Every major genre exists in a state of perpetual reinvention, but the standard tropes of the romantic comedy have largely remained the same ever since silent film gave way to the talkies. Two people, who generally start out with a disregard or dislike of each other, find themselves drawn together by a coincidental set of circumstances, before they fall in love and everyone goes home happy. Despite the sense of familiarity, the rom-com endures because audiences love the mixture of heart and humor that comes with the territory, and Hollywood history is littered with more than a few stone-cold classics. Read on for the 50 best rom-coms of all time.
50. How Stella Got Her Groove Back (1998)
How Stella Got Her Groove Back is far from a masterpiece or a work of art, but it is the equivalent of cinematic comfort food, which is why it’s endured for so long as a perennial rom-com favorite.
Angela Bassett’s title character heads off to Jamaica with her longtime best friend Delilah, where she ends falling for a man half of her age. Hardly a major problem, but the tropes of the genre indicated that some kind of conflict has to be created.
A refreshing spin on seeing a female lead placed opposite a younger male love interest, Kevin Rodney Sullivan’s frothy comedy benefits from a trio of immensely talented stars elevating the proceedings well above formula.
49. Reality Bites (1994)
Ben Stiller’s feature directorial debut is an overlooked and often forgotten rom-com for Generation X, but still boasts a cult following, even though it hasn’t aged particularly well over the last quarter of a century.
Looking at it now, the cast of Stiller, Winona Ryder, Ethan Hawke, Janeane Garofalo and Steve Zahn is a hugely talented ensemble, and it certainly hit the expected beats to satisfy the target audience.
As a snapshot into a certain time period that holds an awful lot of significance for a lot of people, Reality Bites is a winning slice of nostalgia that never tries to over-complicate things or overextend itself.
48. Long Shot (2019)
Jonathan Levine has built a career out of subverting comedic expectations in the likes of The Wackness, Warm Bodies and 50/50, but the filmmaker outdoes himself with the winning Long Shot.
Seth Rogen proves to be a surprisingly capable romantic lead as Fred Flarsky, a journalist who reconnects with his former babysitter and childhood crush, who also happens to be a high-flying politician.
The movies is powered by the sparkling chemistry between Rogen and Charlize Theron, that’s a lot smarter, sharper and more complex that a relatively straightforward rom-com has any right to be.
47. Much Ado About Nothing (1993)
Shakespeare isn’t exactly the first thing that comes to mind when you think of the all-time great romantic comedies, but Kenneth Branagh’s Much Ado About Nothing embraces its nature as a shameless farce and turns out all the better for it.
That’s without even mentioning a cast stacked from top to bottom with talent that includes Branagh himself, Emma Thompson, Kate Beckinsale, Denzel Washington, Keanu Reeves and Michael Keaton.
The cast are more than game, the direction and tone is light and breezy, all combining to form one of the Bard’s best big screen adaptations from a pure entertainment perspective.
46. The 40 Year-Old Virgin (2005)
As Hollywood studio comedy evolved from gross-out to something slightly more complex, Judd Apatow found himself at the forefront of the movement with his massively successful feature debut.
Of course, there are still plenty of d*ck jokes to be found in The 40 Year-Old Virgin, but the plot is layered with genuine emotion, warmth and even some sentimentality thrown in.
Steve Carrell knocks it out of the park in his first major big screen leading role, with the improv-heavy style generating huge laughs as a raft of razor-sharp comics all manage to leave an impression.
45. Forgetting Sarah Marshall (2008)
Balancing romance with raunch, Jason Segel’s stardom from How I Met Your Mother gave him the clout to star in the adaptation of his own screenplay, and he gives a knockout performance.
A struggling musician best known for his famous ex heads on vacation to try and get over the breakup, where he winds up bumping into the titular TV star and her eccentric new boyfriend.
Segel and Russell Brand play off each other extremely well as the disparate personalities who wind up in the same orbit, while Mila Kunis anchors the more outlandish story and comedic elements with her relatable performance as hotel receptionist Rachel Jansen.
44. Something’s Gotta Give (2003)
Rom-com legend Nancy Myers unsurprisingly applied her expertly-honed skills to great effect on Something’s Gotta Give, making the fresh feel familiar in the genre yet again.
Leads Diane Keaton and Jack Nicholson were both nominated for Golden Globes for their performances, with the actress winning the statue after holding her own against the reformed wildman’s charismatic tour de force.
Nicholson expertly plays off his persona as the aging womanizer who discovers to his horror that he’s falling for a woman roughly his own age, while the sheer star power and chemistry is more than enough to compensate for the plot beats you can see coming a mile off.
43. My Best Friend’s Wedding (1997)
Julia Roberts reinforced her credentials as one of the biggest movie stars on the planet by steering My Best Friend’s Wedding to almost $300 million at the box office in another effortlessly commanding performance.
Two childhood friends made a pact to get married if they were still single by the ripe old age of… 28. Unfortunately, Dermot Mulroney’s Michael is set to get married four days before the milestone.
Naturally, Roberts’ Jules decides she’s in love with him, and sets out to try and stop the impending nuptials, before things get increasingly complex. Of course, being a rom-com, things ultimately resolve themselves in the end and everyone gets a happy ending.
42. Jerry Maguire (1996)
As a drama, romantic comedy and sports movie all at once, Jerry Maguire is forced to wear a lot of hats, but peak era Cameron Crowe manages to pull it off with more than a little help from his cast.
Cuba Gooding Jr. Won and Academy Award for Best Supporting Actor, Tom Cruise nabbed a Golden Globe in the lead category, and the movie was nominated for Best Picture at both, which makes it sound like more of a prestige awards contender than a rom-com.
However, the beating heart of the entire film is the dynamic between Cruise’s title hero and Rene Zellweger’s Dorothy, and even if you’ve never seen Jerry Maguire, you already know several of the most famous quotes off by heart.
41. The Wedding Singer (1998)
Adam Sandler has shown on more than one occasion over the last 25 years that there’s many more strings to his bow than the one-not comedy shtick, but he doesn’t show it anywhere near often enough.
The Wedding Singer was arguably the first time he demonstrated true potential as a romantic leading man, and he’s never generated better onscreen chemistry with anyone than the spark he shares with Drew Barrymore.
It’s very inconsistent in terms of tone, but the central romance greatly elevates the material, and the schmaltz and saccharine moments have cemented it as one of the most beloved movies of either star’s career.
40. High Fidelity (2000)
Stephen Frears’ High Fidelity is hardly complicated or profound, but it certainly struck a chord with the intended audiences, and the soundtrack is never going to go out of fashion.
John Cusack stars as the owner of a rundown record store jilted by his girlfriend, leading him to look inward. With a little help from his friends, he ends up finally embracing change and growing up.
Cusack might be the lead, but the supporting cast are every bit as good, with Jack Black giving the breakout performance that took his career to the next level in an unconventional rom-com that still hits all the right notes.
39. My Big Fat Greek Wedding
One of the most unexpected box office smash hits of the 21st Century, My Big Fat Greek Wedding hauled in close to $370 million against a $5 million budget after resonating with audiences in a huge way.
Nia Vardolos wrote the script and also stars as the lead character, torn between happiness and tradition as she falls in love with a man who isn’t the Greek her family were hoping for.
As sharp as it is charming, My Big Fat Greek Wedding pulled off the unique feat of localizing the rom-com and rooting it in a certain aspect of society while still boasting the sort of wide-ranging appeal and relevancy that made the genre so popular in the first place.
38. She’s Gotta Have It (1986)
Spike Lee isn’t the first name that comes to mind when you think of romantic comedy, and She’s Gotta Have It is hardly conventional, but his first feature film definitely ticks many of the boxes required.
Nola Darling can’t decide who she wants to date, so she decides to test the waters with three wildly different guys at the same time, leading to plenty of internal and external conflict as a result.
She’s Gotta Have It displays many of the social and political angles that would go on to define Lee’s career, and it offers a standard Hollywood rom-com wrapped up in the singular talents of a soon-to-be hugely prescient and frequently incendiary filmmaker.
37. Harold And Maude (1971)
The romantic comedy has always tended to be one of Hollywood’s fluffier and less demanding genres, but that isn’t the case when it comes to the pitch-black classic Harold and Maude.
A suicide-obsessed 20-something strikes up a romance with an 80 year-old wild child at a funeral, and together they explore the meaning of life from their vastly different perspectives.
Hal Ashby’s cult classic was a flop at the time it was released, but over the last half a century Harold and Maude is held up as a true cult favorite, and one of the most unusual rom-coms ever made.
36. Amelie (2001)
Audrey Tatou’s title heroine was the personification of the ‘manic pixie dream girl’ long before Hollywood ever got hold of the term in Jean-Pierre Jeunet’s international success story.
A flighty comedy about a woman who manipulates the lives of those around her to create a fantasy world entirely of her own design, Amelie is a complex look at what makes the main character tick, and how her introspection ultimately affects those around her.
A very French and very arthouse concept by design, Amelie nonetheless made major waves with both critics and at the box office that shoots Paris through a vivid and fanciful picturesque lens.
35. Roxanne (1987)
During his 1980s heyday, Steve Martin could barely put a foot wrong from a critical or commercial perspective, even when he made the unusual choice to use Cyrano de Bergerac as the basis for an irreverent studio comedy.
Martin’s C.D. Bales is a small-town fire chief who staunchly refuses to chase after the woman of his dreams, based entirely on the size of his nose, which pretty much sums up the level of absurdity on display.
However, the whole thing is so sweetly romanticized and expertly acted by a cast on top form that it transcends the bizarre premise to serve as a touching, whimsical and frequently hilarious rom-com.
34. The Seven Year Itch (1955)
Billy Wilder’s feature length version of the stage play showed the legendary filmmaker apply his trademark deft touch for blending comedy and romance to fantastic effect.
Tom Ewell’s Richard Sherman sends his wife and son off on vacation to focus on his work, before becoming infatuated with the blonde bombshell that just moved in upstairs, causing him to question the sanctity of his marriage.
Marilyn Monroe is exactly as smoldering as you’d expect in the femme fatale role, and the chemistry between the cast and Wilder’s frequent flights of fancy easily overcome any moral obstacles presented by the questionable premise.
33. To All the Boys I’ve Loved Before (2018)
In recent years, Netflix has made some serious gains in the rom-com market, but none of them have managed to reach a similar level of acclaim as To All the Boys I’ve Loved Before.
Lana Condor gives a star-making performance in the story of a teenager who wreaks self-inflicted havoc on her personal life when her private love letters end up becoming public knowledge, making her life all the more difficult.
There isn’t much to be found in the way of originality, but the whole thing is just so wholesome and charming that it spawned a devoted following, and two sequels have already been shot and are awaiting release.
32. Notting Hill (1999)
Writer Richard Curtis and star Hugh Grant are rom-com stalwarts, so it shouldn’t be a surprise that Notting Hill finds them both on top of their games, with Julia Roberts adding a little A-list stardust for good measure.
Grant’s bookstore owner begins an intense relationship with Roberts’ famous actress, but the obvious differences in their backgrounds and general existences proves to throw up some serious hurdles.
Obviously, because this is a Hollywood rom-com we’re talking about, everyone gets a happy ending in the end, but Notting Hill hits some big crowd-pleasing and familiar beats on its way to making it there.
31. Crazy Rich Asians (2018)
A massive box office phenomenon, Crazy Rich Asians transcended its humble origins to become the highest-grossing romantic comedy of the 2010s, scoring widespread praise from audiences and critics alike.
Journeying into the unknown, Constance Wu’s Rachel Chu discovers her longtime boyfriend is from an incredibly wealthy family and he’s got a reputation as one of Singapore’s most eligible bachelors.
Cultural clashes, an unusual family and the standard romantic hiccups are all par from the course, but the script sings and the cast are more than game for both the sentimentality and slapstick, making Crazy Rich Asians a great time at the movies.
30. 10 Things I Hate About You (1999)
The Taming of the Shrew may have drawn yawns from teenagers in classrooms around the world, but it nonetheless served as the basis for a rom-com that’s still beloved by an entire generation.
A cast of rising stars fronted by Julia Stiles, Heath Ledger and Joseph Gordon-Levitt bring Shakespeare into the world of teen comedy, and in all honesty it works a lot better than it has any right to.
Quick-witted and without an ounce of cynicism, 10 Things I Hate About You is formulaic almost to a tee, but sidesteps the pitfalls that drag down many other rom-coms to stand tall as one of the genre’s cleverest spins.
29. Woman of the Year (1942)
A-listers Katharine Hepburn and Spencer Tracy headline what was viewed as Hollywood’s most progressive populist films at the time, one that ended up being adapted into a long-running Broadway musical.
Hepburn plays the title character, named so for her success as a journalist. Tracy plays her colleague at a New York City newspaper, and the two start off with an intense dislike of each other before inevitably falling in love.
Woman of the Year scored an Academy Award for Best Original Screenplay, which was fully deserved when you didn’t get many movies in the 1940s focused on a successful woman outshining her husband in a professional capacity, putting their marriage at risk in the process.
28. It Happened One Night (1934)
Director Frank Capra, his regular writing collaborator Robert Riskin and star Clark Gable were responsible for countless classics, so it wasn’t any surprise that It Happened One Night turned out as good as it did.
A spoiled heiress marries a pilot that’s only after her money, causing her wealthy father to steal her away on a yacht in an effort to half the union annulled, only Gable’s reporter to fall in love with the young woman he initially only had his eyes on to secure an exclusive story.
One of the most influential rom-coms ever made, the most famous moments from It Happened One Night have been parodied and referenced in countless movies over the last nine decades.
27. Pretty In Pink (1986)
John Hughes knew exactly how to cater to his target audience, and cult classic Pretty in Pink very much follows the typical Brat Pack formula right down to a tee.
Teen icon Molly Ringwald stars as a high school outcast that starts dating one of the popular kids, which causes plenty of tension in her personal and social lives, not least from her best friend.
Jon Cryer plays the quirky pal who harbors a secret affection for the heroine, and while Pretty in Pink hardly breaks new ground from a narrative point of view, writer Hughes and his cast make everything grounded and relatable no matter how many times we’ve seen the scenario play out in the past.
26. Bridget Jones’ Diary (2001)
Sharon Maguire’s adaptation of the Helen Fielding novel took the world by storm, bringing in over $280 million at the box office and turning the title character into a cultural icon for women everywhere.
It also saw Renee Zellweger land the first Academy Award nomination of her career, with the actress balancing the comic beats and the emotional moments to perfection as she finds herself caught between two handsome, charming and very English men.
Bridget Jones Diary’ is technically little more than a plot device as well as a title, but as both a broad metaphor for taking control of your own destiny and a charming studio rom-com it certainly works, and then some.
25. There’s Something About Mary (1998)
The Farrelly brothers may have retained plenty of their signature gross-out style, but There’s Something About Mary also packs in plenty of heart in among the lewd, rude and crude humor.
Cameron Diaz scored a Golden Globe nod for her performance, while the movie itself was nominated for Best Picture in the Comedy or Musical category, both of which were fully deserved.
The leading lady and opposite number Ben Stiller ground the central romance even as the scenarios become increasingly outlandish, and it still holds up as easy viewing when you’re in the mood for a rom-com that balances laughs and romance in equal measure.
24. Pillow Talk (1959)
Golden Age icons Rock Hudson and Doris Day co-starred in several great films together, but Michael Gordon’s all-time great rom-com stands tall as their finest collaboration by far.
A shared telephone line between Hudson’s songwriter and Day’s interior designer sees them at loggerheads, before they find themselves occupying two thirds of a love triangle with Tony Randall’s mutual acquaintance.
Pillow Talk was a major box office success that went on to secure five Academy Award nominations, and in an era where star-powered romantic comedies were ten a penny, the natural chemistry between the leading duo made it easily stand out among a crowded pack.r, sparks fly.
23. The Big Sick (2017)
Husband and wife team Kumail Nanjiani and Emily V. Gordon used the origins of their own romance to craft a crowd-pleasing semi-autobiographical comedy that tackled big themes with plenty of panache.
The Academy Award nominated screenplay played off culture clashes, the difficulties faced by any embryonic relationship, and even threw tragedy and illness into the mix, all based on things Nanjiani and Gordon had experienced themselves.
It very much follows the rom-com template to a tee, but some heartwarming performances and big laughs ensured The Big Sick almost instantly went down in the history books as a modern classic of the genre.
22. Punch-Drunk Love (2002)
The idea of Paul Thomas Anderson and Adam Sandler teaming up for a romantic comedy was enough to pique the curiosity of many viewers, and Punch-Drunk Love ended up delivering the goods.
The leading man gives a career-best performance as a timid business owner under constantly under the thump of his seven sisters, but a passionate love affair sees him come out of his shell.
Inevitably, there are obstacles and issues along the way, mostly caused by an extortionist, but as unconventional as the finished product turned out to be, and there are few entries in the genre that stand out quite as much as the singularly unique Punch-Drunk Love.
21. Working Girl (1998)
An all-star assembly of talent on either side of the camera saw Working Girl’s corporate Cinderella story play incredibly well with both critics and audiences.
Carly Simon’s ‘Let the River Run’ scooped the Academy Award for Best Original Song, while stars Melanie Griffith, Sigourney Weaver and Joan Cusack were all nominated for their performances, along with further recognition in the Best Picture and Best Director categories.
Not a lot of rom-coms double as prestige awards-baiting dramas, but such a tightly-plotted and expertly crafted movie deserved all of the accolades that came its way.
20. Four Weddings and a Funeral (1994)
The first collaboration between writer Richard Curtis and star Hugh Grant remains still holds a special place in the hearts of many audiences, even a quarter of a century after Four Weddings and a Funeral’s signature moments became embedded in pop culture and ripe for parody.
Grant’s foppish charm turned him into a star in the space of 117 minutes, as he fully invests in the idea of fate after spending one night with Andie MacDowell before their paths continue to cross.
A Best Picture nominee and a box office phenomenon, Four Weddings and a Funeral turned the rom-com on its head, and a slew of thinly-veiled imitators saturated the marketplace in almost no time at all, but none of them managed to do it better.
19. You’ve Got Mail (1998)
Tom Hanks and Meg Ryan had already proven that they generated enough electricity to power an entire city, so no matter how dated You’ve Got Mail might be today, it still packs an emotional punch.
The setup is straight out of the rom-com playbook as Ryan’s independent bookseller and Hanks’ owner of a corporate franchise obliviously strike up an online romance despite their frosty interactions in the real world.
Hanks can do the loveable everyman in his sleep, but rom-com royalty Nora Ephron doesn’t shy away from the sentimentality, and if anything uses it to enhance the heightened romantic reality the movie creates for her characters.
18. Palm Springs (2020)
Palm Springs was released exclusively onto Hulu last summer, and as a result a lot of people have been sleeping on what was one of last year’s best movies in any genre, and an instant rom-com classic.
The genre is hardly known for incorporating elements of sci-fi, but the time loop premise results in comedy gold as Andy Samberg ropes Crisitn Milioti into his struggles of reliving the same day over and over again.
The wedding scenario is a fresh spin on the concept, and the always-welcome J.K. Simmons steals every scene he’s in as another unwitting participant, but the burgeoning relationship between the two hugely compatible leads always remains at the forefront of the narrative, much to Palm Springs’ benefit.
17. Pretty Woman (1990)
Some of Pretty Woman’s story points haven’t aged particularly well and it would never make it past the idea stage in 2021, but it remains a seminal entry into the pantheon of classic rom-coms.
It launched Julia Roberts to the top of the Hollywood A-list and she still hasn’t come down over 30 years later, while it even reigned as the highest-grossing R-rated movie ever made for a spell until Terminator 2: Judgement Day came along.
‘Cinderella, except with a prostitute’ doesn’t sound like a light-hearted romp, but the cast have charisma to spare and the glossy Hollywood sheen brightens up a tale that could have turned out very differently in lesser or more cynical hands.
16. Clueless (1995)
A recurring theme throughout this list is that classic literary stories being reinvented and updated as modern day rom-coms has always been a recipe for success, and few did it better than Clueless.
The high school spin on Jane Austen’s Emma still boasts an incredibly loyal and dedicated fanbase to this day, as new generations continue to fall in love with the endlessly quotable and razor-sharp dialogue, brought to life by a cast all on top form.
Clueless went on to launch an entire multimedia empire that included a spinoff show, a stage adaptation, a novel series and comic books, but the feature film is still the only thing that matters.
15. Say Anything… (1989)
Cameron Crowe’s directorial debut marked him out as a rising talent well worth keeping an eye on, as the young filmmaker made it abundantly clear he had his finger on the pulse of youth culture.
The story of high school romance is as timeless and overused as any plotline across any genre, btu John Cusack sells the whole thing with an earnest and charismatic charm that freshens up the tired formula to no end.
The iconic boombox scene alone is enough to burn Say Anything… into the public consciousness, but everyone involved is firing on all cylinders to craft a Gen-X classic that still holds up today.
14. His Girl Friday (1940)
Howard Hawks turned out to be a master of almost every type of movie he lent his impeccable talents to, so it wasn’t surprising that he took to screwball romance like a duck to water.
Cary Grant’s effortless charm dominated the screen, as his New York newspaper editor discovers his ex-wife has become engaged to a new beau. After trying to sabotage her newfound domestic bliss, before they get caught up in a murder investigation.
One of the most influential comedies of the Golden Age, His Girl Friday is light, breezy and snappy, not to mention an engaging mystery and glamorous star-powered comedy all wrapped up in a romance where the dynamics of power are constantly shifting.
13. Bringing Up Baby (1938)
Another classic screwball from director Howard Hawks and star Cary Grant, the suave leading man finds himself up against one of his most formidable big screen opponents in fellow legend Katherine Hepburn.
Grant’s paleontologist is pulling out all of the stops to ensure his museum collects a hefty donation from a wealthy benefactor, but one day before his wedding, he meets Hepburn’s free spirit in a role written specifically for the actress.
Naturally, there’s plenty of mishaps and misadventures along the way, and quite how Bringing Up Baby managed to bomb at the box office remains a mystery given the legacy that it’s left behind.
12. Broadcast News (1987)
A satire of the entertainment industry doesn’t sound like the territory from which a classic romantic comedy would spring, but James L. Brooks is no stranger to tugging at the heartstrings and utilizing a talented cast to their fullest potential.
Brooks’ next film after Terms of Endearment, Broadcast News sees Holly Hunter’s television producer unable to stop herself from being attracted to the news anchor that’s her polar opposite in almost every way.
Her best friend and fellow reporter also harbors a secret affection for her, which complicates matters even further. An insight into the inner workings of the industry that still doubles as a romance at heart, Broadcast News spins many plates but none of them fall, with the result being an awards season favorite that doubles as one of the best movies ever set behind the scenes of TV.
11. Moonstruck (1987)
Cher may have stolen the majority of the headlines for her Academy Award winning performance in the lead role, but Moonstruck is far from just a one-woman show, with the rom-com also nabbing trophies for Best Supporting Actress and Best Original Screenplay.
Cher’s widow accepts a marriage proposal, only to end up falling for her man’s younger brother instead, played by a fresh-faced but still charismatically eccentric Nicolas Cage.
That’s far from the only familial issue that Moonstruck deals with, and it manages to hark back to the glory days of screwball while still succeeding on its own merits as a biting relationship drama.
10. Groundhog Day (1993)
The old saying goes that troubled production often result in the best movies, and that certainly appears to be the case with Groundhog Day, which has become appointment viewing for millions of fans on an annual basis.
Relations between Bill Murray and his director, not to mention Ghostbuster’s co-star, Harold Ramis became so fraught that they didn’t speak to each other again for close to two decades after filming wrapped.
The end result falls somewhere between the rom-com Ramis wanted to make and Murray’s preferred vision for a more cynical and contemplative drama, but Groundhog Day remains an undisputed classic whichever way you want to look at it.
9. Breakfast at Tiffany’s (1961)
Obviously, Mickey Rooney’s portrayal of Mr. Yunioshi is flat-out racist and doesn’t paint the movie in a great light when viewed through a modern lens, but that still doesn’t detract from Breakfast at Tiffany’s status as a titan of the romantic comedy genre.
The feature film adaptation of Truman Capote’s novel follows a young New York society girl who falls for a struggling writer in one of the most iconic films of the 1960s in any genre.
Hepburn’s Holly Golightly became a cinematic icon as well as a stylistic one, with the actress delivering one of her best ever performances in what she described as her most challenging role, given that she was notoriously shy and going for broke as the extroverted heroine.
8. The Princess Bride (1987)
The Princess Bride is almost the living embodiment of a cult classic, and if anything Rob Reiner’s fantasy romance only gets more and more popular with each passing generation that discovers its charms.
A straightforward tale of true love wearing the coats of at least half a dozen genres, Rob Reiner’s postmodern classic is part swashbuckling tale of adventures, part damsel in distress fairy tale but drenched heat to toe in quotable dialogue, memorable characters and no shortage of wit.
There’s been talk of a remake swirling for well over a decade now, but fans would no doubt unanimously reject it on the grounds that there’s only one Princess Bride, and that’s how it should stay.
7. Annie Hall (1977)
Annie Hall wasn’t Woody Allen’s first feature by any means, but it did firmly establish the template the prolific filmmaker would continue to work from ever since, and still does up to this day.
Allen wrote the title role specifically for Diane Keaton, and she rewarded his confidence with an Academy Award winning performance, while the movie itself also picked up gongs for Best Picture, Best Director and Best Original Screenplay.
The tone and style of Annie Hall became hugely influential in American independent cinema over the next decade, but nobody hit the sweet spot between heartfelt romance and downtrodden self-awareness better than Allen did in what’s arguably his best ever movie.
6. The Philadelphia Story (1940)
Cary Grant, Katherine Hepburn and James Stewart are three of the greatest onscreen talents to have ever lived, so fireworks were the bare minimum to be expected when they starred together in a movie.
Not only that, but The Philadelphia Story was produced by the legendary Joseph L. Mankiewicz and directed by Gone with the Wind’s George Cukor, so it isn’t surprising in the slightest that just a star-studded array of talent produced one of the best rom-coms ever made.
Hepburn’s socialite has recently split from her husband, played by Grant on typically charismatic form, and is set to remarry before she crosses paths with both her ex and Stewart’s reporter, throwing her love life into chaos in one of the Golden Age’s brightest comedies.
5. Sleepless in Seattle (1993)
Meg Ryan and Nora Ephron has already proven their rom-com chops four years previously in When Harry Met Sally…, but throwing Tom Hanks into the mix turned out to be a masterstroke.
Hanks’ widower moves to Seattle with his son, who calls into a radio show trying to set his old man up with a new wife, and Ryan’s engaged reporter falls for his emotional story despite being engaged herself.
One letter later, and the stage is set for a rom-com that generated an incredible amount of pathos for the relationship between two leads who spent very little screentime together, but you’re always rooting for them nonetheless.
4. Roman Holiday (1953)
Audrey Hepburn’s first leading role in a Hollywood production saw her rocket to the top of the A-list and win the Academy Award for Best Actress, which isn’t a bad way to introduce yourself.
The actress’ European princess takes a night off royal duties in Rome, only to fall asleep on a park bench and be discovered by Gregory Peck’s American reporter. Once he discovers her lineage, he bets on an exclusive interview, before the inevitable romance kicks in.
Roman Holiday might come close to unabashed slapstick territory with a reliance on easy gags and broad humor, but the sheer star wattage of the leads an intelligent screenplay creates a sense or warmth and tenderness that you can almost feel coming out of the screen.
3. Some Like It Hot (1959)
Two longtime friends witness a Mafia hit and have to flee for their lives in Billy Wilder’s stone cold classic, which boasts a trio of all-time great performances by Tony Curtis, Jack Lemmon and Marilyn Monroe.
Disguising themselves as women, the duo join a jazz group and head to Florida, but as always, plenty of hijinks and shenanigans ensue during their journey, not least of all the mobsters still hot on their tail.
One of the first ever movies selected for preservation in the National Film Registry, Some Like It Hot is an ode to the Golden Age of Hollywood where a lightness of touch and neverending sense of fun permeated all of the biggest star vehicles of the era, but few boasted more in the way of entertainment value than this near-perfect farce.
2. The Apartment (1960)
Billy Wilder again, once more reaffirming his reputation as one of Hollywood’s greatest ever filmmakers by once again upending the conventions of the rom-com in classic fashion.
Jack Lemmon’s insurance worker lends his apartment to his bosses for their extramarital needs, only to find himself disappointed when his boss’ lover turns out to be the woman he’s got the hots for himself.
Forced to choose between the girl he wants and the job he’s been promised, Wilder handles the comedy just as well as the drama with one of the greatest movies ever made in any genre, one that took the box office by storm and won deserved Academy Awards for Best Picture, Director and Screenplay.
1. When Harry Met Sally… (1989)
Rob Reiner may have been the man behind the camera, but Nora Ephron’s screenplay deserves just as much credit for turning When Harry Met Sally… into an instant classic, taking her own career to the next level in the process.
An argument between college buddies over whether or not men and women can be friends without romance getting in the way yield repercussions a decade later when the two title characters reconnect.
When Harry Met Sally… revolutionized the rom-com and brought it kicking and screaming into the modern era by reinventing the tropes for more savvy audiences who wanted more than just beautiful people journeying from Point A to B in their relationship, and in those terms, no other film in the genre has ever done it better.