A Rainy Day in New York Review: In Which Woody Allen Surrenders to His Demons

Few filmmakers plagiarize themselves as flagrantly as Woody Allen does. Though still capable of fashioning strange and daring films, he more often seems content to re-stage triangles between stand-ins and women who embody simplistic wars between purity and decadence and intelligence and frivolity. And judging from many of the films he’s made over the last 30 years, he has no interest in living in modern society—a feeling of alienation and nostalgia that was the literal subject of his Oscar-winning Midnight in Paris.

Allen is drunk on displacement, as he’s always recruiting young actors of the moment to voice sentiments that we’ve been hearing in his films for decades. Does anyone, other than Allen’s protagonists, describe sex as “making love”? And how many millennials are fascinated by Irving Berlin and classic detective movies? Such details are alternately annoying and poignant, as Allen appears to use cinema to build a place in which he feels safe, but in A Rainy Day in New York, such safety leads to revelations as well as complacency.

Like To Rome with Love, A Rainy Day in New York is composed of plot fragments and observations that are so familiar as to feel parodic. Allen’s requisite surrogate here is Gatsby Welles (Timothée Chalamet), a tweed-clad young gambler who’s as willfully anachronistic and unconvincing as his name indicates. Gatsby wins “20 big ones” in a card game not long before his girlfriend, Ashleigh Enright (Elle Fanning), an aspiring journalist, lands an astonishing opportunity: to interview a famous director named Roland Pollard (Liev Schreiber). Inspired by this serendipity, Gatsby treats Ashleigh to a weekend in New York City, where he will share with her all of his favorite haunts, from MoMA to the Met to the iconic hotels and piano bars where he likes to ostensibly play the role of struggling artist. But after getting separated, Gatsby and Ashleigh have respective adventures that test the stability of their relationship.

On the surface, A Rainy Day in New York is a pleasant lark, but it’s possessed of dark, neurotic underpinnings. For one, the name Roland Pollard uncomfortably recalls Roman Polanski, who, like Allen, has been unofficially excommunicated from Hollywood. In certain moments, it’s as if Allen is practically daring his audience to make the cross-association. Roland is probably an alcoholic and immediately takes to the much younger Ashleigh, who resembles an old girlfriend and who physically recalls Mariel Hemingway’s character from Manhattan.

The cruel intimacy of Roland and Ashleigh’s first encounter feels stark and personal—a dangerous exorcism of bitterness that’s nevertheless empathetic to the emotional states of both parties. In the Me Too era, Allen is still quite comfortable with pitiless bimbo clichés, which are transcended by Fanning’s ferocious vulnerability and by the fact that Allen can still write a hell of a dumb blonde joke. (Ashleigh tells Roland that she watches all the American classics, especially the Europeans.) Fanning’s vulnerability fascinatingly meshes with Schreiber’s commanding sense of self-loathing and withdrawal, but Allen soon retreats from his loaded subject matter so as to commemorate his greatest hits.

Though Ashleigh’s story has the potential to push Allen into auto-critical directions, the filmmaker keeps returning to Gatsby, who has to make the usual Allen decision between the prim, proper, and naïve girlfriend and other women who challenge him and satisfy his hunger for fiery, unschooled intelligence and disreputable carnality. As the sassy brunette from Gatsby’s past, a young woman named Chan, Selena Gomez radiates a sensuality that helps to modernize Allen’s occasionally hopeless dialogue, and the filmmaker gives Gatsby and Chan two beautiful moments together: a repeated kiss they must perform for a student film, a performance of passion that gradually becomes real as Gatsby and Chan warm to one another, and an achingly lovely interlude in Chan’s apartment, where Gatsby plays the piano and serenades her. In such sequences, Allen’s obsession with fantasy, with a faux past as an escape portal, transcends shtick by becoming poetry, especially as shot by the cinematographer Vittorio Storaro in tender amber hues that suggest the ultimate dream of New York City.

Eventually, two of Allen’s chief obsessions surface in A Rainy Day in New York, which he manages to cleverly conjoin. Many of Allen’s films, like many of Philip Roth’s novels, are driven by a fantasy of the Madonna-whore that’s rooted in mommy issues. Gatsby is aimless because he resents his mother (Cherry Jones) and the privilege and class she’s afforded him, which is reminiscent of all the past Allen smartasses who’ve yearned for social approval while making superficial gestures of rebellion. These issues of class and sexual fear inform Allen’s ongoing, often tasteless preoccupation with prostitutes as fonts of unexpected wisdom, a trope that’s revisited here when Gatsby brings a professional named Tiffany (Suki Waterhouse) to a family party. This incident leads to Gatsby’s mother admitting that their fortune was built on the early money she made as a prostitute herself, leading to Gatsby’s acceptance of his family as well as himself. With the mother and whore as one here, perhaps Allen can finally free himself of his painstaking fealty to recycling the same quasi-sexist plot over and over again.

Sexual fear, though, isn’t just a governing theme in Allen’s work, it’s also a limitation. After the uncharacteristic carnality of Deconstructing Harry, Match Point, and Vicky Cristina Barcelona, Allen’s ongoing contentment with familiar hang-ups, expressed familiarly, is disappointing. Why can’t Allen’s traditional protagonists ever screw outside of their social class, or have any sex at all? Tiffany is a startlingly erotic presence, but Allen brushes her aside with indifference, and Gatsby is uninterested in her as anything other than an instrument against his mother. A moment in which Ashleigh strips down to her underwear, anticipating sex with a movie star (Diego Luna), is also surprisingly hot, but it leads to another predictable coitus interruptus. A Rainy Day in New York is rich in fascinating signifiers and allusions, but its skittishness is particularly maddening considering that Allen has nothing to artistically prove. Allen may know his demons, but he may have also surrendered to them.