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In 2002, Affleck and Damon starred in Van Sant's experimental drama Gerry, playing two men who get lost while hiking in the desert.
said of Gerry in 2016: "That was an incredible experience.
Opportunities kept presenting themselves that were hard for me to turn down ...
By then, I didn't really have roots at the school or a group of friends." When he later moved to Los Angeles to pursue an acting career in earnest, his first movie role was as a sociopathic teenager in Gus Van Sant's 1995 satirical comedy To Die For.
Even in the midst of Phoenix's most oddball and obsessive torment, it's boring ...And yet in certain kinds of films – this kind – he's 100 percent authentic." However, Stephen Holden of The New York Times felt it "would be a stronger movie if Mr.Affleck had the wherewithal to bare more of the passive-aggressive rage inside ...For his performance as Lee Chandler, a grief-stricken man, he won the Golden Globe, BAFTA and Academy Award for Best Actor, and received a Screen Actors Guild Award nomination.In 2017, Affleck received critical acclaim for his leading role in the supernatural drama film A Ghost Story.
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He later appeared in three Gus Van Sant films – To Die For (1995), Good Will Hunting (1997), and Gerry (2002) – and in Steven Soderbergh's comedy heist trilogy Ocean's Eleven (2001), Ocean's Twelve (2004), and Ocean's Thirteen (2007).