Danny (Paul Rudd) and Wheeler (Seann William Scott) are two salesmen in the greater Los Angeles area for an energy drink, Minotaur. They promote it as a way to keep kids off drugs. Wheeler loves the job. 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 after making one of their presentations at a high school, the duo find that their company truck is being towed for parking in a "No Parking" zone. 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 arrested and the judge sentences the two to a 30 day jail sentence. Beth, however, manages to strike a deal with the judge in which they have to log 150 hours of community service over the next thirty days at the judge's favorite charity, a big-brother style program called Sturdy Wings, led by Gayle Sweeny (Jane Lynch). Gayle, who takes an instant dislike to Danny and Wheeler, 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 to prison. Wheeler is paired up with Ronnie Shields (Bobb'e J. Thompson), a foulmouthed, streetwise miscreant obsessed with breasts who has driven away all the other "Bigs" he has been paired with, while 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 doing that will cost them their jobs and their careers. After a few days they gradually bond with their respective partners; Ronnie takes an interest in Wheeler's favorite band Kiss and discovers that Wheeler shares his obsession with breasts, whilst Danny joins Augie's medieval live action role playing game, LAIRE (Live Action Interactive Role-playing Explorers). At the same time, Danny tries to make up with Beth for his mistakes, but to no avail; Beth must commit to this breakup.
Unfortunately, their success is cut short after Danny gets himself and Augie permanently banned from LAIRE after causing a fight with the "king" and then earns the animosity of Augie's parents after criticizing their hostility towards his interests. Wheeler, meanwhile, takes Ronnie to a party and leaves him unsupervised while 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. In the elevator, Danny berates Wheeler for leaving Ronnie behind while Wheeler scolds him about his whining. The two fight and as they get off, have a falling out.
Danny looks through his closet and finds the battle attire Augie had given him. He then 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 and gets permission from Ronnie's mother to hang out with Ronnie after he gets out of jail.
In the after-battle party, Augie finally hits it off with Esplen, who asks him to become her King, which he accepts, and the two kiss. Gayle, impressed with the pair's efforts, tells them that due to a long standing relationship with the judge, she will be able to get their names cleared. The movie ends with Danny serenading Beth in front of everyone with an off-key and improvised version of the KISS song "Beth" (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) and the two reconcile.
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