There is a certain cruelty to hope, especially when it arrives in the hands of someone who hasn’t earned it. That’s what struck me most watching Roofman—not the robberies, not the escapes, not the myth of a man who slipped through ceiling tiles to steal cash from fast-food chains—but the quiet ache of watching a human being taste belonging for the first time only to slowly poison it with the lie that allowed him to have it. Derek Cianfrance doesn’t treat Jeffrey Winchester like a criminal worth chasing. He treats him like a man worth understanding, which is infinitely more confronting.
Jeffrey doesn’t descend through violence or madness—he descends through longing. He slips out of prison with no real plan, no grand philosophy, just a restless survival instinct and a vague desire to disappear somewhere better. There’s something painfully unexceptional about him, and that’s precisely what makes him dangerous. He isn’t the wolf at the door; he’s the stray dog that finds a home by accident and refuses to leave. When he falls in love with Leigh and quietly folds himself into the warmth of her family, you feel the desperation in him—not for thrill, but for permanence. That need becomes his addiction, and the lie he builds to preserve it becomes his undoing.
Cianfrance understands the emotional gravity of deception, and he resists the cinematic impulse to turn this story into a heist fantasy. Every robbery is incidental; every escape is just logistics. The real story lives inside Jeffrey’s stolen life, inside the moral bruise of pretending to be someone good. Watching him live inside his lie becomes strangely intimate. He makes breakfast. He helps with homework. He fits in. For brief, disarming stretches, you almost forget he's a criminal. You want him to keep the life he built stole. You want the lie to hold, even if its mostly because you want Leigh to have happiness. Bu you know it won’t, and that's without including how ridiculously stupid Jeffrey’s decision making is at times.
What surprised me most was the humour—gentle, sincere, unforced. Not the kind built on quippy writing, but the awkward laughter of human error, of someone genuinely bad at being deceitful. Jeffrey isn’t a smooth criminal—he’s a man of constant near-disaster. He panics. He improvises badly. He talks himself deeper into rooms he can’t get out of. And yet, the comedy never absolves him. It doesn’t soften his crimes. It just lets you feel the strange absurdity of his situation—how a life of felony and false identity can still feel stupidly, unavoidably human. That’s Cianfrance’s magic trick: he doesn’t ask for sympathy, yet he knows exactly when we will feel it.
The film’s social commentary creeps up rather than shouts. Beneath its narrative is a harsh truth about the American appetite for reinvention. This is a country that sells new identities like lottery tickets—go somewhere new, change your name, start again. But the film rejects that fantasy with quiet precision. You don’t get to rewrite your past just because you decide to. You carry it into every room, every smile, every embrace. Jeffrey’s tragedy is not that he was hunted down. His tragedy is that he tried to build real love on false ground, and for a fleeting moment, it worked. That might be worse than if it never had.
Still, the film isn’t without fractures. In its reach for emotional scope, it brushes against threads it doesn’t fully resolve—Jeffrey’s friendship with Steve, the outline of his marriage and child, the finer detail of his crimes as the infamous “Roof Man,” even the psychology of his time in prison. These pieces are present, sometimes powerfully so, but they drift at the edges, hinted at rather than excavated. You sense the larger shape of Jeffrey’s life outside the frame, but sometimes the film spreads itself too thin across fragments instead of choosing one or two wounds to truly open.
But even with that unevenness, Roofman is something rare: a crime film uninterested in crime. A manhunt where the emotional stakes eclipse the legal ones. A tragedy without theatrics. It avoids the easy route at every turn. It refuses moral verdicts. It refuses to tell us what to feel. It simply presents a man who wanted to belong in a world that never asked for him, and shows how longing, when left unchecked, can become a form of violence all its own.
This film stays with you—not because of shock, not because of clever twists, but because it quietly complicates your heart. You root for a man you shouldn’t, then recoil from the pieces of yourself you recognise in him: the fear of being alone, the instinct to hide your damage, the impossible desire to be loved without first becoming truthful. This isn’t Cianfrance at his most devastating, but it is him at his most quietly human. And sometimes, that cuts deeper.
"Roofman" doesn’t soar. It lingers. It broods. It aches. It isn’t flawless, but it means something. And these days, that’s far rarer than it should be.
8/10
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