[1] The film stars Spencer Lofranco, Mary-Louise Parker, Taissa Farmiga, Ving Rhames, and James Woods.

Three years earlier, his mother Tracy attempts to enroll him in school, but he is turned away due to his criminal record and recent stint in a youth detention center.

Crystal seduces James, who soon also meets Sarah, a timid cashier whose father owns a local convenience store.

At a strip club, James and Drew burst into the back office to retrieve owed money for Roc, but it goes awry when they are subdued and beaten by the bouncers.

In the parking lot, James breaks into the man's vehicle and steals a duffel bag full of guns.

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 motel clerk.

The film marked the directorial debut of Trevor White, who co-wrote the screenplay with Lane Shadgett.

[5] In March 2012, Taissa Farmiga joined the cast in the supporting role of Sarah, James' love interest.

[6] The casting of Taboo in the supporting role of Guillermo was reported in late March 2012, while the film was in production.

[9] Shooting also took place in the Baltimore neighborhood of Curtis Bay, at the Maryland House of Correction, and in Brooklyn.

[15] Martin Tsai of the Los Angeles Times wrote, "The core of Jamesy Boy – a juvenile delinquent's inside-the-pen coming of age – follows a too-familiar trajectory: Due to the toxic mix of broken family and corruptive friends, James Burns (Spencer Lofranco) has already earned a tracking device on his ankle and an impressive rap sheet boasting robbery, vandalism, assault and firearm possession.

But it's an unknown, Spencer Lofranco, who makes this gritty chronicle, based on a true story, so memorable... For such a seriously street film, Jamesy Boy has some surprisingly sappy moments.

"[17] The Hollywood Reporter critic John DeFore wrote, "A true story of a young con who turned his life around, Trevor White's Jamesy Boy wants very much to be inspirational.