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Fall In Love: The Playlist's Favorite Romantic Comedies

Photo of Oliver Lyttelton By Oliver Lyttelton | The Playlist April 27, 2012 at 10:56AM

Few genres of film inspire more personal responses than the romantic comedy. Given that you spend a disproportionate time of your life thinking about your romantic woes, it's no surprise that it's remained one of the popular formulas since the dawn of cinema, and while the genre has undisputed classics, you can end up cherishing certain films purely because of their connection to your own life. They can help pull you out of a post break-up tailspin, they can comfort you through unrequited love, and, if a film hits you at the height of your passion for someone, they can end up associated forever, even blinding you to the movie's flaws -- seeing "Elizabethtown" in the midst of first love left this writer swooning after exiting the theater (thankfully, a subsequent rewatch put me straight as to how terrible it is...)
20

Trouble In Paradise
"Trouble In Paradise" (1932)
It may be eighty years old, but few rom-coms since have matched the cleverness, wit, sexiness and sheer joy of the meet-cute (a term that barely holds a candle to the sophistication of the film) that opens Ernst Lubitsch’s “Trouble In Paradise.” The dashing and infamous Gaston Monescu (Herbert Marshall) and the gorgeous Lily (Miriam Hopkins) -- both thieves -- are in Venice, and on a date under the guise of being a Baron and a Countess, but it isn’t long before the crooks realize they are in like-minded company. After they flirt by showing what they have lifted off one another over the course of the evening, Gaston closes the deal with a simple rhetorical question, “You know the man that walked into the bank of Constaninople, and then walked out with the bank of Constantinople?” It’s love. Fast-forward and Gaston and Lily are happily together, scheming their way around Europe, when Gaston sets his eyes on Madame Mariette Colet (Kay Francis), the widowed owner of a lucrative cosmetics company. With more money than she knows what to do with, Gaston wheedles his way into becoming her personal secretary, taking over both her business and personal finances with an end game to make off with as much cash as he can. But of course, he starts falling for her too, and Gaston is forced to choose between his love of money and the love of his life. Based on a play, the film isn’t exactly cinematic, but it hardly matters when the wordplay is as sharp and dazzling as it is here. Marshall carries the film with a confident swagger that makes you believe this man could work his way into the heart and business of a woman in a matter of weeks. And Hopkins and Francis are no mere shells, showing two wildly different women -- one cool and collected, the other impulsive and passionate -- who both have plenty to offer Gaston. It’s a tricky balancing act but the film’s finale, which sees Lubitsch masterfully write his way to an ending that sees all three get what they want and then mirror the opening sequence to top it all off (has pickpocketing ever been done as an act of affection since?), is a total joy to behold. Yes, the film is a total fantasy -- two thieves moving from European capital to another, swindling their way through life -- but Lubitsch knows if the feelings aren’t genuine it won’t work, and by the end of the picture, you really are rooting for Gaston to make the right choice. It’s hard to explain just how brilliant and breezy (the movie runs at a crisp 82 minutes), deeply romantic and laugh out loud funny “Trouble In Paradise” is without just rolling out a bunch of quotes, but this one, spoken by Lily trying to hang on to her man, sums it up best: “Darling, remember, you are Gaston Monescu. You are a crook. I want you as a crook. I love you as a crook. I worship you as a crook. Steal, swindle, rob. Oh, but don't become one of those useless, good-for-nothing gigolos.” Divine. -- Kevin Jagernauth

It Happened One Night
“It Happened One Night” (1934)
While Howard Hawks' “His Girl Friday” is a wonderful almost anti-romantic comedy and perhaps considered the blueprint for couples that have to duke it out before they can fall in love, perhaps an even more pugnacious would-be relationship film is Frank Capra’s “It Happened One Night.” The first film to win all five major Academy Awards (Best Picture, Director, Actor, Actress, and Screenplay and only two other films have done that since), while “It Happened One Night” is often considered a classic romantic comedy, it’s actually quite sarcastic and much more of a traditional screwball comedy with its elbow-to-the-ribs repartees. And to be blunt about it, it’s not that romantic. Clark Gable and Claudette Colbert star as a rakish newspaper reporter and a pampered and recently married heiress who fall for each other on a cross-country trip despite their clashing temperaments. The pair are as mismatched as can be; she’s trying to get out from under her overbearing father’s thumb (who’s trying to annul her marriage) and runs away and he selfishly smells the scoop of the century when he realizes who she is. What ensues are almost corrosive verbal fireworks between the two. He thinks she’s a spoiled brat, and she believes he’s a gruff, self-serving jackass. While they’re both on the mark, this witty, hilarious picture, written by Capra-regular Robert Riskin, makes the most of this unlikely pair with its jagged and droll battle-of-the-sexes humor and unsentimental approach to romance. There’s a lot of deep and understated affection in the comedy, but the way the picture uses diverting sharp barbs to mask those sentiments is incredibly sophisticated for its time. Then again, maybe this movie just indicates that I was born four decades too late. Extra bonus points. I’ve always loved a wisenheimer and Clark Cable’s character in the film is a big influence of one of my most beloved wiseasses of all time: good ol’ Bugs Bunny. -- RP

Two For The Road
“Two For The Road” (1967)
Landing smack-dab in the middle of three '60s films depicting fractured relationships with a French New Wave influence to accompany it (the other two being the Julie Christie vehicles “Darling” and “Petulia”), Stanley Donen's 1967 gem “Two For the Road” excels above the rest by delving beneath its surface romantic-comedy appearance to its characters' romantic desperation underneath. Albert Finney and Audrey Hepburn play the doomed couple in question, wondering over the course of a European vacation about the solution to their marriage crisis, told in a near-experimental non-linear fashion, and the result is a beautiful travelogue, filled with still-relevant insights, a stellar Henry Mancini score, and Frederic Raphael's bold, witty screenplay at its core. The film is dated, sure, but never in an embarrassing way. Hepburn's eccentric fashion choices (read: leather pantsuits) still somehow look incredible, and the slightly stale observations (What kind of people just sit in a restaurant and don't say one word to each other?" Finney asks Hepburn during dinner) are rescued by Finney and Hepburn's flawless chemistry and comedic timing. They aim for that conflicted feeling of simultaneous hatred mixed with undeniable affection, and it's to both actors' credit that they shed any self-image worries to portray it accurately. “Annie Hall” and “Eternal Sunshine of the Spotless Mind” would be nothing without these radical genre attempts, so you owe it to yourself to catch up on this Donen classic, if you haven't already. -- Charlie Schmidlin

High Fidelity
“High Fidelity” (2000)
Is "High Fidelity" a romantic comedy devoid of romance? The main thrust of Stephen Frears’ (seamlessly relocated from London to Chicago) adaptation of Nick Hornby's novel comes when John Cusack’s Rob Gordon splits up with his long-time girlfriend Laura, prompting him to go back and pick over the bones of his Top 5 Break-Ups. It’s all rather more tragic than it is romantic, and as a result the associated comedic moments are dry and sardonic. This is a very different John Cusack romantic lead – while Lloyd Dobler stood outside his girl’s window holding a boombox, the laconic Rob Gordon stands in the same place shouting bitter obscenities. Even as the story progresses and the outlook becomes brighter, the romance is still decidedly lacking in areas which are usually ripe for it – a sex scene and a proposal, in particular. But while the romance may be lacking, the things that you associate with it aren’t. "High Fidelity" is about learning how to love someone, the importance of companionship, and the beauty in two people simply being able to make one another happy. That brings with it an authenticity, which -- coupled with a stunning musical backdrop and a pitch-perfect, fourth-wall breaking performance from John Cusack –- sets it apart from the crowd, while ultimately remaining just as sweet and life-affirming as so many of its peers. -- Joe Cunningham

Harold And Maude
"Harold and Maude" (1971)
As far as loveable rom-com couples go, it's hard to look past Hal Ashby’s "Harold and Maude." It's the kind of film I can't really imagine being made today, with the story centering on the innocent romance between the young death-obsessed Harold (played by Bud Cort) and the 79-year-old and carefree Dame Marjorie “Maude” Chardin (Ruth Gordon). The film's setup of Cat Stevens singing "Don't Be Shy," as Harold methodically goes through the motions of faking his own death, to the complete lack of amusement or shock of his mother who walks in on him, sets the tone beautifully for this romantic comedy, that balances its blackish heart with a sweet first love/coming of age story. Harold and Maude meet at a mutual stranger’s funeral, and Harold falls hard for Maude, who shows him there is more to life than death e.g. flowers, dancing and playing the banjo, which in the hands of a lesser actress would be insufferably twee. Though Cort was in his early 20s when the film was made, his wide-eyed stare and floppy hair make him appear eternally boyish, in contrast with Gordon’s Maude, who is in no way the graceful ageing lady – but as a couple they are incredibly endearing, and the film's effective statement of a deep connection winning over superficiality in the game of love should not be overlooked. Laughs come courtesy of Harold’s idiot mother who tries to set him up with various prospective wives, who he frightens off with more phony, gore-filled suicide attempts so he can instead go on adventures with Maude and her petty-crime sprees. Ashby made the inspired choice of having Cat Stevens soundtrack the film, perfectly underscoring some of the sadder moments, to the point of tears on more than one occasion for this writer. In fact, it's the film's mix of deadpan humour and heartfelt emotions that make it so adorable and continuously watchable. -- Sam Chater

This article is related to: Features, The Five-Year Engagement


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