Stealing Harvard is a dark comedy. John Plummer (Jason Lee) promises his young niece, Noreen (Tammy Blanchard), that he will pay for her college tuition if she works hard after she is disqualified from an elementary spelling bee. Ten years later, John has finally saved up $30,000 to use for a down payment for a house to live in with his fianc''e, Elaine (Leslie Mann). As fate would have it, his niece comes to take up his offer; she has been accepted into Harvard and cannot afford it without Uncle John's help. John doesn't want to let down Noreen nor Elaine, so he seeks alternative ways to make money. His old high school buddy, Duff (Tom Green), convinces him to turn to a life of crime. Duff and John go through many plans and seem to constantly end up empty-handed. Will John keep his financial promise to Noreen, his hard-working niece, or to Elaine, his ditzy fianc''e?