A Rainy Day in New York (2019)

Review of A Rainy Day in New York (2019), directed by Woody Allen

You have no idea how long I’ve actually waited for this movie to come out officially. I’m writing this in the 2020s, when I have already seen the movie two times and have finished my wait, but I was waiting for this movie the minute they officially announced it.

Then they delayed it because wow, Woody Allen is a predator! I was not surprised based on the content of his other movies (Manhattan, I’m looking specifically at you) and how autobiographical he tends to go at times, but I thought they’d drop this movie anyways on some streaming platform.

Instead, they chose to delay it indefinitely in the United States until it came out.

What drew me into this movie originally was the cast. I was extremely interested in a love triangle between Elle Fanning, Selena Gomez, and Timothée Chalamet. I failed to realize, however, that this movie is only about very rich people and thus I would feel extremely disconnected from everyone and everything that’s going on, making me go into a rant immediately after watching it for the first time.

The second time I was a bit more level-headed, but my complaints were largely the same.

Let us begin this review.


Over the course of a single day trip to New York City, one relationship begins to unravel and another begins.

This movie starts at Yardley, a prestigious school in upstate New York that seems to be rich with, well, rich kids and ticks. Our main character is ironically named Gatsby, setting up so many parallels to our doomed protagonist of Fitzgerald’s The Great Gatsby.

He comes from new money in NYC, has been raised to be a major culture snob that basically spews out random classic literature quotes, and he’s dating Ashleigh because her family is much richer than his.

They own banks and she’s from Arizona, she wants to be a journalist, and she’s depicted to be an absolute idiot. Got some misogynistic themes going on here because she’s more ambitious than him. Honestly, she might not be written as a smart cookie, but she’s got something going for her versus just living off of Mommy’s and Daddy’s money.

They decide to take a trip to NYC together, where Gatsby was born, as Ashleigh has been assigned to write about a film director.

This then goes to disaster because Gatsby wanted this to be a nice couple’s trip but is anything but. Ashleigh goes to interview the director but he’s full on having a mental breakdown over his creativity then happens to go missing.

Gatsby then wanders almost every part of the city alone, running into an old high school classmate, then heads down to another classmate’s film set, where he meets Chan.

Chan is the younger sister of his ex-girlfriend, they are told to make out in a car for the film shot, and we’re all entertained by her just roasting him and his kissing skills. I dubbed her the sole voice of reason in this film.

Anyways, we move on with the plot. Gatsby continues wandering and has an existentialist crisis, is forced to go to one of his mother’s parties and hires an escort to pretend to be Ashleigh.

Ashleigh, however, is now cheating on her boyfriend emotionally and almost physically for a famous actor and model, who is also revealed to be cheating on his own girlfriend and lied about having one. We know this because the girlfriend arrives home just as they’re about to have sex.

Every single one of the three main characters is honestly kind of annoying. The only one that I felt like I could like was Chan, but because she went to the same school I graduated from (although I found it absolutely hilarious that a rich local girl studied “design” at the Fashion Institute. She 100% does not look like a design student at FIT, you can pick them out pretty easily). She had this perfect level of snark and could call Gatsby out on his pretentious and idiotic bullshit.

But at the time same time, I don’t know if Chalamet was doing a good acting job in this movie because his character seemed to speak in the same flat tone the entire time and had the personality of a doorknob.

The only redeeming moment in the film for him is at the very end when he breaks up with Ashleigh and just decides to drop out of Yardley, leaving her alone in the carriage.

Chan even calls him out for his fake anarchist bullshit about how he hates the upper class life but he’s so privileged and doesn’t deny the fact he leeches off of his family financially.

I mean good for him that he reconnects with his mother at the end of the film, but I think this just would’ve been a better movie if we had this character development halfway through and we saw who he became.

Ashleigh, however, is just written to be air-headed and honestly completely stupid. Gatsby and her are meant to be complete opposites (he’s pseudo-intellectual while she’s not, he thinks rain is romantic but she hates it, etc.) and that’s the reason why they’re so awful together.

Chan is shown to understand him a bit more, which is good for her, but I honestly don’t see anything in that relationship either. Maybe this would’ve been more convincing if all the actors were better (except Fanning, she did great in this).


Overall Thoughts

Watch for Elle Fanning being an amazing actress and for Chan as a character.

I felt very out of touch with this world because these are uber rich people living in full-on houses and penthouse apartments in Manhattan—that means that they’re very very wealthy. As someone who lived in the New York that consisted of an apartment with a single bed that could only fit in my room, it doesn’t feel familiar to me at all. Maybe this would appeal to people who can relate to this world that the characters live in more, but for me it felt like watching a spectacle.

And maybe that’s intentional and I’m just missing the point. But when I can’t connect to any of these characters, that presents an issue in connecting to their stories. It does indeed have some nice shots of New York in the rain though.

Rating: 1/5

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