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Fall In Love: The Playlist’s Favorite Romantic Comedies

Fall In Love: The Playlist's Favorite Romantic Comedies

Few genres of film inspire more personal responses than the romantic comedy. Given how much of our lives is spent on love and romance (falling into it, falling out of it, chasing it, giving up on it), it’s no surprise that the rom-com has remained one of the most 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…)

Today sees the release of “The Five-Year Engagement,” a Judd Apatow-produced romantic comedy starring Jason Segel and Emily Blunt, and while it doesn’t quite hit the heights of “Annie Hall” and “When Harry Met Sally” that it was aiming for (read our review here), it’s as good a stab at the genre as we’ve had in recent years. To celebrate the film’s release, we decided to acknowledge that personal connection of the genre, and rather than try and pick a definitive list, The Playlist team picked their own personal favorites. Some are classics, some are undersung gems, but all blend laughs and love in a way that’s lingered in the memory. Check our picks out below, and you can let us know what your favorites are in the comments section.

“My Man Godfrey” (1936)
In the pantheon of great screw-ball comedies, “My Man Godfrey” has often been passed over in later years in favor of films like “Bringing Up Baby” and “It Happened One Night.” But ‘Godfrey,’ starring divorced-but-friendly couple William Powell and the luminous Carole Lombard is a gem that should not be overlooked. This Depression comedy features Lombard as the silly, flighty younger daughter of a wealthy family, and the suave, dapper Powell as a homeless man (one of the Forgotten Men of the Depression) whom she hires to help her win a scavenger hunt (yep, he’s one of the spoils) and then to be her family’s butler, where of course she falls in love with him. Powell is at the height of both his comedic and dramatic power — this could be his best role, even better than Nick Charles in “The Thin Man” series, because his character is more grounded and real than the droll detective. He was noticed by Oscar for this one too, one of his three nominations. Of course, as it’s revealed, he’s actually the scion of a wealthy family in Boston, down and out over an affair gone wrong. He keeps Lombard’s Irene at bay, driving her to battiness, and Lombard pulls off the wacky role with panache. Though the Depression issues grounds it firmly in its time, it also keeps the stakes incredibly real within this world of dizzy debutantes. ‘Godfrey’ holds up years down the line, due to Powell and Lombard’s performances, aided in support by the hijinks of the family around them. Scenes with Mother’s Spanish protege Carlos remain hysterically funny, while a romantic scene of Powell and Lombard washing dishes together should be in the canon of iconic romantic scenes in film. You’ll swoon just like Lombard over “My Man Godfrey” (and it’s on Netflix Instant!) — Katie Walsh

“Eternal Sunshine of the Spotless Mind” (2003)
Pigeonholing Michel Gondry’s beautiful, melancholy ode to breaking up as simply a romantic comedy is like calling a Bloody Mary tomato juice. But while rom-com is one ingredient in this genre cocktail that also includes science fiction, comedy, special effects and melodrama (all sprinkled with a heavy dose of dream/nightmare logic), it’s clearly the genre that gonzo screenwriter Charlie Kaufman was most concerned with turning on its head. And does he ever. “Eternal Sunshine of the Spotless Mind” is, for this writer, one of the very best films of the aughts, endlessly rewatchable with something new to be found with every viewing. But also, Kaufman and Gondry (who shared a deserved Oscar win for screenwriting that year, along with Pierre Bismuth) authentically capture the feeling of breaking up and all the messiness that comes with it. Being mostly averse to the romantic comedy genre as it stands today (shitty Katherine Heigl joints, regurgitated indie weepies, et al.), the only thing that could possibly feel different and exciting would be to mash it up with other types of films into something wholly modern. ‘Eternal Sunshine’ was a confluence of many special parts: a near-perfect script, Ellen Kuras’ inventive cinematography, Jon Brion’s perfectly attuned silent film-esque score, Kate Winslet’s finest hour onscreen (she should’ve won the Oscar for this role) and the rest of the spot-on cast. Gondry has yet to match the heights he achieved here. It was the perfect blending of what the inventive but messy French director does best. And yeah, it’s romantic, truthful, funny and sad, sometimes all at once. Sure, it’s many things, but at heart this film is a romantic comedy puzzle that begins in pieces, but by the open-ended climax (will they or won’t they?) forms into a masterwork of genre deconstruction. — Erik McClanahan

“Overboard” (1987)
As far as comedic set-ups go, they don’t get much broader than Garry Marshall’s “Overboard,” wherein Goldie Hawn‘s bitchy heiress falls off her luxury yacht, gets amnesia, and is tricked by Kurt Russell, a lowlife carpenter who previously worked on her boat, into thinking she is his wife (and mother to his four human-tornado kids). In terms of romantic comedy realism, this isn’t going to be mistaken for anything even remotely naturalistic. But it’s really, really funny, and really, really smart (it has a script by wonder woman Leslie Dixon, who wrote everything from “Mrs. Doubtfire” to the terrific “Thomas Crown Affair” remake to last year’s underrated what-if thriller “Limitless“) and the chemistry between Russell and Hawn is palpable and spiky and totally intoxicating. The most striking thing about “Overboard” might be that it succeeds to become a romantic comedy classic in spite of Marshall’s truly awful direction and staging (and the occasionally insufferable Alan Silvestri score). In terms of romantic comedies it hits that sweet spot between wackiness and big-heartedness, exemplified perfectly by the relationship between Hawn and Russell’s devilish kids. (The supporting cast is also top notch — Edward Hermann plays Hawn’s yacht-loving husband in a role that predates his performance in “The Cat’s Meow,” his butler is played by the film’s producer Roddy McDowall.) Also: it’s pretty sexy, especially for a PG-rated comedy the whole family was encouraged to see; Hawn was never prettier and it’s rare in romantic comedies to actually buy that the leads are dying to have sex with each other (in this case, they actually were!). Now if only the studio would release a Blu-ray of the extended cut that you can occasionally catch on TCM. “Overboard” fans would be over the moon. — Drew Taylor

“The Jerk” (1979)
No moment speaks to lovelorn nerds quite as much as the moment in “Freaks And Geeks” when young Sam Weir takes dreamgirl Cindy Sanders to see “The Jerk” only for her to trash the picture and spend the runtime without laughing once. It wasn’t just that Cindy now had rotten taste, but more that she didn’t see the heart busting out between the jokes of “The Jerk.” They couldn’t be friends, yes, but more importantly, they could NEVER be lovers. Although not traditionally considered a “romantic” comedy, there’s no doubt the union of an at-his-peak Steve Martin and the bubbly, warm Bernadette Peters provided the heart for what would have still been a funny, though far less memorable movie. Martin’s Navin Johnson doesn’t exactly have direction until he crosses paths with squeaky voiced Peters as Marie, a kewpie-doll angel that joins him on a beach date both funnier and more romantic than any of Martin’s contemporaries had pulled off. As the two tackle the harmony to “Tonight You Belong To Me,” the heart soars — this was back in the day when a comedy could be more than just a laugh-fest — and the break in action provided a welcome respite from the film’s string of gags. No doubt an entire generation of nerd offspring owes their existence to Mom and Dad watching Martin and Peters hum along like a well-oiled comedy machine. — Gabe Toro

“Reality Bites” (1994)
When in doubt to pick a “favorite,” it’s always safe to default to “the one you’ve seen the most times” and as far as romantic comedies go, for this writer it would have to be “Reality Bites.” I was born in November ‘81 so I just made the Generation X cutoff, though missed the film upon its initial 1994 release. However, a few short years later it became an indispensable part of my high school years, playing on a loop (along with Alfonso Cuarón’s “Great Expectations” and a lot of Radiohead) during a stretch of teenage heartbreaks. Helen Childress’ excellent screenplay pivots between comedy and drama effortlessly, tackling big issues like AIDS and coming out to your parents while still making room for a gas station set dance party to “My Sharona.” (Disappointingly this is Childress’ only screenplay credit to date though there was talk of her reteaming with Stiller on a new project.) Like many guys of my generation, this film was responsible for a massive decade-long crush on Winona Ryder. As Lelaina Pierce, the valedictorian-turned-documentarian, the actress has never been better: intelligent but naive, driven and charming, Ryder’s character was the antithesis of the quirky MPDG’s that would rule the screen in the decade to come. Here she’s pursued by two contrasting love interests: idealistic slacker Troy Dyer (Ethan Hawke, playing what to this day people believe to be a version of himself) and yuppie TV exec, Michael Grates (Ben Stiller, also making his directorial debut). Stiller unselfishly takes the douchebag role and manages to play him as a likeable but misguided counterpoint to Hawke’s flaky rocker Troy, but in the end there can be only one. Featuring ace supporting turns from Janeane Garofalo and Steve Zahn, sharp cinematography by Emmanuel Lubezki and a great soundtrack featuring gems from both the ‘80s (The Knack, Squeeze) and ‘90s (Dinosaur Jr., Lisa Loeb), the film may be a time capsule but it’s one I’m happy to dig up again and again. — Cory Everett

“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” (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” (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” (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” (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

“Bringing Up Baby” (1938)
Boy meets girl. Girl stalks boy in order to get him to look after her leopard. Girl falls in love with boy who’s about to get married. Girl’s dog steals dinosaur bone. Leopard runs away. Boy and girl sent to prison. Boy ends up in a dress. Boy falls in love with girl right back. Not exactly a Garry Marshall movie, but so much the better. Howard Hawks‘ 1938 film neatly followed the template set up by “It Happened One Night” in setting up a boy and a girl — in this case soon-to-be-wed paleontologist David (Cary Grant) and prototypical Manic Pixie Dream Girl heiress Susan (Katharine Hepburn) — to bicker and flirt across a series of adventures before falling in love at the end. But the formula was never quite as perfect as it was here, in part because Hawks retained what’s so often absent in romantic comedies today. Simply, “Bringing Up Baby” is one of the funniest films ever made, riding the outstanding chemistry between Grant and Hepburn, each arguably giving the performance of their careers, through a series of uproarious set pieces. But as funny as the film is, Grant and Hepburn’s courtship feels genuinely hard won, and you don’t question the way that Grant’s defenses gradually come down. It’s also unusually subversive, especially for the era — Grant is increasingly feminized, even to the point of ending up in a dress, while Hepburn was always one of the more masculine starlets, and it’s her that’s doing the pursuing. Maybe it’s not a film that makes you swoon in the way of some of these other choices, but you’ll be too busy battling a chortle-induced hernia to notice. — Oliver Lyttelton

“Annie Hall” (1977)
The moment in “Annie Hall” when Alvy Singer (Woody Allen) tries to recreate the lobster cooking moment that he originally shared with Annie (Diane Keaton) but with a different girl says a lot about the romantic comedy genre itself. Often limited by its conventions, there are times when the romantic comedy genre still seems fresh and inspired and other times, let’s say most of the time, the formula seems dull and flat. When it was released in 1977, “Annie Hall” was a game-changer for the genre, and one of the few to win a Best Picture Oscar. The film also signaled a sea change for Allen, who would begin to transition out of his “early, funny” films and into more serious territory. The reason why the film endures, outside of being hilarious, is its refreshing honesty. While most romantic comedies are focused on showing two people discovering their true love through a series of outrageous misunderstandings, “Annie Hall” watched two people fall in and out of love with one another in a story that didn’t feel completely predestined. Sure, Allen’s Singer starts the movie wondering where things went wrong with Annie, but, in any other romantic comedy, the two leads would find a way to make it work in the end. “Annie Hall” isn’t about pat endings. It’s a comedy about the pursuit of love, and bumps along the way of finding a perfect match. Its honesty about the ups and downs of relationships is something few filmmakers have matched since. — Ryan Gowland

“Broadcast News” (1987)
Much like James L. Brooks did with his comedy-drama “Terms of Endearment,” which saw what could have been a maudlin cancer drama turn into a charming slice of Americana comedy, in 1987’s “Broadcast News” he took a romantic comedy formula we’ve seen in so many films and turned it on its head. The film stars the always affable Holly Hunter as the highly-touted news producer Jane, who’s caught in the middle of the affections of her dear friend Aaron (Albert Brooks) and the handsome news anchorman Tom (William Hurt), and the story film follows Jane’s quest to be seen as sexually attractive in the eyes of Tom. She ignores Aaron’s frequent advances, allowing Brooks to bring sympathy and relatability to a role that’s essentially Duckie from “Pretty In Pink.” In a role that was originally intended for Brooks’ ‘Terms’ lead Debra Winger, Hunter parts from the typically shrill depiction of the hardworking woman that’s been employed in films since, allowing audiences to relinquish in her quest for Aaron’s attention while also sympathizing with her shaky relationship with Aaron. It’s no surprise all three leads walked away with nominations for their performances, along with Brooks for his writing and Best Picture, as well as Martin Scorsese’s regular cinematographer Michael Ballhaus – who lends “Broadcast News” a cinematic look that certainly breaks away from the sitcom-level look of most romantic comedies today. Up until the film’s sweet climax, which lends a grounded realism to the love triangle that sends sparks flying throughout the film’s running time, “Broadcast News” acts as a romantic comedy that surely provides all the laughs, heart, and drama that you find in most Hollywood romcoms these days. — Benjamin Wright

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