Back to IndieWire

11 of the Most Unconventional and Innovative Romantic Comedies

11 of the Most Unconventional and Innovative Romantic Comedies

They Came Together” (out this Friday in select theaters), starring Paul Rudd and Amy Poehler, is a parody of the romantic comedy genre. Rudd stars as Joel, a corporate businessman whose company is threatening to close the small store run by Poehler’s Molly (remind you of the premise of a certain rom-com by the name of “You’ve Got Mail?). The film mocks and twists conventional romantic comedies, turning the tired tropes of films like “Sleepless in Seattle” on its head. But while the mockery of the overused rom-com themes are appreciated, “They Came Together” is not the first of its kind. Check out our list of romantic comedies that have an unconventional or innovative twist. Then let us know what your favorites are in the comments.

READ MORE: David Wain’s ‘They Came Together,’ With Amy Poehler and Paul Rudd, Is a Hilarious Knock On Romantic Comedies
“(500) Days of Summer” Dir. Marc Webb (2009)

The most interesting aspect of Marc Webb’s 2009 romantic comedy—and what makes it unconventional— is that (spoiler alert!) the lead couple doesn’t end up together in the end. Summer (Zooey Deschanel) and Tom’s (Joseph Gordon-Levitt) relationship is presented non-linearly, with jumps back and forth in time. As viewers, we really like Summer and Tom together, and want them to end up happy in the end. But what the story tries to convey, however, is that while one person in a duo may be convinced they have met “the one,” that may not be the case for the other. Don’t worry, things turn out all right in the end, just not in the way that you’d expect. (Casey Cipriani)

“Amélie” Dir. Jean-Pierre Jeunet (2001)

Jean-Pierre Jeunet’s beguiling Gallic hit “Amelie” has originality bursting out of every gorgeously art directed frame. Led by a star-making performance by Audrey Tautou as the film’s titular heroine, “Amelie” centers on a naive and awkward cutie pie living in Paris who goes out of her way to help others, but can’t summon the courage to help herself find love. She does in the end (of course), but the happy ending feels wholly earned. Also, despite being titled “Amelie,” Jeunet is clearly enamored of his entire supporting cast and gives them all a chance to shine and seep into your heart. It’s that rare romantic comedy, full of surprises at every turn, that plays like a classic while paving a new path for the well worn genre. (Nigel M. Smith)

“Annie Hall” Dir Woody Allen (1977)

Leave it to Woody Allen to write one of the few true comedies to win Best Picture at the Academy Awards. How’d he do it? Well, for one, he didn’t try. Allen’s distaste for awards in general is well known, and no one would have called “Annie Hall” Oscar bait had the term been prevalent back in the day. Nevertheless, Allen’s nostalgic reminiscing about his childhood and his most significant relationship won because it struck voters as it struck the rest of the world: unconventionally charming. It’s not your typical love story because it plays with structure and expectations to reach its own unique conclusion. Alvy’s life changed because of Annie, and “Annie Hall” was his ode to that portion of his life. No one told Allen it had to end at a chapel. (Ben Travers)

“Frances Ha” Dir. Noah Baumbach (2012)

The fact that there’s no exact romantic pairing in Noah Baumbach’s “Frances Ha” is why it makes for such a great unconventional romantic comedy. The film, in its exploration of a lost female twenty-something, exemplifies one of the most important aspects of romance: learning to love yourself. In the beginning we see Frances with a dead end job, in a co-dependent relationship with her best friend and as someone unable to be taken seriously. Throughout “Frances Ha” she slowly works her way to adulthood, learning to properly care for herself, make money and manage her relationships. There may be no passionate kiss or rowdy sex scene, but this comedy reminds us of a different type of love. (Eric Eidelstein)

“Kissing Jessica Stein” Dir. Charles Herman-Wurmfeld (2001)

Before Jennifer Westfeldt directed her first feature “Friends With Kids,” she co-penned this winning and insightful romantic comedy about a unlucky in love copy editor, Jessica (Westfeldt), who tries her hand at being bisexual after coming across a personal ad in the newspaper posted by a woman seeking a meaningful relationship (co-writer Heather Juergensen). To Jessica’s surprise, she takes to the ad’s author, Helen, a gallery owner who has her own share of hardships with the opposite sex. Things get messy (as they always do in rom-coms) when one of the pair wrestles with whether she’s in it for the long haul, but the way Westleft and Juergensen deal with the denouement is anything from typical. (Nigel M. Smith)

“Harold and Maude” Dir. Hal Ashby (1971)

If you only watched the first ten minutes of Hal Ashby’s 1971 comedy, you’d think it was a movie obsessed by death, with no business being on a list of romantic comedies. But the film, starring Bud Cort and Ruth Gordon as the ultimate May-December romance, evolves from its grim yet hilarious beginning into one of the sweeter movies ever made about life, and how its pleasures must be absorbed. And that includes love — even an unconventional love like the one Harold and Maude share. (Liz Shannon Miller)

“Lars and the Real Girl” Dir. Craig Gillespie (2007)

Lars (Ryan Gosling) is awkward, closed-off and finds it difficult to socialize with others. One day he informs his family that he’s met a lovely girl on the internet, but when he introduces them to a life-sized doll that he’s ordered from an adult website, they’re pretty sure something is amiss. Is Lars messing with them? Or doe she actually believe this girl is real? Though Lars is romantically attached to “Bianca,” the real romance grows over the course of the film in an unexpected way. (Casey Cipriani)

“Newlyweeds” Dir. Shaka King (2013)

This romantic comedy, as you might imagine, doesn’t play to straight storytelling. It’s more of a collection of vignettes loosely rolled together, poignantly painting the stagnated lives of two arguably ordinary stoners, Lyle (Amari Cheatom) and Nina (Trae Garris), and their touching marriage, oft challenged by their common habit. The storytelling is whimsical and wonderful, but always honest and true. King does not simply look at marijuana and its effect in some juvenile closed-off manner, but with real understanding and care, via Blaxploitation dreams, lost couches and morphing monstrous motions. It’s a smooth trip. (Oliver McMahon)

“Punch-Drunk Love” Dir. Paul Thomas Anderson (2002)

An unconventional love story if there ever was one, Paul Thomas Anderon’s swooning and wonderfully bizarre love story “Punch Drunk Love” centers on Barry, a tormented and troubled novelty supplier (a revelatory Adam Sandler) who finds a kindred spirit in the soft-spoken and doe-eyed Lena (Emily Watson), a co-worker of one of his heinous sisters. They meet after Lena asks Barry to look after her damaged car, then go out on a dinner date where Barry smashes up the bathroom in a blind fit of rage. Rather than recoil in terror, Lena gently observes “your hand is bleeding” and goes on as if nothing bad happened. In Lena, Barry finds a woman who can calm his volatile ways and in Barry, Lena finds a man willing to give himself over to her, mind, body and soul. (Nigel M. Smith)

“Silver Linings Playbook” Dir. David O. Russell (2012)

David O. Russell is never one to play it safe. Despite its romantic comedy trappings, “Silver Linings Playbook” is an O. Russell joint through and through. The comedy plays like all of the filmmaker’s best work — it’s manic, provocative, bursting with life and features career-best performances from its talented ensemble. Bradley Cooper earned his first Oscar nomination as former teacher Pat Solitano, who moves back in with his parents (Robert De Niro and Jacki Weaver, both Oscar-nominated for their work) after a stint in the loony bin. Jennifer Lawrence won the Best Actress Oscar for her incendiary performance as Tiffany, a raven haired dynamo with her own fair share of problems who wins Pat’s heart. Like in all romantic comedies they end up together in the end, but their rocky journey to their happy ending is anything but conventional. (Nigel M. Smith)

“Some Like it Hot” Dir. Billy Wilder (1959)

So “Some Like it Hot” may suffer from a few out-of-date sexist and ethnic tropes, but the hilarious story of two musicians (Tony Curtis and Jack Lemmon) who cross-dress as women to join a traveling band in order to escape the mob, has plenty of unconventionally romantic bits. Naturally both of the men fall for ukelele player Sugar (Marilyn Monroe) and while she can only end up with one of them in the end, how they get there (and who ends up with someone else) is anything but conventional. (Casey Cipriani)

Sign Up: Stay on top of the latest breaking film and TV news! Sign up for our Email Newsletters here.

This Article is related to: Features and tagged , , , ,

Get The Latest IndieWire Alerts And Newsletters Delivered Directly To Your Inbox