The Only Living Pickpocket in New York ★★½

Spiritually, The Only Living Pickpocket in New York feels like a 70s film. One can compare it to something like The Friends of Eddie Coyle with the marvelous Robert Mitchum and this would be apt. But, it feels more akin to a late era Western, one that would star an aging John Wayne who looks around him and the old west he once knew is long gone. He is the last one still out there, riding around with that gun on his hip, everybody he knew either died long ago or permanently put their loyal steed up in the barn. Harry Layman (John Turturro) is the last of that dying breed, a low-level pickpocket who has been arrested so frequently that one of his best friends is a cop, Detective Allan Warren (Giancarlo Esposito). They are both in the twilight of their careers and lives, reminiscing on old faces and united by being past their “planned obsolescence,” boxed up and forgotten about in a city whose heartbeat once matched their own.

Everything has changed over the years. One knows it, but Harry is constantly confronted by the world he refused to adjust to that soon passed him by. Nobody reads magazines anymore, so picking pockets with a magazine disguising one’s hand would make a man stand out in the wrong way. Nobody has cash anymore, just credit cards. His beloved Yoohoo used to be 5 cents and Harry’s refusal to get a cell phone leaves him searching the city for payphones that are in advanced states of disrepair. His latest score, a bag with a watch and some mysterious USB is only partially accessible to him because his fence, pawn shop owner Ben (Steve Buscemi), has one of those old, bulky computers from the 90s that cannot even read the USB. He knows how to deal with the watch, at least, but it is the USB that will cause Harry problems just as every advance in technology over the past 30-or-so years has.

The great existential risk that Harry knows all-too-well from years of watching his cohorts in the business die is picking the wrong pocket and, in this case, Harry stole from the wrong car. Though Dylan (Will Price) is young and smart-mouthed, a Harvard-educated wealthy pain in the ass who thinks he knows everything and speaks like a recently graduated business major, he also has connections. His “family” is the kind one does not steal from and live to tell the tale. When Harry lifted Dylan’s bag, he unwittingly stole a “currency locker” that stores nearly $1,000,000 in cryptocurrency. Now, he must bring it back to Dylan, but he already took it to Ben and then to one of Ben’s connections in Chinatown, only to leave it behind at the latter thinking it to be worthless junk. If he fails to return the USB to Dylan by 4 PM, Harry’s catatonic wife Rosie (Karina Arroyave) is at the mercy of Dylan and his men who have holed up in Harry’s apartment .

The Only Living Pickpocket in New York is less a “love letter to New York City” as one would expect than it is a rumination on time, change, and the generational divide. It is old-fashioned and comfortably so, perhaps indulging too frequently in on-the-nose discussions and caricature-esque depictions of zoomers and boomers alike, but nevertheless a film that stoically looks upon this fabled city and its five boroughs with a wistful eye and a nostalgia for who its inhabitants, especially Harry and his cohorts, once were. It is a far greater look at this than it is as a crime film. Director Noah Segan’s film tries to drum up urgency in its timing, this 4 PM deadline and the risk of Rosie being harmed are plentiful motivation for Harry to jump to the task of retracing his steps then calling in some favors with Detective Warren to get information on everybody he is dealing with. Yet, as The Only Living Pickpocket in New York winds through its plot machinations and tries for some light Uncut Gems-esque thriller elements, it still indulges in being a walk down memory lane. With time ticking down, Harry stops to talk to his estranged daughter Kelly (Tatiana Maslany), knowing he is a dead man for what he has done to Dylan and looking to take account of his life before facing his fate.

This utter lack of urgency is befitting the overall pace and tone of Segan’s film, but is at odds with the forceful plotting and attempts at stirring up drama. In this regard, The Only Living Pickpocket in New York feels uncomfortable with playing to its strengths. This is a film at its best watching Harry work a mark on the subway, chat with Ben, or catch up with Detective Warren. It is best in embracing the strong jazzy score from composer Gary Lionnelli and basking in the glow of time gone-by. The film is a worthy examination of a man whose life is marked by mistakes, a quality that may make him interesting in a film but makes him contemptible and aggravating to have in one’s life; a non-moralizing look at this figure is welcome and compelling. However, as The Only Living Pickpocket in New York tries to find inertia, it overplots itself, developing that story it never really seems interested in pursuing and introducing characters like Dylan that can be hysterical in waxing poetic about the value of AirBnB’s end user license agreement but end up ruining the vibe. This is a wonderful hangout or slice of life film when it wants to be, but it comes with a flat crime thriller side tacked on.

John Turturro gives one of the finest performances of his career as Harry Lehman. It is a performance defined by his mannerisms, his world-weathered way of delivering advice or talking about the old days and the ‘old dog on his last leg’ way of moving through the world. Harry is still sharp and skilled, picking the pocket of a businessman (John Gallagher Jr.) in The Only Living in Pickpocket’s opening scene without the man realizing until later in the day. But, the weight of the world and the way in which he scratches out a living have taken a toll, living pocket-to-pocket and always looking for an angle. Turturro has a sorrow in his eyes, a weariness that really shines in that scene with Kelly but is always there, just sometimes masked with the confidence running through him when he is lining up his next mark. Tatiana Maslany’s brief performance is a showstopper, a more direct dressing down of Harry and men like him, but delivered with an intensity and heartbreak that Maslany sells very well.

An often laid back and melancholic look at the life of a pickpocket and trying to survive in a world one is way past the age of recognizing, The Only Living Pickpocket in New York is a great hang. Harry and those in his orbit provide the film with a wistfulness and a warmth that are immediately endearing. However, as director Noah Segan tries to drum up tension and suspense, The Only Living Pickpocket in New York struggles to shift gears and keep up, falling flat dramatically and feeling increasingly at odds with itself. A great performance from John Turturro anchors it, but the overall package here falls short of its potential.