Boy
Emma
The Gambler
The Clerk

Fifteen years ago, Ben Walker made a decision to leave his college sweetheart and ultimately his faith, in order to pursue a lucrative business opportunity. Now with a high-paying career and a trophy fiancé, he is visited by an angel, who gives him a glimpse into what his life would look like had he followed his calling.

Alicia is a poor girl starting college. Hadley, Julianne and Sydney are three well-off girls in a row house. Classes begin and Alicia is paired with Hadley to work on a sociology class project. At first rejected, Alicia is finally accepted into Hadley's clique where she is introduced to a world of privilege and dangerous thrills. But her attempts to become one of them ultimately land her in the hospital.

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.