I Watched 40 Romantic Comedies. Here's What I Learned.
I’ve started writing a script that is, in large part, about romantic comedies. Though it’s not a direct genre parody (for reasons we’ll get into later), I felt it necessary to become familiar with the storytelling language of romantic comedies. What kinds of characters occupy these stories? How do these movies look? How, in a general sense, do they work?
Of course, I’ve seen a romantic comedy or two before. In the early 2000s, I was a huge fan of the culturally dominate Judd Apatow romantic comedies. (How most of them hold up, I genuinely don’t know. Except for Forgetting Sarah Marshall, which is still incredible.) I’ve also seen a handful of the romantic comedies many consider classics, from the high school romances like Clueless and 10 Things I Hate About You, to a few of the Woody Allen films, to Love Actually, and so on and so forth. (Sorry to bring up Woody Allen, but you kind of have to when you’re talking about the history of this genre. Also, I think Annie Hall is overrated, but that’s for another day.) Also, I watched When Harry Met Sally for the first time relatively recently, and much to my surprise, in this era where the internet has made the term “classic” mean next to nothing, turns out it’s pretty great!
However, there are other “classics” I haven’t seen until now, and I missed most, if not all, of what came in between them. In other words, the romcoms only fans of the genre like that were critically shat upon during their release. (I hate “romcom” by the way, but it’s easy to type.) I hadn’t seen the clichés, and their existence is what I needed to understand. So… I watched forty romantic comedies.
The Movies
Here are the movies I watched, in the order I watched them:
13 Going on 30
How to Lose a Guy in 10 Days
Never Been Kissed
Sleepless in Seattle
Hitch
Bridget Jones’s Diary
You’ve Got Mail
Sweet Home Alabama
Sleeping with Other People
Notting Hill
Two Weeks Notice
Moonstruck
Maid in Manhattan
The Proposal
Set It Up
Serendipity
Friends with Benefits
The Wedding Planner
She’s All That
27 Dresses
Nick and Norah’s Infinite Playlist
To All the Boys I Loved Before
Kate and Leopold
As Good as it Gets
Crazy, Stupid, Love.
What If
It’s Complicated
Isn’t It Romantic?
My Best Friend’s Wedding
Kissing Jessica Stein
Down with Love
Pretty Woman
Four Weddings and a Funeral
Runaway Bride
Fool’s Gold
Something’s Gotta Give
500 Days of Summer
But I’m a Cheerleader
Saving Face
Appropriate Behavior
I had never seen any of these before. (Actually, I had seen 500 Days of Summer once, but due to jet lag and my horrific college sleeping habits, I barely remembered any of it so I didn’t think it counted.) Some turned out to be as expected. Some of them were surprisingly good. Some of them were shockingly bad. Some, such as Down with Love or But I’m a Cheerleader or Appropriate Behavior, turned out not to be romantic comedies so much as super specific pastiche parodies of ‘60s Hollywood comedies or dramedies about relationships or… whatever you want to call But I’m a Cheerleader. (A great movie, by the way.)
I walk away from these movies with a more nuanced understanding of why people like romantic comedies. There are some tropes and commonalities that I genuinely love, and naturally, there’s some stuff I desperately hate. Despite that, I think I have a higher opinion of romantic comedies now than I did before this project, or at least what they could be. So let’s talk about why!
SPOILERS FOR A TON OF MOVIES BELOW!!! Also trailers when the format made it convenient because I find the evolution of trailers interesting.
1. Romantic comedies have more in common with other genres than they’re given credit for.
“Romantic comedies have more in common with other genres than they’re given credit for” implies that I had lower expectations for them than I would if, hypothetically, I was watching forty action movies. And, well… I did. But that had less to do with the content or what I thought were the genre’s ability to tell worthy stories overall. I’m not one of those people on the internet who can only see things through the lens of action movies. Rather, it had more to do with the individual reputation of many of these specific films amongst critics and my friends who like romantic comedies who had a hand in assembling this list.
What I’m really talking about is the kind of story that comes to mind when we think “romantic comedy.” You know, (usually) boy and girl, both of whom are usually white, have a meet cute. (Do people “have a meet cute” or do they “meet cute” as a verb?) At first they don’t get along, and hijinks ensue. Then they get to know one another, and soon, they fall in love. But a wedge drives them apart, be it by outside circumstances or the reveal of a hidden truth or whatever. However, after a romantic gesture or a speech, they realize they’re meant to be together, they kiss, and there’s an implied happily ever after.
Ask a romantic comedy detractor what a romcom is, and they’ll give you a rough version of that answer. And they’re not wrong. That is, if you’re willing to get incredibly reductive and basically ignore act two.
I realize that this may seem like an obvious point to many, but I’m talking about the broader way in which this genre is seen and how we talk about it. Although the stakes are much lower and there are differences in the way these stories are told, romantic comedies, on a core level, aren’t really different from any other genre. They’re still about a person with a flaw and a goal, and in order to achieve said goal, they must overcome that flaw. It’s still your basic Hero with a Thousand Faces stuff, only the aim is not only to wind up with the person you love, but also to overcome the part of yourself that prevented you from falling in love in the first place. There’s a goal, a need, and a want. Just like every other mainstream movie.
Let’s take, for example, 13 Going on 30, the first movie I watched.
It has its fair share of problems, mainly that nobody acts as if Jenna, our rapidly aged protagonist, is behaving strange. There are also umm… uncomfortable questions regarding certain sexual aspects of the movie. (I don’t think the movie directly engages much on that front, but you can’t help but wonder how the filmmakers feel about the ethics of a sexual encounter with a thirteen year old in a thirty year old’s body.) However, I kind of liked this movie! Once Jenna wakes up as her thirty year old self, she learns that all her “friends” are snakes, that she’s having an affair with someone’s husband, that she essentially has no contact with anyone who genuinely had her best interests at heart, including her own parents, and that she’s become a pretty terrible person overall.
It does end with her getting the guy. In this case, the guy is Matt, her childhood friend who was seemingly the only nice person in her life during her adolescence. But it’s really a movie about how being a shitty person won’t make you happy, even if it makes you successful. Once Jenna learns that “popularity” is superficial and “success” isn’t worth it if everyone in your life is awful, she’s free to have healthy relationships, romantic or otherwise, with people who actually care about her. There’s a boy, but there’s also a lesson to be learned.
Another example: It’s Complicated, one of the better movies I watched in this set.
Jane has been divorced from her husband Jake, who cheated on her with his now wife Agness, for a long time. After watching their son graduate from college, Jane and Jake sleep with each other and begin what is technically an affair. But then she meets Adam, an architect working on an extension of her house, who’s charming, kind, and doesn’t have the personality pitfalls of her ex-husband. Thus the titular complication: Does Jane pick Jake, the man she knows down to his core, whom she will always have an emotional attachment to thanks to their kids, but who’s also hurt her in the past and continues to have a selfish streak? Or does Jane pick Adam, the future, a new direction with a different man with different values who hasn’t hurt her? By the end of the movie, we’re rooting for Adam because ultimately, this is a movie about breaking away from old routines and allowing yourself to be open to the new.
None of these things, of course, sound as viscerally exciting as a manly man movie about big beefy dudes shooting and punching each other. But problems in romantic comedies are solved with empathy and emotion, and to me, that means they can be more interesting and likable.
At their worst, however…
2. There’s a shocking amount of cruelty from characters we’re supposed to like.
The first puppy our family ever raised was named Zoey. She was a black lab, and we got her the summer before my sixth grade year. There’s a vast difference between looking at adorable dog photos on the internet and actually buying and raising one. It’s a lot of work, and though you don’t want to admit it, sometimes you wish you didn’t have the responsibility. However, not only did we all grow to love Zoey quickly, in the years after, we got three more dogs: Franny, Nina, and Ella, a yellow, chocolate, and black lab respectively.
Zoey and Franny are no longer with us, but Nina and Ella very much are. I love(d) them all very much. Though this is admittedly a weird and toxic way of saying this, it’s what I feel like saying at the moment, given what I’m about to talk about: There is very little in this world I’m willing to be violent over. I’m scared of confrontation, and most forms of conflict for that matter. But try to harm a hair on one of my dogs, I’m fucking you up. My brother and sister-in-law got a golden labradoodle named Mufinka. (Polish for “little muffin.”) Though I haven’t spent as much time with her as I want to, I’ll fuck you up over her too. I’m not telling you how to feel about any of what I’ve just said. I’m simply stating what will happen.
Ella as a puppy! Chewing on a dog training book, no less!
I mention all this for a simple reason: Oftentimes, we judge characters by their actions, and one of the first things we see the titular Kate of Kate & Leopold do is electrocute her ex-boyfriend’s dog because, at the moment, he’s too busy to give Kate her PalmPilot back. (I’m just old enough to remember how to spell PalmPilot, thank you very much.)
Her ex, Stuart, lives in the apartment directly above her own. She wants her PalmPilot back. She calls him, but he’s too busy, what with having just returned from traveling back in time. (She doesn’t know this, but still.) So, using the dog collar remote she still has, she shocks his dog Bart, an Anatolian Shepherd, to get him to take off the collar so she can shock him as he’s holding it. Said shock, which I remind you was just inflicted on an innocent dog, is powerful enough to knock him to the ground.
This is how we’re getting to know Kate. Up to this point, we had only seen her get stuck in an elevator for less than a minute, go up the fire escape to see why Stuart was making so much noise, see that he was there, and go back to her apartment to call Stuart about the PalmPilot and eventually electrocute his dog. This is the protagonist of the movie. Whom we’re supposed to like. And relate to. And root for. And the movie starts with her shocking a dog. Kate. Whom we supposedly want to wind up with Leopold and not, to pull a random example out of thin air and definitely not the ending I actually wanted, live a horrible life and die alone.
Even the shittiest of screenwriters know Save the fucking Cat goddamn it.
Also, As Good as It Gets begins with Melvin, our protagonist, throwing his neighbor’s beloved dog down the garbage chute. It’s even in the fucking trailer!
In this case, it’s supposed to be hyperbolic. But you’re still throwing a dog down the garbage chute. So, you know… fuck you and any other baby boomer asshole who thought this was funny. It’s not just that I love dogs or I can’t find humor in being mean. As a fan of Armando Iannucci’s shows and films, I love profanity laden insults and spitefulness, and you don’t have to be a dog lover to recognize cruelty when you see it. It’s just a hack joke. (Also, As Good as It Gets is overrated on a variety of levels, but that’s for another time.)
Now that I’ve watched all these movies, I can safely say that my least favorite aspect of romantic comedies is that this type of cruelty is sadly common. Granted, most of them aren’t cruel to dogs in the same way as the previous two examples. And granted, a lot of protagonists in action movies or dramas are actual murderers. But the action genre is not concerned with kindness and empathy in the way romantic comedies can be. Take my dumb reductionist explanation of romantic comedy stories. Why do boy and girl get back together? Because they overcome a flaw, but also because usually on some level, one party recognizes how badly they’ve hurt the feelings of the other, and they want to apologize and make amends. I, for one, find owning up to your mistakes and apologizing touching (at least in theory) not only because apologizing can be very very hard, but because it means that a character has considered the feelings of another. It means growth and kindness are possible.
Thus when a character acts like an asshole in a romantic comedy, it tends to stick out more. And it happens a lot.
Take, for example, How to Lose a Guy in 10 Days.
The premise of the movie is this: After her friend gets dumped, Andie, an advice columnist, sets out to write an article about how to lose a guy in ten days by doing all the things women (apparently) do that drive men away. Meanwhile, Ben makes a bet at his ad agency that he can make any woman fall in love with him, thus proving he knows enough about romance to take over a campaign for a diamond jeweler. Because those two things are related somehow.
Andie and Ben meet. Ben becomes the guy Andie will lose in ten days. Andie becomes the woman Ben will win over for his job. Thus begins a movie that consists, as Ebert put it, of two people “denying their feelings, misleading each other, and causing pain to a trusting heart” that we, the audience, are supposed to find cute and funny. Rock bottom for me was when Andie lures Ben to couple’s counseling, only to have her non-therapist friend play the counselor, the point being to embarrass and annoy him under false pretenses.
How am I supposed to like these people? And why?
Now, let’s take a less obvious example from To All the Boys I’ve Loved Before.
I actually quite liked To All the Boys I’ve Loved Before. However, there’s a thing that drives me insane about this movie. Our protagonist Lara Jean has written a series of love letters that she never intended to send. Kitty, Lara Jean’s eleven year old sister, steals those letters and mails them out. She never apologizes.
Sure, Kitty is eleven. Sure, things work out well for Lara Jean. But the whole point of Kitty’s character is that she’s smart and emotionally mature beyond her years, and she knows right from wrong. We can tell because she waited until Lara Jean was asleep to sneak into her room and steal the letters. For me, it’s hard to overstate how gross a violation of her sister’s trust this is, and it’s something Kitty needs to understand. Later, she owns up to what she did, and the reason she gives is, “You were so lonely, and I could tell Peter (main love interest of the movie and one of the recipients of the letters) liked you and I knew you wouldn’t do anything about it.” When asked why she sent all five letters, she replies, “I thought five chances at a boyfriend was better odds! I miss having him over for dinner!” When Kitty’s out of Lara Jean’s warpath, their older and supposedly wiser sister Margot says to Lara Jean, “Look, her logic was off, but her heart was in the right place.”
Now, I’m usually not one for shouting at my TV. But this time, I shouted, “NO IT ISN’T, YOU FUCKING DUMBASS!” She just said she did it because she missed having Peter over. Even if she didn’t say that, it was callous and cruel to assume Lara Jean was lonely because she’s an introvert (which we learned earlier in the movie), and it’s incorrect to assume that a boyfriend would make Lara Jean happy. I hate how the movie lets Kimmy off the hook without apologizing. I get it. She’s eleven. But actions have consequences, and this is the age where you learn that.
There are plenty more examples I could go at considerable length about. (We’ll be talking about one in particular a little later.) But the question is why are there so many? Of course, it depends on the movie, and I don’t think there’s one reason in particular that covers every bad romantic comedy. But my best guess is that it’s a natural byproduct of personal taste clashing with bad writing. Maybe you’re not as mad at Kitty as I am. Or maybe you’re fine with what Kate did to Stuart’s dog. (Though if you are, then fuck you.) But romantic comedies are designed to make you sensitive, and if these were well written scenes or movies, then they would’ve considered their audience.
3. The best romantic comedies emphasize chemistry over romance.
We’re getting more into the realm of personal taste here. Well, we’ve already been there for a while. But you get what I mean.
By now, I’m sure a lot of you have read Mindy Kaling’s famous and briefly viral article in The New Yorker about the women of romantic comedies. (If not, give it a read! It’s great!) I read it again after watching all these movies, and something she says early on struck me. Specifically, it’s when she says, “I like watching people fall in love onscreen so much that I can suspend my disbelief in the contrived situations that occur only in the heightened world of romantic comedies.” The purpose of this quote is to point out that she’s well aware of the often forced nature of romantic comedy storylines and admit some of their faults. However, what strikes me about this comment is the key phrasing “watching people fall in love.”
Not wind up together. Not have sex (although sex can absolutely be a part of falling in love). But “fall in love.” The reason this strikes me is that she basically identified the trait all of my favorite movies from the list had in common.
I think that a lot of people conjure images of grand gestures and impassioned declarations of love when they think about romantic comedies, and it’s not hard to see why. The word “romance” is right there in the name of the genre. But some people go even more basic. To some, this is the genre where the pretty people kiss at the end, and not much else. Those movies do exist, and they’re shit.
Shit romantic comedies have attraction, but attraction often goes in only one direction. It’s a simple acknowledgment of surface level stimuli. Two people look good and you know the bare minimum about them, so you want them to get together because maybe pretty babies.
What these shit films don’t have is chemistry. Unlike attraction, chemistry goes both ways. It’s achieved not only through mutual attraction, but from communication, be it verbal or physical. It’s an agreement. A shared worldview and a compatible style of socializing. It’s comfort in each other’s company. It’s a key component that must be earned when creating a fictional couple we’re supposed to root for on a level beyond superficiality. It is a vital aspect of love and friendship, not just in a movie, but in real life as well.
Communication. You may be sick of hearing it, but it’s important. Particularly in a genre that’s almost all dialogue.
Of the forty romantic comedies I watched, my favorite one was the 2015 film Sleeping with Other People.
It’s my favorite movie not just because its funny or that Allison Brie and Jason Sudeikis are fantastic or many other aspects I could talk about at exceeding length, but because the chemistry that writer and director Leslye Headland wrote into these characters is so infectious that I’d be willing to spend way more than two hours in their company.
Lainey and Jake meet in college, and later that night, lose their virginities to one another. After college, they meet again at a sex addict’s meeting. Both have problems with monogamy. Jake is a serial womanizer and Lainey is currently the other woman with a married man. (Side note, Adam Scott plays said married man, and he’s so good and so detestable in this movie.) Both are flawed in similar ways, but they communicate well with each other, and we watch as their chemistry flourishes. Both recognize their capacity to hurt one another with their shared flaw, so they agree not to have sex, and for the most part, it’s a healthy relationship that benefits both immensely. But I wanted them to get together so badly it hurt.
Of course, a lot of this is style, as well as the words and direction of Leslye Headland. However, I would say that it’s the respect they have for one another. The way they acknowledge each other’s boundaries. The way they support one another in such a way that it isn’t just punishing the audience and themselves by denying the feelings they have for one another. For the most part, they have each other’s best interest at heart, and every word they say to one another makes you scream, “PLEASE JUST GET TOGETHER ALREADY!!!!!”
Another one of my favorites is the similarly themed Friends with Benefits, a movie I was genuinely surprised by how much I liked.
Were I making a ranked list, I would put it at second or third, and the only reason I like it less than Sleeping with Other People is because there’s some plot choices and jokes I don’t like (which we’ll get to later), as well as a more broad comedic sensibility in general.
Dylan and Jaime, played by Justin Timberlake and Mila Kunis respectively, have an intensely strong chemistry in this movie, and unlike Sleeping with Other People, they have regular sex with each other. Still, a lot of what can be said about Sleeping with Other People can also be said Friends with Benefits, and the later even goes out of its way to reinforce the chemistry with filmmaking technique and editing.
I wish I could find a clip of the scene I’m talking about, but alas, none seems to exist, so I’m going to have to describe it. The opening scene of the movie shows Dylan at work. He then gets a call from, we think, Jaime, as she waits outside a theater. We then cut between Dylan and Jaime as they seemingly talk to one another while Dylan rushes to the theater, and they’re both kind and funny to one another. Then Dylan arrives, and it’s revealed that Dylan was actually talking to his girlfriend Kayla, who’s standing outside the Pantages theater in LA, and Jaime is waiting for her boyfriend Quincy outside a movie theater in NYC.
In this edited conversation, they communicate well and they’re respectful to one another, and I, at least, believed the chemistry I saw on screen. Then it turns out they’re talking to other people, and they both get dumped. Both then lament to their friends, but the two still say similar things that we quickly cut back and forth between. “I’m just going to work and fuck. Like George Clooney.” Says Dylan. “I’m just going to shut myself down emotionally. Like George Clooney.” Says Jaime from across the country. Thanks to the power of editing, we’re already rooting for them to get together, and they haven’t even met yet.
Remember hangout movies? My favorite romantic comedies are essentially those. While most romcoms are less big on setting, they make up for it in transformation and stakes. The transformation comes from overcoming the part of yourself that prevents you from being happy, and the stakes are going back to being alone and miserable while the potential love of your life thinks you’re a dick.
Put it another way: Why is When Harry Met Sally considered by many to be the best romantic comedy ever? Sure, they wind up together and happiness and so on. But everything that comes before that is why you actually care. The parts where the asshole who doesn’t believe in love learns the error of his ways thanks to the woman who he falls in love with.
4. The worst romantic comedies rely on their audience to deflect all their flaws by using “love” and “cuteness” as a shield.
If the best romantic comedies emphasize chemistry, the worst emphasize simple attraction. Again, chemistry. Two people getting to know and care for one another on a non-superficial level as they develop a relationship. Not two compatible looking mannequins acting “cute” at each other.
Let us take Serendipity, one of the worst romantic comedies I’ve ever seen.
Jon and Sara meet at Bloomingdale’s while Christmas shopping. They share a dessert, talk about their relationships, then depart. They meet again moments later. “It’s fate!” Sara decides. They spend a lovely romantic evening together, but when they exchange numbers, the piece of paper gets blown away in the wind. “It’s fate!” Sara decides. So then he writes his name and number on a $5 bill and she in a copy of Love in the Time of Cholera, and if either of these items make their way back into each other lives, then they’ll know it was meant to be. Also, they do this "Will we meet again if we pick the same floor on different elevators in the same building” thing, because one arbitrary test apparently isn’t enough.
This film expects us to root for this relationship, and some do. But what has really been established in all their interactions thus far? They have one or two things in common, and the audience may have some personal ideals and fantasies they project onto these characters and the circumstances they find themselves in. But I personally don’t think there’s anything here other than basic attraction, and I don’t believe in “love at first sight.” Love, in my experience, is built on respect. Something you cannot attain without getting to know the other person and giving said person the time and a reason to develop similar feelings for you.
Still, let’s set logic and screenwriting contrivance aside. Let's imagine that moment, after the elevator scene, where Jon realizes that Sara has disappeared. Let’s imagine his dejectedness on that cold winter night in the cab ride back to his apartment. Jon seems like a smart enough guy. What if he thought about what he just experienced with this woman? He might conclude, for example, that Sara doesn’t really understand the concept of “fate,” as all her tests go against the very concept as fate is, by definition, beyond a person’s control. It may occur to Jon how easily Sara was able to toss him aside for the sake of an abstract concept she doesn’t seem to fully understand, despite the time they spent together, and it may occur to him that Sara might be a bad person. Or at the very least, kind of stupid.
He may reflect on his own behavior as well. Though in a relationship, why was he so quick to pursue this person? Say what you will of monogamy, but I do think you owe people you supposedly love compassion and honesty. Why was he so willing to toss that aside? Maybe, just maybe, he’s also a dick.
Serendipity is a bad movie, but at the very least, it’s basically harmless. The same cannot be said for another film, Crazy, Stupid, Love.
“Offend’ is not a word I use a lot, but this movie sincerely offends me. There is much I deeply hate about Crazy, Stupid, Love., be it several dumb directions the story ultimately takes to the unchallenged and probably unrealized hypocrisy of its characters (particularly Steve Carrel’s) to how much of Ryan Gosling’s character’s dating and sex advice sounds word-for-word like the type of stuff alt-right shitheads peddle to each other on 8chan. Also, “Crazy, Stupid, Love.” is a really fucking stupid title.
But I want to talk about Robbie, the barely teenaged son of Steve Carell’s character Cal and Julianne Moore’s character Emily. Specifically, I want to talk about this scene.
Robbie, you see, is attracted to his seventeen year old babysitter Jessica. She’s made it clear several times in the movie that she does not share his feelings. Nevertheless, he creepily and routinely declares his love for her, sends her creepy texts, makes creepy declarations of love, and is, overall, incredibly creepy. Each and every time, she rejects him. The message finally sinks in, and at the end of the movie, he begins to give a speech during his eighth grade graduation about how he now thinks love is a scam. (A speech, by the way, Jessica is in the crowd to hear, thus once again qualifying as creepy as the speech is essentially directed at her.) Cal then stops him and gives his own speech that essentially says, “Never give up on the woman you’ve arbitrarily decided is the ‘love of your life.’”
Taking his father at his word, Robbie creepily declares his love for Jessica again and also says he doesn’t regret her catching him masturbating earlier and admitting that he thinks of her while he does it. (Which, by the way, is a thing that happened in the movie.) Only this time, for some reason, she laughs and the crowd applauds. Robbie and Jessica don’t wind up together. But she does give him her nudes, which by the way, were meant for his father. (Nothing says, “I love you, older of-age man” than pictures which could potentially get him indicted.)
Why does this movie think that creepily pursuing a girl despite her objections is acceptable? Why did the writers and director then have said girl reward said toxic behavior by giving this underage boy naked pictures of herself to masturbate to? What, in a general sense, the fuck? Simple. Because “love.” Because it’s “cute” and “fun.” Because when it comes to love, you’re apparently allowed to be irrational and sociopathic, and if you have feelings for someone, than such concepts as “respect” or “boundaries” are just gosh darn party poopers. Because these filmmakers are blissfully unaware of what they’re really saying with this movie. Or they’re not, and they just don’t care. Because there are legions of people who don’t want to think about the movies they watch, and they’ll shout down any dissenting opinion by saying, “IT’S CUTE! YOU DON’T BELIEVE IN LOVE! STOP THINKING ABOUT THE MOVIE!” Because this movie doesn’t respect you. Because when it comes to relationships, we, as a society, as a people, as a species, are broken. It’s not hard to witness. Just watch Crazy, Stupid, Love.
Why don’t we have to have these conversations about Sleeping with Other People or Friends with Benefits? Sure, the latter has its own problems, which we’ll get to in a moment. But I would say it’s because these characters actually respect each other, and their relationships go beyond superficiality. Unlike Serendipity or Crazy, Stupid, Love., the writers of these movies actually thought about the message they want to convey. That’s how good movies work.
5. I never got to see certain actors in the romantic comedy periods of their careers. It was odd.
The first time I ever consciously saw Matthew McConaughey in a movie was when I saw Sahara in a theater. Though I had just as much fun making fun of it as seemingly everyone else did at the time, I remember next to nothing about the movie, including whether or not McConaughey himself was particularly good or bad in it. I left the theater, I told my jokes, then I didn’t think about McConaughey again until Tropic Thunder. I thought he was hilarious, and though we can debate when the “McConaissance” began, for me, it was here. Because I haven’t seen him in anything bad since. (Not saying he didn’t do any bad stuff though. I haven’t seen The Dark Tower or The Sea of Trees or any of those.)
Before this romantic comedy thing, I’d seen a grand total of twelve of his projects. (Counting True Detective.) There were movies, like Killer Joe, where I thought he was great despite not particularly caring for the movie itself and there were some, like The Wolf of Wall Street, that don’t need any qualifiers. However, with the exception of Sahara, and I always walked away from his movies thinking, “Man Matthew McConaughey is great. Even if I don’t think he should’ve won the Oscar over Chiwetel Ejiofor.” Then I watched some of his romantic comedies.
Specifically, I’ve seen three of them: How to Lose a Guy in 10 Days, one of the worst movies I watched for the whole set, The Wedding Planner, dull, tedious, and run-of-the-mill, and Fool’s Gold, a romantic comedy with the occasional action scene that’s mostly terrible in ways that, to me, are pretty unremarkable. (It’s one of those “action movies” that didn’t have enough budget, thus it’s mostly talking so they could save money for the big act three action stuff.)
Though McConaughey wasn’t particularly great in any of these films, I don’t think he was particularly terrible either. However, as I watched these movies, I thought about whether or not I would’ve given him the benefit of the doubt if I hadn’t seen his later work first. I don’t think I would’ve. I wasn’t expecting to like any of these movies, but I also didn’t expect to hate How to Lose a Guy in 10 Days as much as I did, nor did I expect to feel almost as negatively about the other two.
I was a fan before I saw these movies, and I’m still a fan now. If anything, these films made me appreciate his later work even more. I didn’t understand why everyone was freaking out over how great an actor McConaughey turned out to be. Now I do. I definitely do.
I had a similar reaction to Julia Roberts’s romantic comedies.
Before I started this project, I had seen nine of her projects. Unlike McConaughey, these projects were more a mixed bag for me. There are films I deeply hate, like Steel Magnolias, there are movies I’m either indifferent to or don’t remember that well, like The Mexican and August: Osage County, and there are projects I like quite a bit, like Erin Brockovich and most recently, the Amazon series Homecoming.
Despite the mixed bag, however, I always thought of her as a prestige actress. Sure, she won on Oscar before I was aware of her work and she’s been nominated three other times. But I always thought she was great. I thought she was incredible in August: Osage County, a movie I didn’t care for. I thought she was incredible in Charlie Wilson’s War, which I need to watch again, but remember her and the other actors quite well. I thought she was particularly incredible in Homecoming and she’s a huge part of why I kind of like the admittedly flawed Ben Is Back. (Go watch the scene where she tells the elderly dementia addled doctor who, back in the day, prescribed her teenaged son the addictive painkillers that turned him into an addict, “I hope you die a horrible death.”)
Now I’ve seen Pretty Woman, My Best Friend’s Wedding, Notting Hill, and Runaway Bride. Of these movies, the only one I feel particularly negative towards is Runaway Bride, mostly for scripting and sensibility reasons. Other than that, I don’t think the gulf in quality between what I had seen of Roberts before and after is as wide as the one in McConaughey’s work. I like Pretty Woman, but I don’t think I love it, I have a bit of a like/hate thing going on with My Best Friend’s Wedding, and there are some creative decisions in Notting Hill that turned me off. But I don’t hate or really even dislike any of them in the way I did with Matthew’s romcoms.
Still, it was strange to see her in this mode. These are the movies that many think define Roberts’s career. To me, they’re more like offshoots. Julia Roberts is an actress you give a lot to chew on, and while she does in Pretty Woman, I’d argue that’s not really the case for the other three. It’s not that she can’t or shouldn’t play a normal person. She does so frequently, often to great results. It’s more that the material she’s given doesn’t rise to the standards I personally hold for her. Again, it’s not that these movies are bad. (Well… Runaway Bride is, but not aggressively so.) It’s that they feel oddly beneath her.
I could go at similar length about the romantic comedies of many actors I’ve now been exposed to. Two that come to mind are Hugh Grant and Sandra Bullock, both of whom have bodies of work I felt mostly positive about until this romantic comedy expedition of mine. (Some of those Sandra Bullock romantic comedies… oh boy.) But I’d mostly be saying the same things, and this article’s getting long as it is.
The point is this: You’ll find great performances in terrible movies. You’ll find terrible performances in otherwise great movies and all types of performances in all types of movies in between. Sandra Bullock or Matthew McConaughey or any number of actors may have made a bunch of movies you don’t like. But there’s a reason they kept getting work: It’s because they’re extraordinarily talented people. Of course, there is such a thing as bad acting. But much of what we call bad acting is really bad screenwriting and, more often, bad directing and in some cases, bad editing.
I thought about this distinction a lot while watching these movies, and moreover, I was reminded of our relationship with actors. A lot of us are under the incorrect assumption that it’s the actor’s job to make the material great. Of course, it’s always welcome when they do, and it’s easy to pin a lot on actors because they’re what we see when we look at the screen. But actors (usually) aren’t writers, they (usually) don’t choose which takes end up in the final product, and most of the time, it’s the director who advises them on how to deliver their lines. Many decisions make a bad film. It’s usually not the actor’s fault. Give them a break every now and then.
6. Nancy Meyers is a treasure.
We’ve talked before about my love of The Intern, but to recap, I think it’s a severely underrated film about getting older, continuing to find purpose in your life, and watching younger people fall into the same traps and heartbreaks you experienced and witnessed, and being there to provide guidance and friendship.
I’ve now watched two more of Nancy Meyers’s films: Something’s Gotta Give and It’s Complicated. My heart still belongs to The Intern, but both of these films are fantastic.
Here’s the thing about Nancy Meyers’s romantic comedies: As opposed to a lot of romcoms, the stories Nancy tells don’t rely on contrivance or bullshit. They unfold naturally at a deliberate pace. Her movies (or at least the ones she’s both written and directed that I’ve seen) are populated with likable and believable human beings, and the ones who stray don’t do so because they’re villains, but because they’re flawed and selfish in fairly common and understandable ways. Unlike many romantic comedies, her films also look fantastic as well. The editing is thought out and stable, there’s more effort put into shot composition, and you get the impression that, although she’s not operating on a blockbuster budget, someone actually wanted to make a film that’s interesting to look at.
I don’t have a point to belabor here. I just want to say that all the movies I’ve seen of her’s have been great, and I intend to watch more. Maybe What Women Want will be the movie that finally breaks the streak. But I can take comfort in the fact that she didn’t write it.
Also, as many have already pointed out, the kitchens in her movies are fucking incredible.
7. Pointing out the clichés is, itself, a cliché.
Somewhere in the middle of all those movies is Isn’t it Romantic?, a 2019 parody of romantic comedies.
Rebel Wilson plays Natalie, a disenchanted repressed architect in a stuffy claustrophobic office with a cynical worldview who, naturally, hates romantic comedies. After being mugged in the subway, she takes a blow to the head, and wakes up in a cliché romantic comedy world. Everything’s brighter, everyone’s unnaturally beautiful, and her existence starts operating by romantic comedy rules.
I was telling a friend about my thoughts on the movie. I said it was funny, but it didn’t really do anything for me beyond that, and I was having trouble understanding why. When she asked what was funny about it, I said, “The clichés it points out are way more specific than the ones people usually list.”
That’s when it hit me. It’s not that pointing out the clichés is the only trick Isn’t It Romantic? has up its sleeves, although I think that’s true for a vast majority of the movie until the last fifteen minutes or so. The problem is that we all know what those clichés are already. All Isn’t It Romantic? was really doing was filling in a gap or two.
Modern romantic comedies are much more self-aware than they were in previous decades. Many of them include a line that goes something like, “This isn’t some romantic comedy where…” and then a cliché gets explained. To All the Boys I’ve Loved Before features a scene where Lara Jean and her fake boyfriend Peter watch Sixteen Candles and comment on the racism while also enjoying the movie. Friends with Benefits has a great running joke where Dylan and Jaime watch and refer to a fictional cliché romantic comedy starring cameo appearances from Jason Segal and Rashida Jones that makes one or two of the jokes later found in Isn’t It Romantic?.
But even if later romantic comedies weren’t as self-aware, as I said, we all already know what the clichés are, and we talk about them all the time. The contrived storylines. The unrealistic expectations of how love works. The color palette and the cheap looks and rushing to the airport to catch the love of your life before that person gets on a plane. I even referenced Mindy Kaling’s article which itself is famous for pointing out the clichés.
At this point in 2019, I think I can say that mocking romantic comedy clichés is, itself, cliché. This is why I don’t want to poke fun at the clichés in my own script. I don’t have any new ones to point out, and I don’t have anything new to say about the ones you already know.
If anything, I’d like us to turn our attention to genres that, in terms of the pure volume of stock creative choices and tropes, are worse than romantic comedies. Specifically, action movies and horror. Of course, we’ve seen movies mocking their clichés as well. Hot Fuzz and Cabin in the Woods come to mind. But I think they deserve more.
8. Romantic comedies have a bizarre relationship with LGBTQ characters.
LGBTQ characters are more visible in the romantic comedy genre than any other I’ve seen up to this point, and there’s something commendable to that, particularly from the films from the ‘90s and the early 2000s when our attitudes about these groups were much less evolved. Rupert Everett’s openly gay character in My Best Friend’s Wedding is one of the only people to tell our scheming protagonist that maybe, just maybe, she’s doing something terrible in trying to sabotage the love of her life’s wedding. There’s Simon Bishop of As Good as it Gets, who helps bring Melvin back to humanity despite his constant homophobic abuse. Matthew and Gareth, as far as I’m concerned, are not only the two most likable characters in Four Weddings and a Funeral, but also the most believable and empathetic relationship as well.
Some of these examples aren’t perfect, and romantic comedies actually staring LGBTQ characters are few, far between, or don’t exist. However, these characters don’t appear in other genres at all. At least romantic comedies acknowledge their existence.
However, we’ve talked already about how everyone knows the romantic comedy clichés, and one of those clichés is the “sassy gay friend.” Isn’t It Romantic? even has a running joke where her neighbor whom she barely knows turns into a caricature of gay men in romantic comedies when she enters romcom world. (It’s more accurate to say that it’s a caricature of the caricature.) This character’s job isn’t really to contribute to the story or offer anything of substance to the proceedings. His job is that of the Shakespearean chorus, but on top of commenting on whatever’s happening in the story, he also throws out some jokes and listens to the problems of the (usually) straight white female protagonist.
I’m a boring straight white guy and I’m a little out of my depth. Some of these portrayals, like the middle-aged gay couple in the otherwise shitty Fool’s Gold, strike me as oddly ahead of its time while also being a bit cartoonish. Others, like some of the gay characters in Nick and Norah’s Infinite Playlist, also ride a weird line between fun and lively and stereotypical and trite. But that’s just me. How accurate or acceptable these portrayals are is a question for an actual gay person to answer.
However, I was expecting the characters. Again, it’s a rather famous cliché. What I was not expecting was the level of gay panic jokes, or the types of jokes where someone points out that doing or liking something “makes them gay” and another character freaks out because, god forbid, they be seen as anything but straight. When I said Friends with Benefits wasn’t perfect, I was referring to these types of jokes. Specifically, there’s a running joke where Dylan freaks out every time someone implies that liking Harry Potter makes them gay. Similarly, my eyes rolled to the back of my head when Jennifer Lopez implied that going to dance classes makes you gay in The Wedding Planner and Will Smith freaks out at Kevin James’s kiss in Hitch.
So on one hand, romantic comedies have more gay characters to varying effect than any other genre. On the other hand, a lot of these representations are unrealistic at best and stereotypical at worst. In the end, I don’t know how I feel about any of this.
But the silver lining is this: I watched four LGBTQ films for this list. Kissing Jessica Stein, But I’m a Cheerleader, Saving Face, and Appropriate Behavior. I didn’t like all of these films. Specifically, I found Kissing Jessica Stein and Saving Face a bit too plain. But I did like the other two quite a bit. (Though I’ll admit I’m stretching a bit in calling them romantic comedies.) And even the ones I didn’t like stood out because all four of these movies go out of their way to break from the norms of the genre.
I’m not sure how I feel about certain aspects of LGBTQ representation in Kissing Jessica Stein. Specifically, I think it can be argued that certain scenes frame same sex attraction as a choice. (Though it does have another gay character call out one of the characters for that very reason.) But it stands out because it’s a grounded character-centric story with no contrivance or heightened romcom shenanigans. But I’m a Cheerleader, while also being hilarious in a very John Waters tongue in cheek way, is about two women falling in love in a gay conversation camp. As such, there’s a heightened sense of stakes, drama, and tension that most romantic comedies don’t strive to achieve. Saving Face dives deeply into the culture of Chinese immigrants in New York, and Appropriate Behavior takes a similar path with the Persian community, while also exploring the quietly shitty and arguably racist behavior of her ex.
There are many reasons, both societal and ethical, as to why we need more of these kind of representations in romantic comedies. But there’s also a pretty simple one as well: They make for better movies. Period.
9. Here’s a simple breakdown of the ones I liked and didn’t like.
Liked
Appropriate Behavior
Bridget Jones’s Diary
But I’m a Cheerleader
Down with Love
Friends with Benefits
It’s Complicated
Pretty Woman
Sleeping with Other People
Something’s Gotta Give
To All the Boys I’ve Loved Before
What If
Sort of Liked
13 Going on 30
Four Weddings and a Funeral
My Best Friend’s Wedding
Saving Face
Indifferent To, But Not Mad At
27 Dresses
Isn’t It Romantic?
Kissing Jessica Stein
Moonstruck
Notting Hill
Set It Up
She’s All That
Sleepless in Seattle
Sweet Home Alabama
You’ve Got Mail
Mostly Disliked
500 Days of Summer
As Good as it Gets
Fool’s Gold
Kate & Leopold
Maid in Manhattan
Never Been Kissed
Nick and Norah’s Infinite Playlist
The Proposal
Runaway Bride
The Wedding Planner
Hated
Crazy, Stupid, Love.
Hitch
How to Lose a Guy in 10 Days
Serendipity
Two Weeks Notice
10. Fuck Crazy, Stupid, Love.
It bears repeating. And I wanted a tenth thing.
