

a Rainy Day in New York (2019)
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Trish Smith
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January 06, 2025
Movie Overview | a Rainy Day in New York (2019)
Two sweethearts find their own meanings to life and love when chance circumstances lead them on different paths over the course of a day.
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User reviews
Beautiful to look at but not much else
Overall rating
3.4
Entertainment Factor
3.0
Story
3.0
Actors Performance
3.0
Cinematography
5.0
Sound Track
3.0
Woody Allen's A Rainy Day in New York arrived amidst a flurry of controversy and mixed expectations. The film, which was completed in 2018 but released in 2019 after significant delays, marked Allen’s return to the romantic comedy genre, a territory he had made iconic with works such as Annie Hall (1977) and Manhattan (1979). Set against the backdrop of the titular rainy city, the film brings together a colorful ensemble cast—led by Timothée Chalamet, Elle Fanning, Selena Gomez, and Jude Law—for a narrative that feels quintessentially Allen in tone, but oddly disconnected in its execution.
At its core, A Rainy Day in New York is a film about young love, the clash of idealism and reality, and the allure of New York City itself. However, it’s also a film laden with Allen’s familiar preoccupations: the complexities of relationships, the search for meaning in a world teeming with superficial distractions, and the fragility of human connection. Despite its elegant production values, charming performances, and intellectual dialogue, the film is weighed down by Allen’s increasingly self-indulgent style, a lack of narrative urgency, and thematic elements that have begun to feel dated, even stale.
Plot Overview
The movie follows Gatsby Welles (Timothée Chalamet), a privileged but thoughtful college student, and his girlfriend Ashleigh Enright (Elle Fanning), a naive and eager journalist, as they arrive in New York City for a weekend getaway. Ashleigh, an aspiring writer, is given an exclusive opportunity to interview an eccentric film director, Roland Pollard (Liev Schreiber), for an article she’s writing. This gives her an excuse to immerse herself in the city’s glamorous intellectual world, leaving Gatsby to navigate the city’s bustling streets alone.
As Ashleigh becomes enmeshed in the world of celebrity, scandal, and art, Gatsby is drawn into his own series of encounters: he reconnects with an ex-girlfriend (Selena Gomez), gets involved in the affairs of his quirky and troubled family, and spends an increasingly stormy day drifting through the city, torn between youthful idealism and the contradictions of the adult world.
The narrative weaves between these two storylines, offering a series of romantic entanglements, misunderstandings, and revelations, all set to the ever-present drizzle of a rainy Manhattan day. Allen’s film captures the city’s distinctive energy: a mix of romantic allure, intellectual pretension, and existential confusion. Yet, despite all the surface-level romance and charm, A Rainy Day in New York never quite takes flight in the way that Allen’s best films do.
Characters and Performances
The performances are one of the film’s most charming aspects. Timothée Chalamet brings a level of sophistication and vulnerability to Gatsby, playing a character who is simultaneously privileged and self-aware. He’s an idealistic young man, yet Chalamet’s natural charisma ensures that Gatsby remains sympathetic even when he’s acting self-absorbed or overly cynical. His portrayal of a young man trying to reconcile his youthful optimism with the jaded world around him feels genuine, though the character himself can come across as a bit naïve at times.
Elle Fanning, as Ashleigh, plays the role of the wide-eyed, ambitious student with charm and grace. Her performance, however, falls into the trap of being too one-dimensional. Ashleigh’s character is written as an idealistic, somewhat vapid aspiring journalist, and while Fanning brings a sweetness to the role, the character lacks the depth and growth that would make her arc feel more substantive. Ashleigh’s immersion into the world of high society and celebrity becomes an allegory for her own loss of innocence, but it feels underdeveloped, given the film’s insistence on Gatsby’s journey as the central focus.
Selena Gomez is a welcome presence as Chan, Gatsby’s ex-girlfriend, a cynical, pragmatic young woman who offers him a grounding influence amidst his romantic confusion. Gomez plays the character with wit and intelligence, offering a refreshing contrast to the more fragile and idealistic Ashleigh. While their interactions are engaging, it’s clear that Chan functions more as a plot device—someone for Gatsby to reflect upon and grow from—rather than a fully fleshed-out character in her own right.
Jude Law plays a charming, somewhat predatory older man, and though his role as a filmmaker does not offer much in terms of new material, he’s an engaging screen presence who adds another layer of complexity to the film’s meditation on love, fame, and the blurred lines between art and life.
New York City as a Character
Like many of Woody Allen's films, A Rainy Day in New York uses New York City itself as a character—its rain-slicked streets, busy sidewalks, and iconic landmarks becoming as much a part of the story as the human interactions. The city is both a place of opportunity and disillusionment, embodying the contradictions of the characters’ own desires. It offers a seductive blend of glamour, chaos, and possibility, while simultaneously exposing the shallowness of ambition and the transience of youthful infatuation.
Cinematographer Vittorio Storaro captures the city in all its grey, rainy beauty. The streets glisten with rain, the neon signs flicker in the wet dusk, and Central Park is both an oasis and a mirage. These lush images are framed with a sense of nostalgia and yearning, evoking the magic of a New York that no longer exists except in the eyes of dreamers like Gatsby. The atmosphere of the city in this film, much like the romance between the characters, feels fleeting and ephemeral—everything is in motion, but nothing seems to last.
Thematic Exploration
Woody Allen’s exploration of relationships, disillusionment, and youthful idealism is hardly new ground for him. In fact, A Rainy Day in New York feels like a rehashing of many of the themes he has previously tackled in his career. At the heart of the film is a central conflict between the desire for romantic fulfillment and the recognition of life’s inherent disappointments. Gatsby’s romantic notions are tested as he grapples with the reality of New York, while Ashleigh’s journey into the world of celebrity journalism highlights the tension between fame and authenticity.
While these themes are by no means tired in themselves, Allen’s handling of them here feels somewhat worn. The dialogue is filled with the usual intellectual musings about love, art, and identity, but the film’s central characters fail to offer anything particularly fresh or insightful. It’s as if Allen is content to coast on the allure of New York and the nostalgia of his previous films without fully interrogating the complexities of the world he is depicting.
The film also feels oddly dated in its portrayal of gender dynamics and romantic relationships. The film’s treatment of Ashleigh, in particular, feels stuck in an older mindset—one in which the young woman’s main conflict revolves around her relationship to a man, rather than her own personal growth or agency. The film’s treatment of women, especially in relation to men like Gatsby and Pollard, suggests a kind of old-school gender imbalance that may feel uncomfortable for contemporary audiences.
Conclusion
“A Rainy Day in New York” is a film that captures the essence of Woody Allen’s filmmaking style—quirky, intellectual, and steeped in a certain romanticism for New York City. While the performances are strong, the plot meanders, and the film lacks the sharpness of Allen’s best work. The film is undoubtedly charming at moments, thanks to its talented cast and the evocative portrayal of the city, but it is ultimately a film that feels overly familiar and strangely hollow. For fans of Allen’s earlier work, there’s something here to appreciate, but for others, the film may come off as an exercise in nostalgia, lacking the insight and vitality that once defined Allen’s films at their peak.
In the end, A Rainy Day in New York is less about romance or relationships than it is about the passage of time and the inability to hold onto fleeting moments of idealism. Like the rainy streets of Manhattan, the film is beautiful to look at but ultimately drenched in melancholy and missed opportunity.
A Simple Romantic Comedy
(Updated: January 04, 2025)
Overall rating
2.8
Entertainment Factor
3.0
Story
3.0
Actors Performance
4.0
Cinematography
2.0
Sound Track
2.0
A Rainy Day In New York is a simple romantic comedy written by Woody Allen, and is about Gatsby Welles, played by Timothée Chalamet , a Yardley College student. When Gatsby learns that his girlfriend, Ashleigh Enright, played by Elle Fanning, is planning to travel to Manhattan to interview a movie director for the college paper, Gatsby plans a romantic weekend with her. Both Gatsby and Ashleigh come from a well-to-do family and Gatsby really is not interested in his college education and the best part of college for him is that he met Ashleigh. When they arrive in Manhattan, Gatsby does not tell his parents, as they are throwing a big party that he does not want to attend. Ashleigh meets the director who invites her to a screening of his new film. Meanwhile Gatsby meets an old high school friend who's shooting a movie, and agrees to participate in a kiss scene with the younger sister of his high school girlfriend. Throughout the rainy New York weekend, both Gatsby and Ashleigh have new experiences and make new discoveries. There are parts of the movie that really don't make sense, some ridiculous lines, many that are supposed to be funny but are not and a few that make the movie unrealistic. The best part of the movie is thinking about a rainy day in New York and the memories that these can conjure up. May be ok for a rainy day at home.
Not one of woody allen's better movies
(Updated: January 04, 2025)
Overall rating
2.2
Entertainment Factor
2.0
Story
2.0
Actors Performance
2.0
Cinematography
3.0
Sound Track
2.0
The appeal of “A Rainy Day in New York,” to the extent it has any, is nostalgia. It has the familiar Woody Allen graphics at the start and, to some degree, has the atmosphere of other, better Woody Allen movies. But it’s mostly a mess — simply off in ways one usually doesn’t see in movies.
The performances seem desperate, as if the actors are compensating for not being directed. The characters make little sense, and their personal dramas are without impact. And no joke, Woody Allen really needs to stop writing about young people, because he has no clue as to how anyone under 40, much less 25, talks and thinks.
That something is wrong with “Rainy Day” is apparent from the first shot. Timothy Chalamet plays a student named Gatsby who goes to a private college in upstate New York. He meets his girlfriend, Ashleigh (played by Elle Fanning), and the two start walking and talking. As the shot lengthens, you can see the actors become increasingly frantic that they might blow the shot and have to start again. They seem under-rehearsed and stiff, and so they push it. The result is an opening that is weird, tin-eared and artificial.
And it gets worse from there.
Gatsby and Ashleigh spend a weekend in New York. She’s a student journalist and has an interview with a major avant-garde director (Liev Schreiber), and Gatsby, who is from New York, wants to show her the city.
Both of them, needless to say, are insanely rich. Rich, like they never once had to think about money. Rich, like they have all the time in the world to complain about being rich. And everybody they know is loaded. “A Rainy Day in New York” takes place in a world in which there are two kinds of people: the ones who matter, and the ones in the shadows that get generous tips from the ones that matter. (Woody needs to get out more.)
As for the story, the less said the better. They go to Manhattan, and the action takes place over the course of a busy 24 hours. Ashleigh meets the director and ends up spending the day in the filmmaker’s circle, and Gatsby runs into the little sister (Selena Gomez) of a woman he once dated.
He tells her that it’s amazing to see her all grown up, and she replies, “You’re not going to start singing ‘Gigi,’ are you?” If you’re not laughing uproariously at that pithy cultural reference, congratulations — it means you’re younger than 100. But the problem isn’t just the line itself, but also the fact that Allen puts it in the mouth of a 20-year-old woman.
This kind of thing happens throughout the movie. Gatsby tells an acquaintance that his girlfriend’s name is Ashleigh, and the person replies, “Ashley Wilkes?” But Ashley (or its variant Ashleigh) has been a popular woman’s name since the 1980s.
In another scene, Gatsby tells someone that Ashleigh is from Arizona, and someone starts making cracks about cowboys and rodeos. But who in 2020 thinks about Arizona in that way? For that matter, what college-age woman would say of her boyfriend, “He’d like to be Sky Masterson?” You know, the gambler from “Guys and Dolls”? Frank Loesser’s musical from 1950? No, that’s not the first reference that would come to a young woman’s mind.
Moreover, here and there, Allen puts supposed laugh lines in the mouths of major characters that undermine their reality. For example, when Ashleigh meets a famous movie heartthrob, she tells him, “My friend thinks you’re the best thing to come along since the morning-after pill.” Fanning tries to make the line work by acting flustered, but she can’t succeed. It’s simply embarrassing.
For the record, I laughed three times, mildly, so Woody Allen can be found, alive, somewhere in this wreckage. He has made too many great movies following bad movies to ever count him out forever. But “A Rainy Day in New York” is not just one of the lesser Woodys, it’s one of the least.
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