When a career criminal's plan for revenge is thwarted by unlikely circumstances, he puts his intended victim's son in his place by putting him in prison...and then joining him.
John Lyshitski, a young man who has been in prison more often than he has not over the entire course of his life, has just been released from what was his third prison sentence. In all three cases, he was sentenced by Judge Nelson Biederman III. As such, John makes it his mission to destroy the judge's life. Unable to do so, John does the next best thing: destroy the life of the judge's privileged thirty year old son, Nelson Biederman IV. In that new mission, John ends up not having to do anything as certain people are out to get Nelson IV, who in the process receives a 3 to 5 year prison sentence. Nelson IV's incarceration should be enough for John, who knows that someone like Nelson IV, ill-equipped mentally for a life behind bars, is easy prey to get beaten, raped and/or killed in prison. But John wants to witness and be at least a small part in Nelson IV's suffering. John's plan is to get busted, charged, and convicted for some crime, and end up in the same prison as Nelson IV's cellmate. John will pretend to be Nelson IV's friend, while truly subverting him at every step along the way to make his life even more miserable than it is by bribing those on the inside including fellow prisoners and guards. Much of what happens goes according to John's plans, but other factors may make his torture of Nelson IV more difficult than anticipated.—Huggo
John Lyshitski is a car stealing slacker, with a weed problem, and has been in Illinois' Rossmore State Penitentiary so many times, he knows its entire population of both staff and cons by their first names. Cursed with the old ill luck of being in the wrong place, at the wrong time, in possession of the wrong car, he's been deemed a lost cause repeat offender in the eyes of everyone else. When the heartless judge, who has been behind most of his sentences, goes to the big court house in the sky, John decides to ruin the man's legacy by having the judge's only offspring, Nelson Biederman IV, thrown in the slammer along with him. Here, the world-class selfish jerk learns a certain old lesson the hard way: Do unto others as you would have others do unto you. But has John gone too far in the payback department?—????
John Lyshitski (Dax Shepard) has spent most of his life being a slimeball, thanks to Judge Nelson Biederman III, who has been giving him hard sentences ever since he stole a car at the age of eight. Now he wants revenge, but finds that the judge died an all too peaceful death three days previous to Johns release from prison.
He turns his attention to Nelson Biederman IIIs 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 Nelsons 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.
Nelson 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.
