Marshals suddenly appear, summoned by the ankle monitor that James triggered, having trespassed the county line.īarrow's computer provides the evidence needed to clear James. When Gayle shoots the life raft, James pulls out a gun he had "keistered" and aims it at Gayle. They try to convince James to run away with them, but he turns them down and heads to a life raft with Darnell.
James unleashes a series of capoeira moves on them before Martin and Alissa arrive, both confessing to the fraud and embezzlement, a scheme that also included Peter. The two sneak onto Martin's yacht to retrieve the computer, only to come across Gayle and his men.
Before he can do so, Darnell arrives in time to convince James to expose Martin. They accept him as one of their own and order him to kill someone as his initiation. Dejected and upset that Darnell lied to him, James returns to the Crenshaw Kings on his own, asking to join. Before they can expose him, Gayle finds them and takes back the computer, informing James that Darnell is not who he thinks is and has never been in prison. They sneak into his office and find the embezzlement records on Martin's computer. James is unable to portray a convincing racist, leading the gang to think he is a cop they threaten to attack James, but Darnell rescues him by bursting in with a flamethrower.Įventually, Darnell and James finally deduce that Martin is the crook, and the reason James is going to prison. However, Darnell's cousin and gang leader Russell ( T.I.) rebuffs James and redirects him to the Alliance of Whites gang. James and Darnell resolve for James to join a local gang called the Crenshaw Kings to gain protection in prison.
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".
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. James King ( Will Ferrell) is an extremely wealthy hedge fund manager at Barrow Funds, engaged to Alissa ( Alison Brie), daughter of his boss Martin Barrow ( Craig T.