John Lyshitski, portrayed by Dax Shepard, has spent a significant portion of his life as a ne'er-do-well, primarily due to the harsh judgments of Judge Nelson Biederman III, who has consistently imposed tough sentences on him since he committed his first crime—stealing a car at just eight years old. Seeking revenge for his turbulent past, John learns that the judge has met an unexpectedly peaceful end mere days before his release from prison.
With his sights set on vengeance, John chooses to target the judge's obnoxious son, Will Arnett, who is known as Nelson Biederman IV. At a ceremony honoring Nelson III, John seizes the opportunity to hop into Nelson IV's BMW, pilfering his spare change, spitting in his coffee, and even finishing off his inhaler. Meanwhile, in the car, Nelson IV has a meltdown—he shouts at his lawyer (who unfortunately has the phone on speaker) and starts belting out a tune, only to discover that his inhaler is empty. In a state of panic, he rushes to a pharmacy, causing chaos by knocking items off the shelves. Mistaken for a junkie robber, he ends up being apprehended by the police after finding an inhaler that they misidentify as a weapon.
Despite the board of directors at the Biederman foundation being tired of Nelson's antics, they decide to let him face the consequences and serve prison time. Unsatisfied with merely witnessing Nelson's incarceration, John plots to join him behind bars, opting to sell marijuana to undercover cops in order to secure himself a matching sentence of three to five years in the same facility as his nemesis. With some bargaining and bribery, John is able to achieve his goal and becomes Nelson's cellmate, pretending to be a supportive friend while secretly scheming to sabotage him.
Contrary to John's ruthless plan, Nelson begins to navigate prison life with surprising success. He encounters Barry, played by Chi McBride, a formidable yet charming gang leader who helps Nelson discover his true self. Barry, with his own romantic flair—exemplified by his taste for smooth jazz and homemade Merlot—becomes an unexpected but endearing companion for Nelson within the confines of prison.
As the year progresses, Nelson appears to hold the title of "top dog" among inmates, ready for his parole hearing. However, John is not about to let his target escape so easily; he resorts to drugging Nelson and marking him with offensive tattoos, a move that leads the parole board to deem him unfit for release. Infuriated by John's betrayal, Nelson retaliates, and a brutal altercation ensues, forcing John to reconsider his plan as he realizes that Nelson has nothing to lose.
In a twist of fate, the duo orchestrates a ruse, injecting each other with a coma-inducing drug, leading the guards and fellow inmates to believe they are dead. After being buried in a graveyard, they are ultimately rescued by Barry, who has secured his release. Fast forward a year: Nelson and Barry have formed a life together and ventured into winemaking. When John arrives unexpectedly, he pressures a critic into giving their wine a favorable review. As the three of them take a scenic drive, they enjoy the rhythmic beats of "Move This" by Technotronic, celebrating their unanticipated bond.
