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James has dinner with Darnell's family and listens to the tale of how he ended up in prison, which is actually just a retelling of the movie Boyz n the Hood. In the chaos, James gets a shiv stuck in his head, after which, Darnell brings James to his home for Rita to treat it. Darnell simulates a prison raid with help from James' domestic staff. James soon after begins to work out harder and faster, makes shivs, learns "keistering" (smuggling contraband in the anus), and seems to be making progress. James can't go through with it and instead tells Darnell that he will keep going and do whatever it takes in order to "get hard".
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With James' training seemingly going nowhere, Darnell suggests that James should prepare in other ways for prison, and takes him to a gay hookup spot to teach James how to perform oral sex in prison. Barrow, the actual crook, believes James is onto him and orders a hitman named Gayle ( Paul Ben-Victor) to monitor him. During the training, James gets in touch with Martin to tell him about his search for help. Darnell, who in actuality has never been to prison and has little experience in fighting, agrees, on the condition James pays him $30,000 Darnell sees it as an opportunity for him and his wife Rita ( Edwina Findley) to finally put their daughter Makayla (Ariana Neal) in a better school, away from the bad neighborhood they live in.ĭarnell's training, which includes pepper-spraying James, re-modelling his house to resemble a maximum security prison and creating multiple scenarios in which he must defend himself, all fail miserably. Shortly after his arrest, James encounters Darnell and, assuming he has been incarcerated before because he is black, begs him for help, requesting to be "toughened up". Over time, James has come to know Darnell Lewis ( Kevin Hart), who operates a small car wash business in the parking lot used by James. On top of this, Alissa leaves James after he suggests the two flee the country together. James is found guilty and subsequently sentenced to ten years in San Quentin State Prison, with the judge (Elliot Grey) allowing him 30 days to get his affairs in order. James' lawyer, Peter Penny ( Greg Germann), urges him to plead guilty for a likely shorter sentence, but James refuses under the belief that he will be exonerated. During an engagement party for James and Alissa, the FBI arrive and arrest James for fraud and embezzlement.
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