10 Best Con Man Movies

There was a period of time in the late 80s/early 90s when, if you wanted an unscrupulous figure to headline your movie, James Woods was the first phone call. His weaselly, slimy, lanky figure combined with his nervous rapid-fire speech pattern made him perfect for any coke dealer's lawyer. At the same time, throw a cigarette in his mouth and a leather jacket over his shoulders and Woods could also pull off badass cop.

Diggstown is a role that lies closer to the former, but Woods as Gabriel Cain brings a sense of gravitas and integrity, alongside the likes of Louis Gosset Jr., Bruce Dern and comic relief Oliver Platt. Sure, he's a sleazebag out to con a town out of money, but he's the lesser of two evils, going up against Dern's local "businessman" (and all that the word implies). The con is barely a con: Gossett Jr. has to go up in the ring against ten men in 24 hours.

The fun that director Michael Ritchie has takes place outside of the makeshift boxing arena, however, with Woods and his ragtag crew conspiring with and scamming the contenders to throw their turn in the ring. It's a film that's unfortunately fallen by the wayside in the ensuing years, but its well-worth your time.