I’m just a writer, standing in front of a reader, asking you to take a look at these 27 romantic comedies. After all, the genre is as timeless as any other. From the earliest days of Hollywood to today, audiences keep returning to these feel-good stories that deliver heart flutters and belly laughs in equal measure.
Whether you’re an actor looking for (onscreen) love, a creator who wants to craft a compelling meet-cute, or just a fan of falling head over heels, this watchlist will give you a rom-com crash course.
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Happily ever after: The characters will go through all sorts of hardship and turmoil, of course, but at the end of the film, they need to end up together. Not only that, but we must believe they’ll stay together for quite some time.
Meet-cute: The cornerstone of the rom-com is that moment when the two main characters meet. Even if the pair have already met or are friends, there should be a scene in which they see each other in a new light. At this point, everything feels full of possibility and adorable.
An unlikely pairing: There’s always something standing in the way of a couple’s happy ending, whether it’s career, family, geography, or just a clash of personalities.
Onscreen Chemistry: Magical Alchemy or Just Good Acting? Sparkling chemistry: The audience needs to be yelling “Now kiss!” at the screen long before the characters themselves figure out that they’re meant to be.
Hilarious side characters: Don’t forget the comedy side of the equation. Though the leads are hopefully funny in their own right, it’s typically the side characters who do the bulk of the comedic heavy lifting. They’re there to point out what the audience is thinking, including all the reasons the two love interests should (or shouldn’t!) be together.
A grand declaration of love: The moment when love overcomes all obstacles should feel big. One character must tell the other that they’re the only one who lights their candle, the only one who floats their boat—preferably either in the rain or in front of a rapt audience.
As Hollywood’s Golden Age really started to shine and the Hays Code required filmmakers to get creative in their innuendo, the rom-com found its footing largely in the form of two-hander screwball comedies. Aspiring actors and creators should watch these films for a master class in chemistry; it’s often not what’s being said but the way two characters bounce barbs back and forth that makes audiences swoon.
“It Happened One Night” (1934)
Before we had 21st century heartthrobs like Matthew McConaughey and Glen Powell, there was Clark Gable. Frank Capra’s film, based on the short story “Night Bus” by Samuel Hopkins Adams, follows recently eloped heiress Ellie Andrews (Claudette Colbert), whose encounter on a bus with newspaper reporter Peter Warne (Gable) sparks an unlikely attraction—and a series of mishaps. Not only did Colbert and Gable receive Academy Awards for their roles, but “It Happened One Night” stands in the history books as the first rom-com to win a best picture Oscar.
“His Girl Friday” (1940)
Cary Grant, one of the most bankable stars of early Hollywood, headlines Howard Hawks’ fast-talking rom-com as Walter Burns, a newspaper editor who convinces his star reporter (and ex-wife) Hildy Johnson (Rosalind Russell) to chase down one last story with him before she gets married and leaves New York. Of course, not only do they get the story, but their efforts also rekindle their lost love.
“The Philadelphia Story” (1940)
Grant once again takes center stage in George Cukor’s tale of second chance romance, opposite Katharine Hepburn in her first major role. The marriage between Dexter Haven (Grant) and Tracy Lord (Hepburn) fell apart because Dexter didn’t measure up to his wife’s standards. However, Tracy soon finds herself torn between her new fiancé (John Howard), the charming reporter (Jimmy Stewart) sent to cover their wedding, and the ex-husband who knows her better than anyone.
“The Shop Around the Corner” (1940)
Audiences today might be more familiar with this film’s 1998 reimagining—Nora Ephron’s “You’ve Got Mail,” starring Tom Hanks and Meg Ryan. But in Ernst Lubitsch’s original, Golden Age icons Stewart and Margaret Sullavan play competing salespeople at a leather goods store who don’t realize they’re also falling in love through the anonymous letters they write to each other.
“Roman Holiday” (1953)
Audrey Hepburn reigned supreme in William Wyler’s film as a princess who falls in love with a gruff American reporter in Rome. And as journalist Joe Bradley (Gregory Peck) circles the story of a lifetime, he must decide what’s more important: his story or his growing fondness for his subject.
“The Apartment” (1960)
Sometimes, romance blooms in the unlikeliest of places; this is the case in Billy Wilder’s “The Apartment.” Bud (Jack Lemmon) is an insurance clerk who lets the higher-ups use his home to cheat on their wives. When the woman Bud likes, Fran (Shirley MacLaine), an elevator operator at his office building, gets caught up in an affair with Bud’s boss (Fred MacMurray), the tangled scenario leads to an endlessly charming romance.
“Breakfast at Tiffany’s” (1961)
In one of her most iconic roles, Hepburn stars as Holly Golightly, a country girl turned New York socialite who winds up falling for her neighbor, struggling scribe Paul Varjak (George Peppard), against the backdrop of the bustling Manhattan social scene. Though Holly’s life seems much more glamorous than Paul’s, the two form a bond as they commiserate between Holly’s many outings and engagements, ultimately realizing that they belong together.
From the mid-80s to the early aughts, the genre ruled the box office and hit creative highs. Watch these movies if you want to deconstruct what makes a truly iconic rom-com moment—from the most quotable conversations to the marquee meet-cutes to firework-launching final confessions.
“Some Kind of Wonderful” (1987)
Unrequited love is one of the genre’s most quintessential tropes, and Howard Deutch’s teen romance does it better than most. Tomboy musician Watts (Mary Stuart Masterson) is in love with her artistic best friend, Keith (Eric Stoltz), but he’s infatuated with popular girl Amanda (Lea Thompson). Not only does the friends-to-lovers pairing eventually come to fruition, but Amanda winds up choosing herself over any of the boys vying for her attention. Truly a modern-day resolution, set decades before the modern day.
“Moonstruck” (1987)
It’s probably already evident that plenty of the rom-coms that stand the test of time are about second chances, which is very much the case with Norman Jewison’s “Moonstruck.” In the weeks leading up to her wedding, the widowed Loretta (Cher) falls for her fiancé’s brother Ronny (Nicolas Cage). This is a film about finding love after losing it once, and realizing you don’t need to settle for a life without passion.
“When Harry Met Sally…” (1989)
Can men and women truly be friends? That is the question posed by Rob Reiner’s “When Harry Met Sally,” a film often touted as the pinnacle of the genre (and for good reason). Over the course of several years, friends Harry Burns (Billy Crystal) and Sally Albright (Ryan) debate that central question—as well as many, many other topics—until they’ve talked themselves into falling in love.
“Pretty Woman” (1990)
Though director Garry Marshall never explicitly said that this classic is based on George Bernard Shaw’s “Pygmalion,” it’s hard to deny the similarities: a high-brow man (Richard Gere) meets a working-class woman (Julia Roberts) and decides to transform her into the version of femininity acceptable to his quadrant of society. While the premise of a sex worker finding love with an uber-wealthy businessman raised some eyebrows, “Pretty Woman” convinced us that Roy Orbison’s words amount to more than meets the eye, and that two characters from opposite sides of the tracks really do deserve true love.
“Sleepless in Seattle” (1993)
It’s rare that a rom-com doesn’t even have the two main love interests meet until the final scene, but that’s the genius of Ephron’s “Sleepless in Seattle.” Bereft widow Sam (Hanks) is thrust into the public eye when his son calls into a radio show, and starry eyed journalist Annie (Ryan) falls head over heels. While Hanks and Ryan have appeared in several movies together, there’s something special about this one—it makes you believe true love can transcend all the logistical issues that stand in its way.
“Four Weddings and a Funeral” (1994)
Sometimes, it takes a few tries for two people to realize they’re meant to be. This is the case in Mike Newell’s “Four Weddings and a Funeral,“ which follows Charles (Hugh Grant) and Carrie (Andie MacDowell) as they run into each other at the titular quintet of events. It’s a classic example of persevering even when the timing is never quite right.
“While You Were Sleeping” (1995)
Rom-coms always throw a curveball at its hopeless romantic leads; Jon Turteltaub’s “While You Were Sleeping” throws several. A train ticket collector, Lucy (Sandra Bullock), tries to save the man she loves from afar, Peter (Peter Gallagher), after he’s pushed onto the tracks. After the incident, not only does the family of the now-comatose Peter mistakenly believe Lucy is his fiancé, but Lucy soon finds herself drawn to his brother, Jack (Bill Pullman). It’s a lot of concept, but Bullock truly holds it together, demonstrating the power of a charismatic lead and dynamite chemistry.
“Notting Hill” (1999)
Audiences love an underdog, and few love interests have ever had the odds stacked against them quite as much as humble bookstore owner William Thacker (Grant) in Roger Michell’s “Notting Hill.” Sparks fly when famous Hollywood actor Anna Scott (Roberts) stumbles upon William’s London shop. It’s not unusual for a rom-com to ask audiences to toss caution to the wind, but this movie truly pushes us to believe in fairytale endings.
“She’s All That” (1999)
Do you know the trope of a geeky girl removing her glasses and suddenly she’s pretty? You can thank Robert Iscove’s “She’s All That” for imprinting that image firmly into the brains of a generation of millennials. In another “Pygmalion” reimagining, popular high school student Zack (Freddie Prinze Jr.) makes a bet with a friend that he can turn introverted art student Laney (Rachael Leigh Cook) into the prom queen. Of course, during the course of his machinations, the two develop feelings for each other.
“10 Things I Hate About You” (1999)
If you think rom-coms are strictly a recent invention, look into how many of the classic films are updated takes on the works of William Shakespeare. In 1999, the playwright’s “The Taming of the Shrew” was adapted into a tangled high school affair in Gil Junger’s “10 Things I Hate About You.” Sophomore Bianca (Larisa Oleynik) can’t date until her rebellious older sister Kat (Julia Stiles) does the same. In a bid to win Bianca’s heart, Cameron (Joseph Gordon-Levitt) hires outcast Patrick (Heath Ledger) to ask Kat out. Those yearning feelings throughout are still universal today, just as they were in the 1990s and 1500s.
“Love & Basketball” (2000)
The romantic comedy and sports drama don’t often overlap, but they’re perfectly combined in Gina Prince-Bythewood’s “Love & Basketball.” Monica (Sanaa Lathan) and Quincy (Omar Epps) are two childhood friends and neighbors who bond over their love of the game. Despite a mutual attraction as kids, their lives take them in different directions. It’s not until they’re adults, still pursuing their shared passion on the court, that they realize they belong together.
“Bridget Jones’s Diary” (2001)
Jane Austen was a writer ahead of her time, as evidenced by the sheer amount of times her novel “Pride and Prejudice” has been adapted, reworked, and rebooted. Perhaps the best example is Sharon Maguire’s “Bridget Jones’s Diary.” Renée Zellweger stars as Bridget, an updated take on Elizabeth Bennett, torn between two men: Mark Darcy (Colin Firth) and Daniel Cleaver (Hugh Grant). While Austen’s works leaned toward drama, this 21st century reimagining brings out the absurdity of its central love triangle.
“Serendipity” (2001)
The idea of fate versus free will gets thoroughly examined in Peter Chelsom’s rom-com that sees Jonathan (John Cusack) and Sara (Kate Beckinsale) leaving their romantic fortunes to chance. In their 20s, both are taken, but chemistry abounds after a meet-cute at a department store during the Christmas rush. Ten years later, they try to track each other down in the infinite chaos of New York City. This one’s for the hopeless romantics who believe there’s someone out there for everyone, despite the obstacles life and time throw in your way.
“How to Lose a Guy in 10 Days” (2003)
We’ve established that destiny and circumstance will try to keep our rom-com leads apart. But what if one character is actively trying to get the other to dump them? In Donald Petrie’s aughts-era classic, columnist Andie (Kate Hudson) tries to force serial womanizer Ben (Matthew McConaughey) to call it quits for a story; he, as part of a bet, is determined to stay committed in order to land a big promotion. The power of megawatt stars like McConaughey and Hudson is that you do believe chemistry would overcome this parade of red flags.
While it may not be the box office juggernaut of old, the spirit of the rom-com is alive and well in Hollywood. If you get caught up in the idea that it’s all been done before, these movies are a testament to the fact that the tropes may remain the same, but the genre cannot be boxed in.
“The Big Sick” (2017)
As rom-coms evolved, the stakes got higher. In Michael Showalter’s “The Big Sick,” Kumail Nanjiani dramatizes the real-life love story of him and his wife, Emily V. Gordon. When his character learns that his ex—and the love of his life—Emily (Zoe Kazan), has a life-threatening disease, he intends to be there for her. The movie deals with much bigger issues than conflicting personalities or simple misunderstandings, asking viewers to take a chance on love no matter the odds.
“Love, Simon” (2018)
While queer love stories have existed from time immemorial, it wasn’t until recently that they got the mainstream treatment. Based on Becky Albertalli’s novel “Simon vs. the Homo Sapiens Agenda,” Greg Berlanti’s coming-of-age film follows a closeted gay high schooler named Simon (Nick Robinson) who falls for an anonymous classmate online. Framing quintessential tropes from the 1980s and ’90s through a queer lens, “Love, Simon” affirms that love stories can be just as corny and overwhelming and magnificent no matter your sexual orientation.
“Set It Up” (2018)
Director Claire Scanlon crafts a classic enemies-to-lovers scenario: Assistants Harper (Zoey Deutch) and Charlie (Powell) try to set up their controlling bosses (played by Lucy Liu and Taye Diggs). This movie is a great example of two characters understanding the assignment while completely missing the point, as they naturally build a better chemistry than the one they’re trying to manufacture.
“To All the Boys I’ve Loved Before” (2018)
While plenty of rom-coms start with a mortifying premise, few rival the inciting incident of Susan Johnson’s “To All the Boys I’ve Loved Before,” based on the novel by Jenny Han. Teenager Lara Jean (Lana Condor) deals with her crushes by writing letters to them that she never intends to mail. Unfortunately, her little sister finds them and sends them to all her past objects of affection. To avoid embarrassment with her current crush, Josh (Israel Broussard), Lara Jean strikes up a fake relationship with another letter recipient, Peter (Noah Centineo). This is more meet-cringe than meet-cute, but it’s hard to deny that from the second those letters hit the mailbox, we’re rooting for our heroine to find love.
“Always Be My Maybe” (2019)
Ali Wong and Randall Park star as childhood friends Sasha and Marcus who reconnect as adults. While Marcus is eager to take things to the next level, Sasha simply doesn’t see him that way (and neither would we, if we were dating Keanu Reeves, or even a fictionalized version of the actor). Nahnatchka Khan’s delightful film is a great example of rom-coms thankfully working to diversify what has largely been a one-demographic genre. While none of the story’s twists and turns are necessarily new, it’s refreshing to see a mainstream American film play with those tropes with nary a white main character in sight.
“Anyone But You” (2023)
Shakespeare, once again! This time, director Will Gluck adapted the Bard’s “Much Ado About Nothing,” one of the best enemies-to-lovers stories of all time. Powell and Sydney Sweeney star as contemporary beautiful people Ben and Bea who fall out after a promising meet-cute. Later, the two are forced to interact when Bea’s sister and Ben’s friend tie the knot. While this version trims away quite a bit of the Shakespearean subplots, the animosity—and simmering attraction—between Bea and Ben does not get watered down in the slightest.
