 Sarah Michelle Gellar plays a Holy Cross 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.