Movie Review – A Rainy Day in New York (2019)

Sometimes a movie just isn’t worth the controversy surrounding it.

That’s not to say A Rainy Day in New York is bad. The problem is just that it’s not a good enough Woody Allen movie to warrant two years of delays and boycotts. Then again, the controversy was never about the movie. I’m not prepared to relitigate the #MeToo scandal and the decades old accusations of child rape that have clung to the Woody Allen name. Kyle Smith already did I better than I ever could so go read him if you want to learn more about that situation.

Needless to say, I’ve watched to check out A Rainy Day in New York for two years. I never expected it would be some masterpiece though. Late period Woody Allen has struggled to find a place of relevance in modern film discussion. His films mostly fall flat as he produces them so quickly that there’s sparsely any refinement to the scripts. Most of the cleverness of his early films has been spent. He only seems to be making annual films to keep himself busy and distracted in his final years of life. He hasn’t had popular and enjoyed films since Midnight in Paris and Blue Jasmine and yet he’s released a film almost every year since.

His state of being THIS out of touch reflects heavily in the dialog for A Rainy Day in New York where supposed millennial hipsters walk around New York City cracking jokes about Gene Kelly and Gone With the Wind. I’m 25 years old and I don’t think I’ve ever heard someone my age use the words “Gene Kelly” or “Turner Classic Movies”. The air of awkwardness and out of touch-ness permeates the film in its entirety. Even the name of it’s lead character is a bad joke: Gatsby Welles.

Trying to evoke the feelings and themes that The Great Gatsby and Citizen Kane bring to mind is hardly a way to get kids to come see your quasi-existential romantic comedy movie…

To my surprise, I did enjoy watching it! I’d go as far as to call it chuckle worthy and charming. It might be “charming” in the same way my Jr. High Choir concerts were “charming” to my parents and nobody else but its “charming“ none the less. The movie looks and feels like a third tier Woody Allen film from the 1970s. This is most evident in its performance which casts Timothée Chalamet as a neurotic, foppish, overly-intellectual Jewish sex-pest wandering through life seeking authenticity and meaning through romance and obscure literature.

Woody Allen literally just wrote one of the most beloved up and coming actors to play a young Woody Allen…

In that mindset, it’s amusing. The movie isn’t some great exploration of love and romance but it has some great moments to it. The film’s plot riffs of the cliches of romantic comedies but goes as far as to effectively make itself into an anti-romance. It sets up its awkward young couple and then separates them as they wander their way through a rainy day in New York City while they get caught up in parallel adventures that stress their relationship to the breaking point.

Woody Allen, being a writer with a love for cleverness and subversion, doesn’t end up building to the cliché kind of ending a movie about two people in New York should be. Given Allen’s lifelong love for Casablanca, it’s not surprising that he wrote a romance movie late in life that comes to the same conclusions about its characters as that film did. The film ends up being a story about why these two characters are a mismatch and now they’ve yet to fully blossom into adults capable of maintaining a relationship with one another.

The movie is hardly scathing though. The movie has far more scathing things to say about the troubling sex life’s of Hollywood stars and directors than it does about lonesome college students. It’s ironic that a movie that fears a director, a screenwriter and an actor individually courting and trying to immorally seduce a young woman would get delayed by a #MeToo scandal. This film might’ve been quite discussed if it had dropped when that cultural discussion was prominent back in 2018.

Regardless, A Rainy Day in New York is a very light and breezy film. The stakes are very low and the only things that are really on the line at any given point are the relationships of the two lead character’s and their mutual romance. You can see the gears turning for the kind of dramatic story Woody Allen was clearly trying to tell but it mostly falls flat. For a Woody Allen romantic comedy, it’s not very romantic and only sporadically funny.

Published by Tyler Hummel

Editor-in-Chief at Cultural Review, College Fix Fellow at Main Street Media, Regular Film Critic for Geeks Under Grace and the New York Sun, Published at ArcDigital, Rebeller, The DailyWire, Hollywood in Toto, Legal Insurrection and The ED Blog, Host of The AntiSocial Network Podcast

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