“The farthest distance in the world is between how it is and how you thought it was going to be,” Cynthia Nixon’s Judith says in the middle of The Only Living Boy in New York, and darn if that’s not true about the movie itself.

It has a great cast. A wonderful director in Marc Webb (500 Days of Summer). A story ripe with possibilities. And yet the movie is an off-putting, depressing tale about malcontents who hate what New York City has become, but don’t do anything to make it better. Webb also shows so little regard for mass appeal that it’s hard to believe he made the first two The Amazing Spider-Man movies. The limited target demo here — New York social elites and those aspiring to be them — will likely (ironically) find the film’s pretentiousness a tad off-putting, making it hard to say what audience will connect with this misbegotten narrative.

Jeff Bridges’ unmistakable voice mumbles over the opening credits about how things were better back in the day. Even the main character, the twenty-something Thomas (a dull Callum Turner), believes “New York has lost its soul.” What exactly he’s basing this assessment on is unclear, but what is clear is that he doesn’t have the life experience to say this. He is a moper — a well-off young adult who hates his publishing mogul father (Pierce Brosnan), worries about his depressed art dealer mother (Nixon), and doesn’t understand why he’s been friend-zoned by his crush Mimi (Kiersey Clemons). Thomas spends so much time feeling lost and sorry for himself that you become convinced that all his dreams could come true and he’d still find life hollow and unfulfilling. Dude, get over yourself.

One night as Thomas tries to get out of Mimi’s friend zone, he spots his father with the beautiful Johanna (Kate Beckinsale) and is shocked to discover they’re having an affair. Unsure of what to do, he follows (stalks) Johanna around the city. Then he has an affair with her himself. If you wonder what exactly Johanna is thinking, you will not be alone.

All the while, Thomas has befriended his new neighbor W.F. (Bridges), who’s a bit nosy but gives sage advice. One must wonder what the great Bridges was thinking working opposite the cardboard box that is Turner, who doesn’t have much screen presence and whose character is a wet blanket. Without a compelling lead, everything in the movie struggles.

At 88 minutes, The Only Living Boy in New York is too short for the type of slow-burn drama it attempts to pull off. The idea of generational differences in New York City is interesting, but Allan Loeb’s script doesn’t do much with it until the conclusion, and by then it’s too late. The end result is a movie that thinks it’s much smarter than it really is, and is there anything worse than a pretentious fool?

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