As Matt Damon prepares for a major 2025, reuniting with Ben Affleck in the Netflix thriller The Rip and starring in Christopher Nolan's IMAX epic The Odyssey, it's the perfect moment to assess the career of one of Hollywood's most dependable leading men. From amnesiac assassins to compromised spies, Damon has consistently chosen intriguing roles that often subvert his all-American image. Here, we rank his 20 finest performances.
The Early Years & Breakthrough Roles
Damon's early work signalled a star who understood his strengths. In 1992's School Ties, he played against type as a vicious antisemitic bully, a far cry from the likeable heroes he would later embody. His commitment was undeniable in 1996's Courage Under Fire, where he lost a drastic 25kg to portray a heroin-addicted Gulf War veteran, a transformation that made Hollywood directors take serious notice.
The real breakthrough came with 1997's Good Will Hunting, the film he co-wrote with Ben Affleck. Damon not only starred as the titular janitor genius but famously stood up to producer Harvey Weinstein to secure Gus Van Sant as director. The gamble paid off, winning them a screenwriting Oscar and creating a Miramax profit powerhouse. This was followed by his memorable, if brief, turn as the rescued soldier in Steven Spielberg's seminal war film, Saving Private Ryan (1998).
Defining a Persona: Antiheroes and Action Stars
Damon truly found his cinematic identity in complex, often morally grey characters. His performance as the duplicitous Tom Ripley in The Talented Mr Ripley (1999) is a masterclass in sinister ambiguity. Critics noted his "smile designed to hide something sinister," proving blandness could be a potent camouflage for menace.
This led perfectly to the role that would define his commercial peak: Jason Bourne. Despite a troubled production, The Bourne Identity (2002) became a slow-burning hit, reinventing the action genre and Damon's career. The sequels, particularly The Bourne Supremacy (2004) and The Bourne Ultimatum (2007) under director Paul Greengrass, perfected a frenetic, grounded style that dominated action cinema for years.
He continued exploring treachery in Martin Scorsese's The Departed (2006) as a gangster mole within the police, and with chilling civility in Robert De Niro's CIA origins story The Good Shepherd (2006).
Collaborations and Character Depth
Damon's frequent collaborations with directors like Steven Soderbergh have yielded some of his most interesting work. They range from the dramatic weight of Contagion (2011)—which found eerie resonance during the Covid pandemic—to the hilarious, deluded whistleblower in The Informant! (2009). Their partnership reached a poignant peak in the Liberace biopic Behind the Candelabra (2013), where Damon captured the frazzled insecurity of lover Scott Thorson.
His work with Gus Van Sant also ventured into daring territory with Gerry (2003), an austere, experimental film about two friends lost in the desert that deliberately stripped away his movie-star persona.
More recently, Damon has shown a knack for supporting roles that steal scenes. His gruff yet warm portrayal of General Leslie Groves in Oppenheimer (2023) provided crucial grounding, while his baleful, treacherous turn as Dr Mann in Interstellar (2014) remains a standout surprise. He earned a third acting Oscar nomination for the survivalist charm of The Martian (2015).
The Unforgettable Highlights
Among his vast filmography, two performances stand at the pinnacle. At number two is his subtly devastating role in Kenneth Lonergan's masterpiece Margaret (2011). As a teacher who sleeps with his student, Damon's portrayal of mute panic and moral collapse is a masterclass in conveying profound regret.
Topping the list is The Talented Mr Ripley. Anthony Minghella's adaptation allowed Damon to craft a Ripley who was less a cool psychopath and more a desperate, awkward social climber. The performance brilliantly amplifies the actor's own perceived insecurities, transforming his everyman quality into something deeply unsettling and unforgettable. It remains the definitive proof that Matt Damon is far more than a reliable hero; he is a actor of remarkable and chilling depth.
The Rip streams on Netflix from 16 January 2025. The Odyssey is released in cinemas on 17 July 2025.
