Harry Lehman is one of the last members of a dying breed. He’s proud to be an old-timer, the kind who still checks out tapes from the local library, listens to the classics on vinyl, and doesn’t know what email is. Despite his occupation being that of a pickpocket, he goes about it in quite a gentlemanly way. He lifts wallets from Wall Street finance bros and other seemingly rude New Yorkers; the only evidence of their interaction comes hours later, when they notice their pockets are a little lighter than they were this morning. Harry still mails their wallets once he’s lifted everything out, sending them through his pawnbroker friend Ben (Steve Buscemi). Much of the cash goes to paying the hospital bills and tipping the nurses and his neighbors for looking after his catatonic wife, Rosie.

Opening with the jazzy lyrics “like a rat in a cage, working minimum wage,” writer/director Noah Segan (a favorite actor of Rian Johnson) transplants Harry’s old-school hustle into the film itself. This is the kind of film John Cassavetes or Sidney Lumet would make: lean and a little mean on the streets, with a short runtime (88 minutes to be exact) and a grainy worldview. Gary Lionelli’s jazzy score underscores a man who’s on the lookout for his next score, which has never exceeded his means. He trades in wallets and watches, procured on the subway and at street corners.

But with everyone now having smartphones, the need for cash and wristwatches has drastically declined. Sure, there are smartwatches, but they don’t carry the same value as a Rolex or Omega. And good luck stealing someone’s smartphone, since it can be tracked immediately from a computer. Harry gets a taste of that future when he accidentally steals a cryptocurrency token from a well-connected frat boy (Will Price) who speaks in phrases like “value add” and “marginal costs.” Those aren’t words for people like Harry, and neither are the millions in cryptocurrency he doesn’t know he stole. But there’s value in it for the new generation, so the predator becomes the prey as they hunt him down through the streets.

Although it seems that Harry is quickly becoming obsolete, that’s never been true of star John Turturro. Despite rarely receiving a substantial leading role or major film awards attention, he’s quietly been at the forefront of American cinema for decades. Not many can boast appearances in films by Spike Lee, the Coen brothers, Robert Redford, Noah Baumbach, Pedro Almodóvar, Ridley Scott, and Guillermo del Toro. Hell, he’s probably the one good thing I’ll concede about Michael Bay’s Transformers films. And then there’s the television work in The Night Of and Severance.

Light on his feet and sharp-witted, Turturro is right at home on the streets of the Big Apple, moving through recognizable parts for audiences familiar with the area. In a nod to how those streets have changed so much over the years, his Do the Right Thing co-star, Giancarlo Esposito, appears as a soon-to-be-retired detective who reminisces about the good old days. Everything feels so impersonal now, locked behind digital paywalls.

The feeling of melancholic nostalgia becomes overplayed by the time the third act arrives. Tatiana Maslany portrays Harry’s estranged daughter, and their reluctant reconnection is based on assumptions and familiar clichés. The plot also relies on some convenient twists and reflects a boomer mentality, suggesting that today’s kids aren’t as good as those in the past. While there may be some truth to that, not everyone can be as effortlessly charming and cool as John Turturro.

Sony Pictures Classics will release The Only Living Pickpocket in New York in select theaters on October 23rd, followed by a nationwide expansion on October 30th.