Ben Affleck vs. Matt Damon: Who'd You Rather? Ben Affleck vs. Matt Damon Who'd You Rather? 3/29/2010 5:00 PM PT Best friends and Oscar winning screenwriters Ben Affleck, 37, and Matt Damon, 39, showed up to the same event in L.A this weekend. Question is ... See Also Richie vs. Rock vs. Jovi: Who'd You Rather? Share on Facebook Share on X Matt Damon Ben Affleck Who'd You Rather?