10 Movies Like A Rainy Day In New York You Need To See

Based on the controversy surrounding Woody Allen, Amazon decided not to release his 2019 film A Rainy Day In New York, which features young stars Selena Gomez, Elle Fanning, and Timothée Chalamet. It’s a rom-com that centers on college students spending a day in Manhattan, as the title suggests. Gatsby Welles (Chalamet) and Ashleigh Enright (Fanning) travel to NYC together as she’s meeting with Roland Pollard (Liev Schreiber), a filmmaker, to interview him for her college newspaper. The young couple splits up for the day and ends up at different parties, and it’s one of those stories where expectations don’t meet reality.

A Rainy Day in New York did get released in Europe, South America, and Asia, but hasn’t gotten great reviews. However, there are other similar movies for people to check out, whether set in NYC or featuring college-aged kids who are trying to figure life out.

10 Autumn In New York (2000)

Released in 2000, this drama features Winona Ryder and Richard Gere. Ryder’s character Charlotte is much younger than Gere’s restaurant owner character Will, as she’s 22 and he’s in his late forties.

This movie captures the spirit of living, working, and falling in love in New York City. It’s much sadder than A Rainy Day In New York but both movies are about a couple spending time in that great city.

9 Palo Alto (2013)

Starring Emma Roberts, this 2013 film is adapted from a book of short stories written by James Franco. It has a similar vibe to A Rainy Day In New York, as it’s about a group of young adults who experience love, sex, and partying. They also seem very lost and like they don’t know what they’re supposed to be doing.

8 200 Cigarettes (1999)

The 1999 movie 200 Cigarettes takes place on one night, New Year’s Eve, and tells a series of stories about people going to a party and trying their best to celebrate the end of the year and the beginning of the next one.

Since it features a party in New York City, it seems similar to A Rainy Day In New York, making it a good choice for movie fans interested in that kind of tale. The movie also features famous faces like Paul Rudd, Courtney Love, Kate Hudson, and Ben Affleck.

7 New York, I Love You (2008)

Anthology TV shows are a lot of fun to watch and sometimes an anthology movie comes around, too. The 2008 movie New York, I Love You is co eleven short movies and tells the stories of people living in NYC and experiencing the range of emotions that love produces.

It has a bit of a Woody Allen feel as it celebrates this beloved, beautiful city the way that his critically acclaimed Manhattan did.

6 While We’re Young (2014)

The 2014 movie While We’re Young tells the story of two couples who are decades apart but have various motivations for hanging out. While Ben Stiller’s Josh and Naomi Watts’ Cornelia love that Jamie (Adam Driver) and Darby (Amanda Seyfried) are young and cool, Jamie has ulterior motives.

This Noah Baumbach movie is all about filmmakers, New York City, and the feeling of being adrift, just like A Rainy Day In New York.

5 The Boy Downstairs (2017)

Want a love story set in NYC? The Boy Downstairs fits the bill perfectly. Released in 2017, the movie follows Diana (Zosia Mamet), who dates Matthew Shear’s character Ben, and the two are very artistic. He wants to make music and she wants to be a writer.

Ben and Diana’s love story gets complicated as she dumps him and he moves in with Meg (Sarah Ramos). It’s an interesting movie about being young, living in the big city, and pursuing art.

4 2 Days In New York (2012)

Looking for another New York City movie? Try 2 Days In New York, starring Chris Rock and Julie Delpy. The movie follows the couple in NYC as they deal with complex issues like race and family. It’s not a traditional or typical romantic comedy, and it goes much deeper.

3 Sidewalks Of New York (2001)

Edward Burns both wrote and directed the movie Sidewalks Of New York, which came out in 2001.

This is one of those movies where the main characters all know each other or have touched each other’s lives in some way. The ensembles stars Burns, Stanley Tucci, Heather Graham, the late Brittany Murphy, David Krumholtz, and Rosario Dawson.

2 Birdman (2014)

Selena Gomez has a part in A Rainy Day In New York as an actress whom Chalamet does a screen test with. While Birdman is a more compelling and also definitely a more creative movie, it is also about acting, making it a great movie for Rainy Day in New York fans to check out.

1 Tiny Furniture (2010)

Before creating Girls, Lena Dunham released her indie film Tiny Furniture in 2010. She wrote, directed, and starred in the movie as Aura, a girl living with her mom in NYC one summer while she’s in college.

Tiny Furniture is about that time in everyone’s lives when everything seems possible and everything is up in the air and yet it seems like it’s impossible not to make tons of mistakes. Aura also has a degree in filmmaking, so the movie has that in common with A Rainy Day In New York.

About The Author

Aya Tsintziras
(1742 Articles Published)

Aya Tsintziras is a freelance writer who writes about pop culture and TV. She has a Political Science degree from the University of Toronto and a Masters of Journalism from Ryerson University. She loves coffee, reading, working out, and watching TV. She lives in Toronto with her husband.

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