The Safdie Brothers have an affection for losers. From repeat offenders to heroin junkies to degenerate gamblers, their preferred kind seems to be those who are inexorably addicted to trouble; ticking time bombs who get roped into chaotic spirals of self-obliteration over and over again. Having built off a successful career out of spiking the viewer’s heart rate manyfold, it’s safe to say that the sibling filmmakers get a kick out of playing cruel God with their flawed creations — throwing them curveballs at every turn only to watch them end up caught between a rock and a hard place.

Predating their breakout hits Good Time and Uncut Gems is the 2009 drama Daddy Longlegs, yet another virtuoso display of guerrilla filmmaking that has largely flown under the radar as a purportedly formative work, which is about to be rediscovered thanks to a new handsome home release courtesy of The Criterion Collection. Though perhaps not as polished or glossy as their subsequent efforts, the film sketches a good deal of the directors’ pet interests and stylish calling cards with all the panache and verve that we’ve grown to expect in their work. Drawing from their own turbulent childhood and filming in their old New York stomping ground, the Safdies gifted us with their most exasperating yet achingly empathetic antihero in their entire catalogue in Lenny (Ronald Bronstein), a middle-aged divorced projectionist loosely based on their actual father.

Lenny, who barely manages to scrape by working night shifts at a Manhattan movie theatre, has to take care of his two kids Sage, 9, and Frey, 7, (Sage and Frey Ranaldo) over the two court-ordered weeks he’s given each year. Fulfilling his parental responsibilities throughout that brief period proves to be an insurmountable challenge for a one-man wrecking crew who can’t even take care of himself, let alone his two sons, on his own.

Sage and Frey, presumably accustomed to an infinitely firmer and more responsible parenting on their mum’s side, seem to initially welcome their dad’s freewheeling spirit — treating their brief stay together like a sort of crazed odyssey through the concrete jungle of New York City. And though it may at first appear that Lenny’s parental incompetence is somewhat compensated for with his over-enthusiasm and contagious playfulness, it soon becomes clear that he’s thoroughly incapable of sticking to the straight and narrow without fumbling himself and everyone around him into insoluble predicaments.

The Safdies’ cracked-mirror vision of the American dream dissolves any boundary between fiction and reality, gliding through Lenny’s everyday life in a stream of quotidian vignettes that bleed into each other in what’s best described as a manic comedy of errors. This bold flouting of narrative cohesion, along with the use of invasive handheld close-ups, amateur casting and diegetic sound, instils the film with a claustrophobic quality that deftly echoes the congestion and frenzied pace of the city that never sleeps.

Whether it’s spending the night in jail, getting mugged or forgetting to pick up his sons from school, Lenny is seen constantly wriggling his way out of snares, greeting every major setback with a shrug of indifference and an impromptu, often ill-advised scheme. The film revels in his jittery dysfunction, feeding off Bronstein’s mercurial presence as we watch his character fail miserably many times over.

A lesser director would have neatly wrapped up the story with a sugar-coated third act where our flawed antihero learns a valuable lesson and comes out of it as a better man, but delivering mawkish melodrama or cathartic closure are nowhere near the Safdies’ prime concerns. Their characters tend to go from A to B without ever finding such a thing as enlightenment or redemption, no matter how desperately they seek it, doomed to live in perpetual ignorance with one foot already in the grave.

The last we see of Lenny is him carrying his belongings around the sidewalk and loading them onto a Roosevelt Island tram, having previously abducted his kids from school long after his custody had reached its eleventh hour. This moral ambiguity and lack of resolution cuts to the very heart of Daddy Longlegs. But where their recent films have seldom allowed their characters an amount of dignity in the face of hardship, the Safdies consciously refuse to reduce Lenny into any sort of one-note caricature, imbuing his character with chutzpah, pathos and off-kilter charisma to the point that you find yourself grudgingly rooting for him.

Admittedly, to feel sympathy for a man who, halfway through the story, drugs his own kids with a heavy dose of sleeping pills because he has to do a night shift and can’t find a babysitter, might be asking too much of the audience. The Safdies certainly know better than to expect our pity, especially for such a remarkably irredeemable human dynamo. But even though it’s hard not to squirm and turn away in disgust whenever Lenny’s reckless negligence actively puts the wellbeing of his sons in peril, the Safdies manage to walk a tightrope between constantly pushing our buttons without coming off as emotionally manipulative at any given point of the film.

It’s only fitting that Daddy Longlegs won the 2010 Independent Spirit John Cassavetes award, named after the patron saint of American independent cinema whose fingerprints are smeared all over this film. One can’t simply watch Lenny without seeing traces of Mabel Longhetti (A Woman Under the Influence), Cosmo Vitelli (The Killing of a Chinese Bookie) and Seymour Moskowitz (Minnie and Moskowitz) among many other of his neurotic leads all over him.

Being likened with Cassavetes’ character studies should of course be taken as the highest compliment. Through his career, the maverick director surveyed the everyday ailments of social misfits, outcasts and freaks alike with brutal honesty, distilling life to its essence and urging the viewer to look past their flaws and find humanity in their plight. Daddy Longlegs, and every other Safdie Brothers film for that matter, is endowed with the same unyielding commitment, seemingly guided by the faith that trying our best is, ultimately, all any of us can do.

Daddy Longlegs is released on Blu-ray by Criterion in a new 4K digital transfer supervised and approved by directors Josh and Benny Safdie on 16 August.