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Damon's career was launched following the success of the film Good Will Hunting (1997) from a screenplay he co-wrote with friend Ben Affleck. The pair won an Academy Award for Best Original Screenplay and a Golden Globe Award for Best Screenplay for their work. Damon has since starred in commercially successful films such as Saving Private Ryan (1998); the Ocean's trilogy; and the first three films in the Bourne series, while also gaining critical acclaim for his performances in dramas such as Syriana (2005), The Good Shepherd (2006), and The Departed (2006). He garnered a Golden Globe nomination for portraying the title character in The Talented Mr. Ripley (1999) and was nominated for an Academy Award for Best Supporting Actor in Invictus (2009).
Van Sant is a two time nominee of the Academy Award for Best Director — for Good Will Hunting (1997) and Milk (2008), both of which were also nominated for Best Picture — and won the Palme d'Or at the Cannes Film Festival for his film Elephant (2003).
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Photo Credit: Walter McBride