Jamesy Boy
James Burns (Spencer Lofranco) is in prison for selling guns, drug possession and illegal possession of a firearm. Some years earlier, his mother Tracy (Mary-Louise Parker) attempts to enroll him in school, but is turned away due to his past in juvenile detention. One night, James meets Crystal (Rosa Salazar) and Drew (Keon Clayton) after they steal from a convenience store, and befriends them. Crystal tells James about Roc (Michael Trotter), a guy they do illegal odd jobs for and offers him a chance to get in on it. James' mother finds out and reminds him that they are close to his legal appeal, but he defies his incarceration by cutting off his ankle bracelet.
James goes to Roc's house asking how he can make money. Roc propositions James to be his getaway driver, then offers a chance to work for him full-time. Later, James and Crystal are horsing around in a convenience store; when James tries to buy cigarettes and liquor, the cashier, Sarah (Taissa Farmiga), tells him to take it as she does not want trouble. Drew and James go to a strip club and Drew points out a man who owes Roc money. Bursting into the man's office, James pulls a gun on him but his thugs break in and beat him up. In the parking lot, James busts the windows out of the man's car and finds a bag of guns. Afterward, James runs into Roc, who orders him to fix the situation.
Meanwhile, James befriends Sarah and begins a relationship with her. He then tries to leave Roc's crew, but Roc tells James that there is a deal going down that night and guilt trips him into going. James and Drew show up to sell the guns he stole, but the police arrive. James escapes to Sarah's house and tells her to pack so they can leave town together. She refuses, leaving him to face his crimes.
In the present day, James makes an enemy in Guillermo (Taboo), who picks on a new inmate, Chris Cesario (Ben Rosenfield). Later, Guillermo's gang attempts to stab James in the shower; during the fight, Chris is mortally wounded instead. James has nightmares from the incident, and takes up poetry in order to block out prison. Worried about Chris, James goes to Lt. Falton (James Woods) to request that Chris be taken out of the yard until his hearing, but Falton refuses. The next day, Guillermo tries to start a fight, but James refuses to join in. Weeks later, Chris hangs himself in the hallway after getting another six years on his sentence. Out of anger, James beats up Guillermo. Later, James starts a fight in the yard, but fellow inmate Conrad (Ving Rhames) breaks it up by telling James that he needs to keep to himself because of his upcoming hearing.
At his hearing, James admits regret over Chris' death and his past decisions; he is subsequently released from prison and gets a job as a janitor. One night, an old acquaintance comes by and offers him some work, but he turns it down. Arriving at Sarah's convenience store, he finds it boarded up. He goes to Sarah's house, but her father says she has moved out. He finds her at a new house that she shares with her fiancé. The two talk about their lives, and James says he may move to New York City. At Sarah's request, he recites some of his poetry for her.
violence, murder, flashback