This feature originally ran in February 2015. We’re reposting it ahead of this year’s Valentine’s Day.
Valentine’s Day, a loved or loathed holiday depending upon one’s relationship status and willingness to succumb to commercialism’s flowers-and-candy paradigm, is nigh. And what better way to celebrate after gift-giving — or throwing a Singles Appreciation party or eating a pint of Häagen-Dazs alone in bed — than by watching a romantic film?
For options, look no further than the steady march of date movies released on Valentine’s Day weekend in recent years: Gnomeo and Juliet (2011), Just Go with It (2011), The Vow (2012), Safe Haven (2013), Beautiful Creatures (2013), Endless Love (2014), About Last Night (2014), Fifty Shades of Grey (2015), Fifty Shades Darker (2017), and, of course, Fifty Shades Freed (2018).
Although celebrations in honor of St. Valentine date back to at least the fifth century AD, Valentine’s Day in the “Hallmark holiday” sense is only a few decades old. As such, films about Valentine’s Day, or those that even include Valentine’s Day as a minor plot point, are surprisingly few and far between.
With this holiday-specific restriction in mind, we did a little digging and came up with a list of eight feature films ranked from worst to best. The list does not include television movies like the Charlie Brown shorts, as cute as they are, nor any films related to the St. Valentine’s Day Massacre of 1929, in which case Some Like It Hot would have made the cut.
Do you have a favorite film set around Valentine’s Day? Let us know in the comments.
I Hate Valentine’s Day (2009)
Remember My Big Fat Greek Wedding? The chemistry between the two leads — then-unknown stage actress Nia Vardalos and Sex and the City’s John Corbett as star-crossed Greek-American and Anglo-Saxon lovers, Toula Portokolos and Ian Miller — coupled with a funny, heartfelt story about ethnic identity and an endearing supporting cast, made it not just the surprise indie hit of 2002, but the highest-grossing romantic comedy of all time.
I Hate Valentine’s Day, which reunites Vardalos and Corbett as onscreen paramours, is not that film. It’s the cracked-out Frankenstein version of that film, as Vardalos’ Genevieve and Corbett’s Greg possess none of the chemistry, not to mention the individual warmth or likability, that made the pairing of Toula and Ian so appealing. Good writing and direction might have saved them, but Vardalos is weak on both counts; as a result, both characters come across as blithering, childish idiots.
Genevieve, who owns a Brooklyn flower shop called Roses for Romance, has a “five-date rule” that she considers breaking after getting to know Greg, who owns a tapas bar called Get on Tapas (woof). The forced humor drags on for what feels like years, while the few scenes featuring Zoe Kazan as Genevieve’s dreamy friend (so good that her character might as well have wandered in from another, much better film) offer only brief glimpses of hope.
The moment of truth for Greg and Genevieve arrives on Valentine’s Day, one year to the day after their story begins. But by that point, the will to care is outstripped by the desire to watch something else, anything else, as a form of brain bleach for the painful second-hand embarrassment of watching two actors stumble through a relationship that even they don’t seem to believe in. —Leah Pickett
There are so many choices for the nadir of post-Scream slasher flicks. I Still Know What You Did Last Summer. Urban Legends one and two. Halloween H20. The entire Dimension Films line-up after 1996. But for the sake of bold claims (and outrageous hyperbole), let’s just say that Jamie Blanks’ Valentine is the bottom of the barrel, the very grimmest of Wes Craven rip-offs. It’s heartless, it’s gutless, it’s not scary, and, worst of all, it stars Denise Richards.
Actually, Katherine Heigl’s in this too. She is the worst of all.
Anyway, Happy Valentine’s Day! Here, yet another lovelorn, love-scorned killer takes on a series of vapid young actors for gore and profit. But see, to drive the Valentine’s theme home, the killer wears a cherub mask. Of course he or she doesn’t wear a cupid diaper – that would just be stupid. Ironic death after death occurs, and oh my God, didn’t America break up with the Scream films already? Do yourself a solid, look at a few clips on YouTube, crack open a box of chocolates, and laugh your heart out. —Blake Goble
My Bloody Valentine 3D (2009)
Movies like My Bloody Valentine 3D make me ashamed of watching horror movies. All base needs are on display: “Let’s give the kids the naughty goods and slap some 3D on it before they realized it was 15 bucks full of nothing.” Not only is it indicative of the modern movie industry’s biggest flaws (nostalgic cash grabbing and 3D for grotesque purposes), but MBV3D is also like cereal comprised entirely of marshmallows.
This is one of those movies that I saw in 2009 with buddies, and their lust for blood and full frontal nudity left me mortified. Never have I ever wanted to grow up more. Thanks for that, Patrick Lussier. My Bloody Valentine 3D isn’t just an eyesore; it’s a palate-destroyer, a waste of time, and its title is a mouthful.
Furthermore, the film’s a hacky, showy remake of a middle-tier horror movie, and most criminally, it hardly elicits the necessary thrills required to hold on to one’s lover. You had one job, Patrick Lussier. Way to screw up everyone’s Valentine’s Day. Oh, wait, this was meant to be camp? Eh, 3D still sucks. —Blake Goble
Valentine’s Day (2010)
For about a year, it appeared as if Garry Marshall was about to make a stupid romantic comedy about every popular holiday in America starring every American idol. Fortunately, he stopped at 2011’s New Year’s Eve. To his ball-bustin’ credit, he did have a reason: In 2010, his ridiculously overstuffed rom-com Valentine’s Day opened nationwide to $52.4 million with final sales tallying over $100 million. “Cha-ching,” he probably said in a blue suit, while screaming at his sister, Penny, about the dog.
Whatever the case, Valentine’s Day is a grossly excessive film with far too many subplots and one too many Hallmark moments that only affirm one’s hesitance with the genre. Even worse, not one star ever escapes into their role; instead, they simply strut and jump and shout at the screen as if to say, “HEY! LOOK! IT’S ME!” The film is more or less an issue of People brought to life for an excruciating 124 minutes.
Still, if you’re into chummy, watered-down, unrealistic fluff, it doesn’t get better. And while the film never earns its unruly cast of A-listers, which includes “Shake It Off” singer Taylor Swift, it’s admittedly fun to watch them all read a script together. Looking at the poster above, I totally forgot Topher Grace was in this, which makes me think I sho— no, no, no, no … maybe? –Michael Roffman
My Bloody Valentine (1981)
Note: This is not to be confused with the awesome Irish rock band. They came out in 1983. Huge difference.
After the successes of Halloween and Black Christmas, you couldn’t turn around without bumping into some thrift-store holiday slasher exported from Canada. There’s April Fool’s Day, New Year’s Evil, Silent Night, Deadly Night, Leprechaun. Has Hollywood no shame? Must they have such disrespect for history and honoring people’s heritage?! Well, come to think of it, America has zero tact or modesty for St. Patrick’s Day either… Okay, fine, a lot of holidays are silly marketing events, but sometimes you get a day off!
Anyways, amidst all those jokey rip-offs, My Bloody Valentine came out in 1981 and has probably lasted longer because of its punny title more than anything it actually does. It’s a cult curiosity. Here’s the premise: There’s a gas-masked killer on the loose slaying couples that celebrate Valentine’s Day. How bitter. Such needless heartbreak, or heart-slash-and-lacerate, rather. If only there was Tinder for this poor and crazed killer back in the ‘80s.
My Bloody Valentine holds its own against a sea of trashy killer movies because of its dark and moody ambience, and it makes a perfect antidote for the lovelorn on Valentine’s. If you can, find the full 99-minute version. —Blake Goble
Sleepless in Seattle (1993)
Sleepless in Seattle feels synonymous with the term “romantic comedy.” It’s as if the entire genre had been building up to that odd moment in June 1993 — only a shy two weeks post-Jurassic Park, mind you — when Nora Ephron, Tom Hanks, and Meg Ryan ruled the theaters. Surprisingly, the late filmmaker’s romp about two nationwide lovers proved to be catnip for America, grossing over $126 million off a $21 million budget, making every Hollywood producer ravenous for tear-stained screenplays in the years following.
But you have to ignore the obvious imitations — including the Sleepless reunion of 1998, You’ve Got Mail — to truly appreciate this film. To be fair, it’s not that hard. Hanks and Ryan are ridiculous together, while the oft-forgotten Bill Pullman adds a bit of camp that’s just So Fucking ’90s. What’s more, there’s a nostalgic charm to the pre-Internet simplicity of this picture, and it’s one of the last films to grasp the majesty of New York City before it was bought and sold by, well, everyone.
If there’s one detriment, however, it’s the little brat playing Hank’s son: Ross Malinger. He isn’t nearly as annoying as he tends to be in the 1995 McDonald’s commercial, Bye Bye Love, but mother of god, he’s an obnoxious wee one, giving credence to why everyone’s sleepless in … yeah, whatever, just know he sucks. The film, though? Not so much. –Michael Roffman
Obvious Child (2014)
In one of the best films from last year, certainly the best romantic comedy, twentysomething Brooklyn comedian Donna Stern (the incomparable Jenny Slate) finds out her boyfriend is cheating on her, bombs on stage, meets a cute, nice guy named Max (Jake Lacy), has a drunken one-night-stand with him, and a few weeks later discovers that she is pregnant. She schedules the abortion for Valentine’s Day.
That the above description translates to a humorous, touching, and even romantic movie-going experience is a testament to not only Slate’s strengths as an actor, but Gillian Robespierre’s ability as a first-time writer-director to draw nuance and sweet, truthful moments out of Donna and Max’s budding relationship.
Throughout Obvious Child, Donna struggles with whether or not to tell Max about her decision to have an abortion. She eventually does open up about her experience on stage — on the night before the procedure, no less — as Max watches from the audience. He looks stunned and walks out before her set is finished, implying that her news was too much for him to handle.
But wait! Not only does Max show up at Donna’s doorstep the next morning with the most adorable bouquet of flowers, but he also goes with her to the clinic and sits with her in the waiting room. It’s the modern romantic gesture equivalent of Billy Crystal running into the New Year’s Eve party to tell Meg Ryan he loves her in When Harry Met Sally or John Cusack holding the boom box over his head to play “In Your Eyes” for Ione Skye in Say Anything.
The film ends with Donna and Max cuddling on the couch and watching Gone with the Wind. Yep, Max is a keeper. Deal, sealed. —Leah Pickett
Eternal Sunshine of the Spotless Mind (2004)
“Why do I fall in love with every woman I see who shows me the least bit of attention?”
Few films hurt like Michel Gondry’s Eternal Sunshine of the Spotless Mind. The 2004 indie cult classic is beautiful, funny, enlightening, inspiring, and downright clever … but it’s also bitter, depressing, nostalgic, sobering, and painful. Anyone who’s ever broken up with a loved one knows the torturous feeling of wanting to think about anyone but them, so there’s something timeless and tangible about watching Joel (Jim Carrey) and Clementine (Kate Winslet) delete one another and then of course immediately regret it.
Gondry won’t ever make a better picture than Eternal Sunshine. And Carrey and Winslet likely won’t find better roles. The ingenuity that fuels this film — from Charlie Kaufman’s witty, heartbreaking screenplay to Gondry’s team of practical effects — is worth studying alone for decades to come. But thematically, that’s where the rare, delicate pieces of chocolate are found, as Kaufman and Gondry dig deep into the risks and spoils and fortunes of love, questioning the basis of attraction and the motives that drive us to and from our loved ones.
Everyone brings their A-game, too. Carrey and Winslet are supported by a stellar, transformative cast that shoot far beyond their star power. A young Mark Ruffalo and a spry Kirsten Dunst add plenty of charm, a meditative performance by Tom Wilkinson injects a dose of authority, a creepy Elijah Wood winds up being the perfect foil, and David Cross has the greatest line about birdhouses ever put to celluloid. And without Jon Brion, the film wouldn’t punch the bruises left by the immaculate imagery, lensed to perfection by Ellen Kuras.
Valentine’s Day is an afterthought in this film, but there aren’t too many productions that capture the mercurial feelings that nag and berate both singles and couples on February 14th. You’ll laugh, you’ll cry, and you’ll probably cry some more. It’s not an easy film to experience, but it’s one of the best to watch. As recent Grammy winner Beck sings here: “Everybody’s got to learn sometime.”
And yes, I know that’s a cover. —Michael Roffman