10 Offbeat Romantic Comedies for Valentine's Day

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  20 Feb 2016 

We’ve gathered together what we think are 10 of the most original films to challenge the conventions of the genre. Some have happy endings, some end in tears or confusion — yet all work an unfamiliar, offbeat magic on the romantic comedy template. There’s no Hallmark rubbish to be found here…

genres
10 Secretary
imdb
rating

7.1

Secretary (2002)

Comedy, Drama, Romance

Based on Mary Gaitskill’s critically-acclaimed short story of the same, Secretary is a dark and deviant romantic comedy about the subjectivity of love, focusing on the idea that love doesn’t necessarily have to be predictable and pain free. It’s a coming-of-age love story about the journey of sexuality, shame and innocence. Like American Beauty and other dark comedies of its sub-genre, Secretary explores taboo concepts in an accessible way that still manages to tease out its controversial messages light-heartedly. It’s understandable, then, that critics might be have been a little divided by a movie that glorifies S&M, self-harm and — perhaps worst of all — inter-office dating.

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A young woman, recently released from a mental hospital, gets a job as a secretary to a demanding lawyer, where their employer-employee relationship turns into a sexual, sadomasochistic one.

actors:
James Spader as E. Edward Grey   Maggie Gyllenhaal as Lee Holloway   Jeremy Davies as Peter   Lesley Ann Warren as Joan Holloway   Stephen McHattie as Burt Holloway   Amy Locane as Lee's Sister  

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9 Punch-Drunk Love
imdb
rating

7.3

Punch-Drunk Love (2002)

Comedy, Drama, Romance

Paul Thomas Anderson’s Punch-Drunk Love tackles the love story between the socially-impaired, emotionally-disturbed Barry Egan (Adam Sandler) and the sweet Lena Leonard (Emily Watson). Barry is not your average male protagonist, spending his days selling toilet plungers and collecting trolley loads full of pudding in order to accrue the attached frequent flyer coupons. He also gets himself into some unusual circumstances, such as calling a phone sex line run by con artists who then pursue and attempt to bully Barry into giving them all of his money. The romance in this film is unique as it speaks its own language; quite unlike that of any rom-com. At one tender moment Barry whispers to Lena: “I’m lookin’ at your face and I just wanna smash it with a sledgehammer… and squeeze it. You’re so pretty.” Isn’t love sweet?

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A beleaguered small-business owner gets a harmonium and embarks on a romantic journey with a mysterious woman.

actors:
Adam Sandler as Barry Egan   Emily Watson as Lena Leonard   Philip Seymour Hoffman as Dean Trumbell   Luis Guzmán as Lance   Mary Lynn Rajskub as Elizabeth   Robert Smigel as Walter the Dentist   Jason Andrews as Operator Carter   Don McManus as Plastic   David Schrempf as Customer #1   Seann Conway as Customer #2   Rico Bueno as Rico   Hazel Mailloux as Rhonda   Karen Kilgariff as Anna   Julie Hermelin as Kathleen   Salvador Curiel as Sal   Jorge Barahona as Jorge   Ernesto Quintero as Ernesto   Julius Steuer as Mechanic   Lisa Spector as Susan   Nicole Gelbard as Nicole   Mia Weinberg as Gilda   Karen Hermelin as Anna   Larry Ring as Steve / Brother-in-Law   Kerry Gelbard as Richard / Brother-in-Law   Ashley Clark as Phone Sex Sister  

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8 Harold and Maude
imdb
rating

8.0

Harold and Maude (1971)

Comedy, Drama, Romance

When people develop relationships with unusual characters in a movie, it’s usually received by the majority of audiences in one of two ways: support or disgust. In rom-com Lars and the Real Girl, we found ourselves encouraging Ryan Gosling to fall in love with his life-sized doll. However, in the case of Harold and Maude, we’re challenged with a love much more confronting than that of a man for his plastic girl. Eccentric and shy young Harold (Bud Cort) passes his time by faking his own suicide attempts and attending funerals at his leisure in his very own hearse. It’s there he meets 79-year-old spontaneous and carefree Maude (Ruth Gordon), who teaches Harold new experiences. No doubt Harold and Maude is a one of a kind, a romantic comedy that tackles the social constructs of ageism behind a clever mask of dark humour and a fascinating (to say the least) love story.

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The young Harold lives in his own world of suicide-attempts and funeral visits to avoid the misery of his current family and home environment. Harold meets an 80-year-old woman named Maude who also lives in her own world yet one in which she is having the time of her life. When the two opposites meet they realize that their differences don’t matter and they become best friends and love each other.

actors:
Ruth Gordon as Maude   Bud Cort as Harold Parker Chasen   Cyril Cusack as Glaucus   Charles Tyner as Uncle Victor   Ellen Geer as Sunshine Doré   Eric Christmas as Priest   G. Wood as Psychiatrist   Judy Engles as Candy Gulf   Shari Summers as Edith Phern   Vivian Pickles as Mrs. Chasen  

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7 2 Days In Paris
imdb
rating

6.8

2 Days In Paris (2007)

Comedy, Romance, Indie

Marion (Julie Delpy) and Jack (Adam Goldberg) have been together happily for two years, but it’s not until a trip to her home in Paris that the relationship is truly tested. Jack becomes jealous and paranoid about Marion’s friendship with her ex-lovers while struggling to relate culturally. His neurosis is compounded by his inability to speak French and his misfortune in some disastrously uncomfortable situations. Channeling both Woody Allen’s ranting comedies and the freeform New Wave cinema of her national pedigree, 2 Days in Paris sees Delpy deconstruct the drama of a modern romance within the guise of an acerbic, off-the-cuff comedy.

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Adam Goldberg delivers "an uproarious study in transatlantic culture panic" as Jack, an anxious, hypochondriac-prone New Yorker vacationing throughout Europe with his breezy, free-spirited Parisian girlfriend, Marion. But when they make a two-day stop in Marion's hometown, the couple's romantic trip takes a turn as Jack is exposed to Marion's sexually perverse and emotionally unstable family.

actors:
Julie Delpy as Marion   Adam Goldberg as Jack   Daniel Brühl as Lucas   Adan Jodorowsky as Mathieu   Alexandre Nahon as Manu   Albert Delpy as Jeannot  

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6 Breakfast at Tiffany's
imdb
rating

7.8

Breakfast at Tiffany's (1961)

Comedy, Drama, Romance

You want offbeat? Plenty of the magic behind the enduring love for this movie can be put down to the eccentricities of its lead characters. Consider that style icon Audrey Hepburn, playing the free-spirited Holly Golightly, is a young runaway living in Manhattan where she gets drunk, goes to strip clubs, stays out all night and lives an independent life completely devoid of responsibility. “We belong to nobody, and nobody belongs to us,” she says. Oh, and she’s also a call girl; lest we forget. Holly sparks up a friendship with her mysterious neighbour (George Peppard) — who also turns out to be a prostitute — and together they tumble into a rocky relationship, in which two commitment-phobes are slowly forced to admit they might have feelings for each other.

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Fortune hunter Holly Golightly finds herself captivated by aspiring writer Paul Varjak, who's moved into her building on a wealthy woman's dime. As romance blooms between Paul and Holly, Doc Golightly shows up on the scene, revealing Holly's past.

actors:
Audrey Hepburn as Holly Golightly   George Peppard as Paul „Fred“ Varjak   Patricia Neal as 2-E (Mrs. Failenson)   Buddy Ebsen as Doc Golightly   Martin Balsam as O. J. Berman   Mickey Rooney as Mr. Yunioshi   José Luis de Villalonga as José da Silva Pereira   John McGiver as Tiffany's salesman   Alan Reed as Sally Tomato   Dorothy Whitney as Mag Wildwood   Beverly Powers as Dancer at nightclub   Stanley Adams as Rusty Trawler   Claude Stroud as Sid Arbuck   Elvia Allman as Librarian   Orangey as Cat  

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5 Amélie
imdb
rating

8.4

Amélie (2001)

Comedy, Romance

Director Jean-Pierre Jeunet (Delicatessen, The City of Lost Children) has a flair for imagining France in a twisted and peculiar light, and it’s on full display in Amélie — the story of a young recluse played with a mesmerising childlike quality by then little-known Audrey Tautou. Amélie is a shy girl who delights in skimming stones, cracking crème brulee and imagining how many people in the world are orgasming at any given moment, while she loves carrying out kind-hearted pranks on the people around her. She’s quite content living in her own fantasy world until chance hitches her fate to Nino Quincampoix (Matthieu Kassovitz), whom she begins to pursue around Paris like the world’s cutest stalker. Amazingly, Amélie was rejected by the Cannes Film Festival because one of the selectors found it “uninteresting”. Go figure.

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At a tiny Parisian café, the adorable yet painfully shy Amélie (Audrey Tautou) accidentally discovers a gift for helping others. Soon Amelie is spending her days as a matchmaker, guardian angel, and all-around do-gooder. But when she bumps into a handsome stranger, will she find the courage to become the star of her very own love story?

actors:
Audrey Tautou as Amélie Poulain   Mathieu Kassovitz as Nino Quincampoix   Rufus as Raphaël Poulain   Jamel Debbouze as Lucien   Claire Maurier as Suzanne   Isabelle Nanty as Georgette   Dominique Pinon as Joseph   Artus De Penguern as Hipolito   Yolande Moreau as Madeleine Wallace   Lorella Cravotta as Amandine Poulain   Serge Merlin as Raymond Dufayel   Clotilde Mollet as Gina   Urbain Cancelier as Collignon   Maurice Bénichou as Dominique Bretodeau   Michel Robin as M. Collignon   Andrée Damant as Mme. Collignon   Claude Perron as Eva   Armelle as Philomène   Ticky Holgado as L'homme dans la photo   Marc Amyot as L'inconnu des photomatons  

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4 Chasing Amy
imdb
rating

7.4

Chasing Amy (1997)

Comedy, Drama, Romance

Basically, the story goes like this: boy meets girl, boy likes girl, boy discovers girl is actually a lesbian. Typically, boy thinks he can “convert” girl. Trouble ensues. Kevin Smith’s highly quotable and unusual take on modern day expectations of love flirts with the idea of sexuality and relationships in a humorous and honest manner. It’s the ultimate tale of unrequited love, dealing cleverly and carefully with some pretty complex and controversial topics. Who could forget gay, black-power advocate Hooper’s wisdom on why he doesn’t feel obligated to stick up for lesbians? “Screw that ‘all for one’ s***, alright? I gotta deal with being a minority in a minority of the minority, and nobody’s supportin’ my ass!”

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Holden and Banky are comic book artists. Everything is going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's a lesbian.

actors:
Ben Affleck as Holden McNeil   Joey Lauren Adams as Alyssa Jones   Dwight Ewell as Hooper LaMont   Scott Mosier as Collector   Ethan Suplee as Fan   Casey Affleck as Little Kid   Jason Mewes as Jay   Brian O'Halloran as Exec. #1   Matt Damon as Exec. #2  

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3 Juno
imdb
rating

7.5

Juno (2007)

Comedy, Drama, Romance

Jason Reitman and Diablo Cody’s Academy Award-winning teen pregnancy comedy is one of the quirkiest — in the best sense of that word — high school flicks in quite some time. Rather than the usual teenage movie caricatures, the movie’s characters reflect the sarcastic but emotionally vulnerable life of real high schoolers (or at least Cody’s imagination, anyway). That is until 16-year-old Juno becomes unexpectedly “Fo’ shizz up the spout” by Michael Cera’s goofy Paulie Bleeker. Romantic comedy of the most offbeat kind results, as the characters try to negotiate both their burgeoning puppy love and Juno’s baby-adopters… all framed within Reitman and Cody’s original little universe.

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A young girl named Juno gets herself pregnant and tries to stand on her own. She soon learns a few lessons about being grown up.

actors:
Ellen Page as Juno MacGuff   Michael Cera as Paulie Bleeker   Jennifer Garner as Vanessa Loring   Jason Bateman as Mark Loring   Allison Janney as Bren MacGuff   J.K. Simmons as Mac MacGuff   Olivia Thirlby as Leah   Eileen Pedde as Gerta Rauss   Rainn Wilson as Rollo   Daniel Clark as Steve Rendazo   Candice Accola as Girl Lab Partner   Aman Johal as Vijay   Eve Harlow as Tough Girl   Valerie Tian as Su-Chin   Emily Perkins as Punk Receptionist  

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2 Eternal Sunshine of the Spotless Mind
imdb
rating

8.4

Eternal Sunshine of the Spotless Mind (2004)

Drama, Science Fiction, Romance

Eternal Sunshine of the Spotless Mind is a story conjured up by two of the most remarkably imaginative and individual filmmakers working in movies — screenwriter Charlie Kaufman and director Michel Gondry. Together they take us on an almost voyeuristic journey inside the fraying relationship between the reserved, nervous Joel (Jim Carrey) and the unpredictable, outgoing Clementine (Kate Winslett). Frustrated, Clementine impulsively has her mind erased of all of her memories of Joel; and the forlorn Joel follows suit. Gondry and Kaufman’s dive into Joel’s subconscious as he tries to cling to his evaporating memories of Clementine is alternately comedic and heart-wrenching — who hasn’t felt the desire to rid ourselves of a painful memory, the hurtful things that we have said, or the vulnerable moments we have shared? Eternal Sunshine challenges our beliefs on love, and asks us if ignorance is indeed bliss…

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A man, Joel Barish, heartbroken that his girlfriend Clementine underwent a procedure to erase him from her memory, decides to do the same. However, as he watches his memories of her fade away, he realizes that he still loves her, and may be too late to correct his mistake.

actors:
Jim Carrey as Joel Barish   Kate Winslet as Clementine Kruczynski   Elijah Wood as Patrick   Mark Ruffalo as Stan   Kirsten Dunst as Mary   Tom Wilkinson as Dr. Howard Mierzwiak   Ryan Whitney as Young Joel   Debbon Ayer as Joel's mother   Gerry Robert Byrne as Train Conducter   Brian Price as Young Bully   Josh Flitter as Young Bully   Paulie Litt as Young Bully   Lola Daehler as Young Clementine   Amir Ali Said as Young Bully   Deirdre O'Connell as Hollis   Lauren Adler as Rollerblader  

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1 Annie Hall
imdb
rating

8.1

Annie Hall (1977)

Comedy, Drama, Romance

Arguably the quintessential Woody Allen comedy and certainly one of the great romances in movies, Annie Hall is also our favourite offbeat rom-com — and one that’s inspired so many others, for both better and worse. Allen’s film retrospectively questions where a failed relationship has gone wrong. As Alvy, a comedian who is re-examining his break up with the frivolous Annie (played by Diane Keaton), Allen overanalyses the ups and downs, the screw ups and the bonds, in a way that attempts to find an upside to the failure of his one true love. Ultimately, Allen’s humour lies in his comedic ability to mock himself. As Alvy says, the reason why he lets his relationship fail is like that “Old Groucho Marx joke” — he doesn’t want to belong to any club that would have him as a member.

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The neurotic New Yorker Woody Allen tells one of the greatest romantic comedies to be set in the city of New York.

actors:
Woody Allen as Alvy Singer   Diane Keaton as Annie Hall   Tony Roberts as Rob   Carol Kane as Allison   Shelley Duvall as Pam   Janet Margolin as Robin   Colleen Dewhurst as Mrs. Hall   Christopher Walken as Duane Hall   Donald Symington as Mr. Hall   Helen Ludlam as Grammy Hall   Mordecai Lawner as Mr. Singer   Joan Neuman as Mrs. Singer   Jonathan Munk as Alvy Singer - Age 9   Dick Cavett as himself   Marshall McLuhan as himself   Jeff Goldblum as Lacey Party Guest   Shelley Hack as Street Stranger (as Shelly Hack)   Beverly D'Angelo as Actress in Rob's TV Show   Tracey Walter as Actor in Rob's TV Show   Sigourney Weaver as Alvy's Date Outside Theatre   Truman Capote as Truman Capote Look-Alike (uncredited)   Laurie Bird as Tony Lacey's Girlfriend  

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