Five-Year Engagement Header

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
"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
“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
"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
“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