Earl's been spending a lot of time helping out the Warden in exchange for time off his sentence, and now he only has about six months left. The Warden confesses that he screwed himself at one of his wife's press conferences, when a tricky reporter tricked him into claiming that he had set up a reconciliation program. If Earl can figure this one out, the Warden will give him a certificate good for six months off his sentence.
Earl searches for just the right inmate to initiate the program, and settles on baby-faced first offender John the Artist, in prison for burning down his parents' home when his meth lab caught fire. Earl asks John to sit down with his parents, which will hopefully lead to an apology and a big hug. John doesn't think his parents will go for it, but if they do, he's in.
Earl sends Joy and Darnell to meet with John's parents, but they don't have much love for their son since he burned up all their possessions. Darnell tells them about last year when Mr. Turtle knocked over a candle and caused a fire in the trailer. They couldn't be in the same room for months, but eventually they talked things over, and now their relationship is stronger than ever. John's parents relent, and agree to meet with their son.
The reconciliation gets underway, but John thinks his parents are supposed to apologize to him. They should also thank him, because the fire was the only time there was any warmth in their house. John's a monster because they ignored him his whole life. He leaves in a fury, and the Warden gives Earl a week to fix things. Earl points out that saying you're sorry and meaning it are two different things, but John's still pissed at his parents because they wouldn't let him go to his prom when he was too stoned to drive.
Since Earl will earn his freedom if John says he's sorry, John wants something big, too, like a prom, or an aircraft carrier. Since the state doesn't have a navy, the Warden uses some of his wife's stationary to get 50 female inmates shipped in for a prison prom. Earl enlists Joy's help, only to realize that a prom is expensive. Joy points out that he still has $24,000 in lottery winnings. Realizing that the prom is his ticket to freedom, Earl signs the check for an underwater wonderland prom with all the trimmings.
The big prom night finally arrives and it's magical. The Warden crowns Earl Prom King, but he relinquishes his throne to John, because without him, the prom never would have happened. The Warden brings back John's parents for another stab at reconciliation. He shows up in his crown, claiming that everyone loves the Prom King except for them because they're fat failures that don't know how to love.
Earl runs after John, who claims that his parents treated him like crap, so now he treats everyone like crap and it's their fault, not his. Something inside of Earl snaps. All he wants to do is make John suffer, so he lights all the paintings in John's cell on fire. John shows up to fight, but Earl knocks him down, claiming that since John treated him like crap, taking away his freedom, now Earl treats everyone else like crap.
Earl's not proud of himself for burning John's paintings. But as John sifts through the ashes, he realizes that he should blame himself for what he did to his parents, and has to make it right. He paints their wedding picture, and then several other family photos that burned in the house fire, and finally John and his family have the best reconciliation they could have hoped for, pleasing the Warden.
The Warden congratulates Earl on his understanding of the criminal mind - he's like some kind of scumbag whisperer. He puts the last six month certificate in Earl's file, wondering what he's going to do without Earl to cover his ass. Earl guesses the Warden will find that out tomorrow, and leaves, sending the Warden into a panic. He begins shredding Earl's certificates...