There are few genres of film more routinely bashed and discarded than romantic comedies. They’re like emo music or fast food. Everyone loves to stick their nose in the air and act like there’s nothing of substance in play, but the truth is there are a few great romantic comedies released every year. More importantly, some of the greatest movies ever made are Rom-Coms, and it’s time we started celebrating them. It’s time we stopped treating the terms “romantic comedy” and “chick flick” as synonyms. Because they’re not. A great romantic comedy should appeal to human beings by offering enough laughs and enough touching moments to please the entire audience, whether they were dragged there by a spouse or not.
The list that follows is CinemaBlend’s definitive comment on the best romantic comedies ever made. It’s littered with beautiful love stories, hysterical lines and even rodents of unusual size. You may not agree with all of our choices, but we can all but guarantee quite a few of your favorites will be on the list.
So, grab your invitation to Bogey Lowenstein’s party, put in some fresh hair gel and grab what she’s having on the way because these are the 30 best romantic comedies ever!
41) Love, Simon (2018)
The Couple: Simon Spier and Bram Greenfield
Story In A Nutshell: A 17-year-old high school student doesn’t know how to come out to his parents, friends, and classmates. If an existential crisis wasn’t enough for the young man, he has also fallen for an anonymous classmate whom he can’t identify.
Why It Works: There are a lot of things about Love, Simon that work, including its cast, heart-felt conversations, and the way it captures the confusion of young love. But the aspect about the 2018 romantic comedy that works the best is the way in which it tells a beautiful story about a boy knowing that he has to find out who he is doing everything that he can to take control of his life to figure that out.
Perfect Quote: “I’m supposed to be the one that decides when and where and how and who knows and how I get to say it — that’s supposed to be my thing! And you took that away from me.”
Rent/Buy Love, Simon on Amazon.
40) To All The Boys I’ve Loved Before (2018)
The Couple: Lara Jean and Peter
Story In A Nutshell: Lara Jean, a shy high school junior has a secret hobby of writing letters to her crushes, but her private pastime (and her life) is blown open when her sister mails them out to five boys.
Why It Works: There is something so fun and refreshing about the concept of To All the Boys I’ve Loved Before that makes it a breath of fresh air for romantic comedies. It’s cleverly written, features some amazing performances by its leads, and overall is just an enjoyable experience. It also makes you look back on those adolescent crushes and secrets for a short trip down memory lane.
Perfect Quote: “I wrote five letters, so don’t go feeling too special.”
Stream To All The Boys I’ve Loved Before on Netflix.
39) Sleeping With Other People (2015)
The Couple: Jake Harper and Lainey Dalton
Story In A Nutshell: Years after losing their virginity to each other at a college dorm party, Jake Harper (Jason Sudeikis) and Lainey Dalton (Alison Brie) run into each other again and become best friends. But soon they find out being “just friends” with someone you’re in love with is no easy task.
Why It Works: Even though Jake Harper and Lainey Dalton aren’t the most likable characters in the history of romantic comedies, the performances by Jason Sudeikis and Alison Brie in Sleeping With Other People makes it to where you can’t help but root for the pair. The movie’s premise isn’t all that unique, but the way the cast has fun with the material makes it work way more than it should.
Perfect Quote: “Lainey: If you want someone to fall for you, you gotta be you. Jake: Yeah, I don’t think I like me enough to introduce him to other people.”
Rent/Buy Sleeping With Other People on Amazon.
38) Chasing Amy (1997)
The Couple: Holden McNeil and Alyssa Jones
Story In A Nutshell: A comic book artist falls in love with a lesbian, despite the objections of all their friends. They’re able to find some happiness, but her past remains an issue.
Why It Works: In theory, Chasing Amy is a about a woman who self-identifies as a lesbian and a straight guy trying to make it work, but deeper than that, it’s about coming to terms with your partner and accepting them for who they are at this very moment in time. Holden and Alyssa get along really well. In a vacuum, they could be very happy for the rest of their lives, but they’re surrounded by people who are used to them behaving in different ways. It’s a frank and fascinating perspective, and it’s one that makes the movie worth watching. Well, that perspective along with Jason Lee hilarity and good old fashioned Jay and Silent Bob jokes.
Perfect Quote: “I love you. And not, not in a friendly way, although I think we’re great friends. And not in a misplaced affection, puppy-dog way, although I’m sure that’s what you’ll call it. I love you. Very, very simple, very truly.”
Rent/Buy Chasing Amy on Amazon.
37) Happiest Season (2020)
The Couple: Abby Holland and Harper Caldwell
Story In A Nutshell: Abby Holland (Kristen Stewart) decides that the perfect time to propose to her girlfriend Harper Caldwell (Mackenzie Davis) is at Harper’s family’s annual holiday party. But the thing is, Harper has yet to come out to her family, which further complicates things.
Why It Works: One of my favorite aspects of this 2020 romantic comedy is the argument it makes about being true to yourself and how only good things can come from honesty (even if it takes a while to get there). We see it with Harper finally coming out to her family as well as with her dad, Ted Caldwell (Victor Garber) finally becoming mayor during the Happiest Season ending. And let’s not forget Dan Levy with his scene-stealing performance as Abby’s best friend John, especially for providing some of the film’s best moments.
Perfect Quote: “Just because Harper isn’t ready doesn’t mean she never will be, and it doesn’t mean she doesn’t love you.”
Stream Happiest Season on Hulu.
36) Licorice Pizza (2021)
The Couple: Alana Kane and Gary Valentine
Story In A Nutshell: Alana Kane (Alaina Haim) and Gary Valentine (Cooper Hoffman) explore life and love in the San Fernando Valley in the early 1970s all while dealing with the drama, temptations, and treacherous situations found within it.
Why It Works: A romantic comedy directed by Paul Thomas Anderson should be enough to sell Licorice Pizza, but it’s the commanding performances by Haim and Hoffman (both of whom have little acting experience) that really makes the Academy Award-nominated film so charming.
Perfect Quote: “I met the girl I’m going to marry one day.”
35. Obvious Child (2014)
The Couple: Donna Stern and Max
Story In A Nutshell: After a one-night stand with Max (Jake Lacy) results in Donna Stern (Jenny Slate) getting pregnant, the struggling stand-up comedian decides the best course of action is to have an abortion. The only thing is she has yet to tell Max and is afraid to do so.
Why It Works: What’s refreshing about Obvious Child is the way it takes a topic like abortion and manages to turn what could have been a dramatic and unsettling experience into one of the best romantic comedies of the past decade. Everything from Gillian Robespierre’s direction to the screenplay she wrote to the performances by Jenny Slate and Jake Lacy all work together to create this hilarious yet honest story of modern love.
Perfect Quote: “I remember seeing a condom, I just don’t know exactly what it did.”
Rent/Buy Obvious Child on Amazon.
34) Palm Springs (2020)
The Couple: Sarah Wilder and Nyles
Story In A Nutshell: Two strangers find themselves stuck in a time loop where they must attend the same wedding over and over again in a seemingly never-ending day.
Why It Works: If Palm Springs were just a time loop movie without the romantic elements it would be good, and the same goes for the other way around, but combining those two genres into one movie makes the Hulu original a modern classic. And outside of the whole time loop business, the movie’s two leads — Andy Samberg and Cristin Milioti — have an undeniable chemistry that makes a good movie into a great romantic comedy.
Perfect Quote: “I hope that blowing ourselves up works, but it’s really irrelevant to me as long as I’m with you, and if it kills us, well, then I’d rather die with you than live in this world without you!”
33) Forgetting Sarah Marshall (2008)
The Couple: Peter Bretter and Rachel Jansen
Story In A Nutshell: A composer gets unexpectedly dumped by his actress girlfriend. To get over her, he takes a trip by himself to Hawaii, only to discover she’s staying in the same hotel with a world famous rock star.
Why It Works: Get past the wacky, contrived premise and just focus on the relationships. Forgetting Sarah Marshall has so much to say about sameness and differences, about the appeal of new and the frustration with old. It gives us real reasons for everyone’s behavior, and it never turns anyone into a complete villain or a complete hero. It lives in the grey areas, even when it comes to its supporting characters, and with an R-rating, it takes advantage of its freedom with consistent, raunchy hilarity.
Perfect Quote: “How you served five years under her, I don’t know. You deserve a medal, or a holiday or at least a cuddle from somebody.”
Rent/Buy Forgetting Sarah Marshall on Amazon.
32) 50 First Dates (2004)
The Couple: Henry Roth and Lucy Whitmore
Story In A Nutshell: Sea life veterinarian and womanizer falls for an amnesiac who forgets who he is every day.
Why It Works: The basic premise of 50 First Dates is kind of sad, and that’s not ignored by the comedy, as we’re introduced to Adam Sandler’s Henry Roth, a guy who harbors no guilt for the way he romances tourists and then sends them packing. Drew Barrymore is a sweet former teacher who has no idea that she’s been reliving the same day over and over, due to brain damage caused by an accident, added to her family’s (and community’s) efforts to play along to spare her the repeated devastation of learning she’s an amnesiac. When Henry comes into her life, he threatens to throw the whole system out of balance. What seems like an ideal situation for him — a woman who might be with him and then completely forget about him the next day — takes a humorous but deeper turn as Henry develops feelings for her. 50 First Dates not only captures that excellent screen chemistry between Barrymore and Sandler, but it also manages to find a very sweet, romantic way of approaching an unusual romance between a veterinarian and a woman with severe short-term memory loss.
Perfect Quote: “So every day you help her to realize what happened and you wait patiently for her to be okay with it… then you get her to fall in love with you again?”
Rent/Buy 50 First Dates on Amazon.
31) Notting Hill (1999)
The Couple: Will Thacker and Anna Scott
Story In A Nutshell: Regular bloke falls for a Hollywood star.
Why It Works: In some ways, Notting Hill is the ultimate fantasy. A regular guy has a run-in with a beautiful celebrity and the two hit it off. They live happily ever after. Not quite. The reality of Anna Scott’s life is a bit more complicated. She’s not as happy as her red carpet smiles would suggest. William Thacker is a bit of normalcy for Anna’s (sur)reality. But this love story has some twists and some great bits of humor as Will and Anna attempt to find a place in each others’ worlds.
Perfect Quote: “After all… I’m just a girl, standing in front of a boy, asking him to love her.”
Rent/Buy Notting Hill on Amazon.
30) Kissing Jessica Stein (2001)
The Couple: Jessica Stein and Helen Cooper
Story In A Nutshell: A copyeditor who has continually struck out with men for most of her life decides to answer a personal ad placed by a bisexual woman who owns an art gallery. Their relationship quickly becomes serious and meaningful, but it’s consistently plagued by insecurities Jessica has related to being with a woman.
Why It Works: Kissing Jessica Stein is fixated just enough on gender politics and societal acceptance to be honest and enlightening, but it’s relaxed and universal enough to cater to a broad audience. In short, it’s a touching movie that has things to say but never twists the plot or the behavior of the characters in order to say them. More importantly, it offers one of the most interesting and beautiful relationships the romantic comedy genre has ever given us.
Perfect Quote: “I was surprised to learn that lesbians accessorized, I didn’t know that.”
Rent/Buy Kissing Jessica Stein on Amazon.
29) Crazy Rich Asians (2018)
The Couple: Rachel Chu and Nick Young
Story In A Nutshell: A woman is unexpectedly thrown into the rich and fabulous culture of Singapore’s upper echelon when she travels with her boyfriend, who happens to be a part of one of the country’s wealthiest families, to attend his best friend’s wedding. She has no idea what she’s about to get into.
Why It Works: Jon M. Chu’s modern-day Cinderella story is a fast and furious display of the rich and famous, but behind all the glitz and glamor is a story about a young woman who’s not willing to back down from her convictions and doesn’t let anyone tell her who she can or can’t love.
Perfect Quote: “I just love Nick so much, I don’t want him to lose his mom again. So I just wanted you to know: that one day – when he marries another lucky girl who is enough for you, and you’re playing with your grandkids while the Tan Huas are blooming, and the birds are chirping – that it was because of me: a poor, raised by a single mother, low class, immigrant nobody.”
Rent/Buy Crazy Rich Asians on Amazon.
28) (500) Days of Summer (2009)
The Couple: Tom Hansen and Summer Finn
Story In A Nutshell: A nonlinear examination of one couple’s romance from start to finish, and beyond.
Why It Works: Not all relationships are meant to go the distance. In fact, some fall apart, leaving one person a complete mess, forced to try to come to grips with what they lost, and what they really had in the first place. (500) Days of Summer isn’t your average love story. In a happier film, we might see Tom and Summer meet, fall in love, accept each others’ differences and finally be together. But this film never intends to stick to the format. Most romantic comedies tell the story about the couple that’s destined to last. Tom and Summer aren’t that couple, but that’s all the more reason why their story should be told, for all its humor and heartache. It’s a love story that ends without the happily ever after, but with the promise that life and love do go on regardless.
Perfect Quote: “It’s these cards and the movies and the pop songs, they’re to blame for all lies and the heartache, everything.”
Stream (500) Days Of Summer on Amazon.
27) The Big Sick (2017)
The Couple: Kumail Nanjiani and Emily Gardner
Story In A Nutshell: A couple’s blossoming relationship is put to the ultimate test when one of them comes down with a serious illness and falls into a coma, leaving the other to pick up the pieces and keep everyone calm.
Why It Works: Kumail Nanjiani and Emily V. Gordon take what was probably the toughest moment of their lives and turn it into an Academy Award-nominated screenplay that perfectly balances comedy and drama to create a one-of-a-kind experience. And then you add Kumail bonding with Emily’s parents (played by Holly Hunter and Ray Romano), which creates some of the movie’s best scenes.
Perfect Quote: “Your driver will be ready as soon as he puts on his pants.”
Stream The Big Sick on Amazon.
26) As Good as it Gets (1997)
The Couple: Melvin Udall and Carol Connell
Story In A Nutshell: An insensitive novelist with OCD begrudgingly gets involved with his neighbor, a waitress, and she teaches him how to be more sensitive.
Why It Works: Melvin Udall is a man who has his life exactly the way he wants it, but circumstances change drastically, due to an assaulted neighbor, a dog that needs to be cared for, and a single-mother waitress who knows how to handle Melvin’s obsessive compulsive tendencies and rude behavior. The romance in As Good as it Gets sort of sneaks up on us, much in the way Carol, Simon and Verdell inch their way into Melvin’s life. Unlike a lot of other romantic comedies, the best of what As Good as it Gets has to offer is less about watching two people fall in love as it is about watching Melvin make the effort to confront his flaws and change himself in order to be the man Carol deserves.
Perfect Quote: “You make me want to be a better man.”
Rent/Buy As Good As It Gets on Amazon.
25) Amelie (2001)
The Couple: Amelie Poulain and Nino Quincampoix
Story In A Nutshell: A quirky French waitress decides to devote her life to secretly making the lives of those around her better through selfless and unexpected acts. Along the way, she realizes she’s in love with a fellow Frenchman whose photo album she discovered.
Why It Works: Amelie has its own pace and feel to it. It’s unapologetically weird and prefers quirky camera angles, striking colors and effective pauses. There are a lot of movies on this list that have more effective love stories that are given more time, but here, we’re able to see Amelie fall in love with the world and with people, and that’s it’s own special take on the romantic comedy.
Perfect Quote: “I like to look for things no one else catches. I hate the way drivers never look at the road in old American movies.”
24) My Best Friend’s Wedding (1997)
The Couple: The Couple: Julianne Potter and Michael O’Neal
Story In A Nutshell: The relationship of two longtime best friends is upended when he announces he’s going to marry another woman. Weirded out and kinda pissed off, she travels to Chicago to break up his wedding and win him for herself.
Why It Works: This movie is Julia Roberts in all her Julia Roberts glory. The poster is a giant picture of her face, and she’s unquestionably the lead character. That being said, My Best Friend’s Wedding gets a ton of great supporting performances and more than anything else, it benefits from being fun. There are some romantic comedies that are meant to teach a larger lesson, and there are some that are meant to be funny, adorable stories about love. This falls into the latter camp, and if it leaves everyone wanting to sing “I Say A Little Prayer”, that’s a win.
Perfect Quote: “I had the strangest dream. I dreamt that some psychopath was trying to break the two of you up.”
Rent/Buy My Best Friend’s Wedding on Amazon.
23) Harold and Maude (1971)
The Couple: Harold Chasen and Maude Chardin
Story In A Nutshell: His hobbies include fake suicides and attending funerals. Her hobbies include music and attending funerals. Together, they begin an utterly bizarre and strangely awesome relationship, despite the fact that she’s 79 and he’s in his early 20s.
Why It Works: It’s so hard to make an original romantic comedy, and yet, every single thing about Harold And Maude is completely its own. Their interests, the way they communicate, even his mode of transportation is tied directly to this film. Yet, at no point does it seem like it’s being weird for the sake of it. These characters, strange as they might be, make complete sense within their little worlds, and it’s beautiful to watch them find and accept each other for exactly who they are.
Perfect Quote: “A lot of people enjoy being dead. But they are not dead, really. They’re just backing away from life.”
Rent/Buy Harold and Maude on Amazon.
22) Crazy, Stupid, Love (2011)
The Couple: Jacob Palmer and Hannah Weaver
Story In A Nutshell: An attractive womanizer takes a 40-something divorcee under his wing only for things to get complicated.
Why It Works: A precursor to what they would pull off a few years later with La La Land, Ryan Gosling and Emma Stone anchor the impressive Crazy, Stupid, Love cast and its story about second chances and new beginnings. The chemistry shared by the two stars is electric to say the least, and helps turn this 2011 romantic comedy into a must watch, either for the first time or another revisit.
Perfect Quote: “I’m so mad at you. I’m really mad at you for what you did. But I’m mad at myself too. Because I should not have jumped out of that car – I should have fought for you. Because you fight for your soul mates.”
Rent/Buy Crazy, Stupid, Love on Amazon.
21) Punch-Drunk Love (2002)
The Couple: Barry Egan and Lena Leonard
Story In A Nutshell: Awkward guy in a blue suit falls for a lovely woman who totally gets him.
Why It Works: Paul Thomas Anderson offers a layer of suspense and intensity to Punch-Drunk Love that almost make it hard to perceive this film as a romantic comedy. But it is romantic and it is funny. Adam Sandler shows us his angrier side as Barry Egan, an awkward underdog of a character who’s determined to turn things around for himself. You get the sense that he’s allowed himself to be held down all of his life, but something is changing. There’s magic in the air. Also airline miles and a lot of pudding. We feel the tension like an electric charge, right from the start. So when he meets Emily Watson’s Lena, their happily ever after seems fated, but there are obstacles in the way, requiring Barry to rise up if he wants to get the girl and keep her.
Perfect Quote: “I have a love in my life. It makes me stronger than anything you can imagine.”
Rent/Buy Punch Drunk Love on Amazon.
20) About Time (2013)
The Couple: Tim and Mary
Story In A Nutshell: Upon turning 21, Tim (Domhnall Gleeson) learns his family secret: the men can travel through time and revisit any day from their past.
Why It Works: If you just watch the trailer or look at the poster for About Time, you will be under the impression that it’s another romantic comedy written by Richard Curtis, but it’s so much more than that. Yeah, romance is a major part of the movie, but tucked away is one of the best father-son stories ever put to film, one that continues to surprise me even after watching this movie nearly a dozen times since its release.
Perfect Quote: I’d only give one piece of advice to anyone marrying. We’re all quite similar in the end. We all get old and tell the same tales too many times. But try and marry someone kind. And this is a kind man with a good heart. I’m not particularly proud of many things in my life, but I am very proud to be the father of my son.
Rent/Buy About Time on Amazon.
19) The Apartment (1960)
The Couple: Bud and Fran
Story In A Nutshell: Office worker loans out his apartment to his bosses so they can shack up with their mistresses, one of whom he falls for.
Why It Works: You don’t really have to look at The Apartment very closely to see that it leans more toward drama than it does comedy, when all is said and done, particularly in its focus on Shirley MacLaine’s Fran, a young elevator attendant who grows increasingly depressed over the adulterous relationship she’s having with Jeff Sheldrake. But there’s humor worked into the story, particularly as it relates to Jack Lemmon’s C.C. “Bud” Baxter, a man hoping that by turning his apartment into a motel room for his bosses and their mistresses, he’ll move up the ranks. A friendship forms between Bud and Fran as she deals with her relationship with Jeff, and he deals with the inconvenience of loaning out his home while waiting for his promotion. It’s the connection between C.C. and Fran that elevates The Apartment to great romcom status, as we see both of them coming to grips with the choices they’ve been making, and what getting ahead is costing them personally.
Perfect Quote: “When you’re in love with a married man, you shouldn’t wear mascara.”
Rent/Buy The Apartment on Amazon.
18) There’s Something About Mary (1998)
The Couple: Ted Stroehmann and Mary Jensen/ Mary Matthews
Story In A Nutshell: An awkward teenager gets invited to prom by the most beautiful girl in school after he sticks up for her mentally handicapped brother. He gets his dick caught in the zipper of his suit before he’s able to go and a decade or so later, decides to track her down to see if he can take her on another date.
Why It Works: There’s Something About Mary is utterly ridiculous, and everyone just rolls with it. That frees the Farrelly brothers up to milk anything and everything for laughs. They make every single man in Mary’s life in love with her. They make every one of their schemes increasingly outrageous. Yet, somehow, they humanize Mary and Ted just enough to give us a relationship we can root for and believe in. It’s the most careful the filmmakers have ever been, and almost twenty years later, it’s still really, really good.
Perfect Quote: “That seems like an awful lot of speed to give one little pooch. Are you sure it won’t kill him?”
Rent/Buy There’s Something About Mary on Amazon.
17) Breakfast At Tiffanys (1961)
The Couple: Holly Golightly and Paul Varjak
Story In A Nutshell: She’s a New York socialite who associates with mobsters and dates a wide range of rich men. Her new neighbor is a struggling writer, but there’s something about him that feels right.
Why It Works: Not all of Breakfast At Tiffany’s works. Any screenings in public are typically preceded and followed by protests over Mickey Rooney’s overtly racist character I.Y. Yunioshi. That being said, what does still work is Holly Golightly, a loveable, selfish and brilliant character, first penned by Truman Capote and perfected here by Audrey Hepburn. She’s the type of woman every man feels compelled to take a shot at, and yet, there’s something really tragic about her too.
Perfect Quote: “You could always tell what kind of a person a man thinks you are by the earrings he gives you.”
Rent/Buy Breakfast at Tiffany’s on Amazon.
16) Better Off Dead (1985)
The Couple: Lane and Monique
Story In A Nutshell: Guy gets dumped and wants to die. A French foreign exchange student cheers him up, fixes his car and teaches him how to ski.
Why It works: Better off Dead revels in the agony of teen heartache through the antics of Lane Myer, a kid who gets dumped by the girl he thinks is the love of his life. The movie somehow manages to find plenty of humor, despite the suicidal overtones thanks to its lead character’s death wish. Lane’s efforts to kill himself are put aside when he teams up with Monique, the French foreign exchange student living with his weird neighbors next door. She lifts his spirits enough to fix up his life and face off against his rival, the douchey but really great skier Roy. Better off Dead is goofy, occasionally dark and a lot of fun. There’s also a musical number involving an animated hamburger because, ’80s.
Perfect Quote: “Go that way, really fast. If something gets in your way, turn.”
15) You’ve Got Mail (1998)
The Couple: Joe Fox and Kathleen Kelly
Story In A Nutshell: A wealthy executive whose family owns a popular mega-chain of bookstores begins an online relationship with a woman who owns a mom and pop bookstore around the corner. Initially, they’re unaware of the other’s true identity, allowing them to feud by day and fall in love by night.
Why It Works: Perhaps more than any other movie on this list, You’ve Got Mail is rigidly dated to a certain time period. Its plot relies completely on the Internet and more specifically, the Internet during that hyper-specific period of time in which adults were cautiously exploring cyberspace (with the help of AOL) and using bizarre email handles not in any way connected to their real names. This movie could never happen now, but the love Hanks and Ryan feel for each other still translates, just as it did when Parfumerie was written in 1937.
Perfect Quote: “The odd thing about this form of communication is that you’re more likely to talk about nothing than something. But I just want to say that all this nothing has meant more to me than so many somethings.”
Rent/Buy You’ve Got Mail on Amazon.
14) The African Queen (1951)
The Couple: Charlie Allnut and Rose Sayer
Story In A Nutshell: He’s a lazy Canadian boat captain. She’s a British missionary grieving after Germans (basically) murdered her brother. Together, they hatch a plan to fight back during World War I.
Why It Works: If you remove the war element, The African Queen picks up on a pretty classic romantic comedy trope. He’s the immature, wild and drunken man who needs a woman’s touch. She’s the straight-laced, overly proper maid who needs a man to jolt her out of her rut. Their crazy adventure down a river in their boat, The African Queen, doesn’t completely hold up, but the fast dialogue and the emotions they feel for each other certainly do.
Perfect Quote: “By the authority vested in me by Kaiser William II, I pronounce you man and wife. Proceed with the execution.”
Rent The African Queen on Amazon.
13) 10 Things I Hate About You (1999)
The Couple: Kat and Patrick
Story In A Nutshell: A modern day take on The Taming of the Shrew, one social outcast is paid to take out another.
Why It Works: 10 Things I Hate About You has solid source material to back it up, as it works a bit of Shakespeare into a high school setting. Heath Ledger is the intimidating Patrick Verona, an outcast who’s offered money to take out a girl by a guy who’s trying to date said girl’s younger sister. Julia Stiles plays Kat with just the right combination of intelligence, beauty and standoffishness, while also leaving some room to show a softer side when Kat inevitably lets her guard down as she falls for Patrick. 10 Things proves to be one of the smarter and more memorable high school-set movies in romcom history, leaving a lasting impression thanks to Stiles and Heath Ledger’s great chemistry, that adorable paintball scene and the teary poem Kat reads when her heart is broken.
Perfect Quote: “I hate the way you’re always right. I hate it when you lie. I hate it when you make me laugh, even worse when you make me cry. I hate it when you’re not around, and the fact that you didn’t call. But mostly I hate the way I don’t hate you. Not even close, not even a little bit, not even at all.”
Rent/Buy 10 Things I Hate About You on Amazon.
12) Love Actually (2003)
The Couple: Jamie and Aurelia, David and Natalie, Jack and Judy, others
Story In A Nutshell: Various types of love are explored among an ensemble of characters, mostly in London.
Why It Works: Love Actually is a beautiful example of an ensemble comedy that’s paced to perfection, building momentum as it tells stories of love and romance from the perspective of a variety of characters around the holiday season. Whether it’s Jamie falling in love with a woman who doesn’t speak English, Natalie falling in love with her boss (the Prime Minister, no less), young Sam falling in love with Joanna, or the more platonic bromance of Billy Mack and his manager Joe, Love Actually delves into all different types of love. Not only does it succeed in keeping its stories organized and entertaining, weaving them together bit by bit as it builds up to its climax, but Love Actually is also really funny.
Perfect Quote: “But you know, the thing about romance is… people only get together right at the very end.”
Rent/Buy Love Actually on Amazon.
11) Say Anything (1989)
The Couple: Lloyd Dobler and Diane Court
Story In A Nutshell: An average guy takes a chance pursuing the girl of his dreams and ends up being exactly what she needs.
Why It Works: It seems like Diane Court is out of Lloyd Dobler’s league. She’s the valedictorian, she has money and a bright future, and she’s beautiful. He’s a good but somewhat underachieving guy who has every reason to be intimidated by her, but Lloyd takes a chance anyway, and it pays off much more than either of them might have imagined. By high school’s social rules, Lloyd and Diane wouldn’t be a good fit for one another, but high school is over and the timing proves to be perfect for a lasting romance, as Say Anything allows us to believe that, despite their differences, by loving each other, Lloyd and Diane will go on to become the best versions of themselves. Say Anything came out in the 1980s. As a teen-focused movie, it’s understandably a bit dated on the surface, but as a wonderful story about two teens falling in love on the brink of adulthood, it’s timeless.
Perfect Quote: “I gave her my heart, she gave me a pen.”
Rent/Buy Say Anything on Amazon.
10) Roxanne (1987)
The Couple: Charlie Bales and Roxanne Kowalski
Story In A Nutshell: A man with a big nose helps a good-looking man without much personality gain the affection of a beautiful woman who thinks he’s the perfect guy.
Why It Works: Steve Martin entertains us with his humorous portrayal of C.D./Charlie, a charismatic small town fire chief with a big nose and a big heart, who falls for the brainy and beautiful Roxanne, a woman looking for the whole package, a man with looks and something interesting to say. Charlie wins our hearts while winning Roxanne’s as he whispers the words she wants to hear through the dim but handsome firefighter Chris. The well-intentioned lie spirals out of Charlie’s control as Roxanne falls for Chris. A modern take on a classic story (Cyrano de Bergerac), Roxanne delivers laughs and smiles as it emphasizes the debate over what matters more, looks or personality.
Perfect Quote: “It’s not the size of the nose that matters, it’s what’s inside that counts!”
9) The Wedding Singer (1998)
The Couple: Robbie Hart and Julia Sullivan
Story In A Nutshell: He’s a wedding singer. She’s a waitress. They both love David Bowie.
Why It Works: Adam Sandler’s characters might be effectively undateable in many of his projects, but in The Wedding Singer, there’s just enough common sense, lovability and eventually, drive behind the emotional outbursts to understand why a cute girl in an awful relationship would fall for him. Here, that cute girl is played by Drew Barrymore in all of her loopy glory, and the romantic chemistry is easily the best of both actors’ careers. They’re a great pair, and with a perfect ‘80s soundtrack, a ton of laughs and great supporting characters, we’re all gonna grow old with The Wedding Singer.
Perfect Quote: “I’ll miss you, kiss you, give you my coat when you are cold. / Need you, feed you, I’ll even let you hold the remote control.”
Rent/Buy The Wedding Singer on Amazon.
8) Silver Linings Playbook (2012)
The Couple: Pat Solatano Jr and Tiffany Maxwell
Story In A Nutshell: Two well-intentioned but emotionally handicapped people meet at the most awkward dinner party ever. They bond over different types of medication and agree to participate in a dance competition together.
Why It Works: The great thing about Silver Linings Playbook is how easy it is for the audience to understand Pat and Tiffany’s relationship and to get why they spend time with each other. To everyone else, they’re broken, screwed up people, but to themselves, they’re just living and playing the hand they were dealt. That’s why they can be so blunt with each other. They would much rather hear the straight truth than listen to the world dance around it.
Perfect Quote: “I saw the way you were looking at me, Pat. You felt it, I felt it, don’t lie. We’re not liars like they are.”
Rent/Buy Silver Linings Playbook on Amazon.
7) The Princess Bride (1987)
The Couple: Westley and Buttercup
Story In A Nutshell: He’s a farm boy turned pirate turned Man In Black, and he’s back to save his true love from the nefarious Prince Humperdinck. A man with six fingers is also involved.
Why It Works: The Princess Bride probably has the best supporting characters of any movie on this list. It’s overflowing with brilliant personalities and loveable ruffians. If the movie were just about Fezzik, Inigo and Vizzini, it would still be great, but fortunately for all of us, it contains one of the most beautiful, naïve and perfect love stories ever written. Nothing will ever stop Westley from returning to the woman he loves, not death machines, not rodents of unusual size and definitely not a battle of wits.
Perfect Quote: “I do not envy you the headache you will have when you awake. But for now, rest well and dream of large women.”
Rent/Buy The Princess Bride on Amazon.
6) City Lights (1931)
The Couple: The Tramp and Flower Girl
Story In A Nutshell: Chaplin’s tramp falls head over heels for a blind woman who sells flowers.
Why It Works: Charlie Chaplin brings romance into the Tramp’s life with this classic tale of a poor man who falls for a blind woman. Through a very simple error, the woman mistakes The Tramp for a millionaire and he encourages the assumption as he goes out of his way to help her. As the Tramp, Chaplin works his charm, adding in creative ways for his character to stumble in his efforts to give this woman a better life, making up for with kindness, determination and a positive attitude, what he lacks in worldly possessions.
Perfect Quote: “Be brave. Face life.”
Rent/Buy City Lights on Amazon.
5) Groundhog Day (1993)
The Couple: Phil Connors and Rita Hanson
Story In A Nutshell: He keeps repeating the same day. She has no idea. They’re destined to fall in love.
Why It Works: At his best, Bill Murray is able to walk the line so carefully between uproarious comedy and honest emotion. Here, he’s able to sell both the inherent ridiculousness of his illogical and impossible situation with the very real feelings most of us would have, and while this isn’t Andie MacDowell’s story exactly, she makes her character just loveable enough to convince the audience her love and affection is a worthwhile goal.
Perfect Quote: “Ned, I would love to stay here and talk with you… but I’m not going to.”
Rent/Buy Groundhog Day on Amazon.
4) Pretty Woman (1990)
The Couple: Edward Lewis and Vivian Ward
Story In A Nutshell: Just your average fairy tale… except the prince is a businessman and the princess is a Hollywood Blvd. prostitute.
Why It Works: Sure, we could focus on the absurdity of staging a romantic story around a call girl and a john, but the charm of Pretty Woman develops from the nature of its characters, particularly as it relates to Edward and Vivian. She treats sex like it’s business. He treats everything like it’s business. Neither enter the story open to romance or a relationship, but the two characters fall in love anyway, during their brief time together, wherein he introduces her to his wealthy lifestyle and she introduces him to the art of relaxation. Maybe it’s not your traditional fairy tale, but the film finds the charm in a story about two people finding exactly what they need in each other.
Perfect Quote: “You and I are such similar creatures Vivian. We both screw people for money.”
Rent/Buy Pretty Woman on Amazon.
3) Annie Hall (1977)
The Couple: Alby Singer and Annie Hall
Story In A Nutshell: He’s a neurotic comedian. She’s a free-spirited singer. They can’t ever get completely on the same page.
Why It Works: Annie Hall is a romantic comedy that focuses mostly on a single relationship, but in many ways, it’s more of a general commentary on love. In just over an hour and a half, it’s able to illustrate reasons why we choose to tie our lives to other people and also to illustrate reasons why well-meaning people sometimes can’t make it work. In addition, it deserves bonus points or perhaps deductions for making Diane Keaton’s androgynous fashion sense a thing, depending on your perspective.
Perfect Quote: “A relationship, I think, is like a shark. You know? It has to constantly move forward or it dies. And I think what we got on our hands is a dead shark.”
Rent/Buy Annie Hall on Amazon.
2) Sleepless in Seattle (1993)
The Couple: Sam Baldwin and Annie Reed
Story In A Nutshell: He’s a widower in Seattle, she’s engaged in Baltimore. They’ve never met, but they’re M.F.E.O.
Why It Works: Inspired by An Affair to Remember, Sleepless in Seattle falls a bit closer to drama than it does comedy, what with its focus on a single father who’s so grief-stricken over the loss of his wife that he can’t sleep. But there is humor and a timeless kind of charm about this story, especially as we watch Annie and Sam separately ponder the concept of soul mates. But it’s really the humor and the romantic notion of destiny in the modern world that allows Sleepless in Seattle to rise above most of the other romantic comedies out there.
Perfect Quote: “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.”
Stream Sleepless in Seattle on Amazon.
1) When Harry Met Sally (1989)
The Couple: Harry Burns and Sally Albright
Story In A Nutshell: A relationship sparks between a man and a woman whose views on sex and love differ drastically.
Why It works: When Harry Met Sally is the ultimate example of how crucial good dialogue can be to a movie, especially as it relates to the combination of comedy and romance. It’s Harry and Sally’s conversations that make this film resonate so well with its audience. Their differing views on love, sex and relationships makes for entertaining banter throughout the film and allow the movie to be about much more than two people who eventually fall for one another. When Harry Met Sally explores the humor and sometimes frustration that comes with love, and the differing views of men and women, while also telling the story about two people destined to be at one another’s side.
Perfect Quote: “I’ll have what she’s having.”
Rent/Buy When Harry Met Sally on Amazon.
Well, there you have our definitive ranking of the best romantic comedy movies ever released, whether they debuted in theaters or on a streaming service. And who knows when the next great romantic comedy will be introduced to us, but if it comes out soon you will find it on our schedule of all the 2022 movie premiere dates.