Stealing Harvard (2002)

Directed by Bruce McCulloch

John and his girlfriend have vowed to marry once they save $30,000 for their dream house. But the minute they achieve their financial goal, John finds out his niece has been accepted at Harvard, and he's reminded of his promise to pay for her tuition (nearly $30,000). John's friend Duff convinces him to turn to petty crime to make the payment … but Duff's hare-brained schemes spin quickly out of control.