9 Movies Featuring BFFs Matt Damon and Ben Affleck

"Jay and Silent Bob Strike Back" is Smith's fifth movie, also set in the Clerks realm, and Jay and Silent Bob take center stage again. Affleck appears as himself, his "Good Will Hunting" character, and as Holden from "Chasing Amy." Damon appears as himself and as Will Hunting. The film's sprawling ensemble includes Carrie Fisher, Jon Stewart, Tracy Morgan, and Alanis Morissette. Adams also reprises her role as Alyssa from "Chasing Amy."