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 duplicitous teachers, Damon has consistently chosen compelling, often morally complex roles. Here, we rank his 20 finest performances.
The Early Years & Breakthrough Roles
Damon's early work hinted at a star in the making, one unafraid of darkness. In School Ties (1992), he played a flagrantly antisemitic bully, an early sign he understood his "bland" persona could be a potent camouflage for beastliness. His dedication was undeniable in Courage Under Fire (1996), where he lost 25kg to play a heroin-addicted Gulf War veteran, a transformative move that made directors take note.
The real breakthrough came with Good Will Hunting (1997). Co-written with Ben Affleck, this drama about an MIT janitor genius won them a screenwriting Oscar. Damon famously stood up to producer Harvey Weinstein to secure Gus Van Sant as director, a gamble that paid off when the film became a Miramax profit powerhouse. This was followed by his star-making turn in Steven Spielberg's Saving Private Ryan (1998), where he memorably popped up from tall grass as the titular soldier after a long search.
Mastering Morally Complex Characters
Damon excels at portraying men whose morals are compromised, a theme running through his best work. In Anthony Minghella's The Talented Mr Ripley (1999), ranked number one, he reinvented Tom Ripley as a preppy, bumbling square who stumbles into murder in 1950s Italy. His performance, layered with insecurity and a sinister smile, proved his blandness was a powerful dramatic tool.
This skill for duplicity shone in The Departed (2006), where he played Colin Sullivan, a gangster deep undercover in the Boston police, and in Margaret (2011), as a teacher whose principles collapse when he sleeps with a student. Even in Syriana (2005), his energy analyst accepts a lucrative contract after his son's death, delivering the caustic line, "How much for my other kid?"
His collaboration with Steven Soderbergh yielded diverse gems: the deluded whistleblower in the farcical The Informant! (2009) and the frazzled lover in the Liberace biopic Behind the Candelabra (2013). In Contagion (2011), he played an everyman surviving a pandemic, a role that found grim resonance during Covid.
Action Hero and Sci-Fi Stalwart
Damon found his defining action role in The Bourne Identity (2002). Despite reshoot rumours, the film was a slow-burning hit that reinvented the spy thriller and cemented his star power. The franchise peaked with The Bourne Supremacy (2004) and The Bourne Ultimatum (2007) under director Paul Greengrass, whose kinetic style and Damon's cultivated intensity created action cinema benchmarks.
He also became a go-to for cerebral sci-fi. In The Martian (2015), he earned a third Oscar nomination as stranded astronaut Mark Watney, balancing survival drama with sassy humour. For Christopher Nolan, he first played the baleful, treacherous Dr Mann in Interstellar (2014), before delivering a beautifully gruff turn as General Leslie Groves in the Oscar-winning Oppenheimer (2023).
Unexpected Gems and Collaborative Ventures
Damon's range is showcased in surprising offbeat projects. He revealed a comic sparkle in the Farrelly brothers' Stuck on You (2003), playing a conjoined twin, and embarked on a minimalist experiment with Gus Van Sant in Gerry (2003), a hypnotic film about being lost in Death Valley. He also delivered an underrated, chilling performance as a CIA founder in Robert De Niro's The Good Shepherd (2006).
From the blockbuster heights of the Bourne series to the intimate character studies of Ripley and Margaret, Matt Damon has built a remarkably varied and enduring career. His reliability stems from a willingness to be unlikable, vulnerable, and complex. With The Rip arriving on 16 January and Nolan's The Odyssey landing on 17 July, his next chapter promises to be just as compelling.
