To Die For (1995)
After bit parts on TV (like a teen RFK in a Camelot mini-series), Affleck heads to Los Angeles and hooks up with Gus Van Sant. Opposite Joaquin Phoenix, Affleck plays his first mumbler: a dumbass kid who helps Nicole Kidman murder her husband.
Good Will Hunting (1997)
After a two-year stint in college (George Washington, Columbia), Casey teams up again with Van Sant, playing the pervert buddy of real-life pal Matt Damon and brother Ben. When the film’s a hit, he watches as Damon and Ben nab Oscars.
Ocean’s 11–13 (2001–07)
Affleck falters after Good Will, with flops like Desert Blue, Drowning Mona, and Committed. But when Luke and Owen Wilson turn down the parts of bumbling brothers in Soderbergh’s heist franchise, Affleck and Scott Caan step in. Fans begin to recognize him.
Gerry (2002)
Affleck and Damon successfully pitch Van Sant on an oblique experiment: Two pals, both called Gerry (the actors’ longtime nickname for “fuckup”), get hopelessly lost in the desert. Damon bullies Affleck, then strangles him. Critics rave—and rant.
Lonesome Jim (2005)
In Steve Buscemi’s shambling indie, Affleck gets strong reviews for his depressive take on the flip side of artistic fame, as a frustrated writer (really, an Applebee’s waiter) who returns home to his mom’s house in Indiana, after failing to make it big in New York.