Everyone has 'moved on', except for Sherman and Jim Levenstein's still understanding father. Little Matt Stiffler wants to join his older brother Steve's business and, after everything Matt has heard from Jim's band-geek wife, he plans to go back to band camp and make a video of his own.
When a bag filled with money goes missing from a casino, the Hitman (Chris O'Donnell) must retrieve it. While he tracks the stash down, the bag changes hands numerous times, finding its way to the Drifter (Jeremy Davies) and the Waitress (Rachael Leigh Cook), among others. As the bag's journey continues, more characters, including the Cop (Michael Rapaport) and the Sheriff (Keith David), get drawn into the winding crime tale, and the search becomes increasingly desperate.