Matt Damon first made his way into the film scene with a minor role in the 1988 film Mystic Pizza, and from there he picked up a steady amount of supporting roles through the early-to-mid 1990s. Though once 1997 rolled around, he soon found himself on top of the world when he starred in Good Will Hunting, which was from a screenplay he co-wrote with Ben Affleck.
Good Will Hunting gained nine Academy Award nominations, coming away with two, including Best Original Screenplay for Damon and Affleck. And from there, Damon’s career quickly rose, shifting from being a supporting player to leading man status. Today, Damon is recognized as one of the top figures in the movie business today, with multiple franchises under his belt, and he even started his own production company, named Pearl Street Films, with Affleck in 2010.
And as Damon’s career went on, his roles became even more critically acclaimed. In addition to his Oscar win for Good Will Hunting’s Best Original Screenplay, he’s been nominated for either Best Actor or Best Supporting Actor four times, and he even got his own star on the Hollywood Walk of Fame in 2007. The latest of Damon’s films to be released is Ford v Ferrari, which already is gaining considerable Oscar buzz, specifically for his acting, along with co-star Christian Bale.
So which of his films are the best? Are all of his more notable films the best ones? Or are there any hidden gems? To coincide with the release of Ford v Ferrari, here’s a look back at ten of Damon’s best movies (in alphabetical order):
1) Contagion
Directed by frequent collaborator Steven Soderbergh, this is an ensemble piece with Damon as one of the key players, that being Mitch Emhoff, a man who seems to be immune to a worldwide disease that contaminates the world, including his wife, played by Gwyneth Paltrow. The film boasts a stacked cast that also includes Jude Law, Laurence Fishburne, Marion Cotillard, and Kate Winslet, all of whom had major subplots of their own. The film is a fine example of Soderbergh’s tight direction, with many scenes filled with close-ups that gave it a claustrophobic feel, as characters would be cut off from the rest of the world as they get infected with the virus, or come close to it. One of Soderbergh’s more recent efforts is also one of his - and Damon’s - finest.
2) The Departed
Martin Scorsese’s a prime example of consistency within the film industry. He’s been cranking out films since 1967, yet you could eliminate his entire filmography pre-2000, and he’d still have multiple classics to his name. One of those is The Departed, which finds Damon as a mole sent to infiltrate the Massachusetts Police Department by crime boss Jack Nicholson, while at the same time, Leonardo DiCaprio - an actual police officer - is sent as a mole to infiltrate Nicholson’s crime operation, with neither mole knowing the other’s true identity. It’s a two and a half hour long saga, but Scorsese fills each and every minute with twists, turns, close calls, and a great sense of mystery. Filled with some standout work from its all-star cast, this is top-tier latter-day Scorsese.
3) Dogma
For quite some time after Good Will Hunting, Damon and Affleck went hand-in-hand as an iconic filmmaking duo, leading the two to be cast as the antagonists in Kevin Smith’s religious comedy Dogma in 1999. The duo star as rogue angels Bartleby and Loki, who find a loophole to get into Heaven after years of being banished, that would lead to the end of humanity. This leads to a team consisting of Linda Fiorentino, Chris Rock, Salma Hayek, and Smith’s most iconic characters Jay and Silent Bob out to stop them. The film was at the center of quite some controversy at the time for what religious groups perceived as blasphemy. Though many of its takes on religion aside, this is an often funny, if a bit overlong at times, film that was a nice balance at the character drama Smith became known for and hilarious over-the-top violent humor, making this one of the stronger entries in Smith’s filmography.
4) Good Will Hunting
Over twenty years later, Damon’s breakout film is still one of his best. Damon stars as the title character, an unrecognized math prodigy who confronts his past and looks towards his future after coming under the wing of a professor played by Robin Williams. While the film featured excellent performances from Damon, Affleck, and Minnie Driver, it was Williams who absolutely stole the show, picking up the other Academy Award win that the film received, and still going on to be known as one of the legendary comedian’s strongest dramatic work. With many of its heartbreaking scenes going on to become iconic, this is a staple of 1990’s filmmaking.
5) The Informant!
Another collaboration between Damon and Soderbergh, this finds Damon as Mark Whitacre, a whistleblower at a food processing company for fixing prices, working with the FBI by wearing a wire to give them the information they need to take the company down, all while dealing with bi-polar disorder and trying to not have a meltdown over the whole ordeal. This is often one of Soderbergh’s most under-looked films, as it was criticized for its comedic take on a character with a personality disorder. Though the film can still be an absolute blast, with an extremely quirky feel that’s spearheaded by Damon’s off-the-wall performance, leading to many laugh-out-loud moments that make it quite a bit of fun.
6) The Martian
One of many films that kept up the recurring joke that we always need to save Matt Damon in a movie, here he stars as an astronaut who get stranded on Mars after a mission goes awry, with his crew realizing after the fact that he’s still alive, and leading a rescue mission to save him. While a sci-fi drama, this was also a very funny film, thanks to plenty of scenes revolving around Damon trying to keep his sanity on Mars, leading him to keeping a video diary where he often puts on an engaging one-man show for the audience. The film is crowd-pleasing in every sense of the word, as the film cuts back and forth extensively between both the chronicles of Damon being stranded on Mars as well as the crew coming to rescue him. This leads to a tense, exciting, and thrilling third act that helps solidify this as a wonderful modern sci-fi film to watch.
7) Saving Private Ryan
The first movie that brought us the “saving Matt Damon” joke. Damon is, like with a few of these other films, the title character here, and he doesn’t show up till nearly the end of the movie. And what’s nice is, despite such a buildup to his appearance, the movie still doesn’t make him feel like just a plot device. He’s still a very fleshed out character, and his own character arc is what drives the remainder of the movie. And it never feels forced, or shoehorned in, nor does it really make the film feel like it goes on for too long. Despite being a nearly three hour movie, the runtime is almost never felt, instead moving at a fairly quick pace. And it carefully balances its lengthy runtime out between intricate character moments and some truly intense action scenes. The opening Normandy Invasion sequence by itself makes this movie worth seeing.
8) Syriana
A giant oil company initiates a shady deal with a smaller oil company, and both the potential social and political effects are felt among many. The film follows multiple story lines, including those revolving around George Clooney, Jeffrey Wright, and Christopher Plummer, among others. Damon plays an energy analyst who is sent by his company to offer his services of an emir, only to get caught up in a much larger war. While this did pick up a Best Supporting Actor award for George Clooney at the Oscars, and did make various critics’ Top Ten lists, this wasn’t as well-received by audiences due to its extremely layered, complex storyline, which can understandably be a turnoff. While the film does have a lot going on, its storytelling is still well-crafted, and it does feature an extensive level of social commentary on the effects of big oil, which is still ultimately relevant today.
9) The Talented Mr. Ripley
Being released only two years after Damon’s star turn in Good Will Hunting, this saw a whole different side of the young actor, going from more good-natured roles to more of an antihero. Damon stars (once again) as the title character, who lies, cheats, commits forgery, and impersonates people. He’s soon recruited by a wealthy socialite to bring his son, played by Jude Law, home. Though things don’t go exactly as planned and Ripley has to do what he does best to get his way out of a tense situation. The film proved early on in Damon’s career that he had some serious range, and that he could take on some truly dark material. The film is filled with various twists and turns and features some great performances from a solid supporting cast that included Gwyneth Paltrow, Cate Blanchett, and Philip Seymour Hoffman.
10) True Grit
It’s rare that a remake would even come anywhere near close to the original, but leave it to the Coen Brothers for being that exception to the rule. The second adaptation of the 1968 novel of the same name, this saw Jeff Bridges step into the role of Rooster Cogburn, the U.S. Marshal once made famous by John Wayne in the previous adaptation in 1969. Damon plays Texas Ranger LaBoeuf, who helps Coburn track down a criminal named Tom Chaney, played by Josh Brolin, after Cogburn was hired by then-newcomer Hailee Steinfeld as the daughter of one of Chaney’s victims. The film was a nice return to the Western for audiences in the 2010’s, as the genre gets considerably less films made these days. And it’s filled with plenty of the Coens’ dark, quirky humor, stunning direction, and fantastic set pieces that make this a modern day classic for the genre.
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