Crime doesn't pay, but neither does watching Trevor White's Jamesy Boy. Across two parallel plotlines, one tracing the titular antihero's life of crime, the other following him on his way out of a subsequent prison sentence, the movie adds up to little more than an interminable bildungsroman, sunk early and often by the desperately miscast Spencer Lofranco. As James, a sweet kid incapable (for reasons largely unexplained) of stopping himself from breaking the law, Lofranco oscillates between dumbfoundedly gazing off into the distance and, in moments of happiness, puckering his lips like he's posing for the cover of a rap album. Despite the constant admonitions of his mother (Mary Louise-Parker, never not appearing like she wants to be somewhere else) that he's this close to cleanly finishing his juvenile parole sentence, James feels marginalized by his bad-boy reputation, and thus skips school, falling in instead with a drug dealer named Roc (Michael Trotter).
James's rough-and-tumble dropout days occupy an extended flashback that eats up more than half of the film's overlong running time. It's clear that White refuses to glamorize James's thug adventures; this would be admirable if the story weren't being told from his perspective. As such, the filmmakers approach every scene with a painfully unimaginative shooting and editing style, so pallid it gives the story an accidental objectivity, and we spend way too much time watching James make bad decisions, knowing they're bad decisions, and patiently waiting for James to realize they're bad decisions. This never happens until a botched heist sees him dropping a duffel bag of guns off at Roc's place, which even Roc concedes is dumb as hell, and by then it's too late for James to escape the cops.
In prison, James stands up on behalf of Chris, a new inmate being terrorized by a vicious prisoner named Guillermo. This leads to a shower-room confrontation where Chris alerts James that Guillermo is sneaking up on him with a knife, and ends up being stabbed in the belly himself. Guillermo walks free, and James learns from a tut-tutting warden (James Woods) that Chris's only crime was stealing a car. Yet despite a relatively minor offense, Chris's sentence is—for reasons unexplained—extended to six years. When he thusly hangs himself in front of the whole prison, James decides he's going to use his next hearing to get out, whatever it takes.
This kind of ethical gerrymandering is all over the film's screenplay: Why would a lightweight like Chris get his sentence doubled, while James—who sold drugs, robbed people, carried guns, and trashed businesses—manages to sweet-talk his way out after three years? White's ridiculous notion of American criminality is neither structural nor poetic; the screenplay picks and chooses as it needs to grease up its inevitable redemption parable. This point is hammered home even harder when James, after finally going straight, runs into a few of his former cronies. Despite having gotten Roc arrested and breaking up the gang, James is greeted with backslaps and hugs—a conclusion so pat and maudlin, it lets the air out of the prior 100 minutes' supposedly advisory bent.