John Plummer's (Jason Lee) rather mundane life is about to take a dramatic detour. Working in the sales department at a medical supply outlet, he has just saved $30,000 with his live-in girlfriend Elaine (Leslie Mann). She wants to make a down payment on a cute little starter home and finalize plans for their wedding. But John's disadvantaged niece is ready to cash in on a long forgotten promise.
In elementary school, Noreen (Tammy Blanchard) lost a class spelling bee. During a rash moment of consolation, Uncle John vowed to pay for her college tuition if she was ever accepted at a good school. Now the dark-haired girl with the trailer trash mother (Megan Mullally) and unknown father has done just that. After tallying all her savings and financial aid, the high school graduate needs only $29,879 from her generous uncle to pay for her first year tuition at Harvard University.
Rather than come clean with his fianc0xE9e about the unexpected debt, John looks for financial assistance from aunts, uncles and a foul-mouthed grandma. Finally he turns to Duff (Tom Green), a dimwitted former high school pal who supplements his landscaping business by procuring liquor and supplying it, at a considerable markup, to teenaged drinkers.
While John's intentions may be honorable, his methods are anything but honest when he lets Duff talk him into a spat of crimes to make some quick currency. Bumbling one robbery attempt after another, the abject thieves soon have Elaine's suspicious father (Dennis Farina) and a zealous police detective (John C. McGinley) closing in on their misadventures.
However a serious shortage of funds isn't the only problem in Stealing Harvard. Expletives and crude anatomical terms abound along with cigarette use and several drug references. Crude sexual jokes include an overly amorous dog, intimacy issues for the soon-to-be married couple, repeated sexual encounters, cross dressing men and lots of skin in a brief shower scene.
With no hope of earning a passing grade, Stealing Harvard is one film families might want to leave out of their upcoming agendas.