Matt Damon's illustrious career has been filled with accolades and box office successes, so finding his best movie isn't an easy task. First turning heads in 1997 with his star-making performance in Good Will Hunting, Damon has never looked back since. With a unique mix of dramas, comedies, and action films, Damon's diverse catalog has helped him become one of the most profitable movie stars in Hollywood history. Aside from his financial success, Damon has never shied away from taking challenging parts, and he was rewarded handsomely with a slew of nominations and wins from the Academy Awards and the Golden Globes.
Making his big screen debut in 1988's Mystic Pizza in a small role, Damon's career quickly began to pick up steam when he landed a co-starring role in the 1996 legal drama, The Rainmaker. Since his monumental collaboration with Ben Affleck on Good Will Hunting, Damon's career began a meteoric rise which hasn't stopped in the quarter-century since the film's release. Amazingly, Damon has never slowed down after becoming a superstar and his 80-plus film output has included massive franchises like the Marvel Cinematic Universe, yet he hasn't been afraid to pay it forward in small indie comedies like 2019's Jay and Silent Bob Reboot as well.
Invictus (2009)
Invictus marked Damon's return to the sports film, years after his appearance in The Legend of Bagger Vance in 2000. The story chronicles the real-life events of the 1995 Rugby World Cup where the host-nation South African Springboks shocks the world with their performance just years after the dismantling of the country's apartheid regime. Damon was known for his leading roles, but his supporting effort as rugby star François Pienaar showed he could do that just as deftly. While not one of the best sports films ever made, Invictus brought the historical drama to life, and Damon snagged a Best Supporting Actor nomination at the Oscars for his performance.
The Informant! (2009)
Matt Damon and director Steven Soderbergh have been frequent collaborators since 2001's Ocean's Eleven, but it was The Informant that really saw the pinnacle of their artistic partnership. The based-on-a-true-story film follows an employee for the ADM corporation who blows the whistle on his employer's price-fixing conspiracy in the 1990s. Damon was praised as Mark Whitacre, and the part demanded every bit of his comedic, and dramatic chops as Mark cracked under the pressure. Though it only garnered a 79% on Rotten Tomatoes, Damon's performance outshone other lesser aspects of the film, and he was nominated for a Golden Globe.
Ford V Ferrari (2019)
Though Ford v Ferrari changed the story's history, it presented a fascinating piece of motorsport lore and showed another side of Matt Damon. Challenged by Ford to create a car that could win at Le Mans, designer Carroll Shelby partners with an eccentric driver to win the race. Graduating to the role of a mature mentor, Damon had come full circle from his younger days. The film made the story accessible to all, and Damon's chemistry with co-star Christian Bale was a large part of its success. Scoring a Best Picture Oscar nomination, Ford v Ferrari also grossed an impressive $225 million (via Box Office Mojo) at the box office.
True Grit (2010)
The Coen brothers' films have been praised for their originality, and it came as a shock to many when they remade the classic western True Grit. After the murder of her father, a precocious young girl enlists a washed-up lawman to help her bring in the perpetrators. Stripped of the original's Hollywood gloss, 2010's True Grit was grimier and truer to author Charles Portis' vision. His co-stars Jeff Bridges and Hailee Steinfeld were the focus, but Damon's turn as LaBoeuf had more layers than Glen Campbell's in the original. The film was a critical and commercial success, though it didn't win any of the 10 Oscars it was nominated for.
Saving Private Ryan (1998)
Steven Spielberg's epic war film Saving Private Ryan was the director's ultimate vision of a blockbuster that also stayed true to history. In the days following WWII's Normandy Invasion, a band of soldiers go behind enemy lines to rescue the last son of the Ryan family. Generally called the best war movie ever made, the film was a titanic undertaking that grossed $480 million (via Box Office Mojo). Even though Damon only appeared as Private Ryan briefly, the young actor stood out among a talented ensemble cast. Ryan was supposed to be a breakout role but he was even better in Good Will Hunting.
The Departed (2006)
Matt Damon's only collaboration with Martin Scorsese was yet another turn in the actor's illustrious career and showed the best of what he had to offer as a performer. Set within the Irish Mafia of Boston, the film follows the Mafia's boss as he flips a police officer to be his spy within the Massachusetts State Police. Usually on the right side of the law, Damon's role as Colin Sullivan allowed the affable everyman to play a conflicted criminal, and he made his mark alongside titans like Jack Nicholson. One of Scorsese's highest-grossing films, The Departed also won the Best Picture Oscar thanks to its impressive ensemble.
The Martian (2015)
If ever a film showed off Matt Damon's box office appeal, it was The Martian, a movie where he largely carried the narrative alone. Stranded on Mars, an astronaut is forced to survive against impossible odds until NASA can devise a plan to rescue him. The fact that Damon earned the Best Actor Oscar nomination was no surprise, and his portrayal of Dr. Mark Watney brought a human component to the science fiction story. Damon's one-man show was a box office smash and grossed a tidy $630 million (via Box Office Mojo) while receiving almost universal critical acclaim for his outstanding performance.
The Talented Mr. Ripley (1999)
Just a few short years after Good Will Hunting made Matt Damon a movie star, his portrayal of Tom Ripley in The Talented Mr. Ripley further established him as a bona fide acting powerhouse. The subversive 1950s period piece follows a huckster named Tom Ripley who attempts to steal the identity of a socialite who had run away from his family responsibilities. Ripley was a part unlike anything Damon had played up to that point, and he was able to turn on the charm while also being a villain. It was one of Damon's few darker roles, and it scored him a Golden Globe nomination for Best Actor.
The Bourne Trilogy (2002-2007)
Matt Damon's career was marked with a slew of critical successes early, and in 2002 he landed the leading role in an action franchise that added another dimension to his career. The Bourne Identity introduced the amnesiac assassin Jason Bourne, and throughout the original trilogy, the titular hero uncovers more and more of his missing memory. Other actors almost played Jason Bourne, but Damon's affability was the perfect ingredient to improve the action hero character. Damon's performance was praised by critics, and his profitability was on full display as each film grossed well over $200 million, with each earning more than the previous one (via Box Office Mojo).
Good Will Hunting (1997)
By 1997, Matt Damon was no stranger in Hollywood thanks to starring roles in films like The Rainmaker, but Good Will Hunting was ostensibly his breakout role. The film centered on Will Hunting, a mathematical genius who worked at MIT as a janitor, and sought the help of a psychiatrist to find his true calling in life. Heady and understated, the movie's small scope allowed for the performances of Damon and his co-star Robin Williams to shine. Aside from starring in the film which earned him the Best Actor Oscar nomination, Damon also co-wrote the screenplay with Ben Affleck, a feat which scored them the Oscar for Best Screenplay.