He turns his attention to Nelson Biederman III’s obnoxious son, Nelson Biederman IV (Will Arnett). At a dedication ceremony for Nelson III, John hops into Nelson's BMW, steals his change, spits in his coffee and uses up his inhaler. In the BMW after the ceremony, Nelson IV yells at his attorney (who has the speakerphone on in the fully occupied board room), starts to sing, and when he goes for the inhaler, finds it empty. He stops at a pharmacy, panicked, and starts knocking items off the shelf in an attempt to find a replacement inhaler. The pharmacy owners think he's another junkie robber, and that the inhaler he finally finds is a tiny pistol, and call the police. Nelson ends up convicted on that robbery and demands that the Biederman foundation call the governor to dismiss his charges. Even though the governor owes the foundation a favor, the board of directors decide to let Nelson go to prison as they have grown tired of his asinine deportment. John is not satisfied with Nelson just going to prison, however, so John decides to join him in prison by selling marijuana to undercover police officers. At his sentencing he pleads guilty to the same judge Nelson IV had, and asks for the same sentence (3-5) at the same prison. After negotiating with the judge and bribing a few guards, he ends up as Nelson’s cellmate, and here he pretends to be his friend, all in an attempt to give him the wrong advice on surviving life in prison.
Somehow, Nelson gets himself out of a numerous array of jams, even discovering that he's gay and meeting the love of his life, gang leader Barry (Chi McBride), a hulking, burly gay caballero with the heart of a dashing romantic hero beating within his massive, hairy torso, as is evident by his liking for smooth jazz (Chuck Mangione is a favorite of his), plying potential romantic partners with his finest toilet-made Merlot, and transforming his prison cell into a candle-lit, rose-bedecked passion parlor.
Neson reaches his one year parole hearing relatively unscathed, and actually the "top dog" in the prison. However, John won't allow his target to escape prison so easily: he drugs Nelson and writes "WHITE POWER" on his forehead and writes two Nazi signs on each of the two sides of his neck. This leads to the parole board deciding that Nelson "needs" more time to be rehabilitated. Infuriated, Nelson brings John up on the act, who confesses to putting Nelson in jail and the two get embroiled in a fight. It's here that John regrets bunking with Nelson when he realizes Nelson has nothing to lose but his will to murder, and John is the target. After an ensuing brawl, the guards set up a death match between the two.
However, John and Nelson secretly conspire and inject each other with a coma-inducing drug. The guards and prisoners believe that they are dead and bury the pair outside in the graveyard. Nelson's lover Barry, who has been let out on parole, digs the two up and they are free, and Nelson and Barry become life partners. One year later, the two same-sex sweethearts set up a winery where a critic is about to fail their wine when John shows up and forces the critic to give them a good review. The gay romantic duo and John take a drive listening to "Move This" by Technotronic.