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The Holy Quartet of Cure-All Romantic Comedies

Combat the cold with these four classic rom-coms.

By Trent EskerPublished 5 years ago 5 min read
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Ah, fall. The temperatures are dropping, the pumpkin spice merch is consuming the racks, and seasonal depression is beginning to rear its ugly head. When the weather gets cold and the Instagram “‘Falling’ in love with you gets better every day <3’ Caucasian-catalogue-couple posts begin to filter in, where does one turn? The answer rests not in sensible, emotionally-sustainable options like exercise or therapy, but in the mindless, heartwarming comforts of your late 90s-early 2000s romantic comedies.

The traditional romantic comedy has long been thought of as a dying genre, which, as a summa cum laude graduate of the Julia Roberts Institute of Cinema, feels like a personal offense. The only rom-coms we get these days are meandering indies about quirky art-school grads grappling with indecision in Williamsburg against a punk rock soundtrack. What happened to the cure-all romantic comedy? What happened to stories about attractive A-listers in obscenely large downtown apartments meeting-cute and falling in love? Let me bring you back to simpler times. Grab a blanket, grab some snacks, splurge for that double bottle of Barefoot Moscato, turn a blind eye to your impending mortality and crippling loneliness, sit back, relax, and let your worries begin to fade. I give you: the Holy Quartet of Cure-All Romantic Comedies.

4. 'The Holiday' (2006)

The Holiday follows two women (Cameron Diaz and Kate Winslet) who agree to swap houses over the holidays in an attempt to escape their grueling jobs and failing relationships. Alternating between the wintry English countryside and sunny Los Angeles, the two women embark on their own unexpected journeys towards fulfillment, redemption, and real love.

I call director Nancy Meyers the Goddess of Comfy, because to refer to her simply by her given name would downplay the mythical, divine influence she’s had on the romantic comedy genre. The Goddess of Comfy doesn’t just create film sets, she creates experiences. The Holiday feels like the plushest, most sumptuous down comforter you’ve ever not been able to afford at Restoration Hardware. The set design is next-level, each location feeling like its own drool-worthy cocktail of HGTV renovation show and Pottery Barn storefront. However, it’s not all about aesthetic. Amidst the rampant interior design porn, Kate Winslet delivers a finely-tuned monologue that works as a profound meditation on moving up and moving on. It’s a warm-and-fuzzy gem with pathos that’s sure to ease any winter blues.

3. 'You’ve Got Mail' (1998)

You’ve Got Mail tells the story of Kathleen Kelly (Meg Ryan), an Upper West Side children’s bookstore owner with impeccable taste in turtlenecks. She lives a double life as Shopgirl, her AOL alter ego, carrying on a cyber-romance with the witty and winning NY152. Kathleen finds her family business in peril when Joe Fox (Tom Hanks) and his big-box bookstore emporium open down the street. Joe Fox, among being a businessman and the biggest DILF of 1998, also just so happens to be Mr. NY152.

Tom Hanks and Meg Ryan are the OG #relationshipgoals. While Sleepless in Seattle is a solid addition to the rom-com realm, You’ve Got Mail is where these two stars (and their natural, warm chemistry) truly shine. This movie is as old-fashioned as they come in the best way possible. It’s unfussy and uncomplicated, poetic in its simplicity. “You’ve Got Mail” gives the kind of viewing experience that’s far too absent these days; the kind that’s built around hope rather than pessimism.

2. 'The Parent Trap' (1998)

Two twin sisters (both played by Lindsay Lohan) who were separated at birth meet for the first time after they’re both sent to the same summer camp. They devise a plot to switch places and reconnect their parents, only to find their best-laid-plans derailed by their father’s new girlfriend.

Where do I even begin on The Parent Trap? Childhood nostalgia is my religion. It’s impossible to not love this movie, from the Goddess of Comfy’s typically resplendent interiors to Lindsay Lohan’s genuine feat of a performance. I don’t understand basic math, but you can bet I’ve memorized the twins’ elaborate handshake top-to-bottom. It all just takes you back and makes you feel at home *clutches Kleenex, face illuminated by the TV, mouths, “Hallie, we’re like sisters,” between hushed sobs). It would’ve cinched first place had it not been for the later-in-life realization that the twins are actually extremely scheming, sadistic sociopaths and should undoubtedly be institutionalized. #JusticeForMeredith

1. 'My Best Friend’s Wedding' (1997)

My Best Friend’s Wedding picks up with successful New York food critic Julianne (Julia Roberts) just as she receives some unwelcome news: her longtime best friend, Michael (Dermt Mulroney), who Jules secretly loves, is engaged. Jules finds herself placed in the middle of a wedding shitstorm, navigating tension with Michael’s bubbly fiancée (Cameron Diaz) and the realization that she has three days to win the love of her life = back before he’s gone for good.

I will stop a total stranger on a busy street just to remind them that My Best Friend’s Wedding remains the greatest romantic comedy of all time. The reason? Instead of settling for archetypes and predictability, My Best Friend’s Wedding gives us fully-formed characters, wry humor, and actual stakes. As trite as it sounds, happy endings don’t come as easily as they do in the movies, if at all. Sometimes the greatest love stories aren’t romantic, but are instead found in the friendships that lift us when we’re lost. In the eternal words of Jules' sidekick George (Rupert Everett), "Maybe there won't be marriage. Maybe there won't be sex. By God, there'll be dancing."

There’s no greater antidote to the Sunday scaries than the knowledge that in trying times, there’s someone out there’s who’s got your back. And that, my friends, is some wisdom that would leave Bridget Jones weeping in her infamous diary.

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