This innovative drama from writer and director James Toback (BUGSY, BLACK AND WHITE) follows the travails of Alan Jensen (Adrian Grenier), a Harvard student determined to live life to the fullest and find the ultimate truth. He gets high regularly, and issleeping with Holy Cross cheerleader Cindy Bandolini (Sarah Michelle Gellar), who also happens to be a mobster's daughter. Simultaneously, Alan is carrying on an illicit affair with his philosophy professor, Chesney Cort (Joey Lauren Adams), a woman witha vast sexual appetite. When his parents lose their Kansas home in a tornado, Alan is desperate to help them financially. He turns to Cindy's father for a loan and is soon entrenched in a high-stakes gambling scheme. But all is not as it seems and Alan soon finds himself in over his head with many aspects of his life: his drug use, the women in his life, and even the FBI. Grenier is endearing as the truth-seeking Alan, and as a tough-talking Mafia princess, Gellar steps far away from her television persona as Buffy the Vampire Slayer. Eric Stoltz and Rebecca Gayheart lend their talents in supporting roles that add to the films twisting storyline.