A Rainy Day in New York sees writer and director Woody Allen (Manhattan, Annie Hall) return to the romantic comedy field of previous hits Vicky Cristina Barcelona and Midnight in Paris, assembling an all-star cast including Timothée Chalamet, Elle Fanning, Selena Gomez, Jude Law, Diego Luna and Liev Schreiber for a charming comedic tale set amid the fast-paced, dizzying streets of Manhattan. 

To celebrate the release of A Rainy Day in New York, we’re taking a look back at five of the best cinematic tales of love set in The Big Apple. 

BREAKFAST AT TIFFANY’S (1961) 

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Poster © Breakfast at Tiffany’s

Released in 1961 and based on the Truman Capote novel of the same name from 1958, Breakfast at Tiffany’s has proved to be one of cinema’s timeless romantic comedies. Hepburn plays Holly Golightly, a naive party girl living in Manhattan, whose path crosses with young Paul (George Peppard) – a young writer and the kept-man of a richer older woman. Cue romantic intrigue, laughs aplenty and of course the memorable scene at Tiffany’s department store. A surefire hit-all round, the film picked up two Academy Awards (with three further nominations) and was a box office smash for studio Paramount. Hepburn wearing the famous black Givenchy dress, with a cat on her shoulder and a cigarette holder in her mouth from the poster, is one of cinema’s all-time iconic images – and the film has continued to delight audiences from its release up until the present day with its timeless tale of New York romance. 

ANNIE HALL (1977)

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Poster © Annie Hall 

New York City native Woody Allen has set many of his movies in his hometown, and his neurotic, fast-talking on-screen persona goes hand-in-hand with the energy of the city. While Manhattan may have a more immediate connection with New York, the relationship between Allen and co-star Diane Keaton in 1977’s Annie Hall has proven timeless in its depiction of the messy intricacies of romantic life. Keaton charms from the offset as idiosyncratic singer Annie, sporting a trend-setting style in Chaplinesque suits – reportedly coming directly from the actress’ own wardrobe. After Annie meets comedian Alvy Singer (Allen) the two fall in love, notably over a masterful comic scene involving a failed attempt at cooking lobsters, and the relationship develops until Alvy’s neuroses and Annie’s emotional growth see the pair eventually come undone. With the jokes arriving thick and fast, it’s one of Allen’s most enduringly funny comedies that also showed a more serious side to the writer and director as he tackled many of life’s bigger questions. Academy Awards for Best Picture and Best Director followed, beating 1977’s big contender Star Wars and showing that as much entertainment can be found on the streets of New York as in a galaxy far, far, away.

WHEN HARRY MET SALLY (1989)

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Poster © Metro-Goldwyn-Mayer Studios Inc. 

No trip to The Big Apple is complete without a visit to Katz’s Delicatessen and a taste of their New York favourite ‘pastrami-on-rye’. Already a favourite with locals, the restaurant gained international fame thanks to When Harry Met Sally and the infamous scene in which Meg Ryan fakes an orgasm at one of the packed diner’s tables leading to the classic punchline from a neighbouring customer, “I’ll have what she’s having”. The film follows the relationship between Billy Crystal’s cynical Harry and eternal optimist Sally. Clashing at first over their differing outlooks on love and sex, the pair continue to have run-ins over the years and a deeper relationship develops between them. When an attraction finally does seem on the cards, Harry runs the risk of losing Sally through reluctance to commit and risk losing their friendship. A grand gesture on New Year’s Eve makes for a classic finale. Written by the talented Nora Ephron, who would go on to pen classics such as Sleepless in Seattle, and from director Rob Reiner who showed he could tug at the heartstrings with fantasy romance The Princess Bride, When Harry Met Sally found Billy Crystal and Meg Ryan on spectacular form as it explored the eternal question, ‘Can men and women ever just be friends?’

YOU’VE GOT MAIL (1998)

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Poster © 1998 – Warner Bros. 

Log on for a classic 90s rom-com about online dating, that predates Tinder! You’ve Got Mail sees Tom Hanks and Meg Ryan star as Joe Fox and Kathleen Kelly, two New York professionals who kindle a relationship in an online chat room using the usernames ‘NY152’ and ‘ShopGirl’. But there’s a catch the two lovebirds don’t know: Kathleen runs a small independent book shop while Joe belongs to the Fox family, owners of a large chain of mega book stores. The hustle and bustle of Manhattan is used to great effect, as it’s slowly revealed that the two frequent the same neighbourhood in the Upper East Side and we see an unforgettable scene in the city’s iconic Central Park. You’ve Got Mail marked the third time Hanks and Ryan had worked together, having previously both starred in Joe Versus the Volcano and 90s rom-com classic Sleepless in Seattle. With great performances from its leads and fun and forward-thinking riff on dating in the digital age, You’ve Got Mail is a rom-com you’re bound to fall in love with. 

AS GOOD AS IT GETS (1997)

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Poster © As Good As It Gets 

Grumpy misanthrope Melvin Udall has a severe case of obsessive-compulsive disorder which leads the best-selling romance novelist to eat at the same New York City restaurant at the same table every day. Luckily for him, that means he gets to enjoy the company of kind waitress Carol Connelly, the only person able to put up with his bad-tempered behaviour. As circumstance forces Melvin to spend more time with his artist neighbour, Carol gets invited along on a road trip with the pair and as the three of them grow closer, Melvin is brought out of his shell leading him to eventually express his feelings for Carol. Melvin may not be a charmer but he’s played by one of Hollywood’s smoothest talkers, Jack Nicholson. Combined with the charm of Helen Hunt, fresh from New York City-set TV rom-com Mad About You, the pair had winning screen chemistry that saw them pick up Best Actor and Actress Oscars. This wasn’t the film’s only mention at the Academy Awards, it received six nominations in total including Best Original Score – Musical or Comedy for Hans Zimmer, a composer better known for his tense strings and work on Christopher Nolan high concept thrillers than he is for romantic orchestral swells!

A Rainy Day in New York is available on Premium On-Demand platforms now.

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Film