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Danny (Paul Rudd) and Wheeler (Seann William Scott) are two salesmen in the greater Los Angeles area for an energy drink, Minotaur, a parody of beverages like Red Bull. They sell it as a way to keep kids off drugs, although ironically, Wheeler smokes marijuana while on break from work. Wheeler loves the job and even dresses in a Minotaur costume. Danny on the other hand, hates the job and possesses a constant negative attitude toward life, which results in the collapse of his relationship with his girlfriend, attorney Beth (Elizabeth Banks). One day while making one of their presentations at a high school, the duo are told that their company truck is being towed. They protest by trying to drive it away from the tow-truck, but they end up driving it up a statue in front of the school.

They are then arrested for destruction of school property, parking in a no parking zone, and assault of a police officer. Upon their arrest, the judge sentences the two to a 30 day jail sentence. Beth, however, manages to strike a deal with the judge giving Danny and Wheeler a deal in which they have to log 150 hours of community service over the next thirty days. The sentence is to be served at the judge's favorite charity, a big-brother style program called Sturdy Wings, led by Gayle Sweeny (Jane Lynch), a recovering cocaine-addict herself. Gayle is aware that their presence at sturdy wings is court-ordered and warns them that if they fail to carry out their tasks to her satisfaction, she will have them sent back to prison. Wheeler is paired up with Ronnie Shields (Bobb'e J. Thompson), a foulmouthed, streetwise miscreant obsessed with breasts. Danny is paired up with Augie Farks (Christopher Mintz-Plasse), a nerdy teenager obsessed with live action role-playing games.

Initially, the pair find their task extremely difficult, with Danny unable to find any common ground with Augie and his narrow interests, and Ronnie taking virtually no interest in Wheeler. The pair initially consider simply completing their sentence in prison, but after a few days they gradually bond with their respective partners; Ronnie takes an interest in Wheeler's favourite band Kiss and discovers that Wheeler shares his obsession with breasts, whilst Danny joins Augie's medieval role playing game, LAIRE.

Unfortunately, their success is cut short after Danny gets himself and Augie permenantly banned from LAIRE after causing a fight with the "king" and then earns the animosity of Augie's parents after criticising their hostility towards his interests. Wheeler, meanwhile, takes Ronnie to a party but leaves him unsupervised whilst he has sex with another guest, resulting in Ronnie walking home by himself. Ronnie's and Augie's parents consequently ask Sturdy Wings to assign them new mentors. As such, the pair are given a court appointment where they will likely be sentenced to some jail time. On their way down from Beth's office, the two fight in the elevator, apparently destroying their friendship.

After looking through his closet and finding the battle attire Augie had given him, Danny goes to the Burger Hole (where the LAIRE King and his men eat before every battle) and asks for forgiveness and to be able to fight in that afternoon's Battle Royale, the final battle of the year. Meanwhile, Wheeler goes to Ronnie's house after many calls and gets permission from Ronnie's mother to hang out with Ronnie after he gets out of jail.

As Augie has been expelled from his nation of Xanthia in LAIRE, Danny, Wheeler, and Ronnie put aside their differences and join him to create a new nation (Kiss-My-Anthia) to fight in the battle, using the Minotaur company car from their original job, even though their participation in the fight will cause them to miss their court hearing and subsequently get a longer sentence. Various members of the nation sacrifice themselves to allow Augie to fight the King in single combat, which Augie wins. However, only seconds into his victory celebration, his crush, Esplen, kills him to become Queen. Augie's parents, having watched him fight in LAIRE, finally accept his interests.

In the after-battle party, Augie finally kisses Esplen and becomes her King. Gayle, impressed with the pair's efforts, tells them that due to a long standing sexual relationship with the judge, she will be able to get their names cleared. The movie ends with Danny serenading Beth in front of everyone (a reference to him saying "getting up in front of a large group of people and singing isn't my idea of fun" at the beginning of the movie).