With “2 Days in New York,” Julie Deply’s hilarious and romantic follow up to her wry comedy “2 Days in Paris,” opening in select theaters today (it’s also currently available on VOD), we’ve decided to share with you 10 of our favorite romantic comedies (though some of our choices are questionably classified as such) set on the island of Manhattan. This list is by no means definitive, so we invite you to share some of your picks below.
“Annie Hall,” the romantic comedy that proved Woody Allen was an auteur of the highest order and did the unthinkable by beating “Star Wars” for the Best Picture Oscar in 1997, still holds up to this day as arguably Allen’s best and most widely accessible film to date. Diane Keaton won a Best Actress Oscar for playing the titular role, a nutty yet totally loveable lounge singer with a fear of initimate relations (she needs to smoke up before sex in order to relax) and the hots for Alvy (Allen), a Jewish comic armed with a earful of self depricating wit. Prior to “Annie Hall,” Allen had established himself as one of the country’s most promising funnymen thanks to “Bananas” and “Sleeper.” “Annie Hall” was the one to prove he could balance drama with the laughs, the perfect combination for any classic romantic comedy.
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Old is gold in “The Apartment,” Billy Wilder’s black and white classic that pairs two of Hollywood’s most iconic stars, Jack Lemmon and Shirley MacLaine, for a romantic dramedy that still packs a bite despite being over 50 years old. Lemmon’s character, C.C Baxter, to achieve ascension in the corporate world, lets four company managers use his Upper West Side apartment for their marital affairs, which isn’t as simple an arrangement as it seems. At the same time, he nurses a love for the elevator operator, played by none other than a wry and wonderful MacLaine. Also starring Fred MacMurray, the film was nominated for ten Oscars at the 33rd annual Academy Awards and won five of them including Best Pictures and Best Director.
“Breakfast at Tiffany’s”
No one captures the wealth, glitz and glam of New York’s Upper East Side than Audrey Hepburn in her critically acclaimed role as socialite Holly Golighty in the 1961 rom-com classic, “Breakfast at Tiffany’s.” Directed by Blake Edwards, this film is largely responsible for making an icon out of Hepburn (it also earned her with an Academy Award nomination for Best Actress). Based on Truman Capote’s novel, the comedy follows a socialite’s race to the top and all the men who come under her charming ways (these include an ex-mobster, a South American millionaire and her real love — a struggling writer and neighbor played by George Peppard).
“Eternal Sunshine of the Spotless Mind”
“Eternal Sunshine of the Spotless Mind” set the gold standard for contemporary films that subvert romantic comedy conventions. Where many rom-coms render viewers numb with their transparent formula, Charlie Kaufman’s narrative labyrinth, blending memories and dreams, was refreshingly stimulating in an era of feeble Heigl and Aniston vehicles. While none of the performances in the film falter, Jim Carrey arguably reached a career high with his portrayal of Joel, a devastated lover revisiting memories in the process of being erased. Michel Gondry’s lush and colorful direction cement the film as a modern classic.
“Kissing Jessica Stein”
Before Jennifer Westfeldt directed her first feature “Friends With Kids,” she co-penned this winning and insightful romantic comedy about a unlucky in love copy editor, Jessica (Westfeldt), who tries her hand at being bisexual after coming across a personal ad in the newspaper posted by a woman seeking a meaningful relationship (co-writer Heather Juergensen). To Jessica’s surprise, she takes to the ad’s author, Helen, a gallery owner who has her own share of hardships with the opposite sex. Things get messy (as they always do in rom-coms) when one of the pair wrestles with whether she’s in it for the long haul, but the way Westleft and Juergensen deal with the denouement is anything from typical.
Woody Allen’s “Manhattan” retains the romantic comedy framework while examining several dark and flawed romances. Building upon “Annie Hall’s” sentimental story of a promising relationship’s painful collapse, “Manhattan” begins with a middle aged writer, Isaac (Allen), being involved with a seventeen year old girl, a romance that both Isaac and the audience know is fundamentally amiss. Beyond the comedic facade are marriages fraught with infidelity and discontent. The black and white film stock and iconic Gershwin soundtrack imbue “Manhattan” with a sense of mythic weight and melancholy that heighten the film’s dramatic moments. Though the film ends with a promise of redemption, the romantic relationships in “Manhattan” leave none unscathed.
Whit Stillman’s debut feature “Metropolitan” examines romance through the lens of one of its greatest farces: debutante culture. Tom, a middle class Princeton student who sees himself as somewhat of a socialist radical, is invited into the company of a group of young New York City socialites, who’s cynicism and jaded malaise easily overcome his intellectual pretenses. The New York City of “Metropolitan” is a stratified one in which the social classes are isolated from each other, each group wondering how the others live. In Whitman’s world, the class warfare consists of a series of verbal skirmishes, and romance gets lost in the cross fire. A naive but endearing socialite named Serena is infatuated with Tom, but for most of the film he’s too caught up in his new way of life and flirtatious ex-girlfriend to notice. It isn’t until Serena takes up with the cartoonish Baron Rick von Slonecker that Tom realizes his feelings for her. Through it all, Whitman’s hyper-articulate, clever and humorous dialogue keeps things moving at a fast clip.
We’ll admit, the set up for “Trick” sounds like a dreadful sitcom on paper, but thanks to a surprising script, stellar supporting work from Tori Spelling (yes, really), and a winning lead in Christian Campbell (brother to Neve), “Trick” is a total treat. The Sundance entry concerns one long night in the lives of Gabriel (Campbell), an aspiring Broadway composer and Mark (John Paul Pitoc), a go-go dancer, as they try to find a place to hookup. Being a romantic comedy, plenty of mayhem ensues thanks to Gabriel’s selfish roommate and his overbearing best friend, Katherine (Spelling), another Broadway hopeful. Will the boys ever find a spot to get it on? Watch, and find out.
“When Harry Met Sally…”
One of the most iconic cinematic contributions from the late, great Nora Ephron, the Ephron-scripted, Rob Reiner-directed “When Harry Met Sally…” is a cornerstone on any romantic comedy list, New York-based or otherwise. It follows Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) through twelve years of chance encounters in the Big Apple. Initally just friends, the inevitable slowly occurs with some classic sequences along the way (Sally faking an orgasm at Katz’s Delicatessan is inarguably the film’s best known scene). One of the most loveable films to come out of a surge of late 1980s rom coms, “When Harry Met Sally…” helped set a very high bar for genre contributions to come.
Another highlight from the late 1980s, Mike Nichols’ “Working Girl” tells the tale of Tess McGill (Melanie Griffith, in her best role), a Staten Island-raised secretary working in the mergers and acquisitions department of a Wall Street investment bank. When her boss Katherine (Sigourney Weaver) breaks her leg, Tess utilizes her absense to make some serious career gains, romancing Tess’s beau Jack (Harrison Ford) along the way. A classic female empowerment story, the film also features fantastic performances from the likes of Joan Cusack and Alec Baldwin, and stands strongly among the best work for director Nichols.
Dema Paxton Fofang, Peter Knegt, Nigel M. Smith and Sri Sridhar contributed to this article.