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The 13 best movies to stream on Valentine’s Day

They might not be the Valentine’s movies you expect, but they’re the ones you deserve.

Feb 29, 2020, 11:56 am*

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Nico Lang

You might hate movie romances, but there’s no denying that they’re a staple of the Valentine’s season. Last year, audiences flocked to the BDSM romance Fifty Shades of Grey, but this year, viewers will be forced to pick between The Choice, yet another product from the endless Nicholas Sparks conveyor belt, and How to Be Single, a slightly tamer offering starring Anastasia Grey herself, Dakota Johnson.

So this Feb. 14, here’s my suggestion: Beat the crowds and don’t waste your money. Stay in with your Apple TV and watch one of these much better offerings currently streaming online. They might not be the Valentine’s movies you expect, but they’re the ones you deserve.

1) The 40-Year-Old Virgin (Amazon Prime)

Over a decade after its release, The 40-Year-Old Virgin is still the best movie Judd Apatow has ever made. Apatow’s directorial debut announced him as the auteur of the thinking-man’s stoner bromance—movies in which aging slackers debate life, love, and the merits of Coldplay while playing video games and sharing a bong.

But the reason that Virgin continues to stand above the pack is that it has something Apatow’s later features often lack: a real sense of vulnerability to them. Virgin is often mislabeled as a “gross-out comedy”—because after all, the movie opens with Andy’s (Steve Carell) morning wood. But it’s written with a naked honesty that’s incredibly rare in studio comedies (or, for that matter, any movies at all). The 40-Year-Old Virgin is filled with characters you know and care about, because you recognize parts of these people in you. You genuinely want them to be find happiness, whether it’s their first lay or the love of their life.

2) About a Boy (Netflix)

If there’s anyone who has a stunning track record in Hollywood, it’s British author Nick Hornby. Hornby’s High Fidelity and Fever Pitch were both successfully adapted to the big screen (even Jimmy Fallon can’t muck up a good script), while Hornby has carved out a niche from himself as one of the best screenwriters in the business—following An Education, Wild, and Brooklyn.

The criminally underrated 2002 comedy About a Boy won’t ruin that sterling reputation anytime soon. Directed by Chris and Paul Weitz, the film is about the unlikely friendship that blossoms between a trust-fund adult (Will, played by Hugh Grant) and the 12-year-old boy, named Marcus (Nicholas Hoult) whom he accidentally meets through a support group for single parents. Will—who is definitely not a father—enrolled as a ruse to meet women but finds himself drawn into Marcus’ life through unexpected circumstances.

About a Boy is Grant fully in “lovable asshole” mode, but there’s a melancholic yearning in his performance missing in his more overtly rakish work (see: Two Weeks Notice). He’s the kind of guy who isn’t nearly as much of a prick as he thinks he is, and the film’s overt cynicism likewise hides unexpected heart.

3) Chasing Amy (Netflix)

Chasing Amy is so much better than every other movie Kevin Smith has ever made that it must have been the result of accidentally getting hit by lightning. A never-better Ben Affleck (yes, even better than in Gone Girl) plays Holden, a comic book artist who develops an attraction to fellow illustrator Amy (Joey Lauren Adams). There’s just one little problem. She’s a lesbian.

Smith’s film has a lot on its mind—from the blurred boundaries between friendships to the mutability of sexuality—but at its core it acknowledges a simple truth: Love is hell. Salon’s Charles Taylor wrote that it depicts romance as a kind of “emotional anarchy”—one that nearly ends in an ill-advised threesome between Amy, Holden, and Banky (Jason Lee), who is struggling to come to terms with his sexuality. But it’s not without its hard-earned rewards. The film’s bittersweet finale is one of the most powerful and honest I’ve ever seen on film.

4) Kicking and Screaming (Hulu)

Noah Baumbach’s directorial debut qualifies as a romantic comedy in that it is both funny and about love. Grover’s (Josh Hamilton) senior year break-up with Jane (The Wonder Years’ Olivia d’Abo), forms the backbone of the narrative—as she leaves him for a writing program in Prague.

Some of the details are unforgivably twee (Jane frequently plays with her retainer and pays people when the stories she tells are dull), but there’s a lot here to fall in love with—including one of the decade’s best casts of young talent. Kicking and Screaming was a veritable who’s-who of the ’90s indie movie scene, featuring Parker Posey, Chris Eigeman, Carlos Jacott, and Eric Stoltz.

These players have a relaxed, easygoing chemistry as a group of best friends who struggle to find themselves after graduating college—or to even leave campus. Kicking and Screaming is about the comfortable rhythms we fall into in our friendships and relationships that make it difficult to move on after they end.

5) The Kids Are All Right (Netflix)

The Kids Are All Right is anything but the movie you will expect it to be going in. When the buzzy Sundance hit debuted in theaters, I expected a light, frothy family comedy that just happened to feature a lesbian couple—Jules (Julianne Moore) and Nic (Annette Bening). What I got instead was an acrid dramedy about infidelity. Jules (Moore) sleeps with the sperm donor that fathered the pair’s children, played Josh Hutcherson and Mia Wasikowska. (Given that said donor is the ever-dreamy Mark Ruffalo, you can’t totally blame her.)

I have friends who hated, hated, hated this movie, but years later, I still can’t get certain scenes out of my mind. Lisa Cholodenko’s script completely nails the neurotic tension inherent in long-term relationships, especially in a restaurant scene where unsaid feelings boil over during a conversation about (what else?) organic farming. “If I hear one person say they love heirloom tomatoes, I’m going to f**king kill myself,” Nic announces. Agreed, Nic. Agreed.

6) The Last Days of Disco (Hulu)

Whit Stillman finally got around to making a proper Austen adaptation with this year’s Love and Friendship, but arguably he’s been making Jane Austen movies his entire career. Since Metropolitan, Stillman’s 1990 debut, the director has shown a keen interest in how social norms and class structures dictate in-group dynamics. In Metropolitan, the characters define themselves as members of the “Urban Haute Bourgeoisie,” wearing their status as a badge of honor.

In his often overlooked 1998 masterpiece, The Last Days of Disco, class is performed not through identity but through endless repartee, as the characters seem to speak only to impress themselves with their wit. The film follows a circle of club-hopping friends in early ’80s New York forever threatened by the possibility of “ferocious pairing off,” as Charlotte (Kate Beckinsale) puts it. Throughout the film, take careful note of Beckinsale’s always too-neat line readings and her character’s meticulous grammar—these things are not an accident.

In Stillman’s world, love is just another game of words.

7) Meet John Doe (Hulu)

I should be putting An Affair to Remember on this list, but either you’ve already watched it and love it or you have not and all the overwritten 200-word blurbs in the world couldn’t convince you. Either way, Cary Grant and Deborah Kerr are going to meet on the Empire State Building just fine on their own.

Instead take a chance on Meet John Doe, one of Frank Capra’s most unheralded entries in his glory of the common man canon. À la My Man Godfrey, this surprisingly dark 1945 satire stars Gary Cooper as John Doe, a down-on-his-luck former baseball player who needs a job. He finds one when a newspaper recruits him to be the face of its John Doe letters—a series of anonymous public grievances penned by a gifted female columnist, Ann Mitchell (played by an always sharp Barbara Stanwyck). Ann believes in the power of the press for change, but not as much as she comes to believe in the man she creates, even as the ruse spins out of control.

8) Notting Hill (Netflix)

Hugh Grant is nothing if not the patron saint of modern romantic comedies—between Bridget Jones’s Diary, Four Weddings and a Funeral, and Sense and Sensibility—but it’s notable that in one of his best films, the love plot doesn’t work at all. I mean no disrespect to Julia Roberts when I say that the film would be much better off if her character simply weren’t in it: I know Anna is supposed to be the most famous person in the world, but does she have to be such a huge jerk? After painfully rejecting William (Grant) twice, she shows up on his doorstep with a pretty speech—as if it’s all cool. I would have told her to get lost.

The more interesting—and quite lovely—film is the romance taking place at the margins, about the love between a group of friends saddled with a lifetime of disappointments. Tony (Richard McCabe) is a failed restaurateur. Bella (Gina McKee), confined to a wheelchair after an accident, can’t conceive a child with her husband. These scenes, however, aren’t depicted as sad but hopeful and even jovial, brimming with a boisterous energy. Whenever the film forgets it’s supposed to be about Will getting the girl, it’s an utter delight.

9) Pride and Prejudice (Netflix)

Joe Wright’s Pride and Prejudice had its work cut out for it. In 1995, the BBC aired a six-part miniseries that would become the definitive Jane Austen adaptation. Starring Jennifer Ehle as Elizabeth Bennet, you likely remember it by the scene where a dripping wet Mr. Darcy (peak Colin Firth) emerges in a white T-shirt after diving in a pond.

But what Wright’s adaptation lacks in moist Colin Firth action it more than makes up for on the strength of a stellar ensemble—featuring Donald Sutherland, Jena Malone, Brenda Blethyn, Rosamund Pike, Carey Mulligan, Judi Dench, and Keira Knightley. Knightley, who had previously starred in the Pirates of the Caribbean films, was a controversial choice to play the second-eldest Bennet sister, but she totally nails it. Brash, outspoken, and fiercely independent, she gives audiences the character they’ve grown to love—even as the film drastically abridges the material for modern audiences.

It’s certainly Pride and Prejudice for the masses, but it’s also spirited and surprisingly sumptuous. Like its BBC predecessor, the film isn’t afraid to make Jane Austen sexy.

10) Punch-Drunk Love (Netflix)

Punch-Drunk Love was simply too great to last. After a career of churning out mindless, low-brow comedies, Adam Sandler made exactly one great movie: Punch-Drunk Love. P.T. Anderson’s difficult-to-pin-down pitch-black-comedy/romance is a total deconstruction of the Sandler type—repressed and angry, prone to bursts of aggression in which he lashes out at those around him. If Roger Ebert once argued that his usual character is like Dr. Jekyll and Mr. Hyde, “cloyingly sweet at some times and a cruel monster at others,” Anderson finally recognizes it.

Instead of playing the hero, Punch-Drunk Love casts Sandler as a tragic, lost soul searching for redemption. His character, Barry Egan, finds that hope in Lena Leonard (Emily Watson), who shares his love of casual cruelty. “I just wanna fuckin’ smash [your face] with a sledgehammer and squeeze it, you’re so pretty,” he tells Lena one morning. She responds: “I want to chew your face, and I want to scoop out your eyes and I want to eat them and chew them and suck on them.”

Punch-Drunk Love is the movie that should have marked a turning point in his career—Sandler’s own shot at a second chance. Unfortunately, we got Jack and Jill and The Ridiculous 6 instead.

11) Roman Holiday (Netflix)

You know a classic romantic comedy still holds up when Hollywood can’t stop remaking it. Surely you’ve seen this movie before: Cooped-up young woman with too many responsibilities meets a dark and handsome man who whisks her away from captivity on a whirlwind adventure. To an extent, it’s the plot of Romancing the Stone, but more directly, the idea was lifted for the Mandy Moore–Matthew Goode “I’m the president’s daughter!” rom-com Chasing Liberty in 2004.

I’d say stick with the original—because how can you improve on Audrey Hepburn and Clark Gable? (Hint: You can’t.) William Wyler (Ben-Hur) directs this 1953 classic about a princess (Hepburn) who enjoys a romantic travelogue with a comely American newsman (Gable), and as in all her films, Hepburn radiates a timeless elegance. The movie sizzles not with sex—Gable, 13 years older, reads more as a father figure than a love interest—but with romance in its purest form.

It’s about the romantic abandon that doesn’t come from love but from experiencing freedom for the first time—the simple joy of biking through Europe with the wind through your hair.

12) Two Lovers (Hulu/Netflix)

With Two Lovers and The Immigrant, James Gray proves himself one of the finest masters of the modern melodrama. Whereas the 1920s-set The Immigrant is an homage to the golden age of moviemaking, Grey’s Two Lovers feels ripped from the cinema of ’70s—from Panic in Needle Park to Sidney Lumet’s Dog Day Afternoon—except that it stars Joaquin Phoenix and Gwyneth Paltrow.

Adapted from a Dostoyevsky short story, the film stars Phoenix as Leonard Kraditor—who is drawn between the blind date his parents set him up with (Vinessa Shaw) and an intriguing neighbor who engaged in an affair with a married man (Paltrow). With self-destructive vigor, Leonard finds himself intoxicated by the woman next door—even as she continually proves herself unavailable. Paltrow and Phoenix are both superb in their roles, infusing their doomed courtship with a raw vivacity.

But Leonard is forced to ask himself: What’s more important, a fleeting romance with someone who he can never be with or a life with the woman he knows is waiting for him? The answer is more complicated than you think.

13) Y Tu Mamá También (Netflix)

Back in the days when video stores were still a thing, I rented Y Tu Mamá También on a recommendation from a friend, not knowing what it was about. Given that it had “Mama” in the title, I figured that meant it was family-friendly and invited my mother to watch it with me. (Cut me some slack; I was 14 and really, really dumb.)

If you’re familiar with the plot of Y Tu Mamá También, you’re aware that decision was a big mistake: The 2001 Mexican-set drama is about a steamy love triangle between Tenoch (Diego Luna); his best friend, Julio (Gael Garcia Bernal); and his cousin’s wife, Luisa (Maribel Verdú), who is dying of cancer. She accepts an invitation with them to go on a road trip to see a secret beach known as “Heaven’s Mouth,” and their journey quickly turns into a tangled mess of erotic fantasy.

The funny thing is that both my mother and I ended up adoring it—although for very different reasons. She liked how boisterous Alfonso Cuarón’s Oscar-nominated screenplay was (loaded with playful, scatalogical banter between carmates), and I enjoyed the film’s sexual politics, with the movie set against a time of governmental and social upheaval. This is a time in Mexican society when Tenoch and Julio’s gay male friends have boyfriends, which makes the pair’s own erotic encounter all the more dangerous.

Fifteen years after its release, Y Tu Mamá También remains a one-movie sexual revolution. Watch it with someone nice and stay inside with a bottle of wine.

Screengrab via hollywoodstreams/YouTube

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*First Published: Feb 9, 2016, 11:00 am