Even a warmed-over, behind-the-times Woody Allen script is going to contain some choice one-liners, and this is a superb cast that knows how to put the right spin on clever dialogue — even when they’re playing thinly drawn characters in a dated and unnecessary story.
I’m sure Allen apologists will say that A Rainy Day in New York was built as a way of self-ridicule with Gatsby’s incredulity towards women always finding older men attractive and filmmakers preying upon ingénues, but nothing in the text suggests that it is.
"A Rainy Day in New York" may not be Woody Allen's best, though it's certainly a step up from many of the painful misfires he's launched in recent years. Despite a somewhat overwritten script, this largely inconsequential romance is breezy, modestly humorous and mildly entertaining, though it could definitely use more (and better) jokes, less overtly conspicuous name-dropping, less regurgitation of themes explored in previous projects, and leads who don't ham it up nearly as much as Timothee Chalamet and Elle Fanning do. To its credit, however, the narrative includes some intriguing little twists and turns, a handful of spot-on one-liners, and fine supporting performances by Liev Schreiber, Jude Law, Rebecca Hall and Cherry Jones. It's something of a letdown to see how this offering turned out given everything that transpired in connection with getting it released, but, considering Allen's track record with recent productions, it's not all that surprising, either.
It is almost a compulsion that I watch nearly every Woody Allen film, in the off chance that, despite his insidious personal background, it’s a home run. In this case, it was undoubtedly the most painfully slow and dreary WA film I’ve encountered. I figured I couldn’t go wrong with a cast like that - Elle Fanning, Selena Gomez, Timothy Chalamet, Jude Law, and on and on. But in a way, this felt like a forced attempt to try to Allen-ify a film with a modern cast in a modern era. The “romanticizing the past” elements of the protagonist felt forced, like the figurative clothes were wearing him. Elle seemed to dim down her authenticity into a very unbelievable character (likely at Allen’s hand, as we know he loves a damsel or a brilliant-but-doesn’t-know-it type). The lonely white rich kid trope is tired, and the lines that Timothy spoke were straight out of an old Allen movie romanticizing the same things and the same city. Selena can do no wrong, so she admittedly carried the movie for me. She seemed to be the only one without rose-colored glasses and a sense of imposter syndrome or naïveté. But as for the rest? Painfully slow, boring, and like a regurgitation of Allen’s best work from the past. And as always, better writing than directing - the characters are always a bit too theatrical to be believable, sharing their monologues aloud, squinting a little too hard when they’re meant to be “thinking.” Sincerely, my harshest (and only) metacritic critique to date.