‘A Rainy Day in New York’: Woody Allen Takes a Half-Hearted Stroll Down His Usual Avenues

Woody Allen has become the most curious example of a controversial director. In aftermath of #MeToo, Allen’s personal life and the shadow of past scandals now cast a cloud over every new release with his name in the credits. Yet, as befitting any of his usual characters, the work itself doesn’t live up to the infamy. After many delays Allen is finally releasing “A Rainy Day in New York,” a movie that on its own should generate no controversy, just a few chuckles and yawns. 

Back into the Allen universe we go, this time with Gatsby Welles (Timothée Chalamet), a wealthy student bored with his picturesque liberal college. He is dating Ashleigh (Elle Fanning), an eternally ebullient student journalist. When Ashleigh gets a chance to journey into Manhattan to interview a big film director, Roland Pollard (Liev Schreiber), Gatsby decides to make a romantic trip out of it. He happens to be a skilled gambler and splurges on a suite and dinner reservations. But once in the city, Ashleigh’s interview with Pollard takes some odd turns with the director running off and Ashleigh going into a typical Allenesque Manhattan odyssey to find him. An annoyed Gatsby is left on his own to wander the city as it begins to rain, catching up with family, distasteful high school classmates and even Chan (Selena Gomez), the younger sister of an ex-girlfriend.

Out of Allen’s recent output, “A Rainy Day in New York” comes closest to the description of a broken record. There’s little vivaciousness to it and feels like Allen locked in a room, obsessing over every theme and quirk he enjoys revisiting. At least there’s the distinction that for once in a long while the main couple are close in age. As drama or comedy there is not much to the story aside from being an odd exercise in nostalgia. While the movie is clearly set in the present, the personalities feel wooden because they’re completely out of time. Gatsby Welles isn’t just privileged and well-bred, he walks, talks and smokes like a spoiled depressive out of the 1920s. In some other movie he might be labeled a “hipster,” especially when he buys a cigarette holder to compliment his style, but it feels more like Allen attempting a half-formed update of his own, wandering semi-intellectual from past films. He’s also unfair to his characters because while Gatsby has some semblance of personality, Ashleigh is reduced to a near ditz. She’s the naïve preppy who squeaks and jumps whenever someone “important” gives her attention. Is Allen just pulling our leg, or is he so detached from modern youth, privileged or not, that he can’t write them as anything other than his own fantasies? The most realistic character is Gomez’s Chan, an aspiring actor who meets Gatsby by chance at a student film shoot, then enjoys nudging at his pretentious shell. 

As with most Allen movies the cast and crew is a gallery of notables. It’s easy to suspect they agreed to this film simply because it’s Woody Allen, not because the screenplay was particularly astounding. Master cinematographer Vittorio Storaro returns, although with a less impressive palette than what he achieved in Allen’s “Wonder Wheel.” Then again, there’s not much to work with when most of the movie is supposed to be set on a rainy day. But Storaro’s gorgeous framing still appears here and there. Why the man who lensed “Apocalypse Now” and “Reds” has apparently only been beholden to Allen and Spanish maestro Carlos Saura for the last two decades is still a mystery. Elle Fanning will never have her welcoming smile lit so masterfully.

Most of “A Rainy Day in New York” recycles the Allen technique of walking through New York City as the characters endure comic hurdles. Mostly this consists of plush interiors and restaurants, with a stop at the Met. But much of it is low-grade comedy that just circles on itself, more as excuses for notable pop ups. For example, after Pollard disappears Ashleigh is left with his screenwriter, Ted Davidoff (Jude Law), who descends into his own crisis when he spots his wife walking into another man’s apartment. Then she falls into the orbit of Pollard’s star, Francisco Vega (Diego Luna), a stereotypical Latin lover who inevitably tries to seduce her. Because this is an Allen movie, all the older men will eventually make some sort of move on Ashleigh. It would be funnier if the dialogue had more wit or bite. Where Allen’s old brilliance for humor slightly shines are in scenes satirizing Hollywood ego, like Pollard acting like the tortured genius, or showing off a sense of absurdity, and Gatbsy’s brother admitting he hates his own fiancé’s laugh. The rest falls flat, even the old gag of someone paying a hooker to pretend to be their girlfriend at a fancy party. 

You don’t need to wonder if Timothée Chalamet and Elle Fanning are up to the task here. They are phoning in dialogue that rarely calls for the efforts of “Call Me by Your Name” or “The Great.” To their credit they do bring to life what Allen has written. Spending time with Gatsby is like walking around with a young preppy bored with his privilege, convinced that a strong vocabulary makes him a tortured soul, while Ashleigh makes the housewives in “Mad Men” look like radical feminists. It’s hard to care, even during the gags like Gatsby suspecting Ashleigh might be two-timing him with Pollard, for no other reason than he’s a film director.

Ironically “A Rainy Day in New York” won’t be showing in NYC theaters, but it is finally opening in select cities after delays stemming from renewed backlashes against Allen, that also caused it to be dropped by its original distributor Amazon as a result. It must be said plainly this is not the kind of movie to risk seeking out amid a pandemic. Even Allen’s diehard fans might be disappointed at how the old pro seems to have pulled this one from the bottom shelf. It rambles and bemoans, then ends with a kiss lacking in any passion. It’s a cloudy film with a desperate need of sunshine.

A Rainy Day in New York” releases Oct. 9 in select cities and Nov. 10 on VOD.