9 Movies Featuring BFFs Matt Damon and Ben Affleck

"Air" marks the first time Affleck has directed Damon, and Affleck also stars in the movie with his bestie. (It's the third time Affleck's directed himself, following 2010's "The Town" and 2012's "Argo.") The movie tells the story of how Nike signed Michael Jordan and began its Air Jordan brand, saving the company and making Jordan a cultural icon. Damon plays marketing executive Sonny Vaccaro with Affleck as Nike founder Phil Knight, and Viola Davis plays Jordan's mother Deloris.