Oscar winner Matt Damon has been one of Hollywood’s most reliable leading men for over two decades. But how many of his titles remain classics? Let’s take a look back at 21 of his greatest films, ranked worst to best.
Though Damon and his childhood friend Ben Affleck became famous by writing their own ticket to fame and fortune with “Good Will Hunting” (1997), the pair had been acting for years before that film became an art house hit, even appearing together in “School Ties” (1992). But it was by returning to their native Boston to tell the inspirational story about a secret math genius (Damon) that put them on the map, winning them an Oscar for Best Original Screenplay and bringing Damon his first Best Actor nomination.
Damon has returned to the Oscar race three times in three different categories: Best Supporting Actor for “Invictus” (2009), Best Actor for “The Martian” (2015) and Best Picture for “Manchester by the Sea” (2016). He won Golden Globes for writing “Good Will Hunting” and for starring in “The Martian,” competing again for acting in “Hunting,” “Invictus,” “The Talented Mr. Ripley” (1999), “The Informant!” (2009) and the TV movie “Behind the Candelabra” (2013). He earned SAG Awards bid as part of the ensembles for “GWH,” “Saving Private Ryan” (1998) and “The Departed” (2006), plus individual acting noms for “Hunting,” “Invictus” and “Candelabra.” “Candelabra,” “The Martian” and “Manchester” all brought him BAFTA bids. On the TV side, he contended at the Emmys for “Candelabra,” “30 Rock,” “Saturday Night Live” and for producing the reality series “Project Greenlight” (four times).
Tour our photo gallery of Damon’s 21 greatest films, including some of the titles listed above, as well as the Jason Bourne series and the “Oceans” trilogy.
– Original text and gallery published in October 2019.