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Fall In Love: The Playlist's Favorite Romantic Comedies

by Oliver Lyttelton
April 27, 2012 10:56 AM
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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

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  • Nia | May 8, 2012 11:08 AMReply

    well its a "omantic comedies" list so why Punch Drunk Love and Berfore Sunrise/Sunset should even be mentioned I dont understand Eternal Sunshine is probably my fav movie - hadnt realized it coukd be considered a rom-com so yeah! I've got a weak point for Bridget Jones 1 and I'm glad Bridesmais wasnt mentioned cause - over-rated much?!

  • Nia | May 8, 2012 11:10 AM

    oh god the typos: "well its a "romantic comedies" list so why Punch Drunk Love and Before Sunrise/Sunset should even be mentioned I dont understand. Eternal Sunshine is probably my fav movie - hadnt realized it could be considered a rom-com so yeah! I've got a weak point for Bridget Jones 1 and I'm glad Bridesmais wasnt mentioned cause - over-rated much?!

  • Lilly | May 3, 2012 2:32 PMReply

    I love My Man Godfrey, William Powell is one of my all-time favorite actors he and Carole Lombard had such great chemistry in that movie. I love the part where she kissed him and he looks at her all befuddled and tries to walk away with as much of his dignity as he can, but you know she got to him.

  • Domi Arcangeli | May 1, 2012 9:27 AMReply

    Uhm... HighFidelity is way overrated, and I hate not seeing "Punch-Drunk Love, by my favorite P.T. Anderson, but again, after seeing-in the same article - Stanley Donen's very charming, but aged and very telephoned mainstream fare like "Two for the Roads",preferred to 2 classic's of the same Time, Schlesinger's much more poignant, unforgettable "Darling" (Best Actress Oscar to Julie Christie and to its Screenplay from the divine Frederic Raphael,who also penned the way minor,if still sophisticated,"Two for the Roads") and,then, one of the most innovative,brilliant,if unsettling, romantic bitter sweet comedies of all time, Richard Lester's masterpiece"Petulia"(1968) starring also Julie Christie (whom by the way, had turned down "Two for the Road" finding it less unique than the other two!) at her very top, and lit by genius Nicolas Roeg,with a dazzling,unforgettable production design by Tony Walton and Dean Tavoularis (Academy Award for Apocalypse Now,1980), well, after such considerations, I am not surprised to see memorable titles left out of much more less memorable others!
    Sorry! It started real well by remembering a real gem, like, 1936's Carol Lombard's classic masterpiece "My Man's Godfrey",but it's been going down, citing a few well known and more conventional films after another!
    By the way, since, we love Julie Christie, hey, i don't know if the true Classic, "Shampoo"(1975), could be really considered somewhat of a romantic comedy also; and,even though there's a lot of romance at the end, the film is more focused on developing its deeply flawed characters,while portraying with incredible Gusto,unfolding with wit and some of the most clever odd moments ever seen in a mainstream huge film,an array of situations that remain classic and still completely true, even today! That yes, was an incredible film who should be cited more often, WOW, if I only think about such a phenomenal script by Robert Towne(probably his very best, right next to "Chinatown") so insightful and disenchanted in describing that riot of a plot, yet always with the firm realism necessary to nail, once and forever, the absolute,corrupted game between love,power,politic's and,of course, hair and appearance, in one of the finest and most sophisticated,haunting portraits of LA, or better, Beverly Hills, ever, and i mean, truly ever filmed,so far,lining up a cast of stars that besides the already cited,Christie, truly divine here,portraying the jaded Jackie Shawn, but also, Warren Beatty, probably at his very peak, both as a movie star and as a clever Producer and strength, behind this incredible film, but also a smashing supporting Cast, featuring some of its Stars' Best Performances ever: Goldie Hawn (truly never so measured and touching as in this one,ever again!), Lee Grant (truly incredible and rightly Awarded by an Oscar for her great supporting turn as the most wealthy and most unhappy of the Beverly Hills wives ever seen on screen!),the outstanding Jack Warden, here also probably getting his most defining role of his long Film and Stage Career, and even Tony Bill and Carrie Fisher, Andrew Stevens or others classic Hollywood's characters directed and cast as their most finest! Hal Ashby ("Harold and Maude" and "Being There", and that's saying something, isn't it?) directed this masterpiece, whose fame, directors and cast should be remembered way more often! If you haven't seen it, this is a MUST!! Forget "High Fidelity", please...... lol

  • jimmiescoffee | April 30, 2012 9:00 PMReply

    i like 'High Fidelity' but think its very overrated.

  • Luke | April 29, 2012 7:00 PMReply

    I was surprised to see Punch-Drunk Love didn't make the list.

  • Lucy | April 29, 2012 6:20 PMReply

    Haha great picks, some of my favorites! :) I agree with some of the other posters Before Sunrise and Before Sunset ( the latter is my favorite) also You've Got Mail I don't know why but that movie is so damn charming.

  • Rosanna | April 29, 2012 12:15 PMReply

    FINALLY you write about the only genre of film worth writing about!

  • Jorinhs | April 28, 2012 7:50 AMReply

    Give a listen at my aternative soundtrack to Eternal:)

  • Milan | April 27, 2012 8:02 PMReply

    Grosse Pointe Blank. That is all.

  • Dan | April 27, 2012 5:35 PMReply

    Fuck overboard. and i agree with whoever said the apartment. that is all.

  • Lou | April 27, 2012 3:33 PMReply

    Definitely, maybe? The neighbour's grass? The apartment? Indiscreet?

  • shark | April 27, 2012 2:19 PMReply

    Really interesting list. Hmmm...if I were restricted to films not listed here for my favorite rom-coms list...

    Down With Love - It's so artificial, and yet that artificiality is its entire point, acknowledging that the battle of the sexes is a silly facade. And Zellweger and McGregor (and Hyde Pierce and Paulson) have NEVER been better. And I can't help but wonder if Pierce and Paulson were deliberately cast, as Pierce is out gay and Paulson is out lesbian.
    Music and Lyrics - Okay, so it's not directed with much flair or anything other than plain competence. That aside, Hugh Grant and Drew Barrymore just WORK. And if nothing else, the music is fucking amazing. I still listen to Pop! Goes My Heart and Way Back into Love all the time.
    Punch-Drunk Love - Well, duh. I don't know what I can say here that hasn't been said elsewhere, but a film that manages to turn Sandler's manchild instincts into a source of strength rather than a crippling flaw is impressive. Also, it's kind of a super-hero film. Or an alien film. Kind of open to interpretation.
    WALL-E - Okay, so it's also an animated science fiction film. But the core story is about a lonely janitor who meets a dream girl and then EARNS her love the hard way, following her across the galaxy and beating his programming just to fulfill HER objective. Okay, granted, you could take it as the ultimate Internet Nice Guy story, but I choose not to, okay?
    Ninotchka - God, I wish Garbo had been a comedy star. Knowing this is her only major comedy role is DEVASTATING, because she takes to it like a fish in water. Or like a conservative politician at an NRA meeting. Well, you get the idea.
    Raising Arizona - Because romantic comedies don't have to be about meet-cutes. Some of the best are about husbands and wives falling back into love with each other, or renewing their commitment, or proving themselves to each other. And I can't think of many screen couples I wanted to succeed while watching the film more than Hi and Ed.
    Adam's Rib - Another terrific dissection of the BATTLE OF THE SEXES. Spencer Tracy was always sort of manly, but he tended to be best at playing deeply empathetic characters with a more feminine sense of understanding for his fellow man, and so his match with Hepburn is screen bliss, a hard-driving woman and a sympathetic man, each testing at the boundaries of their gender while at each other's throats.
    What's Up, Doc? - because before seeing this movie, I hated Barbra Streisand. And now I can't. Also because Ryan O'Neal is a seriously underrated actor (or he was just used well in three masterpieces: Doc, Paper Moon, and Barry Lyndon). And that chase down the streets of San Francisco is pure madcap bliss.
    Moonstruck - I guess I'd have to say Nic Cage was never better than as a goofy romantic figure. I mean, I know it's cheesy and maybe full of stereotypes, but every actor brings these stereotypes into the realm of living, breathing humans. Not just Cage and the divine Cher, but Dukakis, Gardenia, Mahoney, Aiello, and the rest.

  • TheoC | April 27, 2012 12:24 PMReply

    Oh Overboard or "that Kurt Russell date rape movie".

    Nice list all the same.

  • Shala | April 27, 2012 12:17 PMReply

    Corey, I was also born in November '81 and agree with all your sentiments on "Reality Bites". Great list from everyone. Glad to see "Eternal Sunshine" but also disappointed not to see "Before Sunrise/Sunset" probably my favorite of all.

  • Kyle | April 27, 2012 11:28 AMReply

    I agree, You've done a really great job with this, though its a shame to not see Before Sunrise/Sunset or Punch Drunk Love featured (among others)

    Would Rushmore count a romantic comedy? it focuses on a (twisted) love triangle and is damn funny

  • cory everett | April 27, 2012 11:31 AM

    The list was really just each person picking one (as opposed to us collectively deciding our favorites and then everyone writing up one) and mine came down to "Reality Bites" vs. "Punch-Drunk Love." Went with RB just because I've seen it more times.

  • brace | April 27, 2012 11:25 AMReply

    Shakespeare in Love is one of my favorite romantic comedies ever along with these mentioned here.

  • kris | April 27, 2012 11:22 AMReply

    great list. also
    Breakfast at Tiffany's
    Roman Holiday
    The Philadelphia Story
    My Best Friends Wedding

  • anonymous | May 9, 2012 2:34 AM

    "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. "

    What about 500 Days of Summer and Crazy,Stupid Love? They weren't bad.

    " 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."

    A lot of recent romantic comedies really do have mediocre cinematography. I like it when the cinematography actually adds to the movie.

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