Stealing Harvard

In the midst of his carefully crafted life, nice guy John Plummer (Jason Lee) finds himself torn between two morally conflicting desires. On one hand, he yearns to prove his worth as a responsible partner by using his life savings of $30,000 to secure a down payment on a house without accepting financial aid from his wealthy and disapproving father-in-law, Mr. Warner (Dennis Farina). This desire is deeply rooted in John's need to establish an independent identity separate from his fiancée Elaine Warner's (Leslie Mann) affluent family.

On the other hand, John has a long-standing promise to his niece Noreen (Tammy Blanchard), daughter of his "trailer-trash" sister Patty (Megan Mullally), to fund her education at Harvard University. The catch is that Noreen needs an additional $30,000 on top of her grants and scholarships to make it happen. John's conscience is now wracked with the dilemma of disappointing his fiancée by showing he cannot provide for her or letting down his niece, sister, and their circle of friends who look up to him as a role model.

As if this internal conflict weren't enough, John's best friend from high school, Walter "Duff" Duffy (Tom Green), an eccentric loser landscaper with a penchant for getting into trouble, enters the picture. Duff convinces John that stealing $30,000 from one of his wealthy landscaping clients is not only justifiable but also morally sound, as no one would be hurt and the insurance company would ultimately cover the loss. Despite initial reservations, John reluctantly agrees to embark on this dubious adventure with Duff.

However, things take an unexpected turn when they attempt to carry out their plan on a Sunday night at the client's home. As they sneak in, they find themselves face-to-face with the homeowner, Honorable Emmett Cook (Richard Jenkins), who has caught them red-handed and is not pleased. With Duff making a hasty exit, John is left standing alone, staring down the barrel of the homeowner's gun, forced to confront the consequences of his actions and the moral compass he had previously claimed to possess.

As John's predicament deepens, he finds himself in a peculiar situation, with a gun pressed against his temple by Emmett Cook. Rather than being met with violence or incarceration, John is instead coerced into adopting the guise of Cook's late wife, an unexpected role that sees him assume the feminine persona as the two men entwine in a tender "spoon" embrace. This bizarre scenario plays out amidst a backdrop of subtle intimacy, as Cook recounts his longing for his deceased spouse, claiming, "I'm not gay, I just miss my wife." Once John has served his purpose, he is released, only to be confronted by the vigilant Mr. Warner and his keen-eyed canine companion, who misinterpret John's frantic behavior as evidence of an illicit affair.

As the narrative unfolds, John and Duff embark on a series of harebrained escapades, including a botched robbery attempt at a liquor store and a brazen scheme to swindle a ruthless drug lord out of $30,000. Their ruse involves fabricating a tale about running an ecstasy ring, but their plan is foiled when a shrewd police detective (John C. McGinley) closes in on them, always staying one step ahead as he gathers evidence. Meanwhile, Mr. Warner's obsessive quest for proof against John leads him to infiltrate Emmett Cook's home, where he is eventually forced to adopt the same unusual "spoon" pose that initially ensnared John. As Warner rummages through Cook's belongings, he stumbles upon incriminating photographic evidence of John's earlier role-playing antics.

As the truth begins to unravel, John (John) is compelled to reveal the entirety of his extraordinary circumstances to his betrothed, Elaine. The catalyst for this confession is her father's unexpected discovery of a photograph showcasing John in drag alongside Cook, an image that could have far-reaching consequences. However, instead of being outraged by her fiancé's deception, Elaine is struck by John's unwavering dedication to providing for her, shielding her from hurt, and ensuring the educational pursuits of his niece at Harvard. This newfound admiration is accompanied by a profound shift in perspective, as Elaine confides in John that her father's business serves as a treasure trove of wealth, ripe for the taking. United in their desperation, John, Elaine, and Duff conspire to execute a daring heist under the cover of night.

Their plan, however, is foiled by an unexpected participant: Mr. Warner's loyal canine companion, Rex. Initially intent on attacking Duff, Rex becomes inexplicably enamored with his would-be victim, refusing to relinquish his grasp. Duff's frantic attempts to escape are met with failure as Rex remains steadfast in his affections, ultimately leading to a series of comedic misadventures.

As the trio searches for the loot, they stumble upon Mr. Warner, who is promptly apprehended by Detective, mistakenly perceiving him as a burglar. John and Elaine make their escape, only to be pursued by Duff, still being hotly pursued by Rex. In a desperate bid to evade capture, Duff leaps into his van, with Rex hot on his heels. The canine's persistence eventually yields the desired result, leaving Duff at the mercy of Rex's affections.

The authorities finally arrive, and the gang's attempts to flee are foiled. As they face a litany of charges, including breaking and entering, animal cruelty, and attempted vehicular manslaughter (courtesy of Duff's betrayal), John feels his world crumbling around him. However, an unexpected twist awaits as Judge Emmett Cook, a man not unfamiliar with the pair, takes charge of their arraignment.

As fate would have it, John seizes the opportunity to send a defiant message to Cook, scribbling down a bold declaration in his lawyer's notebook and broadcasting it across the courtroom. The makeshift sign boldly threatens to reveal the judge's unconventional desires, sending shockwaves through the proceedings. Cook, taken aback by the sudden revelation, swiftly dismisses all charges against John, effectively freeing him from the clutches of justice.

Meanwhile, Duff surprises everyone with his generosity, parting with his life savings - a whopping $1,000 - to aid John in his time of need. In a bold move, John decides to wager this windfall on a long-shot horse, and against all odds, the underdog triumphs, paying out a staggering 30-to-1 return.

Fast-forward to the future, where John finds himself standing at the altar, exchanging vows with Elaine as their closest friends and family look on. The guest list reads like a who's who of familiar faces: Mr. Warner, Patty, Emmett Cook, and Duff, all gathered to celebrate the union. As the newlyweds embark on their new life together, Noreen sets off to pursue higher education.

In the final scene, John is left pondering the enigma that is Duff, wondering how someone so seemingly unfortunate could have amassed such a considerable fortune. The curtain closes with a hint of intrigue as Duff offers Cook a peculiar proposition - one that promises a substantial payday in exchange for... an unusual form of intimacy.