3. Reindeer Games (2000)
Ben Affleck: You're like a child! What do I keep telling you? You gotta do the safe picture, then you do the art picture... and sometimes you gotta do the payback picture because your friend says you owe him. And then sometimes you gotta go back to the well. Matt Damon: Yeah, and sometimes you do Reindeer Games. Ben Affleck: See, that was just mean!
The above quote is from Jay and Silent Bob Strike Back, and there's good reason that Kevin Smith sought to pick on his pal's baffling decision to star in this inept thriller from the legendary John Frankenheimer. It's another film where Affleck is helpless against the terrible screenplay, which has him traipsing over a non-descript region of Colorado helping a bunch of thugs to rip off a casino. At least he's paired with Charlize Theron, so there is some sexual chemistry in the film, but by and large, it's considered a nadir of both of their careers.