I am the target demographic for romantic comedies – I’m young, single, and a hopeless romantic. I’m truly a sucker for nearly anything that boasts and brags that it is a “rom-com.” I’ll laugh and coo and (if the story is compelling enough) shed a tear. And I’m not exactly sure what it is about romantic comedies that draw a majority of the female population. Is it the inevitably handsome leading man? Is it the love story? Is it the banter and the comedy? If I’m being honest with myself, I think it’s a combination of all of those elements as well as this little added kick: believability. We, as women, have to WANT to become the leading woman in the rom-com. We have to feel like we could be her, or – at the very least – feel like we know someone like her in our lives. Relatability is a key element in any and every story, and it’s never more integral than in a romantic comedy.
There are a LOT of rom-coms out there. I mean… a LOT.
And what’s interesting is that there are a lot of movies that I would typify as a romantic comedy that, say, my friends Kim and Sage and Jaime might not. Every person has their own particular formula for what makes a romantic comedy “great.” My favorite movies will (I guarantee) not all be included in your list of favorite movies. But that’s what makes rom-coms so wonderful: there are a plethora to choose from and each have particular elements that make them stand out from the rest of the pack.
Kim, Sage, Jaime, and I will be discussing our lists in depth this coming week when we kick off our first ever podcast together. So be sure to keep an eye out for that link (and this week for everyone’s respective lists). We’ll probably be debating our selections quite a bit so you don’t want to miss THAT spectacle!
What landed on MY top 15? Click below to find out and be thinking of your own lists as you do! ;)
15. The Princess Bride (1987)
The story in a nutshell: A grandfather reads a story to his sick grandson. It’s a love story between a stable boy named Westley and a princess named Princess Buttercup. Along the way, the pair encounters numerous obstacles to their happiness, the largest being Buttercup’s impending (albeit reluctant) marriage to Prince Humperdinck. In the end, true love prevails, as we are taught that always does.
Why I love it: The Princess Bride is one of those rare films that encompasses it all – wit and humor, satire, action/adventure, comedy, and romance – and bundles it together flawlessly. It’s also one of the few romantic comedies that my male friends enjoy. There’s a beautiful love story, fantastic lines that have stood the test of time (“You keep using that word. I do not think it means what you think it means”/ “My name is Inigo Montoya. You killed my father. Prepare to die.” / “Mawwiage.”), and all of these elements combined make this one of my top favorite romantic comedies.
14. Never Been Kissed (1999)
The story in a nutshell: Josie Gellar grew up teased and tormented, labeled “Josie Grossie” throughout high school. She never truly had a real relationship, and explains to her co-workers that she’s never really been kissed. As an adult, Josie returns to high school, posing as a student for her newspaper assignment and ends up falling in love with her English teacher, Sam. While there, Josie learns a lot about herself, about the people she befriends, and – most importantly – about love.
Why I love it: I first saw this movie when I was at a sleepover and immediately fell in love. I think what I search for in rom-coms is actually pretty simple: a story about a girl who learns something about herself, but who also learns a lot about how to love. Josie is a wonderful character because she has a chance to hit the reset button on her life, for a while. And she takes the opportunities she missed as a teenager because of her insecurities, thinking that maybe – just maybe – she’ll find someone to be happy with. But the beauty of Never Been Kissed is this: it’s just as much of a story of Josie falling in love with Sam as it is a story of Josie learning to love HERSELF. She had to accept that her past is a part of her life in order to move forward and achieve the happiness she’s always wanted and deserved. THAT is a beautiful rom-com message.
13. Love Actually (2003)
The story in a nutshell: It’s Christmas, which means that love is in the air or else dissolving. This movie is a story of ten journeys – journeys of unrequited love, first love, declarations of love, and the love of friendship – that are all connected in a beautiful, intricate web. While not every story has a happy ending, not every love story truly DOES. But that doesn’t mean it’s not one.
Why I love it: There are so many wonderful stories in this movie, and I love seeing films that tie together multiple arcs in a coherent manner. Love Actually is all about – shockingly – love. And what’s wonderful is that it paints a realistic depiction of love. It’s not easy, it’s not always pretty, and sometimes it comes at a cost. But it is ALWAYS worth the risk to put your heart on the line for the person you care most about. And I mean, the iconic scene in this movie (“To me, you are perfect”) will always make me weep.
12. The Wedding Singer (1998)
The story in a nutshell: Robbie Hart is a wedding singer and is engaged to his longtime girlfriend, Linda. Everything seems great… until Linda runs away, the day of their wedding. Now bitter and cynical about love, Robbie continues to play at weddings, where he meets Julia Sullivan and becomes friends with her. There’s only one problem: Julia is engaged to the rather jerkish Glenn Gulia. Slowly but surely, Robbie’s heart begins to soften and he falls in love with Julia. But will she call off her wedding for him?
Why I love it: Even before it was turned into a Broadway musical, I absolutely adored The Wedding Singer. There was something really special about the chemistry that Adam Sandler and Drew Barrymore had together. They were believable as Robbie and Julia. And maybe what I loved most about this movie was that Robbie was a good guy, through and through. He DESERVED Julia and the mistake that he made that pushed her away was one that he made only because he didn’t FEEL like he was enough – because he had been jilted by Linda; because she had told him that his job of being a wedding singer would never be enough for her. And this movie is just so beautiful because Robbie and Julia deserve one another in EVERY sense of the word.
11. Music and Lyrics (2007)
The story in a nutshell: Alex is a washed-up 80s pop star – his band, PoP! has fizzled, leaving him in the dust and forced to relive his former glory. But he gets a shot at fame when his manager asks him to write a song for a young, extremely popular pop star. There’s only one problem: Alex has writers’ block, big time. Enter Sophie, a young woman who majored in creative writing and is watering Alex’s plants. With her lyricism and Alex’s music, the two manage to deliver a song that the pop star, Cora, accepts. But as Alex and Sophie begin to grow closer, creative wedges and past emotional baggage threaten to undo their budding romance.
Why I love it: There’s a reason that both Hugh Grant and Drew Barrymore make multiple appearances on my list, and it’s because they’re both extremely gifted rom-com actors. Hugh Grant often portrays somewhat cynical, calloused, or self-centered male leads, while Drew Barrymore tends to play the endearing, down-to-earth love interest. And what’s wonderful about this movie and their chemistry is something that I love about most romantic comedies: the characters grow and learn from one another. Alex becomes a lot less self-absorbed by the end of the movie. He cares about the promise he made to Sophie and sticks to that promise for her. And Sophie learns to regain her confidence after having it shattered by a former love, thus opening her heart to Alex. That, coupled with the hilarious moments (Hugh Grant can make me laugh in just about anything) and wonderful supporting cast lands this on my list.
10. While You Were Sleeping (1995)
The story in a nutshell: Lucy’s a token collector who leads a pretty lonely life. She has no family, but is enamored with a man who comes to her booth every day. On Christmas, Lucy is working and watches as her crush gets mugged and falls onto the tracks. In a heroic effort, she rescues the man, who is then rushed to the hospital, suffering a coma. When Lucy dreamily muses that she was going to “marry that man,” the nurse and her crush’s (Peter’s) family mistakenly believe that she is his fiancée. Jack – Peter’s brother – isn’t buying that Lucy is Peter’s fiancée. Yet slowly but surely, Jack and Lucy begin to fall for one another. So what will happen when Peter wakes up?
Why I love it: I first discovered this movie while I was home sick one week. My mom came into the room while I was watching it and commented on how she absolutely loved the movie. And truly, this is just such a beautiful, moving, and hilarious movie. Lucy is such a wonderful character because we’re not meant to necessarily pity her – we’re meant to empathize with her, to put ourselves in her position and feel what it’s like to have a group of strangers hold you in their arms as their family. And Bill Pullman does such a wonderful job at fulfilling the role of romantic lead in this movie. He’s sweet and charming, without being overtly so. He’s NORMAL, and I think that’s what the audience is meant to take away from the film. While Lucy idealized (and while we often do the same) this man, Peter, who she never spoke to, her soul mate was so close the entire time.
9. 50 First Dates (2004)
The story in a nutshell: Henry Roth uses his job to his advantage. He’s a veterinarian in Hawaii, after all, and likes to hit on female tourists that he knows he’ll never have to see again, give them a fantastic week, and then come up with an excuse as to why he is unable to continue their relationship. One day, however, in a diner, Henry meets Lucy. She’s beautiful, but a local, which keeps Henry and his womanizing lifestyle at bay. The next day, however, he sees Lucy again and approaches her… except that she has NO recollection of who he is, and becomes extremely nervous and confused when he insists that they met the day prior. Henry learns, thanks to the diner’s owner, that Lucy was involved in a car accident that left her with a type of amnesia – she goes to bed and wakes up the next morning, repeating the same day over and over. Her brother and father keep her stable by reliving that day, October 13th, for her every day. Henry, however, is intent on getting to know Lucy even though it means re-meeting her every day.
Why I love it: Adam Sandler comedies usually surprise me, for one reason: they pack a powerful punch. Years ago, I was on a flight home from Brazil with a high school mission’s team. We thought it would be a good idea – the four or five girls in my row – to begin watching Click at the exact same time. A few hours later, we were SOBBING our eyes out because an emotional twist had sucker punched us from out of nowhere. And that’s what his comedies are quite good at, to be honest. Yes, I often roll my eyes at the innuendos and the cheesy jokes. But behind that façade, 50 First Dates is one of the most touching, wonderful little rom-coms there is. (And the ending is still one of the absolute best things EVER.)
8. Two Weeks Notice (2002)
The story in a nutshell: Lucy is a lawyer. Lucy went to Harvard. Lucy is intelligent. Lucy is… working for a self-centered, entitled man-child named George. She suddenly becomes much more than his employee – she becomes his aide, constantly at his beck and call. In her pent-up frustration, Lucy gives her two weeks notice, visibly shattering George who attempts to convince her to stay and prevent her from being hired elsewhere. For all their bickering, for all his selfishness and her perfectionism, they realize – slowly – that they’ll miss one another and actually make each other better. But will they confront this realization before it’s too late?
Why I love it: Didn’t I say that there was a reason Hugh Grant made my list multiple times? In Two Weeks Notice, his performance is extra noteworthy because of how wonderful and comedic it is. Sandra Bullock absolutely SHINES as Lucy – she’s got sass and wit and intellect, but also baggage that she rarely lets other people see. George is self-absorbed, shallow, and vain. And even though she cannot see an abrupt transformation, Lucy HELPS George become a better person. He tells her that she’s become the voice in his head and he desires to do the right thing because of her. When two people change for the better in a romantic comedy, that is when it is truly worth watching.
7. Sweet Home Alabama (2002)
The story in a nutshell: Melanie Carmichael seems to have it all – the career, the city, the guy, and now the ring, to top it all off. There’s only one problem: she can’t quite have it all yet. After Melanie’s engagement to the son of New York’s mayor, Andrew, she flies back home to Alabama in order to officially get a divorce from her childhood sweetheart who has refused to sign the papers for the last seven years. Melanie isn’t thrilled to be back home, ashamed of her roots and desperate to return to the life she made for herself, but slowly begins to soften in the South and respect the people who have lived their entire lives there and never stopped caring about her. But Melanie is now faced with a choice: does she return to her new life and to Andrew or take a chance on her childhood love?
Why I love it: This rom-com is another one that I first watched at a sleepover and became immediately enamored with. The story is so beautiful because it’s about a girl who tried to forget where she came from, who tried to distance herself from her past, and inevitably realized that she never really lost that part of herself. And just as Melanie tried to start over in New York, she tried to do the same with Jake. She needed to change who she was because she was afraid of who she had been and that she’d always remain a small-town country girl with no opportunities in life. But what Melanie truly realizes is this – don’t write off first loves, don’t try to change who you are, and don’t forget that home isn’t just a town or a state: it is who you are, at your very core. And when Melanie accepted that, she also realized that she had never stopped loving Jake at all.
6. Sleepless in Seattle (1993)
The story in a nutshell: Sam Baldwin is a widower whose son Jonah calls into a local radio station in Seattle on Christmas Eve, explaining how he believes his dad needs to find a new wife. When the radio talk show host requests that Sam be put on the line, he tells the story of how he fell in love with his late wife and hundreds of female listeners across the country are touched by Sam and decide to write to him. One female listener is Annie Reed, who lives in Baltimore. A journalist set to marry her caring but rather dull fiancé, Annie decides to write to Sam as well, feeling a connection to him instantly just by hearing his voice on the radio. What follows is a series of near-misses that culminate in one moment on Valentine’s Day that can only be described as “magical.”
Why I love it: Everything about this movie is flawless, so I don’t really know where to start. Tom Hanks and Meg Ryan are fantastic. The story is comedy, but has some wonderful tear-inducing elements to it (I’m looking at you, Sam’s “magic” speech). It’s a story where you root for each character, where you hope that they find happiness because you know that they deserve it. And Annie? Well Annie is the kind of woman we could very well be, or – at the very least – be friends with. Sam, too, is normal. He’s handsome, for certain, but not overtly so. He’s an architect, not anyone particularly prestigious. Because Sleepless in Seattle, truthfully, is a story about what can happen when you least expect it to. And the bottom line is that it makes you believe that little, inconsequential moments CAN add up to something miraculous.
5. 27 Dresses (2008)
The story in a nutshell: “Always a bridesmaid, never a bride” has never been more appropriate in anyone’s life than it is in Jane’s. She’s a perfectionist, a type-A personality, and a protector of everyone around her. In fact, she is SO loyal that she agrees to be in two different weddings on the same night across town from each other. And that’s where Jane meets Kevin, a handsome but cynical wedding guest who accidentally winds up with Jane’s planner when she leaves it in the back of her cab. Jane, meanwhile, is distracted by the reappearance of her baby sister, Tess, who has just returned to town. At a bar one night, Tess arrives and meets George… and that’s very bad news for Jane who has been in love with George (who is also her boss) since she started working for him. Tess and George begin a whirlwind romance, which slowly eats away at Jane. But as weeks tick by, Jane finds herself building a bantering friendship with Kevin. The question is: will Jane ultimately find her happiness or constantly settle for making everyone but herself happy?
Why I love it: I’m a lot like Jane. I’m the oldest sibling, I take care of everyone, and I have yet to have my real “moment.” And what I love about this movie is that it takes a trope (a woman having a seemingly unrequited crush on her boss for years) and turns it on its head. Similarly, rather than evolve a selfish character into one that is more selfless, 27 Dresses is all about Jane learning to let go of control – to let other people, like her sister Tess, make mistakes. She learns how to say no to people, how to stand up for herself, and KEVIN is the one to teach her that. He truly learns to love and care about her. And it’s beautiful in its irony: she’s the one who always takes care of others, but when she’s finally able to let go – to let others live and learn for themselves – there is someone right there to finally take care of her.
4. The Proposal (2009)
The story in a nutshell: Andrew works for Margaret Tate in New York City. She’s a cold, calculating, and relentless boss, but she’s one of the best in the publishing world and Andrew is seeking to publish his manuscript eventually. When Margaret is informed that her visa will be expiring and she’ll be deported back to Canada, the woman hatches a plan – she will force Andrew to pose as her fiancé in order to stay in the country. The pair meets with an immigration agent who informs them of the trouble they will be in, should their marriage be anything other than legitimate. Margaret and Andrew claim that they are in love and – to prove their devotion to the plan – Andrew and Margaret return to Andrew’s home state of Alaska for his grandmother’s 90th birthday. Though they initially despise one another, Margaret learns how to be vulnerable, to open herself up to having a family and love and Andrew learns to see another side of Margaret as well.
Why I love it: Sandra Bullock can do no wrong, in my book. And – paired with Ryan Reynolds – she utterly shone in The Proposal. I love Andrew and Margaret’s relationship at the beginning of the movie. They are truly antagonistic toward each other, which makes the end of the movie all the more fulfilling. Their love is gradual in this film, and beautiful because of that. There are some genuinely HYSTERICAL moments, but also some really touching ones. And it’s Margaret who learns how to soften, how to open herself up, how to become vulnerable. This endears her toward the audience and Andrew as well, who begins to realize that there is more to her than she allows others to see. And as he learns more about her, he begins to fall in love with her. (Ryan Reynolds in this movie, guys. I’m telling you.)
3. The Holiday (2006)
Why I love it: Jaime and I text each other around October each year, without fail, to tell the other that The Holiday is on TBS. Never mind the fact that they will play this particular movie for four months straight, we HAVE to inform one another when it is airing. I love The Holiday, and not just because I was introduced to it AND Love Actually during a girls’ movie night in college. I love it because I always related to Iris (“You, I can tell, are a leading lady. But for some reason you’re behaving like the best friend.”) on a fundamental level. I love that she grows confident in herself throughout the course of the film – how she evolves from being desperate and depressed to courageous and happy. Similarly, Amanda began the film rather cold and unfeeling toward relationships. She heavily guards her heart because of baggage from her parents’ divorce, and doesn’t allow herself to ever become emotional. And then she meets Graham who is sensitive and caring and also a bit wild at heart still… and she begins to open herself up to the possibility of something real and meaningful. I LOVE the shot of Amanda crying in the car, I truly and honestly do. It’s one of my favorite things about this movie because of how telling and poignant it is. (Except for Jack Black. He completely and utterly stole my heart during this film.)
2. You’ve Got Mail (1998)
The story in a nutshell: Joe Fox and Kathleen Kelly have never met. It’s probably for the best, too, since Joe is a part of the Fox family – a family of wealthy men who own bookstore chains that are trying to buy out and shut down small, family-owned bookstores like Kathleen’s. Joe and Kathleen don’t know one another in “real life”: they’re fairly close to one another online, though, having met in a chat room where they’re referred to as “NY152” and “Shopgirl” respectively. And that’s perfect because both have significant others in their lives so they can’t possibly fall in love with someone they’ve never actually met… right? But when Joe and Kathleen DO meet in real life, they immediately clash, cannot stand one another, and – most importantly – don’t know the others’ Internet pseudonyms. What follows is less of a story of “boy meets girl” than it is “boy and girl learn from each other and then fall in love.” And it’s brilliant.
Why I love it: What can I possibly say about this movie, apart from the fact that it is one of my favorite romantic comedies of all time? I will ALWAYS re-watch when it is on television, no matter what time of day it is. I can quote most of the movie by heart. I still laugh at the jokes, I still ache when Kathleen gets stood up by Joe, I still celebrate when she insults him because he – ironically, as “NY152” taught her to stand up for herself (is that becoming a theme thread in my favorite rom-com list?). I still swoon at the ending, and I still love every little detail about this film. It so perfectly embodies what a great romantic comedy should have – likeable, but flawed leading men and women; a compelling conflict; multiple resolutions; a plethora of supporting characters to anchor the leads; wit and satire; and an ending to make women place their hands over their hearts and sigh. They just don’t make them like this anymore, kiddos.
1. How to Lose a Guy in 10 Days (2003)
The story in a nutshell: Andie Anderson is a successful journalist, thriving as Composure Magazine’s “how to” columnist. But Andie is passionate about politics and social issues, and is looking to cover more hard-hitting stories. Her boss assures her that she’ll have freer rein… right after she writes a new how-to piece based on friend and columnist Michelle’s personal life. Andie’s assignment is to write about what women do wrong in relationships – “How to Lose a Guy in 10 Days,” she decides to call it. Meanwhile, Benjamin Barry wants to be given more responsibility at HIS job and seeks to pitch a diamond campaign to his boss. His boss agrees, once Ben displays his confidence in his ability to get any woman to fall for him, and – through some manipulation by his envious female co-workers – Ben meets Andie in a bar and the two begin a 10-day relationship in which Ben tries his hardest to draw Andie in, while she tries her hardest to drive him away (without, of course, either knowing the others’ motives). And yet, somehow they begin to fall in love, which makes everything a lot more complicated.
Why I love it: This is the film that I will watch forever. I own it on DVD, but I’ll always watch it when it’s on Bravo. I saw the film in theatres when it was released ten years ago (has it really been THAT long?) and I consider it to be my favorite romantic comedy because it nails absolutely EVERYTHING it sets out to accomplish. It wanted to provide plenty of laughs? It succeeded. It wanted to make us swoon? It hit the mark. It wanted us to feel invested in Ben and Andie’s lives? It did just that. It made the SUPPORTING characters have significant purpose outside of merely supporting the leads? It did. It threw high stake after high stake at the characters? Yes. It grew Andie and Ben into better people? I do believe so. I think what I truly love about How to Lose a Guy in 10 Days is that it’s not just a “feel-good” comedy, though I do feel great after the credits roll and everyone gets their happy ending. It’s a story about men vs. women, which is something that I don’t think, at least, happens a lot in rom-coms. Usually we only see the romantic comedy from the female perspective, but this rom-com contrasted Andie and Ben and their respective friends really well. Though How to Lose a Guy in 10 Days may not nab the coveted top spot on most lists, it definitely remains at the top of mine.
Now that I’ve selected fifteen movies that rank as my favorite romantic comedies of all time, what movies land on YOUR list? Hit the comments below or tweet me and let me know your selections. And, as always, have a great week. And happy 4th of July to all of my American friends! :)