Won: Two Oscars for Best Original Screenplay (Matt Damon and Ben Affleck) and for Best Supporting Actor (Robin Williams), 1998 Probably the esoteric Gus Van Sant's most straightforward film, Good Will Hunting won two of the nine Academy Awards it was nominated for back in 1998, triumphing in the Original Screenplay and Supporting Actor categories for Matt Damon and Ben Affleck, and Robin Williams, respectively. The former of those wins came as something as a surprise, with Affleck and Damon, relative unknowns, especially in screenwriting circles, winning for their very first screenplay, beating out veterans like Woody Allen (for Deconstructing Harry) and James L. Brooks (for As Good As It Gets ) to elatedly take home the Oscar. The latter was much more expected, with Robin Williams winning an Oscar at the fourth time of asking (he'd previously been nominated for Good Morning, Vietnam; Dead Poets Society; and The Fisher King), the actor here getting a nod in the Supporting category for the first time. In a strong field that included the likes of Burt Reynolds' and Robert Forsters' renaissance turns in Boogie Nights and Jackie Brown (respectively), Williams probably just deserved to win, his performance one of the most touching of the '90s.
