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Deck the Halls With New York’s Greatest Christmas Movies

It’s the most wonderful time of the year in New York City — when the throngs of tourists crowding decked-out store windows threaten to devolve into a stampede at any moment, and the waffle cone filled with mysterious chicken chunks you bought at a holiday market that shall remain nameless brings on a DEFCON 1, 24-hour stomach crisis. (That second thing? Happened to me, last week. Be careful out there.) But from Dyker Lights to Radio City, there’s something extra magical about Christmas in the city, a phenomenon of which Hollywood has taken note. Here are seven of our very favorite New York–centric Christmas movies. Can’t you smell the chestnuts roasting on an open street cart already?

Christmas in Connecticut (1945)
Don’t be fooled by its title: This Warner Bros. classic is very New York. Elizabeth Lane (Barbara Stanwyck) leads a professional double life, writing a popular newspaper food column in the persona of a married mother living on a farm in Connecticut. In reality, she’s actually just a champion scammer. Our proto-lifestyle blogger heroine lives alone in her tiny Manhattan apartment and never cooks — instead, she orders in from the restaurant downstairs, whose proprietor ghost-writes Elizabeth’s recipes for her. Her publisher, unaware of Elizabeth’s true life circumstances, demands she host a war hero at her (nonexistent) family home for Christmas. Her sort-of boyfriend offers up his Connecticut farm and his hand in marriage to help with the ruse. They even borrow a neighbor’s baby. When the soldier arrives, though, he turns out to be unexpectedly hunky. It is crazy that there hasn’t been an Instagram-age remake of this movie.

Home Alone 2: Lost in New York (1992)
Ah, 1992! When anybody, even a small child, could just wander onto any old plane going anywhere and no one would say so much as a “bah humbug.” For a second consecutive year, Kevin McCallister (Macaulay Culkin) gets separated from his family when they leave on their Christmas vacation. This time, he ends up all by himself in New York City, in a swanky suite at the Plaza Hotel, no less. Let Home Alone 2’s tear-jerking mother-and-child reunion beside the Rockefeller Center Christmas tree serve as a heartwarming reminder of the meaning of the holiday. And let the rest of the movie serve as a chilling reminder that the creepy businessman who gave you directions in a hotel lobby could one day become the president of the United States.

Scrooged (1988)
Frank Cross (Bill Murray) is the ultimate Manhattan Scrooge, a power-hungry TV network executive planning a sexy, action-packed, and altogether family-unfriendly live musical production of A Christmas Carol. Lo and behold, Frank gets the Charles Dickens treatment himself. The New York Dolls’ David Johansen is a delight as the Checker cab–driving Ghost of Christmas Past, but Carol Kane’s violent fairy version of the Ghost of Christmas Present is possibly the single most compelling reason to revisit this dark comedy.

Eyes Wide Shut (1999)
Erotic thrillers sure are an underrepresented genre of Christmas movie. You might have forgotten amid all the nudity, but Stanley Kubrick’s final film very much takes place during the holiday season, which apparently has rendered everyone in the five boroughs both extremely horny and extremely terrifying. The warm Christmas lights and wreaths of Greenwich Village — the streets of which Kubrick meticulously re-created in a London film studio, having dispatched envoys across the Atlantic to measure their exact dimensions — serve as an unexpectedly chilling backdrop for the journey Bill (Tom Cruise) takes through Kubrick’s paranoid fever dream. By the end of Eyes Wide Shut, the bright colors and oversize teddy bears of the packed FAO Schwarz–like toy store where Bill and Alice (Nicole Kidman) take their daughter shopping somehow seem just as obscene as the movie’s infamous orgy.

Serendipity (2001)
Just as much a Christmas movie as it is a rom-com, Serendipity begins just five days before the holiday, when Jonathan (John Cusack) and Sara (Kate Beckinsale) meet cute over the last pair of black cashmere gloves at a jammed-to-capacity Bloomingdale’s. The one romantic night they share is a solid itinerary for anyone visiting New York City in December: ice skating in Central Park, joyriding the elevators in the Waldorf Astoria, and frozen hot chocolate at Serendipity 3. That said, it’s worth noting that the main characters in Serendipity did not have to wait in line at Serendipity, given that in their universe the movie Serendipity had not yet come out. Rude.

Elf (2003)
What Miracle on 34th Street did for Santa, Elf does for the big guy’s little helpers. Buddy (Will Ferrell), a human raised as an elf, travels from the North Pole to New York City to track down his long-lost biological dad, Sonny Corleone (James Caan). Buddy finds himself a fish out of water at the department store Santa Land where he accidentally lands a job, but he saves Christmas when the real Santa’s sleigh crashes in Central Park. Come for Buddy perilously squeezing his way through Lincoln Tunnel traffic on foot; stay for Buddy losing his mind with excitement over the “World’s Best Cup of Coffee” sign on a nondescript diner.

The Night Before (2015)
For more than a decade, Isaac, Ethan, and Chris (Seth Rogen, Joseph Gordon-Levitt, and Anthony Mackie) have gotten together every Christmas Eve to drink enough booze to turn the rest of the reindeers’ noses red. But now that the men have grown older and drifted apart, they have just one last chance to track down the fabled, invitation-only Nutcracker Ball, a mega-party that turns out to be accessed via the freezer in the back of an unassuming bodega. This all-of-the-drugs-fueled riff on A Christmas Carol takes the best friends from the holiday glitz of Fifth Avenue to the dive bars of Alphabet City, with stops in between to perform Kanye West’s “Runaway” on the FAO Schwarz keyboard and to puke in the middle of midnight mass at St. Bartholomew’s.

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Fate Is Enough

Now that irony is dead, it’s a sanctioned pleasure to embrace Serendipity, shopworn fluff as regressive as its namesake Upper East Side dessert parlor. Amiable Jonathan (John Cusack) and British Sara (Kate Beckinsale, accent intact after the last days of Pearl Harbor) retire to the precious patisserie after meeting way too cute at Bloomie’s, each trying to snag the last pair of black cashmere gloves for a significant other. Sara recites her moony faith in destiny, to her companion’s chagrin; instead of exchanging surnames and phone numbers like normal people, Jonathan must jot the contact info across a five-spot (immediately spent and dispersed), Sara onto the flyleaf of Love in the Time of Cholera (hocked the next day). Fate will bring them together, or it won’t.

It takes García Márquez’s parted couple half a century to reunite; Serendipity has no time for such dawdling, jumping a few years to the eve of Jonathan’s wedding (to a doelike Bridget Moynahan) and the night Sara (now a straight-talking Bay Area therapist) gets engaged to an oboist with Yanni-sized ambitions. (San Francisco apparently treats its oboists like minor deities.) Before you can say “Julia Roberts movie,” Jonathan starts reading traces of Sara everywhere and enlists his best man in a last-ditch search (yielding the grad-school-incubated line “Maybe the absence of signs is a sign”). Meanwhile his beloved comes to New York and checks into the Waldorf, coincidentally the site of Jonathan’s impending nuptials. Book, bill, and other pieces fall into place; the heart wants what it wants, and love conquers all, including any guilt for throwing over your betrothed.

Like the gruesome You’ve Got Mail, Serendipity trots out tourist-friendly backdrops—Wollman Rink somehow ceilinged by stars, Chelsea Piers simply a fancy driving range—but it’s oddly pleasurable to see the city in this prelapsarian light. At the clinch, as magic-realist snow falls in spring, the fussy soundtrack gives way to a Nick Drake song so pretty that all is forgiven. Serendipity is the most romantic New York movie since August’s Happy Accidents.