Review - A Rainy Day in New York

February 20, 2020

A Rainy Day in New York – US, 2019

Timothee Chalamet is 24, and in Woody Allen’s latest film, he plays a character who is around that age. That would mean that his character, a college student by the name of Gatsby Welles, would have been born around 1996. If we assume that his mother, played by Cherry Jones, was born at least thirty years prior to that, that would put her birth somewhere around 1966, meaning she became a legal adult in the late 1980s. I mention this because very little about those years and the experiences had by most people of those generations gel with the world that Woody Allen presents us with in his latest film, A Rainy Day in New York.

In the beginning of the film, Gatsby’s girlfriend, Ashleigh (Elle Fanning), learns that she has been granted an interview in New York with a famously reclusive independent film director named Roland Pollard, despite the fact that she writes for a college newspaper that hardly anyone has likely heard of. Gatsby, being the great guy and New York native that he is, determines to go along and make a glorious weekend of it – grand hotels, museums with some of the world’s finest exhibitions of art, and restaurants that few ordinary people would be able to afford an appetizer at. He can afford it not because he is from a wealthy family, which he is, but because he recently won $20,000 gambling, so – he reasons – he has money to burn.

And their weekend is truly amazing, so much so that by the end of the movie they are on their way to that magical land known as “Happily Ever After.” I’m kidding, of course, for what romantic comedy has ever had its characters go to a big city like New York and come back stronger. Owen Wilson couldn’t do it in Midnight in Paris; Cary Grant couldn’t do it in An Affair to Remember; and Christopher Reeve couldn’t do it in Switching Channels. And if Superman can’t do it, what hope does a mere mortal like Gatsby have? His odds of success are further reduced by the fact that his character is a young version of the standard Woody Allen role featured in so many of Allen’s earlier films. In other words, Gatsby is neurotic, artistic, extremely knowledgeable, and capable of dropping the names of famous entertainers at any moment. The latter works when Allen does it because of his age and the fact that he’s Woody Allen; here it is off-putting. In one scene, Gatsby drops a line from a song written in 1932 and interprets his girlfriend’s ignorance of it as evidence that they are an awkward match. Because, really, what self-respecting millennial doesn’t recognize show tunes from the 1930s?

Once in New York, Gatsby and Ashleigh go on separate journeys of discovery. His involves family, friends, and an old female acquaintance whose personality could not be more different than that of his girlfriend. As for Ashleigh, she finds herself surrounded by Hollywood bigwigs and she’ll eventually have to choose between a life in that world and Gatsby. Along the way, we meet a number of interesting, somewhat undeveloped characters, such as Gatsby’s brother Hunter (Will Rogers) and his finance; a screenwriter played by Jude Law; and an A-list actor named Francisco Vega (Diego Luna). Each of these characters either complicates the intended fun of Gatsby’s weekend or creates temptation for Ashleigh.

Perhaps the most memorable character is Chan Tyrell, played by Selena Gomez, precisely because she is the least out of place. In other words, her character feels real for these times. She is unabashedly opinionated, unapologetically sarcastic, and often brutally honest. Gatsby used to date Chan’s older sister, and in one scene, she tells Gatsby that her sister used to rate his kisses; she doesn’t inflate the number to lessen the blow to his ego. Ouch.

The scenes with Gatsby and Chan work well, so well that I found myself wishing the movie were just about them. It’s refreshing to see a character who is as blunt as Chan, calling a spade a spade and pointing out rather large inconsistencies between Gatsby’s words and actions. Chalamet and Gomez play well off each other, yet their scenes together are few and far between, and that prevents them from adequately reflecting the beginnings of true feelings. Sure, their connection is stronger than that of Gatsby and Ashleigh, but their disconnect was apparent from the very first scene. Gatsby and Chan have enough connection for a first date, but a second seems far from guaranteed.

As I watched A Rainy Day in New York, I began to sense that Woody Allen had made a film abut young people that only older people would fully appreciate. Earlier I mentioned that Gatsby would have been born in the late 1990s. Thus, if he were indeed exposed to independent films and Broadway at that time, wouldn’t he name-drop famous people from that time period, people such as Yimou Zhang, Stephen Soderberg, Spike Lee, Jim Jarmusch, Robert Altman, Steven Sondheim, and Andrew Lloyd Webber, all of whom were active during the years in which Gatsby would have been discovering the arts? Instead, both he and his former classmates bring up people like Grace Kelly and Jean Renoir. I just didn’t buy it.

There‘s another problem with the film, and that has to do with its celebrity characters. There was a time when a young woman being pursued by a Hollywood figure would have seemed perfectly innocent, when Hollywood was seen a land of opportunity, a place where talent got you places and the fairy-tale ending was possible. Alas, those days are gone. Nowadays, audiences are more likely to view a director who pursues a much younger reporter after only knowing her for thirty minutes as a predator, and they’re likely to be equally critical when they see a young female character simply shrug her shoulders and hide after learning that a man lied to her about being single. They might rightly ask why she isn’t angry and exposing him as the jerk he is. It’s a good question and not one that earlier audiences would always have thought to ask.

I’m being negative here, perhaps more than I intended to be. In truth, I didn’t hate the film. It is humorous in parts, and some of the situations Ashleigh finds herself in are quite fun. I also enjoyed every moment in which Chan is onscreen, for she infects the film with energy and vitality. The film’s biggest fault is Gatsby and the way he is written. Simply put, the only person who can play “Woody Allen” is Woody Allen. And if he’s no longer available, perhaps it is time for the character to be retired. (in theaters outside the United States)

2 and a half stars