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What are the most important elements of a romantic comedy movie? The first is probably that it’s on film, but that’s a given. The second is that it is romantic, and third is it needs to have jokes. All of these edicts are no-brainers given the very words used in the phrase “romantic comedy movie,” but when it comes to the 45 movies Decider chose for their list of best rom-coms of all time, there’s something a little extra.
Is it that they’re funnier? More romantic? More specific in terms of the situation of the comedy, whether it’s an ill-advised bet, a time loop, or something else? Perhaps it’s as simple as the chemistry between the leads, which is why iconic couples like Tom Hanks and Meg Ryan have been paired up so frequently. Or it might just be the singular stars, like Ryan and Julia Roberts, who bring the heat wherever they go. Whatever that secret ingredient is, every single one of the movies on this list has it — from When Harry Met Sally, to Can’t Buy Me Love, and everything in between.
So how did we determine this list? First, every member of the Decider staff submitted their top ten picks for the best romantic comedies of all time. Those were ranked, weighted, culled together, and then where necessary, voted on in tie-breakers. Some movies, those that were perhaps more of romantic dramas than romantic comedies, didn’t make the list. Others were just ranked too low, or on not enough lists, to be included. Ultimately though, our number one was far and away the top romantic comedy picked by the entire staff. But don’t worry, there are surprises, too.
Read on for the definitive list of the best romantic comedies of all time… At least until next Valentine’s Day.
'Can't Buy Me Love'
Does the concept of 1987’s Can’t Buy Me Love, which finds a nerd played by Patrick Dempsey paying a cheerleader played by Amanda Peterson $1000 to pretend to be his girlfriend hold up to 2023 standards? Well, no, and not just because it’s impossible to picture Patrick Dempsey as a nerd. Still, the chemistry between the leads is undeniable, and the last scene, which (spoiler) finds the two kissing on a tractor as the title song plays is iconic.
'Obvious Child'
Jenny freakin’ Slate, everybody! The comedian and actor leads this romantic comedy about a stand up comedian, Donna, in New York City who is dumped by her boyfriend right before a set. Even worse, he left her for her friend. Fresh on the prowl, Donna hooks up with a new guy and finds that he’s a lot more interested in her than she is with him. This causes a ton of awkwardness between the two, especially after Donna casually moves on to another person. Eventually, she finds out that she is pregnant and decides to proceed with an abortion and is conflicted with how to involve Guy #1. The movie features a few fun twists and a more natural perspective on love than others within the genre. — Raven Brunner
'Long Shot'
In Long Shot, one of our greatest modern action stars (Charlize Theron) trades in her War Rig and labrys ax for a presidential campaign and a second-chance romance with Seth Rogen. Their chemistry is surprisingly great, and the movie’s tagline — “Feel Something Different” — couldn’t be more apt. It’s definitely less conventional than the classics of the genre, but that’s what makes it so interesting. That’s also due, in part, to a murderers’ row of a supporting cast that includes Bob Odenkirk, June Diane Raphael, Andy Serkis, Alexander Skarsgård, and O’Shea Jackson Jr. — Angela Tricario
'My Best Friend's Wedding'
If there’s one indisputable rule of romantic comedies, it’s that Julia Roberts gets the guy… Right? My Best Friend’s Wedding challenged this ironclad law by thrusting Roberts into the situation of the title, pitting her against a charming Cameron Diaz for the love of Dermot Mulroney. Add in a breakout performance by Rupert Everett, and you have a cast game to challenge the tropes of rom-coms; while still leaning into them at the same time.
'The Apartment'
The Apartment is both a euphoric and sobering study of the relationship between an office drone (Jack Lemmon) and an elevator operator (Shirley MacLaine). Sure, the main plot involves Lemmon’s low-level insurance clerk loaning out his apartment to the execs so they can have affairs, but that doesn’t compare to the chemistry between Lemmon and MacLaine as opposites thrown together by fate but kept apart by everything else. This moody holiday romance film captured and preserved the cold of a mid-century Christmas — especially the feeling of isolation and hopelessness that go hand in hand with the holly and the jolly. — Brett White
'Just Friends'
The Proposal may be Ryan Reynolds’ best-known rom-com, but don’t you dare sleep on the cozy comforts of Just Friends. The delightful film centers on Chris Brander (Reynolds), a formerly obese high school student turned successful record producer who returns to his hometown and begins hanging out with his old high school crush (Amy Smart). A fun, silly romp with heart to spare, Just Friends is a perfect lazy Saturday night date movie. — Josh Sorokach
'Jersey Girl' (1992)
Not to be confused with Kevin Smith’s 2004 comedy, the original Jersey Girl is a winning 1992 rom-com for the bridge and tunnel crowd. The luminous Jami Gertz stars as the big-haired, big-hearted Toby, a pre-school teacher with ambitious dreams, who longs to date a classy Manhattanite. She soon encounters the handsome Sal (Dylan McDermott) when she accidentally drives into his Mercedes-Benz—a classic meet-cute. The two begin to date, but will their drastically different worlds keep them apart? You’ll have to watch and find out! Jersey Girl is one of the great New York rom-coms featuring memorable performances and delightfully ’90s hair and costuming. — Karen Kemmerle
'Crazy Rich Asians'
Endlessly romantic and laugh-out-loud hilarious, Crazy Rich Asians casts Constance Wu as an American professor who travels with her boyfriend (Henry Golding) to a wedding in Spingapore, only to discover his family isn’t just rich: they’re crazy rich. The culture clash starts immediately, and Wu and Golding eat up every moment they’re on screen. Now, where’s that sequel we were promised?
'She's The Man'
In a hilarious modern-day twist on Shakespeare’s Twelfth Night, She’s The Man follows Viola (Amanda Bynes) on a quest to impersonate her twin brother Sebastian and prove she can make the starting lineup of a men’s soccer team. After Viola receives a convincing makeover, she takes Sebastian’s spot at boarding school and gets her head in the game. But when she starts crushing on her new roommate, the team’s star player Duke (Channing Tatum), her plan spectacularly spirals out of control. From start to finish, She’s The Man is a delightful, outrageously quote-able romp. Bynes shines in the unconventional rom-com role, and she and Tatum prove they’re one hell of a team. Let’s not forget She’s The Man is also the movie that launched Tatum’s career, and for that we’ll be eternally grateful. — Nicole Gallucci
'You've Got Mail'
Is it even really Valentine’s Day if you don’t spend it with rom-com king and queen Tom Hanks and Meg Ryan? Nora Ephron’s classic modern update to The Shop Around the Corner, You’ve Got Mail is a catfish love story before catfishing was ever a word. Ryan stars as an independent bookstore owner, who strikes up an online romance with a dreamy man, not realizing he’s actually her professional rival. Sure, the references to AOL are dated, but that’s half the fun of this classic, feel-good romantic comedy. – Anna Menta
'Always Be My Maybe'
Randall Park and Ali Wong as childhood friends who realize maybe they have something more going on? You love to see it. You also love to see an absolute incredible cameo by Keanu Reeves that launched a thousand GIFs, and whip-smart, often incredibly weird jokes throughout the movie. With chemistry like this, fingers crossed Park and Wong do another rom-com soon.
'Much Ado About Nothing'
We all love a good rom-com updating of Shakespeare, but what about — bear with us here — a good rom-com that doesn’t update Shakespeare? Starring Kenneth Branagh and Emma Thompson at the peak of their charming abilities, Much Ado About Nothing proves why the bard’s words have survived — and thrived — at this point, for centuries. Class dismissed!
'Crazy, Stupid, Love'
This Is Us creator Dan Fogelman’s 2011 rom-com, Crazy, Stupid, Love, follows 40-something suburban dad and husband Cal Weaver (Steve Carell) in crisis. After Cal’s wife Emily (Julianne Moore) reveals she cheated on him and wants a divorce, the womanizing Jacob Palmer (Ryan Gosling) steps in to give him a crash-course in confidence and modern-day dating. As Cal 2.0 emerges, Jacob meets Hannah (Emma Stone) — a girl who makes him reevaluate his aversion to commitment — and the film’s various (admittedly problematic) storylines converge to create pure chaos. Crazy, Stupid, Love’s undeniable charisma comes from its winsome cast. And though this is the film where Stone and Gosling recreate the famous Dirty Dancing lift, their casual bedroom banter emerges as the film’s most romantic scene. — Nicole Gallucci
'Moonstruck'
When you think “Christmas rom-com,” a film like Moonstruck might not spring to mind, but that’s exactly what this Oscar-winning flick is. Cher plays Loretta Castorini, a young widow about to marry her long-time boyfriend Johnny. While he’s overseas tending to his dying mother, she extends an olive branch to his estranged younger brother Ronny. However, when Ronny falls hard for Loretta, she discovers a wellspring of passion she didn’t know she had. Moonstruck is a film about living life to the fullest and loving as hard as you can. — Meghan O’Keefe
'Charade'
A romantic comedy starring Audrey Hepburn and Cary Grant — that’s gotta be a lark, right? Charade is a whole lot of fun, from that jazzy opening title sequence to the final identity reveal, but this is a romantic comedy that’s also mysterious and thrilling. Instead of playing a straightforward love story, Grant and Hepburn are dropped into a murder mystery where neither can trust each other — and they definitely can’t trust the cadre of criminals hot on their heels. But if you think foul play and life-threatening circumstances are gonna keep people as hot as Audrey Hepburn and Cary Grant from falling head over heels for each other, think again. — Brett White
'Notting Hill'
A classic “they’re from two different worlds” story, Julia Roberts plays, well, Julia Roberts, essentially, a massive movie star who happens to stop in a small bookshop owned by Hugh Grant. After they quickly bond — and kiss — they spark up a romance that just couldn’t ever work… Or could it? You can’t do much better than Julia Roberts and Hugh Grant in a rom-com, and this is a classic for a reason.
'But I'm a Cheerleader'
By now, Natasha Lyonne has developed a reputation for being endlessly, effortlessly cool. That’s partially why Jamie Babbit’s black comedy is such a blast. Lyonne stars as Megan, a 17-year-old who’s sent to a conversion therapy camp due to her interest in vegetarianism and Melissa Etheridge. It’s only after she enters this starkly pink and blue world that she discovers that she really is gay. And do you know who her love interest is? Clea DuVall. Also starring RuPaul, Melanie Lynskey, and Bud Cort, this is one cult hit that delivers so much more than its wide-eyed name implies. — Kayla Cobb
'Something Borrowed'
Kate Hudson and Ginnfer Godwin play two lifelong best friends in denial of their conflicting personalities. Based on Emily Giffin’s book of the same name, this 2005 comedy follows Hudson’s Darcy as she prepares to get married with her bestie, Godwin’s Rachel, at her side. Rachel has always been okay with being a second choice to Darcy, but finds herself at a crossroads when met with her long-going crush on her friend’s fiance and the rising tension between the engaged couple. The movie is super messy and is bound to spark Team Darcy/Team Rachel arguments when watched with a group, but it’s a top-tier choice for the single people out there! — Raven Brunner
'Imagine Me & You'
Sadly, the number of romantic comedies centered on queer relationships are few and far between. But if you’re a queer woman, you probably know about Imagine Me & You, which stars Game of Thrones queen Lena Headey as Luce, a florist who falls for a woman named Rachel (Piper Perabo). The plot may feel a tad dated—Rachel is married to a man and thinks she’s straight, leaning into the “straight woman leaves her husband for a lesbian” stereotype—but the slow burn chemistry between Heady and Perabo is irresistible. You’re a wanker, number nine! – Anna Menta
'Forgetting Sarah Marshall'
Forgetting Sarah Marshall is an exceptionally written rom-com that perfectly captures the intricacies of a well-crafted love triangle. Penned by Jason Segel, the film centers on Peter Bretter. a composer who takes a Hawaiian vacation to recover from his recent break-up with TV star girlfriend Sarah Marshall (Kristen Bell). But wouldn’t you know it, Sarah’s staying at the same resort with her new rocker boyfriend Aldous Snow (Russell Brand). The love triangle that eventually develops between Peter, Sarah, and receptionist Rachel Jansen (Mila Kunis) is a nuanced portrayal of romance that casts aside broad archetypes to focus on genuine characters. It’s an endlessly charming film that confidently embraces the muddled awkwardness of love and loss. — Josh Sorokach
'Mrs. Winterbourne'
A light heartened remake of the Barbara Stanwyck classic No Man Of Her Own, Mrs. Winterbourne is one of the most underrated rom-coms of the ’90s. Starring Ricki Lake, Brendan Fraser, and Shirley MacLaine, this breeze of a film follows the loveable, lower-class and pregnant Connie (Lake) who is mistaken for a rich man’s widow after a train crash. Stuck with a newborn and few options, Connie takes on Patricia Winterbourne’s identity when the family of her dead “husband”—his intimidating mother Grace (MacLaine) and his snobbish brother Bill (Fraser)—takes her in. Connie/Patricia slowly wins them over, and Bill can’t help but fall in love even after he has deduced her real identity. With its classic screwball elements, charming performances and a passionate tango sequence, Mrs. Winterbourne is the perfect stream for a date night in. — Karen Kemmerle
'Legally Blonde'
Before she was a book club and producing mogul, Reese Witherspoon was feminist icon Elle Woods, the sorority girl who got into Harvard Law. (What, like it’s hard?) The Legally Blonde script—written by Karen McCullah Lutz and Kirsten Smith—is brilliant because it disguises itself as an early 2000s gimmicky rom-com, when it’s actually a fairly radical clapback against misogynistic stereotypes. Yes, women do contain multitudes, and if you ever forget it, just remember Elle Woods walking in slow motion out of those courtroom doors to Hoku’s “Perfect Day.” No wonder Luke Wilson fell in love with her. – Anna Menta
'The Cutting Edge'
The Cutting Edge is an under-appreciated ’90s classic. This dreamboat of a movie stars the enchanting duo of Moira Kelly and D.B. Sweeney as reluctant figure skating partners who attempt to capture Olympic gold. The plot is ridiculous in the best possible way, the leads have palpable chemistry, and the film exudes a jaunty rom-com charisma that’ll keep you thoroughly entertained throughout the movie. One of the many reasons The Cutting Edge has endured is because it embraces the fact that rom-coms are supposed to be fun. If you want to kick back, relax, and get lost in a charming, entertaining flick, The Cutting Edge is a gold medal option. — Josh Sorokach
'Only You'
A ‘90s romantic comedy starring Robert Downey Jr. and Marisa Tomei? Sign me up! Only You is a movie for the dreamers and the hopeless romantics. The story follows a woman who has spent her entire life convinced that her soulmate is named Damon Bradley after a series of spiritual revelations. As she grows older, she abandons the belief and finds herself engaged to a man – not named Damon – but she unravels her future plans after learning that her fiance has a high school friend with the sought-after name. She rushes to Rome, in hopes of finding true love, and ends up on another unconventional path to love. Come for the cast, stay for the melodramatic airport scenes. — Raven Brunner
'It Happened One Night'
Besides being one of the greatest films of all time, It Happened One Night is also the template for the rom-com genre itself. The 1934 film has an heiress on the run (and married to the wrong man), a down-on-his-luck reporter (lying about his job), tons of hilarious banter, and an enemies to lovers story. But what really makes the film so iconic is the incendiary chemistry between leads Clark Gable and Claudette Colbert. You can still feel the heat after all these years. — Meghan O’Keefe
'Broadcast News'
From director and writer James L. Brooks, Broadcast News is the rare rom-com that is far from fluff. Starring Holly Hunter, William Hurt and Albert Brooks, Broadcast News takes on everything from sexual assault to media layoffs, while still layering in some inappropriate workplace attraction that nonetheless sets off sparks.
'Uptown Girls'
Not many people can recall the very day in 2022 when “Sheets of Egyptian Cotton” from the Uptown Girls soundtrack was removed from Apple Music, but I can… because I used to listen to it every day while getting ready for work. Not only does Uptown Girls offer some sweet tunes, but it is also an easy, relatable watch that follows a young woman having to learn to grow up amid financial challenges, a flaky romance, and a new job. Despite being nearly 20 years old, the movie remains the perfect representation of being in your twenties – the fun, party nights plagued with lingering fears of aging, commitment, and the future. Brittany Murphy plays 22-year-old Molly Gunn. Her parents died when she was a child and left her with all of their riches. One night, she discovers that her family accountant embezzled her savings and she is evicted from her apartment. As she struggles to land on her feet, she falls in love with an up-and-coming rock star Neal Fox (Jesse Spencer) and accepts a job as a nanny (to a young Dakota Fanning). Her relationship with Neal grows rocky as he climbs the social ladder with only one goal in mind: to become famous. After they split, Neal realizes that Molly was his muse – but is it too late? — Raven Brunner
'The Proposal'
Andrew Paxton has just about no concept of work-life balance when he agrees to marry his pushy corporate boss, Margaret, just to keep her from being deported to Canada. Ten years his senior, and totally not his type, Andrew must believably justify his relationship with Margaret to his family (and himself) or risk losing his job. Starring Sandra Bullock and Ryan Reynolds as the awkwardly mismatched couple, The Proposal is a hilarious reminder that sometimes, with a little bit of pressure, opposites really can attract. — Kara VanDooijeweert
'Set It Up'
If rom-coms live or die by the chemistry between the leads, Set It Up will live forever thanks to the crackling chemistry between Glen Powell and Zoey Deutch. From their meet not-so-cute, to the days and nights they spend plotting to set their bosses up, to the inevitable third act “break up,” you’ll spend the whole movie yelling JUST KISS ALREADY! at your TV. — Angela Tricarico
'Palm Springs'
Palm Springs presents an incredibly compelling case for Andy Samberg: rom-com lead, after over a decade of mostly un-romantic comedic roles. He’s pitch perfect here alongside his love interest in the movie, Cristin Milioti. Palm Springs is an interesting take on the Groundhog Day-esque time loop which sees both characters stuck in the same time loop. Throw in an unhinged J.K. Simmons in a supporting role, and you’ve struck rom-com gold. — Angela Tricarico
'13 Going on 30'
As someone who received a VHS tape of 13 Going on 30 for my 13th birthday, I may be a tad biased when I declare it one of the best movies, of any genre, of all time. But, c’mon! Jennifer Garner delivers a career-best performance as a 13-year-old in 1987 who magically gets transported to the year 2004, into the body of her 30-year-old self. Her wide-eyed innonence at the cutthroat world of early 2000s NYC media never gets old. When she takes the train home to visit her parents, set to Billy Joel’s “Vienna”? I’m tearing up just picturing it. And then there’s the epic chemistry between Garner and Mark Ruffalo (the peak era of Mark Ruffalo). “Jenna, I’ve always loved you,” remains the most romantic line of my childhood. – Anna Menta
'Clueless'
The best part about Amy Heckerling’s Clueless is that Cher (Alicia Silverstone) never pretends to be anything that she’s not. Cher is hot, popular, smart, beloved, and wealthy, and she never once questions that she’s any of these things. Much like Jane Austen’s Emma, her only real flaw is that she’s, well, clueless. Rom-coms don’t always need to have the highest stakes. Sometimes they can just be about fashionable divas who learn exactly one life lesson and score Paul Rudd as a boyfriend in the process. This 1995 gem delivers all the high school camp you could want while also serving as a lovely story about friendship that never drifts into catty territory. — Kayla Cobb
'High Fidelity'
High Fidelity is a film obsessed with Top 5 lists and an intense form of music snobbery that’s only hilarious when it’s coming from Jack Black. When Rob (John Cusack at his best) faces yet another disastrous breakup, he decides to revisit his top five breakups of all time in an attempt to figure out why things keep getting screwed up. What came first, the music or the misery? That’s the heady question that opens High Fidelity, and it also the hook that reels in everyone who’s ever been brave (or foolish) enough to inextricably link their feelings for another person with a playlist. — Brett White
'To All the Boys I've Loved Before'
Woah, woah, woah, you might say: since its release on Netflix, the hit adaptation of Jenny Han’s books has spawned two mixed results sequels that complicated the pure, innocent romantic relationship between Peter Kavinsky (Noah Centineo) and Lara Jean Covey (Lana Condor). But the original film is unimpeachable. Centineo is the perfect puppy dog jock. Condor is an effusive fount of joyous nerdy light. Along with crisp, pastel direction by Susan Johnson, the story of a girl who accidentally sends letters to her crushes, and the guy who helps her (sort of) get out of the situation is exactly the sort of plot that rom-com dreams are made of.
'Sleeping With Other People'
Alison Brie once told Decider that Sleeping With Other People was a past project she felt deserved more love, and she’s absolutely correct. The underrated 2015 rom-com stars Brie as Lainey and Jason Sudeikis as Jake, two people who slept together in college and reunite 12 years later in a sex addiction treatment class. In bonding over messy love lives and commitment issues, the two embark on a unique friendship that they vow to keep platonic despite a wild attraction to one another. Written and directed by Leslye Headland, with Will Ferrell and Adam McKay as producers, Sleeping With Other People is hilarious, sexy, and full of heart. Brie and Sudeikis share palpable chemistry, and cameos from Adam Scott, Adam Brody, Amanda Peet, Natasha Lyonne, Jason Mantzoukas, and more cement a top-tier cast. Sleeping With Other People gives the beloved friends to lover trope a fresh twist, and Sudeikis’ hand kissing scene deserves a spot in the rom-com hall of fame. — Nicole Gallucci
'Bridget Jones's Diary'
Do you want to know why this loose adaptation of Pride and Prejudice has stood the test of time? It’s because it’s relatable. Renée Zellweger plays the leading lady we all secretly are: She has ambitious plans to lose weight that will never come to fruition, a smoking addiction, and for the life of her she can’t stop flirting with guys she knows she shouldn’t. Forget all the girls who are not-so-secretly gorgeous but happen to wear glasses. Bridget Jones is our chaotic idol. — Kayla Cobb
'The Holiday'
Despite its name, The Holiday is a charming feel-good film that can (and should) be enjoyed year-round. After two unlucky-in-love strangers Iris (Kate Winselet) and Amanda (Cameon Diaz) meet through a home-exchange website, they leave their problems behind and swap lives for the holidays. Iris heads to an LA mansion, Amanda vacates to a cozy cottage in England, and the two lost souls quickly find themselves — and love — again. Jude Law, Jack Black, and the late Eli Wallach exude charm as The Holiday‘s leading men. Hans Zimmer’s beautiful score simultaneously moves and delights. And the perfect rom-com balance of serious, swoonworthy, and silly is achieved by offsetting character heart-to-hearts and deep moments of introspection with, say, a “Mr. Brightside” dance party and the unveiling of Mr. Napkinhead. You’ll laugh, you’ll cry, you’ll crave fettuccini. If The Holiday were a melody, Nancy Meyers used only the good notes. — Nicole Gallucci
'The Wedding Singer'
There’s no such thing as a perfect rom-com, but The Wedding Singer is pretty damn close. Starring the winsome duo of Adam Sandler and Drew Barrymore, the film follows the bewitching romance between a heartbroken wedding singer (Sandler) who promises to help a waitress (Barrymore) plan her wedding. Few movies balance zany laugh-out-loud moments (shout-out to Jon Lovitz performing “Ladies’ Night!”) with genuine pockets of heartfelt sincerity with more aplomb than this iconic beacon of romance. We want to grow old with you, Wedding Singer. — Josh Sorokach
'Fire Island'
At this point, who hasn’t seen the viral “No, the defense is wrong!” clip? This 2022 romantic comedy, written by and starring Joel Kim Booster, offers loads of fun and sickly sweet romance. Fire Island follows a group of gay friends on vacation to New York’s “gay village” Fire Island. While visiting their “house mother” Erin (Margaret Cho), she reveals that she is selling her house, which puts a bummer on the group’s party plans, but they proceed to try and make a few more lasting memories. This brings them to meet a vacationing doctor named Charlie (James Scully) who invites them to hang out with his rich friends. The story becomes a sordid tale of romance and classism as true intentions are revealed and another love interest is introduced – and through it all, there’s still the ongoing ambiance of needing one last hurrah. In addition to the star-studded cast, Conrad Ricamora gives a standout performance, effortlessly achieving the challenging duality of playing a douchebag who’s not really a douchebag. — Raven Brunner
'Scott Pilgrim Vs. The World'
Baby boomers have When Harry Met Sally, Generation X has High Fidelity, and millennials have Scott Pilgrim vs. the World. Edgar Wright’s adaptation of Bryan Lee O’Malley’s graphic novel opus was ahead of its time in 2010. It takes queer characters, meme-able moments, irreverent jokes (“Bread makes you fat?!”), the insight of a Tumblr essay, and the unmistakable ennui of the time and crams it into a love story (or a like like story) between two millennial greats: Michael Cera and Mary Elizabeth Winstead. With its fast-cutting of pop culture riddled gags and 8-bit surrealist storytelling, the kind of visual language that would dominate social media in the following decade, Scott Pilgrim literally spoke to a generation. — Brett White
'Say Anything...'
Are there any ten more devastating words in the English language than, “I gave her my heart, she gave me a pen”? Written and directed by Cameron Crowe, in his feature debut, Say Anything… announced a bold new talent onto the scene that also presaged a spate of slacker comedies that would be released over the next decade. But what makes the movie work, other than being plugged into the voice of a generation, is the chemistry between leads John Cusack (donning an iconic trenchcoat) and Ione Skye, as well as a stellar supporting cast including Joan Cusack, John Mahoney, a hilarious Lili Taylor and many more. If you’ve ever thought about playing “In Your Eyes” on a boombox outside the window of the one you love — and you definitely have at least thought about it — you have Say Anything… to thank.
'Pretty Woman'
What list of the best rom-coms of all time would be complete without Garry Marshall’s Pretty Woman? In what is still the most charismatic performance of her long career, Julia Roberts (at just 23-years-old!) plays Vivian Ward, a hooker with a heart of gold, who is hired by corporate raider Edward Lewis (Richard Gere), to spend the week with him attending various corporate events. Over the course of a few days, they flirt (“I would have paid four.”), they laugh (“Slippery little suckers.”), they shop (“Big mistake. Big. Huge!”), they kiss (!) and fall in love. Beautifully acted, endlessly quotable, and totally swoon worthy, Pretty Woman is a modern fairytale, complete with a suited knight in a white stretch limo. — Karen Kemmerle
'The Princess Bride'
The Princess Bride nails the two most important parts of the rom-com genre: the romance and the comedy. Okay, yeah, sure, that might sound easy, but I defy you to come up with a purer cinematic love story than that of Westley and Buttercup or a film full of so many hysterical punchlines. The Princess Bride is an enchanting fairy tale that fully embraces the joy of both love and laughter. — Meghan O’Keefe
'The Big Sick'
Based on Kumail Nanjiani and Emily V. Gordon’s real-life experiences as a couple dealing with interracial romance and one of them falling ill (that would be Emily), The Big Sick is a refreshing, surprising rom-com that manages to balance some extremely heavy issues with multiple laugh-out-loud funny moments in nearly every scene. Nanjiani has since gone on to dominate the world of action movies, but he’s never been better than opposite Zoe Kazan as the fictional Emily. And as a bonus, this is one of the rare films that not only understands how the comedy scene works, but actually manages to make scenes involving stand-up comedy both authentic and hilarious.
'When Harry Met Sally'
It’s been said hundreds of times before, but there’s simply no way around the fact that When Harry Met Sally is the greatest romantic comedy of all time. Writer Nora Ephron and director Rob Reiner delivered the ideal blend of hilarious and romantic 34 years ago, and no one has been able to top it since. Harry and Sally—played perfectly by Billy Crystal and Meg Ryan—are the quintessential enemies-to-friends-to-lovers. There is no character vs. plot; the characters are the plot. There is no waiting for the movie to get to the good stuff, because it’s all the good stuff. That first banter over an 18-hour car ride, that late-night phone call to watch Casablanca together, that fake orgasm in Katz’s Delicatessen, that failed double-date, that first night together, that speech on New Year’s Eve—all of it. How could you forget a single shot, when every scene is so deliciously romantic and so refreshingly fun? It’s all the best parts of a romantic comedy and none of the worst. – Anna Menta
