13 Anti-Valentine’s Day Films

Movies Lists Valentine's Day

Oh, Valentine’s Day. A time when love is in the air, couples express their undying affection for one another and PDA and conception run amok.

As with everything, however, there’s a flip side to this coin. For every wide-eyed romantic looking to put his or her love on the line, there is the eye-rolling cynic denouncing the holiday as absurd and superfluous. These are the people for whom the statement “Valentine’s Day was invented by Hallmark to sell cards” becomes a personal mantra. And, let’s face it, anyone whose ever been burned by rejection or found themselves just plain sick of their friends using the occasion as an excuse to suck face all day, has felt at least a twinge of nausea whenever February 14 comes rolling around.

Well, for those not looking to be stuck alone at home watching a marathon of Sleepless in Seattle on TNT, here’s a list for you. It compiles the films perfectly designed for those disillusioned or made bitter by love’s hurtful sting.

13. The Break-Up (2006)
At the time of its release, The Break-Up appeared to draw more attention for the burgeoning relationship between co-stars Vince Vaughn and Jennifer Anniston than for its actual quality. Certainly, the trailer did little to assure moviegoers that the film would be anything but a goofy romp in which Vaughn’s and Anniston’s characters pull increasingly wacky pranks on each other in order to seize control of their impressive Chicago condo. And while the movie is not without its goofy moments (Anniston’s in-the-closet brother leading the dinner table in an a capella version of “Owner of a Lonely Heart” is a notable example), director Peyton Reed and screenwriters Jeremy Garelick and Jay Lavender successfully crafted a dramedy that deftly explores the resulting chaos that follows an emotional break-up. Say what you will about Vince Vaughn and his occasional overbearing, frat-boy persona, here he displays genuine vulnerability and sadness. Anniston also brings her A-game, demonstrating that she deserves much better than the material often given to her. Moreover, the on-screen fights occasionally feel so real that the idea that the two leads actually hooked up during filming seems downright unnatural.

12. Ruby Sparks (2012)
In his review for the much-maligned Cameron Crowe project Elizabethtown, AV Club writer Nathan Rabin coined the now ubiquitous phrase “Manic Pixie Dream Girl.” Writing about the film’s female lead (played by Kirsten Dunst), Rabin highlighted the archetype of the lively, quirky girl who becomes a shot in the arm to her dour and/or depressed male lead. Written by and co-starring Zoe Kazan, Ruby Sparks seems to have been created specifically as a reaction to this type of character. Paul Dano plays a writer who, drowning in the shadow of his early-in-life success, ends up writing his own Manic Pixie Dream Girl as a form of therapy. To his surprise, his creation springs to life. What seems to be the ideal relationship, however, grows complicated when reality rears its ugly head. The long-awaited follow-up to directors Jonathan Dayton and Valerie Faris’ Oscar-winning, Sundance breakout hit Little Miss Sunshine, the film begins innocently enough before descending into a very dark and, in one particularly horrific scene, highly disturbing tale of obsession and the madness that comes from one’s paralyzing need for control over the chaos of life.

11. In the Realm of the Senses (1976)
Read the true story that this Criterion-approved Japanese-French film based its plotline on and you’ll have an idea why it would make for the worst kind of Valentine’s Day viewing. Directed by the late Nagisa Oshima, the film revolves around the perverse relationship between a hotel maid and the employer who molests her. This tryst leads to an intense, long-term sexual affair where the two indulge in every kind of experimentation you can imagine. This destructive coupling eventually climaxes (hehe) in a series of events so depraved that I won’t dare spoil them here. Naturally, the film caused no end of controversy, not only for its sexually explicit content but for the fact that the two leads were performing non-simulated sex.

10. The War of the Roses (1989)
Never has the phrase “love is a battlefield” been taken more literally than in Danny Devito’s sophomore directorial outing. An acerbic black comedy based on a 1981 novel of the same name, The War of the Roses stars Michael Douglas and Kathleen Turner as a well-to-do couple whose crumbling marriage becomes a launching pad for a vicious, no-holds-barred war for control of their home and possessions. Simultaneously hilarious and gleefully mean-spirited, the film acts as an excellent double feature with Romancing the Stone, an adventure-romance film also starring Douglas and Turner (albeit, one with a much happier outcome).

9. Bad Timing (1980)
Nicolas Roeg’s Bad Timing does not begin promisingly. In Vienna, the beautiful Milena (Theresa Russell) is rushed to the hospital after suffering what appears to be a fatal overdose. At her side is Alex (Art Garfunkel), her American psychiatrist and (as we soon learn) her lover. Under heavy police interrogation, Alex weaves a tale of a most perverse and twisted love affair. It’s a story of obsession and domination. Slammed by many at the time of its release, one official from the film’s U.K. distribution company famously dubbed it “a sick film made by sick people for sick people.” Nevertheless, its reputation has grown in recent years, culminating in a Criterion Collection release. Still, this toxic romance remains a brutal, disconcerting narrative to sit through. You’ll certainly not be able to shake certain images of Art Garfunkel after it’s all over.

8. (500) Days of Summer (2009)
“This is a story of boy meets girl. But you should known in advance, this is not a love story,” intones the voiceover at the start of this bittersweet romantic comedy. True to those words, what unfolds is not quite the light, sunshine-y narrative indicated by the film’s vibrant color spectrum. Subverting notions of the typical rom-com, Summer acknowledges the all-too-true notion that sometimes, without definite rhythm or reason, a relationship can just not work out—no matter how badly you want it to. The film’s non-linear structure — which jumps back and forth across the titular 500 days between the couple’s initial meeting, their breakup and the point where lead character Tom (Joseph Gordon-Levitt) can finally move on with his life — helps to emphasize the delicate nature of romantic relationships and how perception means everything. Speaking of perception, who hasn’t been in the position so accurately displayed in the film’s devastating “Expectations vs. Reality” sequence?

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7. Sleepwalk with Me (2012)
Mike Birbiglia’s directorial debut is a Portrait of the Comedian as an Awkward Stand Up. Throughout the film, we witness Birbiglia’s dramatic surrogate, Matt Pandamiglio, slowly transition from telling stiff, half-baked jokes to weaving insightful and humorous anecdotes based on his life and relationships. The problem? As his comedic voice flourishes, his relationship with his long-term girlfriend (Lauren Ambrose) begins to rapidly disintegrate. Based on Birbiglia’s one-man Broadway show of the same name as well as his first book, Sleepwalk with Me is a small movie but an effective and poignant one nonetheless. In a Reddit AMA with co-producer Ira Glass, one user even informed the This American Life host that seeing the movie with his wife led to them addressing their long-dormant problems and ending their marriage that very night.

6. Closer (2004)
Directed by the legendary Mike Nichols, this adaptation of Patrick Marber’s award-winning play of the same name is a scathing, cynical sneer at modern-day relationships, starring a quartet of some of the most hateful, insensitive characters ever put to film. Needless to say infidelities, broken trust and shattered promises abound. Natalie Portman earned her first Oscar nomination as perhaps the most innocent and naïve of the four (who just happens to be a stripper). Clive Owen, however, shines as the crass, boorish dentist prone to proclaiming whatever pops into his sick mind (he’s also probably the most honest one in the group). A venomous Valentine if there ever was one, Closer remains one of the worst first-date movies ever made.

5. Husbands & Wives (1992)
As with several entries on this list, Woody Allen’s 1992 domestic drama was overshadowed by behind-the-scenes drama. Prior to the film’s release, Allen’s relationship with longtime partner (and co-star) Mia Farrow went up in smoke after it was revealed that he’d been engaging in a sexual affair with her 19-year-old adopted daughter. With this news still fresh in the tabloids, the narrative, which displays marital discord in all its ugly glory, inevitably invited real-life parallels. Allen’s use of handheld, documentary-like camerawork only serves to highlight the bleakness and harsh reality of the situation. While films such as Annie Hall and Manhattan will always stand as major apexes in Allen’s career, Husbands & Wives serves as an underrated masterpiece in his lengthy filmography.

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4. Brief Encounter (1945)
For most, the name David Lean evokes images of sprawling, three-plus hour epic masterpieces such as Lawrence of Arabia or The Bridge Over River Kwai. Yet perhaps one of the British’s director’s most powerful outings is a small-scale movie about a doomed relationship that barely clocks in under 90 minutes. Celia Johnson stars as a bored British housewife who finds herself drawn to a married doctor that she meets at a train station. Over the course of several weeks, the two soon realize their relationship and attraction to each other is far from innocuous. Based on a one-act play by Noël Coward, Brief Encounter paints a dreary look at traditional British marriages and examines the depressing concept of knowing that the one you truly love might have been yours under different circumstances.

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3. Scenes from a Marriage (1973)
No one does angst-ridden relationship dramas quite like Sweden’s Ingmar Bergman. This one is no exception. Made on a shoestring budget and featuring Bergman’s trademark penchant for claustrophobic close-ups and long, soul-baring monologues, the original Swedish TV miniseries ran almost five hours in length. Released as a three-hour cut in U.S. cinemas, the film still proved to be a gut-wrenching examination of a failed marriage. Funny enough, the film becomes notorious in its home country when, in the wake of its release, there was a rapid spike in Scandinavian divorce rates.

2. Blue Valentine (2011)
Blue Valentine is actually two movies. In one, Dean (Ryan Gosling) and Cindy (Michelle Williams) are two lost souls who find solace in each other’s company. Cindy has emotional baggage stemming from familial trauma whereas Dean is the charming free spirit ready to make the pain go away. When Cindy finds herself pregnant, Dean becomes her emotional support and the two eventually decide to marry. This tale of young love is juxtaposed sharply against the future versions of Dean and Cindy—aged, tired and weary beings who are mere shells of their former exuberant selves. The child, which originally drove them together, now appears to be the last remaining link in their deteriorating relationship. Though one can easily find signs of impending disaster in the early scenes, it does not make watching the slow but inevitable collapse of their marriage any less traumatizing.

1. Eternal Sunshine of the Spotless Mind (2004)
Yes, yes, between landing a high spot on Paste’s Top 50 Films of the Decade list as well as one on The 50 Movies on Netflix Instant list, it seems like there should be some kind of penalty box reserved for Eternal Sunshine. To that I say — can’t fault a masterpiece for being too good.

Unlike other entries in the list, Eternal Sunshine begins with the signature couple already broken up and heart broken. Desperate to rid himself of the memories of the break-up (and, by extension, the pain), Joel enlists a company that specializes in wiping away such memories. Of course, in the middle of the procedure, Joel realizes that some memories are worth holding onto, regardless of the hurt. Though much of the film has Joel and Clementine yearning for each other in their own ways, it’s the story’s conclusion that potentially turns this cerebral romantic dramedy into a cosmic tragedy.

While we, as viewers, want more than anything for the oddball coupling of Jim Carrey’s reserved Joel and Kate Winslet’s vivacious Clementine to work itself out, the fact remains that we’ve seen that the two are woefully incompatible in the long run. Thus, though the end leaves the couple with the optimistic hope that they can turn their situation around, the film’s final shot appears to tell a different story. As credits roll, we see Joel and Clementine frolicking around in the snow. Then the image is repeated again. And again. And again. While director Michel Gondry has stated that he had no grand intention, the repetition of the shot carries an unmistakable implication: Joel and Clementine are trapped in a Sisyphean cycle wherein they break up, wipe their minds then repeat the same process over and over again. Writer Charlie Kaufman’s original draft, which shows an elder Joel and Clementine meeting each other “for the first time” once again, leads some credence to the argument. Whatever the real story, Eternal Sunshine of the Spotless Mind has safely secured itself as a modern day classic, even if it’s not the cheeriest movie for a romantic movie-night.

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