Film Overview
A young couple arrive in Manhattan expecting a romantic weekend together and instead spend the day moving through completely separate adventures involving filmmakers, actors, old friends, family secrets and a great deal of rain.
Timothée Chalamet plays Gatsby, a New Yorker attending college outside the city and far more attached to Manhattan than to his academic life.
Elle Fanning plays his girlfriend Ashleigh, an aspiring journalist who has been given the opportunity to interview celebrated film director Roland Pollard, played by Liev Schreiber.
Gatsby imagines the assignment will occupy only a small part of their weekend. Instead, Ashleigh becomes drawn into Pollard’s creative crisis, encounters his screenwriter Ted Davidoff and eventually movie star Francisco Vega, played by Diego Luna.
Left alone, Gatsby encounters Chan, played by Selena Gomez, the younger sister of a former girlfriend. Their increasingly easy connection begins challenging his assumptions about both Ashleigh and the life he wants.
Vittorio Storaro photographs Manhattan through rain, hotel windows and warm interiors, while Erroll Garner, Bing Crosby and Conal Fowkes create an old-fashioned musical New York surrounding characters considerably younger than the songs accompanying them.
Watch A Rainy Day in New York
My Review
The Manhattan weekend Gatsby planned and the one New York gives him instead
A Rainy Day in New York is built around a very Allen idea: somebody carefully plans a romantic Manhattan weekend and the city spends the next day ignoring the itinerary.
Gatsby has already constructed the weekend in his head. There will be hotels, restaurants, walks and the particular version of New York he wants Ashleigh to understand.
She only needs to complete one interview.
Naturally, the interview consumes almost the entire day.
Gatsby arrives with a plan for New York. New York has its own schedule.
Timothée Chalamet plays Gatsby as somebody whose nostalgia has arrived several decades before old age. He is young but emotionally attached to an older Manhattan of piano bars, elegant hotels and standards.
He dislikes college partly because it places him outside the cultural world in which he feels most himself.
Ashleigh is different. She is enthusiastic, open and delighted by the access journalism suddenly provides.
The day exposes that difference much more effectively than an argument between them could.
Elle Fanning is very funny as Ashleigh because she does not enter the film looking for an adventure. Events simply keep escalating around her.
The Pollard interview becomes a screening, the screening becomes a search for the missing director, and the search introduces her to increasingly glamorous members of the film world.
Liev Schreiber, Jude Law and Diego Luna create three different versions of movie-industry sophistication around somebody who remains slightly amazed to be included.
Ashleigh’s innocence is less stupidity than openness to whatever happens next.
Ashleigh keeps missing Gatsby because every cancelled plan turns into a better story for the journalist she wants to become.
Selena Gomez gives the film its sharpest dialogue as Chan. She and Gatsby have history through her sister, which means there is no need for the careful social performance required by a first meeting.
They can irritate one another immediately.
That familiarity gradually becomes attraction because Chan understands Gatsby’s relationship with the city in a way Ashleigh does not.
She does not need Manhattan explained to her.
The scenes with Gatsby’s family deepen the character more than I expected. His relationship with his mother is built partly around resistance to the polished world she represents.
Then he learns something about her past that complicates the image he has spent years carrying.
Again, the film is about assumptions being corrected by a day that refuses to follow the expected version.
Gatsby’s mother turns out to contain a history he had never imagined because children are often remarkably confident that parents began existing only shortly before they were born.
Gatsby thinks he knows Manhattan and thinks he knows his mother. The weekend quietly demonstrates how incomplete both maps are.
Storaro makes the rain beautiful without turning the city unreal. Streets shine, windows glow and the grey exterior light makes cafés and bars feel even warmer.
The Pierre, the Met, Bemelmans Bar and Central Park belong to Gatsby’s preferred version of New York: cultured, expensive and slightly outside contemporary time.
Loquasto’s interiors reinforce that feeling. Gatsby is effectively attempting to live inside a Manhattan inherited from music, movies and family memory.
The rain helps. Sunshine would make the city too ordinary.
The soundtrack may be the strongest expression of Gatsby’s personality. Bing Crosby opens with I Got Lucky in the Rain, a title that already tells us the weather is going to become opportunity rather than inconvenience.
Erroll Garner dominates much of the remaining music: The Best Things in Life Are Free, Will You Still Be Mine?, Misty and others.
Then Gatsby himself sings Everything Happens to Me, with Conal Fowkes at the piano.
It is almost comically perfect for a character spending the day watching his planned weekend disappear.
Everything Happens to Me is Gatsby’s complaint and, by the end, probably the best thing that could have happened to him.
The final romantic choice is deliberately simple. Gatsby and Ashleigh have not suffered a dramatic betrayal requiring an enormous confrontation.
They have simply discovered that spending one day apart reveals how differently they respond to the world.
Chan fits naturally into the city Gatsby wants to inhabit. Ashleigh’s appetite pulls her elsewhere.
Sometimes incompatibility does not require a villain.
The clock sequence gives the ending exactly the kind of old-fashioned romantic gesture Gatsby has wanted all along, but with the person he did not expect.
That is why the film’s nostalgia works for me. It is not simply Allen photographing another attractive Manhattan.
Gatsby himself is nostalgic, and the story gradually asks whether he can find someone who wants to inhabit that imaginative New York with him.
He can. It just is not the person who arrived on the train.
Gatsby finally gets his romantic New York ending. He simply cast the wrong leading lady when he planned the weekend.
Cast and Characters
Timothée Chalamet
A young New Yorker far more interested in Manhattan, music and poker than in the college life he is supposed to be building.
Elle Fanning
Gatsby’s enthusiastic girlfriend, whose journalism assignment unexpectedly takes over their entire weekend.
Selena Gomez
The younger sister of Gatsby’s former girlfriend, whose sharp humour and familiarity with New York gradually pull him in another direction.
Liev Schreiber
A celebrated filmmaker whose creative crisis turns Ashleigh’s straightforward interview into something much larger.
Jude Law
Pollard’s screenwriter, who brings Ashleigh further inside the director’s increasingly chaotic day.
Diego Luna
A glamorous movie star whose encounter with Ashleigh pushes her improvised New York adventure even further from Gatsby’s plan.
Old New York songs accompany two very young people getting lost in Manhattan
Bing Crosby, Erroll Garner and Conal Fowkes create a deliberately old-fashioned musical city completely aligned with Gatsby’s personality.
Everything Happens to Me
Gatsby sings the standard with Conal Fowkes at the piano. The title is both a complaint about the collapsing weekend and a clue that the disruptions may ultimately be exactly what he needs.
The music belongs to the city Gatsby wishes still existed
Garner supplies a large part of the film’s jazz soundtrack, with recordings including Misty, Undecided and I’ve Got the World on a String.
Bing Crosby’s opening song makes the rain itself part of the romantic promise.
I Got Lucky in the Rain
The opening song turns bad weather into the possibility of good fortune before the story has begun.
Misty
One of Garner’s defining compositions is an irresistible choice for a film built around rainy Manhattan romance.
Will You Still Be Mine?
The title neatly anticipates the question Gatsby and Ashleigh’s weekend will eventually force them to answer.
I’ve Got the World on a String
Another great standard surrounding characters whose plans suggest they have considerably less control than the song promises.
Locations
The film moves through an unmistakably Allen Manhattan of museums, grand hotels, downtown streets, Central Park and one particularly important piano bar.
The Pierre
The Fifth Avenue hotel belongs naturally to Gatsby’s polished and nostalgic version of Manhattan.
Metropolitan Museum of Art
The Met appears within the cultural geography Gatsby considers essential to a proper New York weekend.
Bemelmans Bar
The legendary Upper East Side bar gives the film one of its strongest links to the older Manhattan of Gatsby’s imagination.
Central Park Zoo
The park remains part of the constantly shifting route Gatsby takes once his original schedule collapses.
Walker’s
The Varick Street restaurant is among the real downtown locations used during the production.
A City in the Rain
Storaro uses rain, reflected street light and warm interiors to make the city itself the atmosphere connecting Gatsby and Chan.
Awards and Recognition
Vittorio Storaro
The film continues the visually rich collaboration begun with Café Society and developed through Wonder Wheel.
A Full Manhattan Return
After several films set partly or entirely outside the city, Allen again builds an entire romantic comedy around Manhattan.
Erroll Garner
The pianist’s recordings dominate the soundtrack and give Gatsby’s New York its strongly nostalgic musical character.
Timothée Chalamet at the Piano
Gatsby’s performance of Everything Happens to Me makes the soundtrack part of the character rather than simply accompaniment.
International Theatrical Run
The film began its theatrical life internationally in 2019 before later receiving North American distribution.
Another New York Romance
The film returns Allen to rain-soaked streets, jazz standards, Central Park and the idea that Manhattan can rearrange a relationship in a single day.