14 Romantic Comedies That Won't Make You Cringe

Say what you want about Valentine’s Day, but at this point it’s become unavoidable. Popular culture, your local drug store and your partner (both sexes are equally guilty) instill the importance of the Hallmark holiday as the end-all be-all of romantic dates on the calendar.

For folks who can’t stand all the sappy love games, suck it up. You may feel sheepishly unoriginal or love sick come Valentine’s Day, but we’ve come up with a list of films that transcend the genre and will get even the non-romantics in the mood for February 14.

Grosse Pointe Blank (1997)
Director: George Armitage

As a stalwart of romantic comedies that can appeal to nearly all viewers, none of John Cusack’s gushing oeuvre has been more subversive or genuinely lovable than Grosse Pointe Blank, aka the one where a hitman goes to his high school reunion and wins back Minnie Driver after slaughtering Dan Aykryod with a TV set. The quintessential rom-com reaction to Pulp Fiction’s violence-meets-meta-comedy hysteria that swept through Hollywood during the 1990s, this hard-R flick features Cusack’s affably neurotic Martin Q. Blank murdering competition with a fountain pen and proposing marriage while dripping in the blood of Aykroyd, Azaria, and other wacky goofs who got in the way. Often times acidic toward the notion of nostalgia and teen romance, this backward-looking 1997 film still finds its inner-John Hughes long enough to mourn the passing of ‘80s high school glory while also serving as its own time capsule for ‘90s rom-com and Tarantino-lite staples. Plus, Cusack and Driver are absolutely adorable as they work through their problems, just as Cusack simultaneously works his way through the hometown’s dwindling population.

High Fidelity (2000)
Director: Stephen Frears

Then again, none of Cusack’s work has more honesty and poignancy than High Fidelity. The 2000 Stephen Frears adaptation of a Nick Hornby novel is the coming-of-age saga of a Gen-Xer who discovers how late in life that moment can be. Much like the crossroads of a music industry that has long said goodbye to vinyl and is only now on the cusp of the true digital revolution, Rob Gordon (Cusack) works at a record store specializing in actual records, a perennial hipster before that was a thing. The sometime-DJ has to come to grips with the fact that being a slacker ceased being cool after 30 or that cheating on his pregnant girlfriend Laura, prior to her abortion, is more than adequate grounds for dumping. But this is still a Cusack film, and the two are able to bond over real, hard-won emotions, underscored by a little slow-jamming goodness provided by Jack Black as the angrier, funnier slacker also manning the store. This is proof positive that even John Cusack films have to grow up and deal with romance that is anything but idyllic, even if the movie is truly ideal.  

Intolerable Cruelty (2003)
Directors: George and Ethan Coen

For those who view Valentine’s Day as the most cynically abhorrent time of the year, we have good news: the Coen Brothers likely agree with you. They’d also probably find it lovely! After all, their single, fanged romantic comedy, Intolerable Cruelty, wears its heart on its sleeve, shouting unabashed emotionalism from the top of the proverbial Everest like a beaconing Tenzing and Edmund. Of course, it does this with a tongue firmly planted in its cheek. The story of what happens when L.A.’s most ruthless divorce attorney (George Clooney) falls in love with his client’s spouse (Catherine Zeta-Jones), Intolerable Cruelty is the most Hollywood of the Coens’ catalogue since it honors the kind of old school star vehicles that used to make the studios sparkle. However, this is still a Coen Brothers movie, so there is at least one attempted murder required—leading to both stars eventually hiring the same hitman to assassinate one another. It’s simply adorable! As is Billy Bob Thorton’s pseudo-George W. Bush impression.

When Harry Met Sally… (1989)
Director: Rob Reiner

I am sure you’ve heard this one before: once upon a time, When Harry met Sally…but sometimes the best jokes bear repeating. A simple tip of the hat to the hopeless romantics in everyone, Rob Reiner and Nora Ephron’s New York minute romance takes about 12 years to get going when Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) share a cross-country road trip that dovetails into a decade-long friendship after the many coincidences and incidences pile up. Can a man and a woman be just friends? Sure, but perhaps not when they reach the point where they’re faking orgasms together in a Jewish Delicatessen. We all would like to have a little bit of what she’s having.  

Breakfast at Tiffany’s (1961)
Director: Blake Edwards

Arguably the essential romantic comedy, Breakfast at Tiffany’s is the culmination of perfect parts creating an even more perfect whole. Lighter than bubbly, and more enduring than its downbeat Truman Capote source material, Breakfast captures the intangible yearning of every great fairy tale ever told for the post-industrial, urbane world. The story of Holly Golightly, the ultimate Manhattan Good Time Girl, it could have been either Capote’s tragedy of a desperate creature named Lulu Mae losing all in her frantic climb to the social summit, or likely the sanitized poppy yé-yé chic laugher Paramount expected for its glistening Audrey Hepburn marquee. Instead, comic genius Blake Edwards reveals his unapologetic sentimentality in a movie that walks the line between farce and melodrama to one of the most satisfying happy endings of all time. And this celluloid daydream is achieved largely due to the iconic performance of Hepburn in a signature role that was the complete opposite of her previous demure good girl personas, but every bit as hauntingly metropolitan as Henry Mancini’s ethereal “Moon River” melody that drifts over the picture like a lingering perfume. The scandalous yarn of how a call-girl and a married woman’s kept man could find love in a New York rain storm is so perfect that it can wash away even the most uncomfortable undertones from Mickey Rooney’s bit playing. Sumptuously decadent and wistfully open-hearted, they simply don’t make ‘em like this anymore.

Silver Linings Playbook (2012)
Director: David O. Russell

Yet, sometimes they do. Finding a high-minded, middle-budgeted romantic comedy (or dramedy), which used to be a staple of the Hollywood dream factory, has become practically impossible over the last 10 or 15 years. The industry fluctuates between micro and mountainous budgeted fare that promises big rewards, with nary a thought for anything in between. Even formulaic, safe, and faceless “rom-coms,” marketed simply on the supposed value of faces, are fading with every passing year. Thus, Silver Linings Playbook is something of a small miracle in all its dysfunctional glory. As affecting as it is inappropriately hysterical, this one came from the heart for writer-director David O. Russell. Meant to be an earnest boost of confidence for his bipolar son, Russell’s film, just like Matthew Quick’s novel, captures a beautiful clarity about understanding mental health and creates an even broader portrait for a whole generation of post-Great Recession millennials coping with diminished expectations. Because even for the wonderfully acted Pat (Bradley Cooper) and Tiffany (Jennifer Lawrence), two abrasive individuals who have been dealt a crummy hand by life, a silver lining is only a cha-cha away, making all the loss, mental anguish, and judging eyes in their childhood homes worth it. A celebration about the healing power of family, friends, and football, Silver Linings Playbook is the most feel-good big screen romance in years.

The Princess Bride (1987)
Director: Rob Reiner

Today, the fantasy genre is the realm of serious storytelling, which is usually dominated by men with even more serious beards. But before fantasy got so high on itself, it also served as a genre for humor, lightness, and sometimes romance. Rob Reiner found all of the above in this 1987 classic that depicts the strained courtship of Westley (Cary Elwes) and Princess Buttercup (Robin Wright). Her title is actually a formality, because she's the people's princess when assigned the role of intended bride for the dastardly Humperdinck (Chris Sarandon). Fortunately, before he can murder for his own gain, Westley returns in a Zorro mask and with a fierce reputation as the "Dread Pirate Roberts." Together, they will overcome quicksand, fire pits, the steepest hills in Florin, and rodents of unusual size (I don't think they really exist). Most of all though, it is a beautifully mushy beating heart that will make all the castle storming, all the Sicilian drinking games, and all the fun of meeting Inigo Montoya (Mandy Patinkin) and Fezzik (André the Giant) worth it. Since the invention of the kiss, there have been five kisses that were rated the most passionate, the most pure. This one left them all behind.

Eternal Sunshine of The Spotless Mind (2004)
Director: Michel Gondry

How do you get the drumming misery of a failed relationship out of your head? Easy. Erase it. The premise of Eternal Sunshine of the Spotless Mind asks you to believe that this wonderful science exists to let those who can’t help but fret on a failed romantic endeavor move on. In committing his talent to the Academy Award winning screenplay for Eternal Sunshine, Jim Carey made a successful transition into serious role after earning a boatload of cash per wacky facial expression in the 90s. At times trippy and feverishly discordant, the film is an ode to the places within the mind that store memories both big and small. It’s what you do with those memories that help shape the perception of a relationship but for Carey’s Joel, it seems as though the loss of his darling Clementine (played exceptionally well by Kate Winslet) is too much for his brain to chew on. With an extraordinary supporting cast, Eternal Sunshine examines a fictional realm we can only dream of and has us wishing that we could recount more love stories that were erased. 

Forgetting Sarah Marshall (2008)

Director: Nicholas Stoller

In a reality where erasing your ex doesn’t exist, keeping the girl of your dreams out of your head can be depression inducing and seeing her on primetime television has to be down right infuriating. Jason Segal wrote himself into the perfect role as the down-on-his-luck boyfriend who’s ditched for an aging rock star. The film really has it all. Russell Brand sings. Jonah Hill makes a hilarious appearance. There’s a Dracula-based opera. And oh, did we forget to mention that Kristen Bell AND Mila Kunis share screen time? We rest our case.

Lars and the Real Girl (2007)
Director: Craig Gillespie

Love isn’t always cheery rainbows and butterflies like you see in the movies. Here’s a film that grapples with people’s perception of relationships and attempts to redefine the idea of a support system. Ryan Gosling received a Golden Globe nomination for his role as Lars Lindstrom, a socially awkward individual that finds companionship in a life-sized plastic doll he names Bianca. It’s a powerful performance by Gosling but the real message of the film is conveyed through how Lars’ town is able to rally around his relationship with an inanimate object. The film has its darker moments but at its core, Lars and the Real Girl is a romantic dramedy that is lighthearted and an ideal watch for those looking to stray from the ordinary.

Groundhog Day (1993)
Director: Harold Ramis

Let’s use our imaginations and pretend you didn’t watch Groundhog Day on cable television on the actual day Punxsutawney Phil saw his shadow. Regardless of what day in February it is, Groundhog Day is an ideal romantic comedy to watch. The film transcended an easily forgettable holiday and found something romantic in being caught in between the seasons. It was also an ingenious marketing move to corner the market on Groundhog Day, considering other holidays like Halloween and Christmas are already locked down. Residual checks for the film’s cast and crew will flow in until the end of time. So what’s all the fuss about? In one of Bill Murray’s many classic roles, he plays Phil Connors, a self-loathing TV reporter trapped in a time loop that forces him to relive Groundhog Day over and over. It’s rumored that the writers of the film intended the time loop to last more than 40 years, giving Connors just enough time to successfully court the lovely Rita (Andie MacDowell). Groundhog Day is charming, thought-provoking and if you’re in the market for a piece of movie history, the cozy bed and breakfast that was used to shoot the film was recently put up for sale. 

Garden State (2004)
Director: Zack Braff

For some, the Grammy-winning Garden State soundtrack alone is enough to make you fall in love with the next person you lay your eyes on. The hand-selected soundtrack was just one of the many reasons why Zack Braff’s writing and directional debut is widely seen as a cult classic. The former Scrubs leading man also stars in the indie dark comedy as Andrew Largeman, a fringe Hollywood actor who returns to home to New Jersey to mourn the death of his mother. Largeman heads back to the Garden State to feel something, as his life has been one over-medicated haze. In balancing the broken relationship with his father, the death of his mother and his homecoming as a middling celebrity, Largeman finds solace in Natalie Portman’s Sam, the other half to Largeman’s tortured soul. Garden State has the right amount of quotable hijinks and perfectly spontaneous displays of raw anxiety and affection to satisfy anyone in the viewing party. Like most romantic comedies, Garden State ends with the tired cliché of the airport decision, but Braff’s spin on it, coupled with this song, should be enough to stir up a tear.

Chasing Amy (1997)
Director: Kevin Smith 

Straight out of the Kevin Smith universe comes a film that pushes the boundaries of sexual exploration and on a deeper level, questions what truly constitutes love. Ben Affleck stars as Holden, a New Jersey comic book artist who falls for a lipstick lesbian from Manhattan named Alyssa (you later find out who the titular Amy is). It’s a love story unlike any other on this list not because of the nature of their forbidden relationship, but Chasing Amy digs into the underlying fears and tensions of jumping into a relationship and slowly unraveling each partner’s past. It’s a necessary game all couples eventually have to play, but Smith cuts into these emotions with care, crafting a dark and humorous take on what it means to learn how to love.

Say Anything (1989)
Director: Cameron Crowe

There's so much to love about Say Anything, and it's all been discussed virtually to death, but we'll do our best. John Cusack (yes, him again) and Ione Skye are the quintessential mismatched romantic pair during that one magical summer that nearly everyone experienced: the one between high school graduation and before college. Say Anything's timeless appeal has a lot to do with Cusack and Skye, arguably the most genuinely likable pairing ever seen in this kind of film, but it's enhanced by a supporting cast that includes the always welcome John Mahoney, a young Jeremy Piven, Joan Cusack, and Homer Simpson himself, Dan Castellaneta. Cameron Crowe's dialogue and direction make the romance feel authentic, and there are plenty of genuine laughs throughout. And then there's that soundtrack! Like the memorable tunes in Cameron Crowe's later music-centric works like Singles and Almost Famous, Say Anything's soundtrack runs the gamut between classics (the song that launched countless high school slow dances and make-out sessions, Peter Gabriel's "In Your Eyes") and deep cuts (The Replacements' moody, off-kilter "Within Your Reach"). Is it possible that Crowe never topped this one?  

Enjoy Valentine's Day! Hopefully Cupid hits you square in the butt! 

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