Duff (Tom Green) and John (Jason Lee) are best friends, but couldnt be more different. Duff is a confirmed under-achiever and a lifelong bad influence on John. John is a practical, hard working guy who only wants to marry his longtime girlfriend Elaine (Leslie Mann). Elaine and John have vowed to marry once they save $30,000 for their dream house. After years of struggle, John and Elaine can finally afford to walk down the aisle and into their dream house until Johns sister Patty (Megan Mullally) calls with the unbelievable news that his niece Noreen has been accepted at Northern University. Wedding bells are silenced as Patty reminds John of his promise to pay for his nieces college tuition, which costs $29,829 and is due in two weeks! Unable to tell his girlfriend, John turns to his friend Duff to help him make an additional $30,000 in two weeks. Duff, who is no fan of Elaines, convinces John to make a short-term commitment to petty crime. Johns life quickly unravels as each of Duffs hare-brained schemes spin out of control.