Harvard Man (2002)

A comedy which follows Alan, a Harvard student indulging in all of life's more interesting vices--illicit sex, drugs and high-stakes gambling, with a little Heidegger thrown in for good measure. Tempted by cheerleader-seductress-mob daughter Cindy Bandolini, Alan gets in too deep and finds himself in danger of losing a lot more than his scholarship when the tables are turned. The affair that Alan is having with his philosophy professor complicates matters further, when her sexual predilections get in the way. Furthermore, Alan starts fixing games for profit and starts indulges in drugs. But when the game-fixing plans go awry, Alan must outsmart the cheerleader, her father, and the FBI.