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Thomas Webb’s life post-grad seems to be filled with likely struggles. Played by Callum Turner, he worries about his bipolar mother, disappoints his father, and he feels confounded by Mimi’s (Kiersey Clemons) unreciprocated romantic feelings. Tucked away in the Lower East Side far away from his wealthy parents, Thomas realizes that New York has lost its soul. That is until a new neighbor moves into his building and immediately becomes of interest to Thomas.

W.F. Gerald (Jeff Bridges) offers advice and alcohol to Thomas throughout the film. The dynamic between the two is odd but charming, as W.F. tries to help Thomas navigate his relationship with Mimi. After a night on the town, he sees his recently distant father, the owner of a publishing house, out and about with another woman.

The other woman is Johanna (Kate Beckinsale), a British transplant who works in freelance publishing with Thomas’ father. Beckinsale’s character, in fairly typical fashion, is portrayed as a flirtatious and seductive woman. Her initial interest in Thomas feels like a game that is carried out for the majority of the film, and seems to be the only plausible way that she would ever be interest in Thomas anyhow.

The Only Living Boy in New York is an examination of relationships, where romantic, sexual, and familial boundaries are blurred. In his attempt to save his parents’ crumbling relationship, Thomas and Johanna begin having an affair. The idea of a father and son both sleeping with the same woman is hard to wrap your brain around in theory, and even eerier when played out on the big screen.

Thomas’ character development is infuriating, as his decisions seem to always be fueled by selfish desires. I remain unconvinced that he interfered with his father’s affair in order to protect his mother, but rather to reciprocate his father’s disappointment in a concrete and tangible way. Furthermore, Thomas is a sexually frustrated 20-something who initially uses Johanna to get back at Mimi for her lack of romantic feelings for him. Unsurprisingly, he is a wealthy and kid who feels like the world is out to get him. He is supposedly so plagued with the idea that New York’s culture is dying out, though seems too self absorbed for that to be the case. Thomas could have had depth, but the directors do not have the wisdom to imbue it.

Clocking in at just an hour and 28 minutes, The Only Living Boy in New York was a short movie, but not terribly fast paced. Plus, it is nonetheless a long time to contend with Thomas’ entitlement. It’s definitely an interesting interpretation of the Simon and Garfunkel song. I did see the familial twist coming at the end, but it felt like the most important/enjoyable part of the film came – and gone too quickly. The cast was talented, and any film with Cynthia Nixon is worth watching at least once.