Stealing Harvard

Stealing Harvard working title, Uncle is a 2002 American crime comedy film directed by Bruce McCulloch and written by Martin Hynes and Peter Tolan, about a man who resorts to crime to pay for his nieces Harvard tuition. The film stars Jason Lee and Tom Green with Leslie Mann, Dennis Farina, Richard Jenkins, John C. McGinley, Tammy Blanchard, and Megan Mullally.

John confides in his friend Walter Duff Duffy Tom Green, a landscaper. He convinces John to steal from one of his rich clients, who keeps large amounts of cash in an unlocked safe. The pair set off to steal the cash, but Duff runs away when lights come on in the home, leaving John to get caught by Emmett Cook Richard Jenkins. Cook forces John to crossdress and roleplay the part of Cooks late wife as the two men lie in bed and spoon. Eventually, after taking an incriminating photograph of John, Cook releases him. As he is leaving, Mr. Warner rides by and takes note of Johns panicked behavior, believing that he has caught John in an affair.Further capers ensue as John and Duff try to rob a liquor store and later attempt to con a drug lord out of 30,000 by concocting a phony story about running an ecstasy ring. A police detective John C. McGinley is on to John and Duff, but never has enough evidence to actually pin any of the crimes on them. Meanwhile, Mr. Warner breaks into Cooks residence in order to get evidence against John, and once Cook catches him, he is forced to spoon as well. Before leaving, Warner finds the photo of John from the album, which he then gives to Elaine. ........

Source: Wikipedia