Engaged to the beautiful Elaine (Leslie Mann) and saving up to buy their dream house, John (Jason Lee) appears to have it all. But when his sister shows him a videotape in which he promises to pay for his niece's college education, he finds himself desperate for thirty thousand dollars. Recruiting his slightly psychopathic friend Duff (Tom Green) to help him come up with some fast cash, John quickly discovers that he's only making things worse for himself. After a bumbled mini-mart hold-up and a house burglary gone terribly wrong, John's descent into a life of crime takes even more outrageous turns for the worse. After he eventually comes clean with Elaine, she hatches a plan to rob her father's (Dennis Farina) home healthcare business. As the trio breaks into the Homespital offices, a maniacal police detective (John C. McGinley) and Elaine's father both make their move...