Rudy Duncan (Ben Affleck) has spent 6 years in jail for auto theft. He and his cellmate Nick (James Frain) are just days away from being paroled, when Nick is killed by another inmate. Rudy, is released from prison by as he boards the bus into town he passes a woman who meets the description of Nick’s romantic pen pal, Ashley (Charlize Theron). Knowing that Ashley and Nick have never met, Rudy decides to pretend to be Nick and be rewarded with some female attention. However, Ashley’s crooked brother Gabriel (Gary Sinise) has anxiously been waiting for Nick to be released from prison. He has plans of knocking off a casino that Nick once worked for. Rudy, unable to reveal his true identity is forced to play the part of Nick and aid in the robbery. What could go wrong with this set up?