A Rainy Day in New York (2019)

Last updated:
October 27, 2025

A Rainy Day in New York is a 2019 romantic comedy written and directed by Woody Allen. The film captures a whimsical and bittersweet story about young love, fate, and the charming unpredictability of New York City. It’s both a tribute to classic Hollywood romance and a reflection on youthful confusion in the face of adult realities.

Table of Contents

Detailed Summary

Introduction: The Plan

The story follows Gatsby Welles (Timothée Chalamet), a smart but restless college student from a wealthy background, and his girlfriend Ashleigh Enright (Elle Fanning), an innocent and enthusiastic journalism major. They plan a romantic weekend in New York City when Ashleigh scores an interview with a famous film director for the student newspaper. Gatsby, thrilled by the idea, arranges a perfect getaway full of luxury, fine dining, and jazz.

Ashleigh Meets the Filmmaker

Things immediately start to unravel when Ashleigh’s interview with the eccentric director Roland Pollard (Liev Schreiber) spirals out of control. Pollard, in the midst of an existential crisis, decides to disappear, dragging Ashleigh into his chaotic world of celebrity and artistic drama. She soon crosses paths with screenwriter Ted Davidoff (Jude Law), whose own marriage is falling apart, and later with actor Francisco Vega (Diego Luna), a notorious Hollywood playboy. Ashleigh finds herself drawn into the glitzy, seductive chaos of show business.

Gatsby’s Unexpected Encounters

Meanwhile, Gatsby’s romantic weekend takes a completely different turn. While waiting for Ashleigh, he runs into Shannon (Selena Gomez), the younger sister of his ex-girlfriend. The two share witty banter, and despite their differences, there’s a growing spark between them. Throughout the day, Gatsby drifts from one encounter to another: playing poker, visiting his parents, and reflecting on his dissatisfaction with his privileged life.

The Rain as a Motif

The title’s rainy weather isn’t just literal—it mirrors Gatsby’s internal mood. The rain symbolizes unpredictability, emotional turmoil, and change. As he navigates the city, Gatsby begins to question his relationship, his future, and what love truly means. The rain accompanies every revelation, underscoring the melancholic beauty of self-discovery.

Movie Ending

The film culminates in a heartfelt and quietly devastating finale. Ashleigh, after a wild day of cinematic misadventures, spends the night with the charming actor Francisco Vega. She’s caught in the allure of fame and glamour, oblivious to how much she’s hurt Gatsby. When she finally meets Gatsby again, she confesses her chaotic day but glosses over the more compromising details. Gatsby, however, isn’t naïve—he senses the truth.

Realizing they no longer belong together, Gatsby ends the relationship. He decides to skip the fancy dinner he had planned and instead wanders through Central Park, lost in thought. There, under the rain, he unexpectedly meets Shannon again. The two share a quiet, intimate conversation beneath the park’s clock tower, where they had shared a previous kiss earlier in the film.

In the final moments, as the rain gently falls, they share a look that suggests a new beginning. Gatsby’s face lights up with understanding—sometimes love doesn’t arrive as planned, but it can still find you in the most unexpected way. The film ends with them walking off together, leaving the city lights glowing behind them, perfectly encapsulating the film’s romantic melancholy.

Are There Post-Credits Scenes?

No, A Rainy Day in New York does not feature any post-credits scenes. Once the credits roll, the story is complete, ending on its quiet, hopeful note.

Type of Movie

The film is a romantic comedy-drama, filled with elements of coming-of-age, satire, and urban romanticism. It’s distinctly “Woody Allen” in tone—cerebral, nostalgic, and peppered with humor that hides genuine emotional insight.

Cast

Timothée Chalamet as Gatsby Welles
Elle Fanning as Ashleigh Enright
Selena Gomez as Shannon
Jude Law as Ted Davidoff
Liev Schreiber as Roland Pollard
Diego Luna as Francisco Vega
Cherry Jones as Mrs. Welles

Film Music and Composer

The film’s music features classic jazz pieces and a soft, nostalgic score composed by Erroll Garner, whose iconic song “I’m in the Mood for Love” recurs throughout the movie. The soundtrack perfectly complements the film’s romantic, rainy-day atmosphere, evoking the golden age of New York cinema.

Filming Locations

A Rainy Day in New York was filmed entirely in New York City, across iconic locations such as:

The Carlyle Hotel – where Gatsby and Ashleigh stay, symbolizing upper-class sophistication.
Central Park – the heart of the film’s romantic imagery, particularly the final scene.
The Metropolitan Museum of Art – featured in Gatsby’s wandering moments, connecting his love of culture to his search for meaning.
The Plaza Hotel and The Village – representing both Gatsby’s elite world and the bohemian charm of the city.

The city isn’t just a backdrop—it’s a living character, full of charm, irony, and mood, influencing every decision the characters make.

Awards and Nominations

While the film didn’t receive major international awards, it found particular appreciation in Europe, especially in Italy and France, where Woody Allen’s work remains widely respected. It won modest recognition for cinematography and Chalamet’s performance at smaller film festivals.

Behind the Scenes Insights

The film’s release was delayed due to distribution issues following controversies surrounding Woody Allen.
Timothée Chalamet donated his salary from the film to charity, which sparked media attention.
Woody Allen described the movie as a “light, romantic escape” inspired by classic New York films like Breakfast at Tiffany’s.
Despite the rain-soaked aesthetic, some of the rainy scenes were shot under artificial rain on unexpectedly sunny days.
Elle Fanning improvised parts of her dialogue to make Ashleigh sound more spontaneous and naive.

Inspirations and References

The movie draws heavy inspiration from Woody Allen’s own earlier films, such as Manhattan (1979) and Annie Hall (1977). It also references:

F. Scott Fitzgerald’s The Great Gatsby — the protagonist’s name and themes of wealth and disillusionment.
Classic screwball comedies from the 1930s and 40s.
The romantic chaos of Breakfast at Tiffany’s.

Alternate Endings and Deleted Scenes

There are no confirmed alternate endings, but early drafts reportedly contained a slightly different finale where Gatsby leaves New York alone, without reconnecting with Shannon. This was changed to give the movie a softer, more hopeful closure. A few deleted scenes involved extended sequences of Ashleigh’s misadventures with Francisco Vega, which were cut to tighten pacing.

Book Adaptations and Differences

The film isn’t based on a novel, but it carries the literary tone and narrative style of classic American literature, with introspective monologues and poetic dialogue reminiscent of Fitzgerald or Salinger.

Memorable Scenes and Quotes

Key Scenes

Ashleigh’s chaotic interview turning into a wild day with the director.
Gatsby and Shannon’s sarcastic, flirtatious banter in the car.
The rain-soaked final meeting under the park clock tower.
Gatsby playing piano at The Carlyle, lost in thought as jazz fills the room.

Iconic Quotes

Gatsby: “I’m a romantic realist. I like to dream, but I like to know what’s real.”
Ashleigh: “Life is like a movie—you never know if it’s a comedy or a tragedy until the ending.”
Shannon: “You think too much for someone who’s trying to have fun.”
Gatsby: “A rainy day in New York is still better than a sunny day anywhere else.”

Easter Eggs and Hidden Details

The clock tower in the final scene symbolizes time, fate, and missed opportunities—a recurring motif in Allen’s films.
The jazz piano motif echoes themes from Manhattan and Café Society.
Gatsby’s last name “Welles” might nod to Orson Welles, another filmmaker obsessed with wealth and moral ambiguity.
The film posters glimpsed in Pollard’s studio reference fictional titles inspired by Allen’s own career.

Trivia

Woody Allen shot the film in only 35 days.
The movie’s title went through multiple versions before settling on A Rainy Day in New York.
Selena Gomez described working with Chalamet as “like acting in a jazz scene—improvised and alive.”
The film’s cinematographer, Vittorio Storaro, used warm lighting to contrast the gray, rainy setting.

Why Watch?

Watch A Rainy Day in New York if you love romantic, dialogue-driven stories set in atmospheric cityscapes. It’s ideal for fans of wistful love stories, jazz-infused soundtracks, and characters who stumble through heartbreak while trying to find themselves. It’s a nostalgic, beautifully shot film that celebrates both love and loneliness.

A Rainy Day in New York (2019)