A Rainy Day in New York is Mismatched Nostalgia

Image courtesy of Signature Entertainment

For anyone who’s heard one of the countless monologues in a Woody Allen film, you may have found yourself asking “who in the world talks like that?” Well, that’s him. That’s the dithering panache of the quintessential New York filmmaker and master screenwriter. Hurdles, though, come with him and his new movie A Rainy Day in New York as it debuts on Amazon Prime October 9th after long delays amid a heap of personal and professional controversies surrounding the production during the #MeToo movement. This writing piece (and every single one I ever write) separates the man from the medium. Film reviews are for films. The rest belongs in an louder editorial sections, and rightfully so in his case.

Like him or not, the man can sure put words together and stuff poetry into peoples’ mouths. When he used to cast himself delivering those diatribes and long conversations, the semantics fit the persona perfectly. With Allen aging out of his usual middle-aged hopeless romantic leading man roles, the pairings between the acting vessels in his place and his scripted ravings do not always ideally match.

Appealing as it may be, swinging from the affable to the morose, that mismatch is the glaring irregularity found in A Rainy Day in New York. The flow of uptown affluence and worldly whims spoken by the central figures of the film is perky and magnetizing. The words enchant to no end, yet are staggeringly uncharacteristic when you watch them coming from a cast of 20-somethings, even if they are played by talents like Timothée Chalamet, Elle Fanning, and Selena Gomez.

You’re back to the question of “who talks like that,” and your answer is almost certainly not a single young person you know of this current decade or century. They might as well be talking in Shakespearean English for cutesy theatre instead of acting their age and era. Even the most cultivated retro Millennial you could ever concoct or discover couldn’t and wouldn’t talk like Woody Allen. That’s where the fizz doesn’t flow, despite the winsome look of every layer of A Rainy Day in New York.

Chalamet, the Call Me By Your Name Oscar nominee, plays Gatsby Welles, a brash senior at the fictional Yardley College in upstate New York. Clad in his wool blazer and sneakers, he’s an intellectual smoothie who was cast out of his native Manhattan by his mother (Cherry Jones) for liberal arts refinement. It hasn’t taken. The whip-smart nonconformist enjoys the vices of gambling, cigarettes, and booze while longing for the classic haunts of Old New York that he misses terribly while stranded in the sticks.

Because this an Allen film, therefore shadowing his own personality traits, Gatsby is eccentric to the nth degree in his urban playground of hostility and paranoia. His cultured character is hot-and-cold, with actions and choices clashing his creative dreams with rank pessimism. Timothée plays this with the appropriate frazzle and fluster. The dashing and shifty actor eats this kind of measured material up, and even croons an old standard over piano for us. Chalamet’s Allen proxy laments lines like “Find some brilliant way to ruin my life” or “I need a drink, a cigarette, and a Berlin ballad,” among many others, with smirking persuasion.

Ashleigh sits in a small theater watching a screening with the director and screenwriter.
Image courtesy of Signature Entertainment

On Gatsby’s arm is the bouncy and breathy Ashleigh Enright (Fanning). She’s an aspiring journalist who’s more than a bit of a gullible ditz. Ashleigh is credentialed to interview a notable and temperamental indie filmmaker (Liev Schreiber) in the big city and Gatsby jumps at the chance to blow some poker winnings on a lavish weekend away together. While on her assignment, Ashleigh gets roped into a tailspin of a scoop that separates her from Gatsby over the course of their meticulously planned day. Meanwhile, he dodges family and runs into the little sister (Gomez) of a former high school girlfriend who might have an old crush on him.

The Big Apple swank delivered by location manager Christie Mullen is all over A Rainy Day in New York. The city sells itself. From the Bing Crosby opening number and through the many lovely jazz selections of Erroll Garner, the tone of it all is very genial. Old school three-time Oscar-winning cinematographer Vittorio Storaro (Apocalypse Now!) fawns over the name stars within the angles and antiquities crafted by Allen regular Santo Loquasto and decorated by TV vet Sarah Dennis. Costume designer Suzy Benzinger gives everyone threads that can handle being drenched in showers of precipitation and style.

Gatsby and Chan talk outside a museum entrance.
Image courtesy of Signature Entertainment

The brininess cutting the sweetness of this celluloid rainwater is, again, the mismatched maturity roots. While the worldliness is quaint, it is extreme and beyond what the roles can accomplish. Even if the spirited actors, try as they may, rise to flirt with that level, they are woefully out of place, especially when saddled with Allen’s signature placement of odd fidgets, manifested here in dorky laughs, hiccup gags, and more. A blurry hodgepodge like that can take one right out of even a very winning romantic picture.

A cloistered senior artist like Woody Allen cannot write a credible 2020 youth, but he can write “his” youth with gusto. Advance this story by going backwards rather than dilute an unflattering present. Shave off the cell phones, turn this movie’s clock back 40-plus years, and every beat of A Rainy Day in New York would be identically the same, only gloriously better. That is because the talent would meet the nostalgia instead of vice versa. Put “their” age in “your” age, not the other way around.

Written by Don Shanahan

DON SHANAHAN is a Chicago-based Rotten Tomatoes-approved film critic writing here on Film Obsessive as the Editor-in-Chief and Content Supervisor for the film department. He also writes for his own website, Every Movie Has a Lesson. Don is one of the hosts of the Cinephile Hissy Fit Podcast on the Ruminations Radio Network and sponsored by Film Obsessive. As a school teacher by day, Don writes his movie reviews with life lessons in mind, from the serious to the farcical. He is a proud director and one of the founders of the Chicago Indie Critics and a voting member of the nationally-recognized Critics Choice Association, Online Film Critics Society, North American Film Critics Association, International Film Society Critics Association, Internet Film Critics Society, Online Film and TV Association, and the Celebrity Movie Awards.

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