The Only Living Pickpocket in New York follows Harry Lehman (John Turturro), an old-school hustler who slides through life in the city with his charm, connections and lubricating palms with cash. But life isn’t necessarily easy for the quintessential New Yorker. Though he makes a living hauling green bills and wristwatches, he also spends his days caring for his terminally ill wife. Still, he’s able to get by… until one unfortunate night when he lifts the wrong wallet. Now, the old school thief must try to navigate a new school world that feels entirely foreign to him, just so he can keep what he already has.

Directed by Noah Segan, Pickpocket scores big as it steals your heart. Backed by sublime work from Turturro, this is a story that feels torn between the past and future. It’s current and timeless at the same time. It’s also undeniably beautiful.

Here, Turturro offers some of the best work of his career. Stepping into Harry’s loafers, there’s an ease to his demeanour that’s built upon familiarity. Despite his criminal ‘work’, Harry isn’t a man looking for a big score. Instead, he treats his skills like a day job. He has regrets from his past but, in general, he’s entirely comfortable in his own skin.

And Turturro slides into Harry’s world with a subtle sadness that speaks to a life that’s passed him by. There’s a humility within his performance that breathes life into Harry’s world. He’s compassionate but calculating; experienced but still maintains a slight playfulness about him. (Without giving spoilers, Turturro absolutely sparkles within his dance sequence, a moment that speaks volumes about the things that matter most to his character.)

In short, you cannot help but fall in love with Harry.

Admittedly, it sounds cliché to suggest that New York is a character in the film but, in this case, it does apply. Here, the city itself feels like it’s also in transition between old and new. Yes, it looks the same but, on the ground, it’s getting faster. More chaotic. Very quickly, New York is giving way to the next generation of powerbrokers and Harry is falling behind.

As a result, his greatest battle isn’t within himself. It’s against the clock. Though he has his ‘ways’ that still work for him, the world has long moved on past him. He has no use for computers and email. He can’t use smartphones and doesn’t understand digital currency.

They don’t even make his brand of watch anymore.

He’s an analog man in a digital world. And that’s what makes his encounter with his young opponents so terrifying. He’s seen their types before… but, this time, he doesn’t understand their world at all. (It’s worth pointing out that the film’s title is The Only Living Pickpocket, suggesting that he’s a dying breed.)

And, for what it’s worth, Harry isn’t alone in this situation. Ben, Allen and the rest of Harry’s compatriots all find themselves (mostly) lost in the new digital New York. They can navigate slightly better than their pickpocket friend, but they also know that they don’t belong anymore. Like Harry, their stories feel like they’re coming to a close.

Yet Pickpocket speaks about Harry’s world as more than simply nostalgic. There’s a wisdom embedded within the ‘old ways’ that comes through. Harry may not understand how to live in the new world, but he still knows how to do what he does better than anyone else around. And he’s happy to pass that on to those who are willing to listen.

The problem is that there aren’t many people who are.

Even so, Last Pickpocket recognizes the importance of those who have come before. This is a story that showcases society’s willingness to overlook—and undervalue—a generation that remains unable to adapt, celebrating their giftings and recognizing the ways that we push people to the side for the sake of convenience. (And incidentally, the film would make a fascinating double header with Dafoe’s superb performance in the recent Late Fame.) As such, there’s a subtle beauty about Pickpocket that makes it endearing and a heartbeat of compassion that gives it life.

The Only Living Pickpocket in New York is available in theatres on Friday, October 23rd, 2026.