are the films that he probably regrets making? Read on to find out.

Worst: The Brothers Grimm

You've no doubt heard of "Cinderella," "Little Red Riding Hood," "Rapunzel," "Sleeping Beauty," and "Snow White," classic stories that have been adapted many times over the years. These are just a handful of the many tales chronicled by 19th-century brothers Jacob and Wilhelm Grimm. 2005's "The Brothers Grimm," starring Matt Damon as Will and Heath Ledger as Jake, is about these two cultural academics. Well, sort of. It's based on a version of the real-life brothers so fictitious it could've been one of their fairy tales.

In this movie, the brothers are traveling conmen in French-occupied Germany. They use their deep knowledge of local legends to trick people into paying them to get rid of dark spirits. However, they eventually stumble across an actual threat — the Mirror Queen, who kills young women to steal their beauty and life force. This, of course, forces our two heroes to grow and make some sacrifices to save innocent lives.

It sounds pretty creative, and a lot of effort went into making this version of the story work out. Unfortunately, it's not a well-executed film. "'The Brothers Grimm' is full of beautiful imagery, but the story is labored and less than enchanting," says the Rotten Tomatoes critics consensus. Veteran film critic Roger Ebert called the film "an invention without pattern, chasing itself around the screen without finding a plot. The movie seems like a style in search of a purpose, with a story we might not care about."

Best: The Bourne Ultimatum

You can't list the best Matt Damon movies without at least mentioning the Bourne series, based on Robert Ludlum's novels. Damon stars as Jason Bourne, a former CIA agent who tries to recapture his memory after the organization tries and fails to assassinate him for abandoning an immoral job. 2002's "The Bourne Identity" follows the titular character as he tries to retrace the bloody steps of his life. He continues his mission in 2004's "The Bourne Supremacy," which was also a hit with critics, per Rotten Tomatoes. But it's the third movie in the series, 2007's "The Bourne Ultimatum," that takes the top prize on this list.

This movie sees Bourne fighting across the planet to stay ahead of his hunters, hot on his trail and itching to finish the job. The infamous shaky-cam action is a bit stomach-turning after all these years, but there's no denying that between the plotting, performances, and set pieces, this is about as solid an action-thriller as you'll find anywhere. The Rotten Tomatoes critics consensus has all the info you'll need if you're thinking of giving it a watch: "'The Bourne Ultimatum' is an intelligent, finely tuned non-stop thrill ride. Another strong performance from Matt Damon and sharp camerawork from Paul Greengrass make this the finest installment of the Bourne trilogy."

Worst: The Great Wall

Matt Damon is a leading man who appears in big, high-concept films, including action and sci-fi pictures. But he usually fronts dramas or more prestigious blockbusters, rather than CGI schlock. So it was definitely weird to see his face on posters for 2017's "The Great Wall," a VFX-heavy monster movie directed by Zhang Yimou in which aliens attack the Great Wall of China during the medieval period.

Damon plays William Garin, a European mercenary who gets imprisoned in the wall after getting caught sneaking around the Song dynasty in search of gunpowder. He gets forced to help his captors ward of waves of generic space... wolves? Dinosaurs? We're not sure how to describe the Tao Tei monsters featured here, other than "stupid looking." So, yeah. Not your typical Damon material. It was also disappointing to see a white guy leading a mostly Asian cast in a story about Asian cultures, traditions, history, and landmarks. But that's Hollywood for you.

Luckily, you don't have to watch this movie! Most people didn't, as evidenced by its status as a massive box office bomb. Not only did it lose an embarrassing $74.5 million, according to Deadline, but Rotten Tomatoes says it got a chilly reception from critics and audiences alike.

Best: True Grit

It's always risky to remake an older film. If it's a classic and you're trying to capitalize on its enduring popularity, you have to deal with angry fans who want their beloved material left alone. If it's a lousy property that you think you can improve upon, it probably doesn't come with fans attached, and you're left wondering what the point is. But 2010's "True Grit," starring Jeff Bridges as Marshal Rooster Cogburn and Hailee Steinfeld as young Mattie Ross (who hires the former to avenge her father's murder), managed to thread the needle just right.

We suppose the Coen Brothers, fresh off the 2007 Western thriller "No Country for Old Men," had something to do with this one being as good as it was. Damon himself wasn't the star of the movie, but he got plenty of well-used screen time as Texas Ranger LaBoeuf, who is also on the trail of the murderer (Josh Brolin's Tom Chaney). Roger Ebert was one of several critics who praised the nuance Damon brought to the role. "Glen Campbell had the role earlier, and was right for the tone of that film. Damon plays it on a more ominous note. His LaBoeuf isn't sidekick material. He and Cogburn have long-standing issues. Nor, we discover, is LaBoeuf a man of simple loyalty."

Worst: All the Pretty Horses

Based on Cormac McCarthy's novel of the same name, the Billy Bob Thornton-directed "All the Pretty Horses" looks like a Lifetime movie with all the cowboy hats and lovey-dovey glances that co-stars Matt Damon and Penelope Cruz share. It sounds even more like a Lifetime movie when you read the plot summary. Essentially, a young homeless cowboy embarks on a journey of self-discovery when his mother sells the Texas ranch he grew up on. He finds a job as a cattle wrangler for a ranch owner and ends up falling in love with the rancher's daughter. Then you watch the movie and realize you were wrong: Most Lifetime movies are actually better.

The film is rushed, soulless, and predictable, yet doesn't seem to be aware of its shortcomings. The dialogue is stiff and forced. Multiple scenes feature inexplicable and painfully artsy shots (like close-ups of horse eyeballs or people staring directly at the camera) that ruin the pacing. We get the impression the movie thinks it has something important to say, but we just can't figure out what it is.

Lisa Schwarzbaum ripped this sappy drama to shreds in her review for Entertainment Weekly. "Faced with a choice of blunt instruments with which to beat a good book into a bad movie, director Billy Bob Thornton chooses heavy, random, arty imagery and a leaden pace to thwack 'All the Pretty Horses.'"

Best: The Martian

Getting stranded on Mars is a death sentence, unless your name is Mark Watney and you're a skilled botanist. Based on Andy Weir's 2011 novel of the same name, "The Martian" follows Watney's fight for survival after a dust storm on Mars forces his NASA crewmates to leave him for dead. With nothing but a damaged shelter and his own wits, Watney has to farm, manufacture water, and find a way to communicate with Earth before it's too late.

The filmmaking is solid, and the performances from the supporting cast (including Jessica Chastain and Jeff Daniels) are wonderful. According to Science ABC, the story (like the book behind it) is far more accurate than most sci-fi films. In fact, it's such a well-researched love letter to science and the men and women who wield it that it's hard to call it science "fiction" at all, even though we must technically put it in that category. But the true star here is Matt Damon, who anchors the concept and turns in one of his most accomplished and likeable performances ever.

The Rotten Tomatoes critics consensus sums up the film's overwhelming critical acclaim: "Smart, thrilling, and surprisingly funny, 'The Martian' offers a faithful adaptation of the bestselling book that brings out the best in leading man Matt Damon and director Ridley Scott."

Worst: The Monuments Men

Between "Saving Private Ryan," "Interstellar," "The Departed," "Good Will Hunting," and "Contagion," Matt Damon has been part of some of the most amazing ensemble casts ever. So when it was announced he was joining Bill Murray, John Goodman, and George Clooney (who also directs) in a late-WWII period piece, it seemed like another hit was coming. Sadly, "The Monuments Men" was anything but. The story follows American soldiers who fight to stop the Nazis from destroying priceless works of art as revenge for their now imminent defeat.

One of the problems with this uneven film is that there's too much to do and too little time. "There are far too many characters, so the screenplay splits them up into little groups and sends them off on various errands," wrote Alex von Tunzelmann, a historian who reviewed the movie for The Guardian (and who collected receipts on the film's many historical failings). "Some of these [errands] are more exciting than others — but they do not add up to a satisfying plot. A TV series might have been a better vehicle for the 'monuments men' stories than a feature film."

Another big problem here is the fact that the movie expects the audience to care about art when death and destruction is bringing Europe to its knees. "It's hard to have fun with Hitler and the Third Reich given all the Jews that died during World War II," said The Wrap.

Best: Ford v Ferrari

You probably think of America when you think of auto racing, but there was a time not so long ago when the United States was about as dominant in that sport as it is now with soccer. Ford wanted to change all that by building the GT40, which they hoped could finally beat the dominant Italian team and their Ferrari supercars (who, per Britannica, had won the 24 Hours of Le Mans every year from 1960 to 1965). "Ford v Ferrari" tells that story with all the rousing energy of the best sports dramas. The movie manages to be excellent without avoiding complex ideas or holding your hand through the story.

The writing is tight, the filmmaking is wonderful, Christian Bale is great as Ken Miles (the GT40's test driver), and Matt Damon is terrific as Carroll Shelby (the experimental car's designer). Unsurprisingly given the talent involved, the movie got lots of award nominations (including best picture at the Oscars). It took home Academy Awards for editing and sound mixing, as well as trophies at the BAFTAs and Screen Actors Guild Awards. The Rotten Tomatoes critics consensus sums it up perfectly: "'Ford v Ferrari' delivers all the polished auto action audiences will expect — and balances it with enough gripping human drama to satisfy non-racing enthusiasts."

Worst: Suburbicon

In director George Clooney's 2017's crime comedy "Suburbicon," Matt Damon plays a family man whose seemingly peaceful suburban neighborhood is actually beset by crime and corruption. Damon isn't the only talented actor in this movie, with the likes of Julianne Moore (who plays Damon's paraplegic wife as well as her twin sister) and Oscar Isaac also taking part. On top of that, the film was co-written by the Coen Brothers. And yet... oof.

"Suburbicon" is a jumble of ideas from all over the place that flopped hard at the box office, making less than $6 million domestically. It was panned by critics and regular moviegoers alike (it has a critical score of 28% on Rotten Tomatoes and an audience score of just 25%), making it another let down for Clooney and for Damon. Everyone involved had good intentions, but Clooney hits viewers over the head with his message. "'Suburbicon' is just too obvious in its satirical depiction of the dubious morality and social inequality behind the squeaky-clean façade of post-war American life," said The Hollywood Reporter's David Rooney.

Best: The Departed

The first film to earn Martin Scorsese a well-desreved Oscar, "The Departed" follows a mob boss who plants a mole in the Massachusetts State Police. At the same time, the cops hide a rat in the mob boss' organization. Both sides figure out what's happening (but not who's who), and all sorts of hyperviolent shenanigans ensue. The movie boasts one of the most impressive ensemble casts ever assembled: Jack Nicholson, Leonardo DiCaprio, Martin Sheen, Mark Wahlberg, Alec Baldwin, Vera Farmiga, Ray Winstone, and, of course, Matt Damon are all present. Aided by a tremendous script and the guidance of a seasoned mob movie master in the director's chair, everyone's firing on all cylinders until the last clip is empty.

Damon plays Staff Sergeant Colin Sullivan, a clean-cut cop secretly feeding information to his real boss in the local Irish mob, Nicholson's Frank Costello. DiCaprio (playing Billy Costigan Jr., the police department rat in Costello's crew) and Nicholson get to scream, shout, and ham it up to their heart's content. Damon plays it closer to the chest, but he's no less mesmerizing to watch. "Featuring outstanding work from an excellent cast," reads the Rotten Tomatoes critics consensus, "'The Departed' is a thoroughly engrossing gangster drama with the gritty authenticity and soupy morality we come to expect from Martin Scorsese."

Worst: The Legend of Bagger Vance

"The Legend of Bagger Vance" stars Will Smith as the titular golf caddie. When Adele Invergordon (Charlize Theron) announces a Depression-era golf tournament to raise money for her struggling family, Vance agrees to coach former champion Rannulph Junuh (Matt Damon) back to his former status as a pro to be reckoned with. It's a sweet story with lots of smiles, laughs, and plenty of charming wisdom from Vance, who always knows just what to say. The thing is, none of that is a compliment. The movie is far too sugary and relies too heavily on clichés to cover up its uninteresting characters, sloppy writing, and the racist, insulting character of Vance himself.

"In 'The Legend of Bagger Vance,' one of the more embarrassing movies in recent history, Will Smith plays a magical Black caddie who helps Matt Damon win a golf tournament and the heart of Charlize Theron — in 1930s Georgia, no less," said Time magazine when the film dropped back in 2000. "You'd think Smith would have used his powers to, oh, I don't know, stop a lynching or two." To make matters worse, critics didn't like the movie even without the "Magic Black person" nonsense, calling it out for lousy dialogue and flat characters. This offensive dud holds a (generous) rating of 43% on Rotten Tomatoes.

Best: Good Will Hunting

1997's "Good Will Hunting" is about a brilliant young underachiever (Hunting, played by Matt Damon) who is too arrogant (and secretly afraid) to realize his nearly limitless potential. Luckily, he's got friends in the fight against himself: His best pal Chuckie (Ben Affleck) and his court-ordered therapist Sean (Robin Williams). Sean's professional approach is to give Hunting the tools to examine the roots of his issues, confront his trauma, and challenge him to, well, challenge himself. Chuckie's approach is to call his buddy an idiot for wasting his maths talents. It's not clear which way is more effective, but in the end, Hunting takes a chance on himself and grows as a character.

It's pretty clichéd stuff at times, but it works. Why? Because the writing is great and the performances are top-notch. You might be able to predict the ending from the first frame of the movie, but between the "How 'bout them apples?" line, Sean's speech to Will in the park, the "It's not your fault" scene, and several other moments, the movie earns the right to end however it pleases. The film was nominated for nine Oscars, winning two: Williams scooped the award for best supporting actor, while Damon and Affleck won for their screenplay.