‘A Rainy Day in New York’ Movie Review: Woody Allen’s Biggest Mess Yet

Woody Allen does not get enough criticism — a controversial thing to say, sure, given the central role he plays in the never-ending scandal of his life. What I mean is that the allegations surrounding him have, in recent years at least, largely overshadowed how much he has regressed as a filmmaker.

His recent features — with Café Society being perhaps the most heinous offender among them — have been completely lifeless, devoid of anything even remotely resembling the comic genius he so deftly showcased several decades ago. Never one for slack, however, Allen has set a new bar of awful for himself with A Rainy Day in New York.

The film centers around one Gatsby Welles (given a performance that lives up to the faux-pomp of the name ‘Gatsby’ by Timothée Chalamet), a brilliant college student with a well-advertised rebellious streak that seems to be expressed primarily through betting on horses and winning high-stakes poker games. When his girlfriend Ashleigh (Elle Fanning, what’re you doing?) is tasked to go into New York City, Gatsby decides to tag along and show Ashleigh the beautiful city he once called home.

To say that the film goes downhill from here would be to ascribe to it a gradualness it simply does not possess. Every character is completely awful, with Gatsby being perhaps the most grating: all he does is talk about how much he loves New York, but his familiarity with it seems to come entirely from a Time Out article written in 2009. For Gatsby, SoHo is “full of hipsters” and the Upper East Side remains the last vestige of civilized urban life.

It’s completely confounding that this movie is set in the present day given Allen’s obvious contempt for modern times: Gatsby smokes through a cigarette filter, every phrase spoken is some kind of campy witticism, all women wear skirts and sweaters, and everyone is white. Never has New York been less faithfully represented onscreen, and yet Allen still insists on making the city a “character” in this pitiful exercise in escapism.

I won’t describe the plot any further, but I will give a partial list of the clichés employed: prostitute with a heart of gold (two of them actually!), mid-career artist going through a professional crisis of confidence (two of those too!), character who is naturally “gifted” at gambling for no discernible reason, and, of course, two characters who speak exactly the way Allen does eventually getting together by the end. An end that is, by the way, one of the most elitist romantic endings I’ve ever seen onscreen.

Most of the cast is visibly trying; I think Jude Law is the only one that at all succeeds. Selena Gomez drowns her lines in a weird faux-nasal Hepburn-esque accent and Liev Schreiber is, well, there. That this movie even exists should be a testament to how great of an artist Woody Allen once was. From any other director, a script this bad could never have even gotten a second look, and we likely would’ve been better off for it.