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The Best Romantic Comedies of the 21st Century (So Far)

By Dustin Rowles | Lists | December 13, 2016 |

By Dustin Rowles | Lists | December 13, 2016 |

Today marks the 20th Anniversary ofJerry Maguire, and over on Bustle, they wrote a think piece calling the Cameron Crow movie the last great adult romantic comedy. That sounded insane to me, but as I looked over the offerings from the last 16 years, they may be right. There have been good romantic comedies since — and some very good — but it would be hard to argue that any were as good as Maguire.

Looking over this century’s romantic comedies, I also ended up piecing together the best in the genre since 2000, a few years before studios stopped churning one or two out every quarter. I’m not sure what happened to the romcoms — I think 27 Dresses may have killed them — but the appetite for funny romantic movies isn’t quite what it used to be. Apparently, all the lame high-concept ideas have already been used.

For the sake of scope, this list is limited to studio romantic comedies, because the indie world continues to produce quality romantic comedies like What If?, In a World, Lars and the Real Girl, Obvious Child, Safety Not Guaranteed, Ruby Sparks, The One I Love and enough others to inspire its own separate list.

High Fidelity — John Cusack counts down through the top five break ups of his whole life, and there’s some great music along the way. This movie has a lot to say about relationships and messing things up and being unhappy and making terrible decisions so let it wash over you, take it all in and meditate on it. Also featuring one of the only times that Smog has appeared on a soundtrack, so a nice perk for those who care at all about the Bill Callahan/Joanna Newsom break-up spectacle (one out of every million people).

(500) Days of Summer — It’s a story about love, but it’s not a love story. Tom falls hard for Summer, but Summer - for reasons unexplained at first — is slightly detached. She wants to keep it casual. We know from the outset that they break up at least once, on day 288. And we see the days leading up to the break-up, which are intercut with the days subsequent to it, a brilliant chronological device that allows us to see the long-term consequences of a certain statement or gesture in a more immediate sense. Tom and Summer’s relationship travels from the idle talk of two co-workers who obviously have an affection for one another through the courtship and up to the relationship’s more cemented status before the floor is pulled out from under Tom. Then it explores the stages of heartbreak - the denial, the deconstruction, the wallowing self-pity, and the attempts to resurrect the relationship. But it does so without ever getting maudlin — 500 Days of Summer remains a breezy fast and emotionally exuberant film from the first minute to the last.

Trainwreck— What Schumer really gives us here is a painfully honest portrait of a person finding herself. When her relationship goes through those late-second act bumps (which aren’t really spoilers, because you know the formula here, right?), Amy finds her whole life shifting. Her once totally fulfilling life is suddenly anything but. Her family is in a patch of distanced weirdness, her work life is nothing but a drain, and her sexual hookups… well, let’s just say those start to be more trouble than they’re worth. What’s so impressive about this movie, though, is that it manages to avoid the expected slut shame you would expect from these changes. Amy doesn’t have a *grand realization* that she’s wasted her whorish life being a filthy trollop. She just… changes. Like we all change. Her choices weren’t wrong, they just aren’t what fits her anymore. And that evolution is handled with such a light touch that it’s natural and beautiful, and a subtly realistic reflection of what we all go through with every new development in our lives.

About Time — What’s it about? How are the performances? Is the cinematography good? Does any of that matter, really? It’s not the kind of movie where that stuff counts. It’s an emotionally driven movie specifically designed to make you fall in love with your own life again. If you’re in love, whether it’s new love, honeymoon love, or the love of a couple that has been together for 50 years, it’s probably going to feel like an intensely personal movie, like it was a movie MADE SPECIFICALLY FOR YOU. You’ll love it for the same reason you love “The Luckiest,” even though it’s an unabashedly hokey, sentimental song that cool people make fun of because, gah, how predictable. But those are the best movies, the ones where we get so lost that the details become irrelevant, the ones that remind us how much we love the ones were with, and the more you love them, the more power About Love will have over you. It is not for cynics. It is not for critics. It’s not for the cool. Cerebrally, it probably wouldn’t hold up to close scrutiny. But emotionally, there are no holes in About Time; it is a semi-sonic blast of feels that that will trigger every node of happiness and ache and affection inside of you and leave you exposed and vunlerable and smiling through a puddle of tears like a goddamn mad man.

Silver Linings Playbook — The truly terrible title may be one of the worst of its year. I get it, it has to do with football and with silver linings and stuff, but come on. It’s hard to say and a million syllables. But don’t let a terrible title keep you from Silver Linings Playbook. There’s warmth, laughter, community and joy to be found here amidst the ruins. When we have nothing left to lose we find ourselves at our most authentic, and emerge from these moments of alchemy wiser, changed.


Crazy, Stupid, Love — If you can temper your groans — and the movie is good enough that it’s not hard to do so — Crazy, Stupid, Love is a sweet, low-key love story, the absolute best movie you could hope for given the circumstances. Steve Carell is likable and lovely, Ryan Gosling is douchebag-charming, Emma Stone is sweet and endearing, and Julianne Moore is, well, she’s in it. The performances are so remarkable, and the direction is so sure handed that, despite your brain’s many misgivings, it’s an easy film to like.

Easy A — Will Gluck’s Easy A is a 21st century teen comedy, and maybe the first really good one at that. It doesn’t borrow the archetypes of those ’80s standard bearers — there’s no expositional scene establishing where the various cliques are seated at the lunch table. It presents high school for what I expect it must be now: an amorphous body of singular cliques — teenagers too busy self-identifying to align with anyone else, except in such a way as to self-identify. And so they selfishly align with Olive Penderghast (Emma Stone), a self-proclaimed nobody who is not really a nobody. You know she’s not because, when she lies to her best friend about losing her virginity, everyone in the school knows it by the end of the day. And they know it because possessing that information — and exaggerating it — is their way of valuing their own self-worth, which no one cares about because their only concern is with themselves.

The ProposalThe Proposal is the rare rom-com that doesn’t feel as though it began with a pitch, a title, and the two leads before the script was even written. Granted, it’s still constrained by that formulism, but there’s a lot of life going on in those gaps. Much of that magic comes in the form of Ryan Reynolds, who has finally gotten a role that not only takes advantage of his physique, but more importantly, his droll sarcasm and the ability to naturally deliver a cutting remark with impeccable timing — it’s a heady combination of the likable Reynolds from Definitely, Maybe and the romantic version of the wry, deadpan Reynolds in Blade Trinity. And though it’s the unlikeliest of pairs, there’s an actual easy-going and sweet chemistry between Reynolds and Sandra Bullock (sans snort!), who finally gets to express what many of us have known lies beneath her gauzy button-cute, dewy façade: Her inner, simpering bitch.

Forgetting Sarah MarshallForgetting Sarah Marshall is funny, sweet, and almost predictably wonderful at walking the line between comedy and drama as it lays out a story broad enough to be relatable but special enough to raise the characters from emotional place-holders and make them fresh, empathetic, and completely enjoyable.


Definitely, Maybe — Ryan Reynolds, naturally, is as charming as ever here, but for once, he’s actually given a role he can do something with — he’s not forced to resort to sarcastic wisecracks or camera mugging to make a film tolerable. And the three love interests — Weisz, Banks, and Fisher — are all so goddamn likable that you’d almost be happy to see him end up with any of the three, though it does become apparent that just one is right for him. Ultimately, I fell for Definitely, Maybe because, as best a movie of this ilk can, it dealt fairly with the complexities of relationships and love, and did so without cheap jokes, pratfalls, or a multitude of forced contrivances. It is, in a word, relentlessly sweet. And sure: There are a few mawkishly sentimental lines that may make some of you cringe, but that’s the nature of romance, isn’t it? When you’re in love, somehow it’s the cheesy lines that are always the most heartfelt.

Knocked UpKnocked Up sets itself apart from the other great comedies of this century, Old School, Wedding Crashers and even 40-Year-Old Virgin — because Apatow injects some real authenticity into the last hour, which makes the payoff feel less tacked on and more sweetly rewarding. I can scarcely ever remember feeling so moved by a movie that, just an hour before, had me projectile ejaculating Icee from my nostrils. Apatow does something amazing here — he doesn’t play up the childbirth for laughs, he mines the real emotions that flow out of it. There is something achingly genuine and sincere about Apatow’s approach, creating a situation that makes it possible to show the endearing side a group of scene-stealing geeks who just so happen to enjoy playing Murderball in hospital wheelchairs.

Love Actually — We have written extensively about Love Actually. There’s no point in choosing a blurb from just one post. Read them all.

Sweet Home AlabamaSweet Home Alabama, somehow reaches into that deeply buried Southern spirit of mine. I don’t know why. It’s a crap movie, and even those who will admit a certain guilty fondness for it, will concede that it’s a crap movie. There are a few nice flourishes hither and yon, but it’s hardly representative of the South. And yet, no other film can make me as homesick as Sweet Home Alabama,

Bridget Jones’s DiaryBridget Jones has become a contemporary comedy classic, a go-to for girls nights, and an inspiration for generations of women who feel like a “wanton sex goddess” one moment, and a utter disaster the next. We—like Mark Darcy—like Bridget very much, just as she is.

Going The Distance Movie.jpg

Going the DistanceGoing the Distance is not a brilliant romantic comedy, but it’s a fun one, and at times — thanks to Sudeikis and Day — completely hilarious. Best of all, however, is that it doesn’t completely sacrifice character for laughs and even manages to squeeze in a few honest moments that will ring true to anyone who has attempted to make a long-distance relationship work.