Woody Allen Breaks Stunning New Ground in ‘A Rainy Day In New York’

Just kidding, it’s the same old schtick

Wet with romance and soggy with outdated references, A Rainy Day in New York strains to be a full-hearted look at human folly. It’s a portrait of attraction—to love, to fame, to money, to impossible ideals—that’s more wispy than wise. But there’s still some structural integrity to the screwball premise of star-crossed lovers and mismatched paramours pinballing through a 24-hour Manhattan reverie.

A RAINY DAY IN NEW YORK ★★★(3/5 stars)
Directed by: Woody Allen
Written by: Woody Allen
Starring:  Timothée Chalamet, Elle Fanning, Selena Gomez, Jude Law, Diego Luna, Liev Schreiber
Running time: 92 min

Did I mention that allegedly-pedophilic and investigated-but-cleared Hollywood pariah Woody Allen directed it? That’s the reason this Amazon-dumped 2018 movie is finally seeing daylight. After an international release last year, and a perfunctory, Covid-crippled theatrical U.S. release last month, it’s now streaming digitally. If your opinions of the longtime auteur are hardened, if your mind is officially closed and his work doesn’t merit discussion, then I’m surprised you’ve read this far.

Like any enduring brand or legacy franchise, Allen’s films, especially the comedies, generally meet for-better-or-for-worse baseline expectations: sex-obsessed neurotic men, ditzy ripe women, postcard-perfect exteriors, stunning apartments, and a fatalistic ennui leavened with happy accidents. He’s been churning out variations on a theme for more than fifty years. And, like anything that lasts more than half a century, his cultural shorthand becomes long in the tooth.

In this case, the pop allusions and casual repartee in A Rainy Day In New York are so maddeningly out-of-step, so embarrassingly tone-deaf, they’re actually kind of quaint. At times it feels like this was a script that Allen slated for 1980 but then lost in a drawer for 40 years. The main character, a disaffected know-it-all college student (Timothée Chalamet), is literally named Gatsby Welles. Really? He says things like “My horse came in this weekend” and refers to tony Ivy League universities as “joints.” He’s the type of guy who asks, “Can I play your piano?” and then accompanies himself singing “Everything Happens to Me” in his best Chet Baker sigh. Dude seriously buys a cigarette holder. And starts using it. With a straight face. It’s enough to make Holden Caufield vomit.

A Rainy Day In New York
‘Would you like to see my negatives?’–Older man macks on younger woman in Woody Allen’s ‘A Rainy Day In New York’.

This being a Woody Allen film, Gatsby is dating a comely airheaded co-ed named Ashleigh Enright, played by Elle Fanning. They’re at fictional Yardley College, just a few hours’ drive from his hometown of New York City. She lands an interview with self-important film director Roland Pollard (Liev Schreiber) for the school newspaper. Only hitch is that it’s in Manhattan. But that’s fine, because Gatsby just won $20,000 playing poker the previous weekend. Again, really? But whatever.

He offers to give her a swoony trip to the Big Apple: a suite at the Pierre and dinner at Daniel, plus a quick stop at the Weegee exhibit at MoMA and drinks at Bemelmans Bar. Gatsby’s version of a New York weekend reads like a tony website’s recommendations for moneyed blue-haired tourists. But yeah, sure, college kids would probably like those things too.

She says yes, they go to the big city, and hijinks ensue that keep the duo separated for the rest of the day. She tells Pollard that “film’s my total thing” and espouses her love for cinematic giants. Cue dusty name-dropping of hoary masters like Renoir, De Sica, and Kurosawa. Pollard, being tortured, disappears on a Courvoisier bender—who does that?—so Ashleigh and Pollard’s screenwriter Ted (Jude Law) try to track him down. That leads to Ted discovering his wife’s infidelity and Ashleigh stumbling into the orbit of Mexican heartthrob actor Francisco Vega (Diego Luna).

Meanwhile, Gatsby bumps into an obnoxious frenemy who references Gone with the Wind and Grace Kelly in the span of five minutes—no no no—and tells him about a mutual buddy shooting a student film a few blocks away. This buddy ropes Gatsby into acting in the film, and suddenly Gatsby has to kiss sassy raven-haired beauty Chan Tyrell (Selena Gomez), the fetching younger sister of his old flame. She quickly mentions ‘Gigi’, to further establish this odd parallel universe where people only watch TCM. They hit it off—she’s cheeky, bright, doesn’t suffer fools—and he wonders if she isn’t maybe his soul mate.

This latest fetishistic ode to the filmmaker’s favorite city is creatively pallid compared to previous peaks of his uneven career. That said, it’s self-aware enough for Gatsby to be described as “searching for a romantic dream from a vanished age.” And it’s knowing enough to drop casually profound asides like “the world is full of tragic little deal-breakers.” Is there an unfortunate mother/whore plot twist that would make Freud proud? Yes. But there’s also a searching story about a wayward young man who thinks he has it all figured out when he’s only just starting to realize how deeply ignorant he really is.

Describing a new Woody Allen movie as bad is just lazy. It’s also fashionable—just as de rigueur as saying, back in the day, that a forgettable ’80s film like Radio Days or a ’90s trifle like Manhattan Murder Mystery was good. They aren’t, and they weren’t back then either. But among his prodigious output are solid, sometimes stunning works. A Rainy Day in New York fits squarely in the lower-middle bracket: eyerolling contrivances, grimace-inducing caricatures, but more than a few cute zingers and occasionally even a touching insight or two. Is it worth watching? To paraphrase Annie Hall: the success of Allen’s continued output, despite all his off-screen personal mishegoss and on-screen misogynistic schtick, really depends on how badly viewers need the eggs.

Looks like another Rainy Day In New York.

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Stephen Garrett

Stephen Garrett is the former film editor of 'Time Out New York’ and has written about the movie industry for more than 20 years. A Rotten Tomatoes certified reviewer, Garrett is also the founder of Jump Cut, a marketing company that creates trailers and posters for independent, foreign-language, and documentary films.

One thought on “Woody Allen Breaks Stunning New Ground in ‘A Rainy Day In New York’

  • November 29, 2020 at 12:49 pm

    This is hilarious. Thank you, Stephen Garrett.


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