John (Jason Lee) leads a simple and happy life. He has beautiful fiancée and an assistant manger position at his future father-in-law's company. Everything seems perfect, until John's favourite nice surprises him with her acceptance to Harvard University and he's reminded of a long forgotten oath he made to foot the bill! Desperate, John turns to his hare-brained and half-witted best friend Duff (Tom Green) for advice. Thinking far outside of the box, Duff convinces John that they must temporarily lead a life of crime to raise the needed cash!