When Nina returns from Hell with the information Sam needs, he challenges the Devil to the game he's best at. However, when it comes to a draw, Andi is forced to make the ultimate sacrifice.
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Sam ends up working for a company run by the Devil that handles the corruption of souls. When Mr. Oliver contacts Sam from Hell and tells him he has the information he needs to break his contract with the Devil, the gang decides to use the company's Hell portal to get Nina through to obtain the information. Meanwhile, Sock tries to date a demon who has the ability to be anything he desires.
Sam, Sock, and Andi go after their old high school teacher, Mr. Sprong, assuming he is the current soul they are trying to catch. The only problem? Mr. Sprong is still alive, and none too happy when the boys take him hostage to try to convince him not to press charges.
Sam is tasked with getting Gary, a spoiled rich guy the Devil wants, to sign a contract selling his soul. Unfortunately, Gary is too clever, and manages to avoid all Sam's attempts to get him to sign on the dotted line. Meanwhile, three's company and five's a crowd when Nina and Morgan both move in with the guys at Sock's house, and Andi regrets letting Sock have a bachelor party at the Work Bench.
Sam is sent to the home of the Devil's lover Sally so that she can teach him more of the "family business." She initially refuses, but realizing she can possibly help him out of his contract, Sam asks her to teach him anyways. Meanwhile, Ben tries to deal with Nina after their breakup, and Sam's father decides to surf the Internet.
Sam continues his quest to find Alan, who he believes can help him get out of his contract with the Devil. Meanwhile, the Devil forces Sam and Morgan to compete to see who will become his heir, and Nina wants to meet Ben's grandmother.
Sam is forced to once again take Morgan on a soul catch, but Morgan takes off, leaving Sam to once again do all the work. This time, Sam has to return an unjustly condemned soul who wants to satisfy one wish: to lose his virginity. Meanwhile, Nina offers to take Ben flying, and Sam tries to make up with Andi.
Sam is sent on a road trip to catch a soul, and he takes the gang along. When he gets to the town, however, he finds that a tentacled beast has taken over.
Sam, Sock, and Ben turn to Tony for help when an escaped soul leaves her baby behind. Morgan lets slip to Andi that Sam is really the Devil's son. And Sock considers chemical castration to deal with his lust for his half-sister.
The Devil takes Sam to the police station and introduces him to Morgan, whom he calls his son. Now, Sam and the gang are tasked with hanging out with Morgan and showing him the ropes.
Sam must capture a former boxer by using boxing gloves as a vessel. Meanwhile, Andi is awarded a promotion at the Work Bench.
Sam finds it hard to concentrate on his new assignment because of his fascination with how Alan broke out of his deal with the Devil. However, Alan disappears when the two of them are attacked by demons. Meanwhile, a demon becomes infatuated with Ben.
Sam and the boys return from a road trip and discover that they have been fired from their jobs and evicted from their apartment. Meanwhile, Andi refuses to patch things up with Sam, and The Devil returns with a new assignment.
