Jason Lee and Tom Green star in this overlooked comedy from 2002 about a guy having to find a way to steal $30,000 so his niece can go to Harvard since he'd promised to pay for her College education years prior.
John's (Lee) uncharacteristic turn to a life of crime backfires early on when he hires the help of his friend Walter (Green), a moronic loser with consistently bad ideas. It doesn't help that John's girlfriend Elaine (Leslie Mann) has spent all their money on a downpayment for a house and that her father (the late, great Dennis Farina) hates John with a passion. With Lee and Green as the two leads, plus the involvement of Mann, Stealing Harvard might have confused cinemagoers back in the day in that it was neither a Kevin Smith film, a Judd Apatow film or a Tom Green-centric farce in the vein of Freddie Got Fingered. It feels like a film destined for the mid-to-late 90's which was frozen in the ice and thawed about 5 years too late for anyone to care.
All this is unfortunate since, against all odds, Stealing Harvard is rather good. The duo's attempts at finding the money are entertaining as they are initially caught by Richard Jenkins trying to empty his safe and forced to wear women's clothing and take pictures with him, then they hire Chris Penn's criminal who leads a messy bank robbery and finally try to steal from Elaine's father. While it's obvious that John should have probably just said he had no money early on rather then embark on this goofy journey, his misadventures are so amusingly misguided it doesn't matter. Green steals the show and has a ball making Walter sound as sure-of-himself and clueless at the same time then having him bungle every mission. The film is very funny, has a really good cast and delivers on a shaky premise more than you'd expect it to.
It may have not been an instant classic upon its release and most people forget the film even exists but Stealing Harvard is nevertheless an underrated comedy with a lot going for it. If you're a fan of the people involved, you won't be disappointed so try not to pay attention to the negative feedback surrounding the film since it all feels more anti-Tom Green driven than genuine.