Like every rational person, I am well-versed in the art of watching romantic comedies. And I’ve seen them all: from the terrible, overly cheesy films to the ones that are so well-done, you don’t even want to mention them in the same breath as some of the other drivel that makes up the genre. I watch them all eagerly, and let myself get completely wrapped up in the sentimentality that drives them all. Romantic comedies get a bad wrap for being unrealistic and falsely building up expectations, but there’s so much more to it than that. In fact, some of the best romantic comedies are the ones that don’t follow those stereotypes at all, to the point where they might not even seem like romantic comedies at first glance. Sure, a formula has developed, but really, every good romantic comedy stands on its own, and has its own definition of what it means to fall in love. Ultimately, my definition of a romantic comedy (and what defines a film as such) is one that puts two characters on a journey that ends with both falling in love and becoming the person they need to become in order to have a happy and sustainable relationship.
A few friends and myself have decided to start a podcast, and our inaugural episode will feature a discussion of romantic comedies. To preclude that discussion, Kim, Sage, Jenn, and I came up with our top 15 favorite romantic comedies (and all their picks can be found by clicking their respective names!). This list took a while to come up with, and is probably one of the hardest things I’ve ever done. So without further ado, here it is: my fifteen favorite romantic comedies.
15. Silver Linings Playbook (2012)
“The only way you can beat my crazy was by doing something crazy yourself. Thank you. I love you. I knew it the minute I met you. I’m sorry it took so long for me to catch up. I just got stuck.”
After being released from a court-ordered stay in a mental health facility, Pat (Bradley Cooper) struggles with his return to his normal life. His friend sets him up with his sister-in-law Tiffany (Jennifer Lawrence), but the two, both suffering from mental illness and instability, find countless flaws within each other. But they quickly realize they need each other: Tiffany needs a dance partner for a competition she’s always wanted to enter, and Pat needs to prove to his estranged wife that he can be dependable.
Silver Linings Playbook is the youngest film on my list, and received tons of attention last year, including Oscar nominations for every acting category and Best Picture, among others (and a win for Jennifer Lawrence). I think you’ll see a trend in my list where I often favor films that aren’t just romantic comedies; in fact, at first glance, Silver Linings Playbook isn’t a romantic comedy at all (and in fact, it’s only so low on my list because its status as a romantic comedy isn’t something that jumps out to me right away). At times, it’s incredibly dark, and the focus isn’t on Pat’s growing romantic feelings for Tiffany, but his growing connections to the world around him. But Tiffany is a huge grounding force for Pat; she helps him let go of his need to win back his wife and allows him to cut loose and have fun. You don’t want Pat and Tiffany to fall in love for the sake of watching people fall in love; you want them to fall in love because it genuinely seems like it would be good for them. One of the biggest draws of romantic comedies is the idea of fantasy; you want to see the characters find each other and fall in love because you want to fall in love. But Pat and Tiffany are both suffering from deep-seeded issues, and are on heavy medication and under serious pressure from their families to show signs that they’re improving. There’s no fantasy here; you don’t want to be Pat or Tiffany. But you want the best for them, and at the end of the film, it’s clear that starting a relationship is the best decision either of them could make.
14. Sleepless in Seattle (1993)
“Well, it was a million tiny little things that, when you added them all up, they meant we were supposed to be together… and I knew it. I knew it the very first time I touched her. It was like coming home… only to no home I’d ever known… I was just taking her hand to help her out of a car and I knew. It was like… magic.”
Annie (Meg Ryan) believes in love: a magical, fantastical, life-changing sort of love. So when she hears Sam (Tom Hanks) reluctantly talking to a radio show about how strongly and completely he loves his late wife, she joins a slew of women who send him letters in the hopes of attracting his attention. Sam’s son Jonah finds Annie’s letter and wants his father to pick her, going so far as to arrange a meeting on the observation deck of the Empire State Building.
Sleepless in Seattle is a quintessential rom-com, and one of the defining films in the decade that defined the genre. And it features the first partnership of Tom Hanks and Meg Ryan, a duo so great, they still haven’t been topped as the king and queen of rom-coms. And the best thing about the movie: the two main characters don’t meet until the very last scene. Sure, they see each other from afar, and Annie is very aware of Sam’s existence, but it completely changes up the standard trajectory of a romantic comedy, where the moment the two characters meet drives the entire plot into motion. Because this movie isn’t about waiting for two characters to realize they’ve met their soulmate, or trying to accept the fact that they want to settle down with this other person; this movie is about the thrill of the chase, about how exciting it can be when there’s a new presence in your life. It’s about possibilities, and how the beginning steps of a relationship where anything can happen can be just as exciting as the stages when you realize what will happen. It’s a movie that celebrates love, one that lets you sit back and get carried away by fantasy.
13. Friends With Kids (2011)
“Please, please, just let me fuck the shit out of you right now. And if you’re not convinced afterwards that I am into you in every possible way a person can be into another person, then I promise I will never try to kiss you, or fuck you, or impregnate you ever again, as long as I live.”
After seeing how having children has changed their friends’ personalities and relationships, best friends Julie (Jennifer Westfeldt) and Jason (Adam Scott) reveal that they want children, but don’t want it to affect their relationship with their future partners. Jason suggests that they have a child together, a plan none of their friends support. But they adapt well to co-parenting, happily raising their son Joe together, and soon find themselves in serious relationships. This film questions what it means to be a family, and how confusing intimate (but platonic) relationships can be.
This was a recent addition to my list, and I only decided to add it after I saw Netflix had Friends With Kids under romantic comedies. It hadn’t occurred to me that it was, because the structure is very different from most romantic comedies: the idea of the characters being in love with each other doesn’t come into it until near the end of the film. In fact, the bulk of the film is about how close Julie and Jason are because they’re not in a romantic relationship. But after seeing it listed as a romantic comedy (and getting confirmation that it’s on one of my friends’ lists), I realized that it has more in common with a traditional romantic comedy than I thought. If the most basic description of the romantic comedy genre is that it features characters’ paths as they fall in love with each other and undergo changes that allow them to enter a mature, long-term relationship, then this film 100% qualifies. Sure, the film focuses on Julie and Jason’s separate lives, and how happy they are as best friends who raise a child together, but over time, you see how unfulfilled they are with that. They begin the film as emotionally stunted people (and maybe stay that way for a while), and you watch these two people slowly realize just how much they need the other, and how much they want – and need – their relationship to become more.
12. (500) Days of Summer (2009)
“Just because she likes the same bizarro crap you do doesn’t mean she’s your soul mate.”
Told through nonlinear glimpses into the relationship between Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel), (500) Days of Summer is maybe the least romantic comedy of all the films on my list. The film chronicles every step of their relationship, from the time they meet through Tom’s crush that borderlines on obsessive, to their casual relationship and break-up.
(500) Days of Summer is such an interesting film because at the end of it, you don’t want Tom and Summer to be together. But it’s kind of hard to realize that; I think everyone sides with Tom on their first viewing and hates Summer for leaving him when clearly he cares about her, and for pulling away when he was putting so much into this relationship. But then you realize that Tom’s not the good guy here. Summer didn’t want a serious relationship, and that’s not a bad thing; Tom’s the one who couldn’t let go, and who refused to move on from a girl who refused to change herself into what he wanted her to be. But, at the same time, it’s not a bad thing to want Tom and Summer to end up together before you realize how unhealthy his feelings are for her; it takes the conventions of rom-coms and uses them against you, to create a couple that seems perfect and then slowly tears that down. But ultimately, it’s still a film about love, and how overwhelming it can be. And it’s not negative toward the whole concept; Summer does fall in love, after all, just not with the leading man. This film suggests at a larger world for its characters, one that we only get a glimpse into over these 500 days. Summer finds her own leading man, one who isn’t part of Tom’s story, suggesting that every part of life can be a great story.
11. You’ve Got Mail (1998)
“I would have asked for your number, and I wouldn’t have been able to wait twenty-four hours before calling you and saying, ‘Hey, how about… oh, how about some coffee or, you know, drinks or dinner or a movie… for as long as we both shall live?’”
Kathleen Kelly (Meg Ryan) and Joe Fox (Tom Hanks) talk multiple times a day over email – only they have no clue of the other’s identity. So when they meet in person and Kathleen learns that Joe’s family owns a large chain of bookstores that’s threatening to put her small, family-owned children’s bookstore out of business, they instantly hate each other. While fighting over business, the two still talk online, and give each other advice on how deal with their problems. After finally making plans to meet up in person, Joe realizes the identity of his online friend, a fact he uses to his advantage.
You’ve Got Mail might be one of the only movies on my list that feature not just protagonists who dislike each other for a good portion of the movie, but protagonists whose lives outside their romantic interests are heavily featured. The entire plot is hinged on the contradictory nature of the characters’ professions, giving a new layer of depth to what could have just been a light, fun comedy about two people falling in love. It’s completely character-driven, and both characters – not just these character types, but these specific people – are absolutely integral to the plot. I think this is what makes it one of the quintessential films of the genre; it doesn’t just celebrate love itself, but the people who are falling in love and the journey they have to go on. And unlike a lot of other rom-coms, the conflicts in this film are very real, and would absolutely be detrimental in real life. In other words, they’re not kept apart just for the sake of being kept apart. It’s smart and a great movie all on its own, not just a pinnacle of the genre.
10. Crazy Stupid Love (2011)
“I met a girl. I’m spending all my time with her and she is a game changer.”
Crazy Stupid Love intertwines four or five love stories, but it does it so well, you don’t even realize it’s doing it. After Cal’s (Steve Carell) wife Emily (Julianne Moore) tells him she had an affair and wants a divorce, he meets Jacob (Ryan Gosling), who helps him learn how to present himself and meet women in an attempt to move on from his failed marriage. Then Jacob, a notorious ladies’ man, meets Hannah (Emma Stone), and finds himself in a serious relationship with no desire to go back to his old life. All of the stories are complicated, unconventional, and about how much love hurts.
All right, let’s get it out of the way: Ryan Gosling’s performance in this movie might just be the single greatest thing ever committed to film. Okay, moving on now. I’ve always been a fan of movies that can intertwine multiple storylines, but it’s never been done quite like this. Throughout the film, we see different love stories in various stages – there’s Cal and Emily, whose marriage is falling apart, then Jacob and Hannah, who meet once before finally acting on their attraction from each other, then four or five other relationships that are doomed to fail, some even before they begin. And it focuses on so many kinds of love: the love a man has for his wife of over twenty years, the first love felt by a young boy…There’s something for everyone, and when all the storylines finally connect by the end of the film, you see just how important every character was to telling this story. Like (500) Days of Summer, every character in this has their own plot going on, which means there aren’t really any secondary or supporting characters. There’s so much heart at the center of this film, and it leaves you with the message that love is (as the title suggests) crazy, stupid, and makes you act similarly; but it’s so, so worth it.
9. Never Been Kissed (1999)
“All I can tell you is that when you’re my age, guys will be lined up around the corner for you.” “You have to say that because you’re my teacher.” “Actually, I shouldn’t say that because I’m your teacher.”
After a miserable high school experience, Josie Geller (Drew Barrymore) works as a newspaper copy editor, and done everything she can to move on from her terrible memories of being a teenager. But then her boss forces her to work on an undercover assignment – at a high school. Her old insecurities come out and she finds it hard to connect to her new classmates. The only person she really connects with is her teacher, Sam (Michael Vartan), but getting too close to him means risking blowing her cover. After her brother Rob (David Arquette) enrolls at the school and helps her become friends with the popular kids, Josie has her story, but has to choose between it and Sam.
I think we all know that May/December romances are the best thing in the world, but this movie offers an even better option: a fake May/December romance, since Josie is really 25 but Sam thinks she’s 17. But there’s so much more going on, especially with Josie’s struggle to accept herself for who she is, and to leave behind the image of “Josie Grossie,” her nickname in high school. It’s such a great high school movie, because it features the standard questions about identity and love and everything, including the standard trope of a teenage girl waiting for her first love and first kiss. Her second chance at high school lets her become the person she always wanted to be as a teenager – but, much like high school itself and adolescence, it has to end. In this case, it’ll end either when Josie has her story or if she blows the whole thing, giving the story much higher stakes than a typical high school comedy. And then there’s Sam, who connects with Josie because of her maturity, but of course, neither of them can act on their feelings. Again, it’s a movie with real stakes, not just something thrown in for the sake of creating drama. There’s such a great vulnerability to Josie, which is painfully evident in the film’s iconic ending scene, when, after having revealed her true age and reason for being at the school, she stands in the middle of the baseball field and waits for Sam to come kiss her – her very first kiss, a fact she’s embarrassed to admit. It’s one of the few movies from this genre or time period that equates teenagers with adults, by nature of the fact that, in this case, an adult becomes a teenager. Josie has the exact same problems as her classmates, but her second chance gives her the courage to finally do something about it and become the person she’s always wanted to be. And, apparently, that person is one who makes out with Michael Vartan on baseball fields. I feel a kinship with her.
8. The Holiday (2006)
“Iris, in the movies, we have leading ladies and we have the best friend. You, I can tell, are a leading lady, but for some reason, you’re behaving like the best friend.”
The Holiday is probably technically a Christmas movie, but don’t tell anyone. You can totally watch it any day of the year, like I do. Iris (Kate Winslet) has decided to move on from her ex-boyfriend Jasper (Rufus Sewell), who has remained a huge part of her life since their break-up, despite his new relationship. She finally gives up after he announces his engagement, and discovers a home exchange website where you switch homes, cars, everything, with someone. She decides to switch homes with Amanda (Cameron Diaz), a woman from Los Angeles who wants to get away after breaking up with her long-term boyfriend who cheated on her. Amanda arrives at Iris’ cottage in Surrey and meets Iris’ brother Graham (Jude Law) on her very first night. Graham shows up drunk, forgetting that his sister isn’t home, and the two wind up sleeping together and starting a relationship, despite the fact that Amanda is only visiting for two weeks. Meanwhile, Iris meets Miles (Jack Black), and starts a friendship with him and Amanda’s elderly neighbor, who they discover is a retired but incredibly well-known Hollywood screenwriter. Both storylines are about love, of course, but more importantly, about the bonds that can be created in a short time, and the sorts of relationships that can’t be forgotten about.
Jenn and I have been friends for a long time, and over the course of that friendship, we’ve developed a few rules. For example, any and all pictures of Jake Johnson discovered on Tumblr need to immediately be sent to the other. Another is that we will always text each other when certain movies are on TV. The Holiday is one of those films. No matter how many times I watch it (and I watch it a lot, especially during Christmastime), I’ll never get tired of it. It’s a long movie, almost two and a half hours, because it spends so much time building up the relationships between Amanda and Graham, and Iris and Miles. You get such a strong sense of how the two couples relate to each other and why they like each other, something that can often be glossed over in romantic comedies. More importantly, you understand exactly how hard it will be for the two women to return home at the end of their holiday, because you know exactly what they’ll be leaving behind. It’s one of the best feel-good films of all time, one that never loses its charm, no matter how many times I watch it.
7. Clueless (1995)
“I am totally butt crazy in love with Josh.”
Based on Jane Austen’s Emma, Clueless is the story of Cher Horowitz, a vapid valley girl who enjoys helping those less fortunate than her – whether it be people in need of a makeover or in need of being set up romantically, Cher will do whatever it takes to help those in need. She helps her new friend Tai (Brittany Murphy) fit in at school, and tries to set her up with Elton (Jeremy Sisto), who, as it turns out, is only tolerating Tai’s attention because it’ll get him close to Cher. But her matchmaking is rendered moot when Tai reveals she has a crush on Cher’s ex-stepbrother Josh (Paul Rudd), who, Cher eventually realizes, is a total Baldwin.
I don’t want to be overdramatic here, but Clueless is the greatest movie ever, okay. I watched it countless times growing up, and to this day, it’s still probably my favorite 90s movie. It was the predecessor to Mean Girls, a film so quotable that, if you’re a fan, you probably know every line. I think we’ve all yelled “You’re a virgin who can’t drive” at a friend in the heat of an argument. But beyond its humor, Clueless is a movie with heart. Cher is dedicated to helping others, and even though she’s a little blind and selfish about it, she has a good heart. And with so many couples around her, some that she even set up herself, you can’t help but feel bad for her as she tries to find love and fails. She views the world so clearly and optimistically that you can’t help but share her vision, so when she realizes that she’s in love with Josh and the fountains swell up behind her, it’s like watching a freaking unicorn being born, okay, because Cher Horowitz deserves love and happiness, and Paul Rudd with his stupid face* is the perfect match for her.
*Fun fact: This film came out in 1995, and Paul Rudd still looks exactly the same. It’s been eighteen years and the man has not aged. Fuck Paul Rudd**, is what I’m saying.
**In more ways than one.
6. Say Anything (1989)
“I gave her my heart and she gave me a pen.”
Unlike some other films on my list, Say Anything is focused singularly on the love story between Lloyd Dobler (John Cusack) and Diane Court (Ione Skye). And, okay, yeah, it’s a little…weird sometimes. The summer after they graduate from high school, Lloyd decides to ask Diane on a date, despite the fact that they’ve never spoken and she was their class valedictorian and he’s convinced she’s too good for him. But for some reason, she says yes, and over the summer, the two fall in love.
Say Anything is such an interesting movie for me, because it’s one of my top 10 favorite films of all time, but I don’t think it’s really a universally entertaining film. For one thing, Diane Court is terrible. Terrible. Really just awful. Part of the reason that she’s so awful is that the film glorifies Lloyd, whose adoration of Diane is made abundantly clear from the very first scene. And, okay, realistically, Lloyd’s kind of the problem here: he’s kind of clingy, and can’t let go of Diane even after she breaks up with him for totally valid reasons, and he literally and verbally says that he doesn’t want to do anything in his life but be with Diane. And it’s great. Say Anything never fails to remind you that it’s about teenagers falling in love for the first time, so it’s easy to forgive them when they say things they don’t quite mean or do things that might be considered slightly creepy in other contexts. But John Cusack plays Lloyd so earnestly that it’s completely endearing when he says that all he wants to do is be with Diane because he’s good at it. This is a boy completely and utterly head over heels for Diane, and you can’t help but get swept up in the fantasy of the film and fall in love with Lloyd Dobler. He’s kind of the perfect example of a movie boyfriend: you watch the movie and sigh deeply and say you wish someone loved you like Lloyd loves Diane, but in reality, having a boyfriend like that would probably creep you out. But you forgive his imperfections, just as you forgive Diane’s (well, maybe some people do. I really don’t like Diane), because ultimately, this is a film about two people who should not be together. His friends don’t think they belong together, her father doesn’t think they belong together…The only people who think Lloyd and Diane should be together are Lloyd and Diane. So it’s easy to forgive the constant moments throughout when the two aren’t meshing, or when their relationship seems rough and ill-fitting, because when everything finally gels at the end, you see that they might be perfect for each other after all.
5. How to Lose a Guy in 10 Days (2003)
“True or false: All’s fair in love and war.” “True.” “Great answer.” “Good question.”
Andie Anderson (Kate Hudson) is the “how to” girl at Composure Magazine. She comes up with her new story, How to Lose a Guy in 10 Days, just as Benjamin Barry (Matthew McConaughey), an advertising executive), starts a bet with his coworkers that he can make a woman fall in love with him in ten days. Having visited the magazine earlier that day and heard about Andie’s article, Ben’s coworkers choose Andie as the woman for Ben. The two begin dating and seeing each other every day, but starting the day after they meet, Andie begins acting crazy, going through some of the clichéd mistakes girls make that drive men away. But she grows frustrated when Ben doesn’t break up with her, leading her to up her game and do whatever she can to get rid of him. Somehow, at the end of their ten days together, they realize that they’ve fallen in love with each other – which becomes a problem when they learn of the other’s ulterior motive.
This is another movie that I always watch with Jenn when it’s on TV. Kate Hudson and Matthew McConaughey tried to become the Meg Ryan and Tom Hanks of the 2000s, and it would have worked if they had chosen a movie like this for their second pairing. But no one cares about Fool’s Gold, especially not when their first partnership is as great as this. How to Lose a Guy in 10 Days is over the top, hilarious, and genuinely romantic – something a lot of romantic comedies seem to forget about these days. Though it’s a clear competition between Andie and Ben, it’s impossible to choose a side. It’s such an interesting dynamic because their true personalities aren’t being presented for the bulk of the film, so while you root for them to get together, you can’t possibly root for the versions of them that are actually together, if that makes sense. The only way they can feasibly have a healthy relationship is if they’re truly acting like themselves – but that requires both of them finding out about the other’s mission, which could ruin any chance of a relationship. That tension keeps the viewer invested, and makes the few genuine moments between Andie and Ben (including their time together at his parents’ house. Specifically in his parents’ bathroom) so exciting and painful to watch. It’s also incredibly quotable, and gave me many phrases that I’ll drop into casual conversation (“Frost this!” and “I love you, Binky, but I do not have to like you right now” in particular). This film has everything a great romantic comedy needs, including an ending chase scene that leads to a declaration of their true feelings. As every classic film should have.
4. The Princess Bride (1987)
“Death cannot stop true love. All it can do is delay it for a while.”
The main plot of the film is a framed narrative set around an old man reading a bedtime story to his sick grandson. Within the world of the film, The Princess Bride is an old fairy tale that features love, adventure, tragedy, and revenge. It’s the story of Buttercup (Robin Wright), a girl who falls in love with Westley (Cary Elwes), a worker on her family’s farm who has no money to his name. He sets off to travel in an attempt to earn some money to secure a future with Buttercup, but after some time, she hears that his ship was attacked by pirates and that he’s been killed. Five years later, before Buttercup marries Prince Humperdinck (Chris Sarandon), she’s kidnapped by three men who inform her they plan to kill her. But they’re followed by a mysterious man in black who seems set on rescuing the princess. Three guesses who that man is.
My mom used to watch this movie with my sister and I all the time when we were growing up. And I loved it: it had a princess, sword fights, and a bad word. It was everything a seven-year-old girl could want. As I got older, I realized that it’s actually, like, a great and celebrated movie because of its wit, and I remember my reaction upon hearing that it’s considered one of the greatest comedies of all time: “Oh. Wait, it’s funny?” I hadn’t seen it in a while at that point, so I very quickly rewatched it and realized, oh yeah, this is one of the greatest movies I’ve ever seen. But even before I had developed a sense of taste in films, I fell in love with this movie. Its appearance as a fairy tale makes it easy for everyone to enjoy, but it’s only once you’ve gotten older and have gained an appreciation for other romantic comedies that you can understand what makes Buttercup and Westley’s story so great. If movies are about surrendering yourself to a fantasy, The Princess Bride provides the ultimate escape.
3. Love Actually (2003)
“With any luck, by next year – I’ll be going out with one of these girls. But for now, let me say – Without hope or agenda – Just because it’s Christmas – And at Christmas you tell the truth – To me, you are perfect – And my wasted heart will love you – Until you look like this.”
Hopefully, we’ve all seen Love Actually, so I’m gonna spare you a plot summary. Love Actually is probably the most quintessential romantic comedy of the last decade, and yet, it’s not always a romantic comedy. With so many storylines, it’s easy to pick favorites and attach to some over others, because there are just so many different kinds of love represented. Obviously, the best is Mark and Juliet, which isn’t even a love story at all. The theme is best represented throughout by Rowan Atkinson’s character, a possibly magical presence that enables the growth of certain storylines. There’s a sense of magic and possibility around Christmas, one that can make life seem like a fairy tale. You can fall in love with someone in the span of a few weeks, despite a language barrier, or tell your best friend’s wife you love her to the pre-recorded songs of carolers. Anything can happen in a movie like this, and it proves that no matter what, love actually is all around.
2. Friends With Benefits (2011)
“You said you wanted your life to be like a movie.” “Oh, no, no –“ “Shut up, it’s not what you think. Jamie, will you be my best friend again?” “This is so lame.” “Oh, I know. It’s some Prince Charming shit, though, right?”
In 2011, two films about people becoming friends with benefits came out. One of them wasn’t good. The other one gave us like a million sex scenes with Justin Timberlake and Mila Kunis. Friends With Benefits explores the relationship between Dylan and Jamie, two friends who decide to start sleeping together, confident that they can handle a purely physical relationship. Spoiler alert: they can’t.
I know, I know, barely any good romantic comedies were made after 2003 or 2004, but this is one of the few that reminds us that the genre still has a fighting chance. If anything, the decline of the genre is what makes this film possible. It’s incredibly self-aware, and both characters comment on romantic comedy clichés throughout the film – while eventually starting to fall victim to those standard tropes themselves. We all know the best movies are the ones that are about movies, and this is the best kind of all: a movie about romantic comedies. Also, Justin Timberlake’s ass, so.
Like most people, I scream “GPOY” every time a movie character does something that I relate to even slightly, but Jamie is the true representation of us all. She watches romantic comedies obsessively, knowing that they’re cheesy and unrealistic and something you would never, ever want for yourself…But she also cries at their endings, and becomes completely wrapped up in them. Basically, we are all Jamie (much more literally, in my case. That’s a name joke. BOOM). She serves as the best kind of audience surrogate, the one who is strong and determined and successful (and, much like You’ve Got Mail, this might be one of the most character-driven films the genre has to offer. Like Joe and Kathleen, Dylan and Jamie meet through work, and the pressures of their job are a constant conflict throughout the film, and are a huge factor in how they finally come together), but she’s not afraid to watch these movies and get swept away by them. She understands the greatness of romantic comedies: no matter how cheesy they can seem, they appeal to something in all of us, and let us vicariously experience things we might otherwise never get to.
1. When Harry Met Sally (1989)
“I love that you get cold when it’s 71 degrees out. I love that it takes you an hour and a half to order a sandwich. I love that you get a little crinkle above your nose when you’re looking at me like I’m nuts. I love that after I spend the day with you, I can still smell your perfume on my clothes. And I love that you are the last person I want to talk to before I go to sleep at night. And it’s not because I’m lonely, and it’s not because it’s New Year’s Eve. I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.”
Here’s how you know this is the greatest movie of all time: it appears as #1 on three out of the four lists we’ve posted, and that’s only because Jenn hasn’t seen it.
Kim said this was a mic drop moment – no explanation needs to be given for why it’s the greatest romantic comedy of all time. It just is. When Harry Met Sally is the ultimate romantic fantasy: what would happen if you fell in love with your best friend? The answer, of course, is that it would take place slowly over a few years, during which your feelings would change from absolute contempt to eventual friendship, with some very awkward interactions thrown in. And that’s what makes When Harry Met Sally so wonderful: it still has the escapist elements of a romantic comedy, but it feels real. You’re following Harry and Sally on this journey, knowing exactly what each step means for them. There’s a very real sense during some of the more dramatic moments that this really could be the end of their friendship. In fact, because it defined so many classic romantic comedy moments and tropes, it’s unlike any other film in the genre, it’s easy to forget that you pretty much know exactly how it’s gonna end. Now, it’s a story that’s been told a million times, but when you watch it, you forget that you’ve ever seen it before – because you haven’t, not like this. Everything about this movie is perfect, and without it, the romantic comedy genre as we know it would be drastically different.
There you have it, folks! What are your favorite romantic comedies, and how do you define the genre? Make sure to check out our podcast next week when we discuss this in excruciating detail!