Sarah Michelle Gellar plays a Boston College cheerleader named Cindy who is dating the point guard for the Harvard basketball team. Her father is a mob boss, and she gets her boyfriend Alan (played by Adrian Grenier) mixed up in sports betting. Joey Lauren Adams plays Alan's philosophy professor with whom Alan's got something going on the side. Eric Stoltz is an undercover FBI agent infiltrating Cindy's father's mafia operations. Rebecca Gayheart plays Stoltz' co-FBI agent/girlfriend, and Ray Allen plays Grenier's Harvard teammate.