A RAINY DAY IN NEW YORK-- 3 STARS

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 brilliance of the quintessential New York filmmaker and master screenwriter. The man can sure put words together and stuff poetry in 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 Allen’s new film A Rainy Day in New York debuting on Amazon Prime October 9th. 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. 

LESSON #1: ACT “THEIR” AGE-- 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. 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. 

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.

LESSON #2: FIND SOME BRILLIANT WAY TO RUIN YOUR LIFE-- Because this an Allen film 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 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 a line like this lesson title or “I need a drink, a cigarette, and a Berlin ballad,” among many others, with smirking persuasion. 

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. 

LESSON #3: ACT “YOUR” AGE-- 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.