3 out of 5 stars

I’m not a fan of Woody Allen’s films, with the exception of Blue Jasmine (2013), although I attribute my appreciation more to Cate Blanchett. While accepting Allen as a filmmaking legend, his work is too light on narrative for my taste. A Rainy Day in New York has the same look and feel of many of his previous films, but more interesting is his depiction of New York, which strays from his usual fascination with grand skylines. Instead, it focuses on little nooks in the East Village and elegant apartments overlooking Central Park under gloomy skies. One might not realise this dreary city is even New York if it weren’t in the title.

Despite what one may think of Woody Allen and the sexual assault allegations that continue to haunt him, the actors he’s assembled at least make this worth seeing, particularly Elle Fanning and a surprisingly good turn by Selena Gomez (who nails playing an entitled but smart and self-aware Upper East Side rich girl.) It is ironic, however, that the movie’s older male characters lust for significantly younger women (Fanning’s character pulls out ID to prove she’s 21 and not 15).

A Rainy Day in New York lacks a meaty plot but what story there is focuses on a young couple, Gatsby (Timothee Chalamet) and Ashleigh (Fanning), both studying upstate at the fictional Yardley College. They plan to spend a weekend in New York City so Ashleigh can interview a prominent filmmaker for her first story as an aspiring journalist. They stay at the prestigious Pierre Hotel and plan to have drinks at the Carlisle so Gatsby can show off the luxe version of the metropolis he absorbed from his upbringing. Ashleigh is originally from Tuscan and her only impression of New York, thus far, is from a trip she took years ago with her family, who couldn’t believe the cheap Rolex watches and designer purses being sold on street corners. She’s so out of touch she still doesn’t realise these were fakes.

Gatsby describes New York as a hostile city full of paranoia and anxiety, claiming “you’re here or nowhere”, clearly believing it’s the centre of the universe… and it just might be the centre of his. Chalamet plays Gatsby with pretentious flair, exuding the attitude of a ‘woe-is-me’ spoiled kid. I loathed him. Allen would have you believe it’s more likely for these modern-day lovers to carry their cigarettes with elongated holders than it is to post a photo to Instagram. Gatsby grew up in a refined and well-educated family, but he was seemingly sheltered from every aspect of life that emerged since the 1950s! Everything he says sounds like a carefully crafted sentence from an F. Scott Fitzgerald or J.D. Salinger novel. I don’t care how classy, nobody speaks this way today.

For someone who doesn’t have an identified passion or career path, Gatsby has a lot to say about the old pals he encounters making student films and his mom’s vast network of successful acquaintances and friends, for whom she’s throwing a gala he’s trying to avoid. He also expresses a sense of paranoia toward Ashleigh. When she postpones lunch with him, Gatsby believes something bad must have happened to her.

Ironically, it’s Gatsby’s behaviour that’s cause for concern as he agonises over Ashleigh being up to “funny business” and even assumes she’s broken up with him at one point. He’s the one having a somewhat too-involved day with Shannon (Gomez), reminiscing about the past with her while trotting around The Met, and even sharing a kiss for a scene in a student film. The timing of the kiss coincides with the downpour that New York is subjected to for the rest of the day, symbolically.

Ashleigh’s interview with a filmmaker Roland Pollard (an unsubtle reference to Roman Polanski) is the reason the pair are in the Big Apple. Pollard invites Ashleigh to a screening of his film, which he’s severely unhappy with and upset with his screenwriter Ted Davidoff (Jude Law). Near the end of the screening, Pollard leaves in an exasperated mess of embarrassment for his own work, while Ted and Ashleigh set off across Manhattan searching for him. This is the start of Ashleigh’s own Manhattan adventure. She’s not fazed in the slightest by the unique people and events she encounters, just rolls with the action and makes the most of every second. Even when she does express a little star-struck awe, she’s quick to snap back to focusing on her journalism. Her passion and drive, unaffected by stardom, unintentionally captivates many famous New Yorkers. 

Her bubbly, adventurous attitude contrasts nicely with Gatsby’s. If Gatsby is the rain, then Ashleigh is Manhattan. He ponders how moody the weather is and how nice it would be to take a ferry ride, while she doesn’t even notice the weather because she’s so absorbed in work, which is becoming bigger and better the further she falls down the city’s rabbit hole.

A Rainy Day in New York may lack a structured plot (beyond the exceptionally different day the pair end up having apart), but the journey of these two characters through the city is captivating. Ashleigh gets to wander around Kaufman Studios. Gatsby ventures over to his ex-girlfriend’s apartment with her younger sister, Shannon. But along with the lack of plot, there’s not much character development or depth… as how much can really happen in a single day? Especially one that doesn’t seem that out of the ordinary for anyone but Ashleigh! Even with her eventful encounters, she’s never more than the heart-eyed determined careerist she started out as.

If there’s a highlight to this movie, it’s the moment Gatsby shares with his mother in a moving monologue that gave me goosebumps. Cherry Jones (whom I’ve been watching in Defending Jacob recently) may not have a lot of screen time here, but she’s so memorable. She scolds Gatsby for bringing a prostitute to her party, who’s pretending to be Ashleigh. She describes it as an act of hostility toward her, reminiscent of the way Gatsby describes New York at the beginning of the film. Perhaps proof that your perspective can have far-reaching effects on your own situation and actions.

A Rainy Day in New York is unquestionably beautiful. The number of long single takes, especially between Gatsby and the friends he visits, offer a great opportunity to capitalize on the architecture of New York’s luxurious homes. The camera work is impressive and the set design is wonderful. The film had me longing to relive my own adventures in New York on this scale, while also reminded me I’ll probably never be so lucky… if knowing these types of self-absorbed folk can be described lucky? 

Gatsby is obsessed with “the life”, fully aware of high-class culture and taste, never afraid to name-drop artist Jean-Michel Basquiat or be critical of what others consider exceptional, which he may do to define his own individuality. He dresses the part, in a tweed blazer and he gestures with his cigarette in a dated holder, but he’s still faced with his own dullness and monotony when Ashleigh disappears on her own adventure. No matter how much he looks the part, action, work, and talent will always trump being self-aware and thinking he’s deserving just because he was raised around it. Gatsby’s nothing more than an interloper in other people’s lives bobbing around for meaningless visits. A woefully accurate metaphor for this film in Woody Allen’s filmography.

A Rainy Day in New York is ultimately mediocre, dripping with Woody Allen’s voice we’re all-too-familiar with by now. There’s nothing new or different here. It’s as pretentious as its lead character. It almost seems as if Allen is criticizing everyone in the audience who isn’t as well accomplished or relevant as himself. It might also be interpreted as a feeble attempt to normalise the rumours surrounding him. 

At times I wondered if this film was intentionally trying to show dated characters navigating a modern New York, but that idea is offset by Ashleigh—who has nothing timely about her. I don’t think even Allen knows what time period this story occurs in, or he’s understandably out of touch with the youth of today as a man in his eighties. This representation of New York is a hybrid of the romanticised olden times city and the modern-day one.

This is a film about young students; people nowhere near their peak in life, but with a lust for the world and what it has to offer. Their actions are based simply on their reactions and emotions to whatever they encounter. One can pull apart their decision-making and personalities, but Ashleigh and Gatsby are simply reacting to their surroundings, propelled by impulse, unsure who they are during one rainy day in New York. It’s a day that certainly won’t impact the rest of their lives, but it’ll “be a wonderful story to tell the grandkids.” That’s a stretch.

USA | 2019 | 92 MINUTES | 2.00:1 | COLOUR | ENGLISH

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Cast & Crew

writer & director: Woody Allen.
starring: Timothée Chalamet, Elle Fanning, Selena Gomez, Jude Law, Diego Luna & Liev Schreiber.