It’s easy to forget just how formidable Woody Allen’s Oscar history is. Not only is he the most-nominated screenwriter, with sixteen bids, he’s also tied for fourth place in the directing category with seven. He won three prizes for Best Original Screenplay, for the three films that earned Best Picture nominations: Annie Hall, Hannah and Her Sisters, and Midnight in Paris. Annie Hall of course won the top prize for 1977.
Allen has made nearly fifty films, and by my count, I’ve seen a third of those. A good portion of them are from the last two decades, which is hardly considered his golden period. Of his contemporary pictures, I was most wowed by Match Point, which was a dramatic departure from his typical tone as well as a geographical departure from his beloved New York City. But his most recent, Wonder Wheel, was a dud as the closing night selection for the New York Film Festival back in 2017. Interestingly, Allen has two films premiering this month...
One of them, Rifkin’s Festival, is only being released in Spain and Italy, so I don’t know if we’ll ever get to see it in the United States. The other, A Rainy Day in New York, will be quietly opening this Friday in select (open) American theaters since many people consider Allen to be persona non grata.
In the latter, Gatsby (Timothée Chalamet) is a pretentious college student who jumps at the opportunity to accompany his girlfriend Ashleigh (Elle Fanning) on a trip into New York City so that she can interview a notorious director (Liev Schreiber). When they arrive, his plans to provide a whirlwind tour of all the classics are quickly derailed as new “scoops” present themselves to Ashleigh, including a ride-along with a movie writer (Jude Law) and a run-in with a famous actor (Diego Luna). Gatsby is left to his own devices, reencountering relics of his past as he tries to keep himself busy, including his mother (Cherry Jones) and Chan (Selena Gomez), the younger sister of an ex-girlfriend.
Allen last appeared as an actor in Crisis in Six Scenes, his peculiar six-episode miniseries for Amazon Prime in 2016 that costarred Miley Cyrus. He’s found a formidable surrogate for his mannerisms in Chalamet, who is probably more charming than Allen ever was on screen but expresses the same self-involved overconfidence that makes him difficult to tolerate. Fanning, a stellar lead in last season’s best TV show, The Great, plays Ashleigh as a typical Allen female, brilliant and well-spoken but equally naïve about the intentions of others. Allen’s peculiar selection of another pop star for his latest project proves to be fine, as Gomez handles the material she’s given sufficiently. It’s worth noting that all three performers are considerably younger than Allen was when he first began starring in his earliest films, though each feels like a faithful fit to their part.
Updating his ensemble with hot, up-and-coming actors absolutely makes sense, and it’s something that Allen has been doing for the past twenty years as he has gradually handed over the leading parts to others. But what he hasn’t done is to modernize the way his characters speak and experience the world around them. The idea that even the most precocious of teenagers would use words and expressions like those Gatsby, Ashleigh, and Chan do is far-fetched, and it’s as they’ve stepped right out of the 1970s and emerged in the present day. Gatsby’s concerned reaction when Ashleigh mentions the wrong hotel as their rendezvous point is overdramatic given that they both have working cell phones, and Ashleigh’s magical adventures during her day in New York may feel like a dream, but we know they’re real when TV news airs paparazzi footage that Gatsby can watch live in his lavish hotel room.
This film is like a living anachronism, with its millennial/Gen Z protagonists visiting a historical remnant where film crews close down New York City streets and are able to shoot scenes without interruption, and where people behave as if technological innovations haven’t changed the way they see or interact with the world. It’s an idyllic and welcome trip, one that captures the beauty of New York in a way that it doesn’t always transmit anymore in cinema. There’s nothing particularly fresh or earth-shattering that’s explored here, but for a filmmaker who’s written countless love-hate letters to New York City, it’s a surprisingly engaging and entertaining experience.