Two films ago, with “Café Society,” Woody Allen opened Cannes. Last time out, with 2017’s “Wonder Wheel,” he closed the New York Film Festival. His latest film, the first casualty of the squealing-brakes reversal when Amazon Studios pulled out of their four-picture deal with the scandal-buffeted director, premiered a month ago in one Eastern European territory prior to a spotty regional rollout and an opening slot at France’s upcoming Deauville Festival of American Film. With the greatest of respect to Deauville, not to mention the nation of Poland, the herky-jerk release of “A Rainy Day In New York” would seem like a step down. Until you watch it and realize it may be significantly more generous than the film merits.

Despite featuring some of the best actors of their respective generations, “A Rainy Day in New York” feels like a film born of profound creative exhaustion. It is a retread of territory Allen has extensively covered before, but while the same can be said about almost all of his late-career work, seldom have the gears ground quite so loudly, and never before has the writing felt this chronically out-of-phase with the era it depicts. Allen’s last two films had period settings, which lessened the potential for anachronisms jarring to the modern eye. But the protagonists of “A Rainy Day in New York” are Gen Y/Z bright young things, inhabiting an apparently contemporary America, yet they model behavior that would be fustily out-of-date if they were in their late fifties, in the late 1950s. This is supposedly 2019, but a butler bearing a telegram on a silver salver would seem more plausible than, say, a WhatsApp conversation.

The romantic lead is played by the charming Timothée Chalamet, who needs every ounce of his casually quizzical, floppy-haired sensitivity to convince us he is not constantly being thrown through upper-floor windows when people discover his character’s name is Gatsby Welles. Gatsby, apparently borne back ceaselessly into a past where 23-year-olds wear tweed and use a pop-culture lexicon composed entirely of Cole Porter aphorisms, is a brilliant, wealthy but directionless Manhattanite attending leafy, fictional Yardley College. He effortlessly wins thousands of dollars every time he sits in on a poker game, and is dating journalism major and fan of preppy sweater/skirt combinations Ashleigh (Elle Fanning).

If Chalamet’s Gatsby is a reanimated extinct creature — Holden Caulfield as played by a peculiarly refined dodo, perhaps — Ashleigh is a unicorn, entirely mythological. She’s a worldly naif; a competent, careerist ditz; a serious-minded student who somehow mistakes the song lyric “In the roaring traffic’s boom/In the silence of my lonely room” for Shakespeare — from the Bard’s well-known series of traffic sonnets, presumably. But mostly, she’s a wealthy, luminous pageant queen from Arizona whose acute journalistic insight, coupled impossibly to her guileless, breathy admiration might just rescue Roland Pollard (Liev Schreiber), the Great Director she’s in Manhattan to interview, from his existential crisis.

This all spoils Gatsby’s plans for a weekend of fancy meals, upscale hotels and evening cocktails listening to jazz piano while avoiding his mother’s snooty soirée. Ashleigh goes off on an extended caper involving the unfinished film’s screenwriter (Jude Law), his faithless wife (Rebecca Hall) and a famous heartthrob (Diego Luna) who completes the trio of age-inappropriate men vying for her flighty attentions. Meanwhile, Gatsby roams the streets of Manhattan in a funk and ends up starring in a friend’s short film, in which, poor lad, he has to kiss Shannon (Selena Gomez), the little sister of a girl he used to date.

Gomez comes out the best of the younger cast, husking her way through some of the films better lines, like her amused reaction when Gatsby tells her his girlfriend is from Tucson: “What do you guys talk about? Cactus?” And yes, that really is one of the funnier moments: Elsewhere the jokes that do land come down awkwardly, usually at the expense of one of the harpies, hookers or heartbreakers who comprise the film’s women, like Shannon’s sister, who “performed oral sex at a Bar Mitzvah”; or Gatsby’s brother’s fiancée (Annaleigh Ashford) with her irritating laugh; or the sex worker (Kelly Rohrbach) Gatsby hires to impersonate Ashleigh, who, arf arf, “can’t be expected to live hand to mouth.”

Still, unfunniness is only the most obviously dispiriting attribute of “A Rainy Day in New York.” Side characters are underdeveloped and bizarrely inconsequential, like Gatsby’s school friend (Ben Warheit) who shows up just to coin the sick burn “Turner Classic wimp” and to immediately relate the name “Ashleigh” to Ashley Wilkes from “Gone With the Wind,” because this is an alternate America that apparently has not produced female Ashley/Ashleigh/Ashlees in bulk in the decades since 1939. Even Vittorio Storaro’s usually luscious cinematography feels tired and unconsidered: It is wet and gray outside but the windows let in enough sunshine to bathe the interiors in a glow so honeyed it’s practically sticky. Scenes are blocked unevenly, sometimes cramming actors into unnatural proximity despite the spaciousness of the sets, in an unsuccessful effort, perhaps, to summon some chemistry. It doesn’t work, and with many of the performers apparently riffing on Allen’s own over-emphasized gesticulations, there’s a low-level anxiety that they might clock each other accidentally.

Eventually, it becomes quite infuriating that Fanning, especially, can be so lovely and so game and so thoughtlessly abandoned, given no consistent notes to play and sent down the undignified dead-ends of a storyline that has no place to go and nothing to do when it gets there. The screenplay discards her characterization again and again, like it’s a gum wrapper stuck to a shoe, even while the camera moons over her — the gaze here, except for an ill-advised scene that contrives to have her end up in her underwear, is less pervy than strangely fawning, and entirely uncomprehending.

It’s mercilessly clear just how far Allen’s sensibilities are, not only from the millennial generation he’s ostensibly describing but also from the women of his own back catalogue (some of the most indelible, wonderful, idiosyncratic female characters in the American canon) and almost as depressingly, from the intensely romantic vision he always used to communicate of his other great muse, Manhattan. It’s “A Rainy Day in New York” indeed, but it doesn’t just rain, it pours.