Matt Damon has always had a knack for playing extraordinary leading men in movies. His casting as the cunning, resourceful Odysseus in Christopher Nolan’s The Odysseymakes perfect sense once we consider Damon’s decades-spanning filmography. Films like Good Will Hunting (1997), The Talented Mr. Ripley (1999), and the Bourne(2002-2016) series showcase Damon’s incredible range in playing larger-than-life characters with varying moral compasses.