The Best Romantic Comedies Of All-Time

Meg Ryan and Billy Crystal in When Harry Met Sally
(Image credit: Castle Rock Entertainment)

What makes a good romantic comedy? Is it the style of humor? The location where it takes place? The soundtrack? Surely, most will agree that the chemistry between the love interests is crucial. In fact, based on our picks for the absolute best romantic comedies of all time, a lot of factors come into play when identifying what makes us laugh or swoon or even tear up a bit if the mood is right. So let’s get on to the list. Those of us at CinemaBlend with a passion for rom-coms got together and rated our picks for the absolute best romantic comedy movies of all time… 

John Cusack in High Fidelity

(Image credit: Buena Vista)

50. High Fidelity

When talking about meet-cutes, there are few movies that could make a list of rom-coms that are more sad sack than High Fidelity. But the Nick Hornby book-turned-film manages to be very funny, much of it due to the performance from John Cusack as Rob, whom one roots for despite his obvious poor understanding of the ladies in his life. The movie is carried along by an A+ soundtrack, a zany performance from Jack Black, and surprising turns from ‘90s icons Catherine Zeta Jones, Tim Robbins, Joan Cusack, Lisa Bonet and more. It’s a great movie to curl up with in the winter and an even better movie to throw on after a break up. Watch, this rundown will now sell five copies. 

Steve Carell and Ryan Gosling in Crazy Stupid Love

(Image credit: Warner Bros.)

49. Crazy Stupid Love

Crazy Stupid Love is surprising in the best way. It tells the story of Cal (Steve Carell), who is dealing with a divorce from his wife Emily (Julianne Moore), and his friend Jacob (Ryan Gosling) is teaching him to be a playboy while dealing with his own love life after Hannah (Emma Stone) rocks his world. 

From re-creating the Dirty Dancing lift to what might be one of the greatest plot twists ever, the laughs come at a mile a minute in this film, and it’s pure joy. Also, how could we forget, this movie brought Emma Stone and Ryan Gosling together for the first time, and for that, we’re eternally grateful. 

Adam Sandler and Drew Barrymore sitting around a fire.

(Image credit: Columbia Pictures)

48. 50 First Dates

Adam Sandler can and has made his share of rom coms over the years, but there’s something particularly magical about what happens when he and Drew Barrymore fall in love on screen. The 2004 Hawaii-set 50 First Dates is plenty goofy, as Sandler’s Henry learns that his crush, Barrymore’s Lucy, will – due to a brain injury from an accident in her past – forget him all over again every morning. The concept creates all sorts of setups for funny quips, but finds staying power in how it inspired a unique love story all about patience and acceptance.  Plus, you know a movie is iconic when it recontextualizes The Beach Boys’ “Wouldn’t It Be Nice” and The Wizard Of Oz’s “Somewhere Over the Rainbow” in a way that will have one never hearing them the same again, without recalling Henry and Lucy’s quirky love story anyway. 

Jennifer Garner in 13 Going on 30.

(Image credit: Sony Pictures)

47. 13 Going On 30

13 Going on 30 turns twenty in 2024, if you can believe it, and now, we’re cementing it as one of the best romantic comedies out there. The film follows a young teen who wishes to be “thirty, flirty and thriving,” only to wake up one morning to find her wish has come true. She’s thirty and living in New York City, working at a fashion magazine. 

While the romance in 13 Going on 30 takes a bit of a backseat in comparison to the life lessons Jenna is taught (like don’t try to change yourself for others), it’s still one that makes us smile. The 13 Going on 30 cast is great, and Jennifer Garner and Mark Ruffalo have chemistry that is tough to beat. 

Drew Barrymore and Michael Vartan on roller coaster in Never Been Kissed

(Image credit: Twentieth Century Fox)

46. Never Been Kissed

Never Been Kissed is an ode to the awkward high school nerds. The ones who may have been late-bloomers but eventually found their spotlight. Drew Barrymore is another queen of the romantic comedy world. She always delivers a charismatic performance and creates likable heroines. 

Her characters are never without flaws but that makes them more appealing. Barrymore’s Josie bumbles her way through high school (again) in a very funny but sweet way. Michael Vartan and Barrymore’s chemistry is really what makes the film such a great romantic comedy. The final moments of Never Been Kissed make you kick and twirl your hair with glee. 

Jason Segel and Mila Kunis staring in shock as they stand next to a hotel check-in desk.

(Image credit: Universal Pictures)

45. Forgetting Sarah Marshall

Forgetting Sarah Marshall is way more than its top-of-the-line embarrassing breakup scene where Jason Segel’s Peter, well, bares his peter because he’s so shocked by the end of his five-year romance with Sarah (Kristen Bell). Aside from hilarious performances from Segel, Bell, Mila Kunis, and a number of other funny people, the story of attempting to move past a relationship that wasn’t as perfect as you’d previously thought while unexpectedly falling for someone else when you really think you’re not ready is one lots of people can likely relate to. Laugh-out-loud funny and heartwarming is how we like our rom-coms, and this is an R-rated comedy that still delivers big time.

Molly Ringwald in Pretty in Pink

(Image credit: Paramount Pictures)

44. Pretty In Pink

Howard Deutch’s Pretty In Pink has one of the best movie soundtracks with songs like “Please Please Please Let Me Get What I Want” by The Smiths and the titular track by The Psychedelic Furs, but it’s the story at the center of this “Brat Pack” classic that makes it so charming. Written by John Hughes, the film follows Andie Walsh (Molly Ringwald) as she begins to venture outside of her social group after falling for Blane McDonnagh (Andrew McCarthy), a popular prep from her high school.

The clash of cultures, ideals, and social classes leads the high school senior on a remarkable journey where she sets out to find out who she really is and what she wants out of life.

Keira Knightley and Chiwetel Ejiofor in Love Actually

(Image credit: Universal Pictures)

43. Love Actually

Why settle for one love story when you can have ten? Love Actually explores a spectrum of different types of love through its loosely connected characters, and while there’s plenty of romance to be found, there’s also grief, anger and heartbreak. It’s no surprise that this has become a Christmas classic — and is one of the best movies of the 2000s — as legendary rom-com director Richard Curtis assembled an astonishing ensemble cast that includes Hugh Grant, Emma Thompson, Alan Rickman, Liam Neeson and Colin Firth, to name just a few. Not all of Love Actually’s stories resonate with every viewer, but with so much going on, everybody’s sure to find something to love.

Nick Robinson and Keiynan Lonsdale on a ferris wheel in Love, Simon

(Image credit: 20th Century Fox)

42. Love, Simon

Love, Simon was a massive deal when it was released because it was the first movie by a major Hollywood studio to focus on a gay teenage romance. Nick Robinson plays Simon, a high school senior who is coming to terms with his sexuality. Not yet ready to come out, Simon finds himself exchanging anonymous emails with a fellow gay classmate whom he begins to fall for. 

The movie includes a swooning romance with one of the best grand gestures at the end, but it also explores the nature of coming out and how complicated that can be, even though the people in Simon’s life are supportive. It’s safe to say there wouldn’t be as many LGBTQ+ romantic comedies if it wasn’t for this one. 

Renee Zellweger and Colin Firth in Bridget Jones's Diary

(Image credit: Universal Pictures)

41. Bridget Jones's Diary

This early-aughts retelling of one of literature’s greatest romantic comedies—Jane Austen’s Pride and Prejudice—gave us a plucky heroine for the ages in Ms. Jones, a thirtysomething London singleton played to perfection by Renée Zellweger. It’s rare when a rom-com performance gets acknowledgment from the Academy, but Zellweger’s turn as the clumsy, chain-smoking yet utterly charming lass earned her a much-deserved Oscar nomination. 

In the Sharon Maguire-directed comedy, our usually unlucky-in-love leading lady finds herself in the middle of a love triangle featuring two very eligible (and very British) bachelors: Hugh Grant’s rakish Daniel Cleaver and Colin Firth’s mysterious Mark Darcy. The latter has a leg up, though, because he likes Bridget just the way she is. And so do we.

Cooper Hoffman running with Alana Haim in Licorice Pizza

(Image credit: United Artists Releasing)

40. Licorice Pizza

PT Anderson’s Licorice Pizza gives us a romance we’re not sure if we should be rooting for. The age gap, life circumstances, morals and common sense should push Alana and Gary apart, but through waterbed schemes, acting dreams and his relentless determination, they’re repeatedly drawn together, despite her better instincts. It’s awkward and uncomfortable but also vibrant and full of life in a way that thoughtfully shows just how many similarities and differences there are between your teenage years and your twenties. Plus, acting newbies Cooper Hoffman (the son of Philip Seymour Hoffman) and Alana Haim are both fantastic, and the film features an absolutely unhinged supporting turn from Bradley Cooper that needs to be seen.

Henry Golding and Constance Wu in Crazy Rich Asians

(Image credit: Warner Bros.)

39. Crazy Rich Asians

Based on the novel of the same name and directed by Jon M. Chu, Crazy Rich Asians was a huge rom-com when it released in 2018, telling the story of a young woman who has to travel to Singapore to meet her fiance’s family – only to find out that they are incredibly rich. 

Crazy Rich Asians tells a story that aims to make you laugh but also make you swoon at the same time at the undeniable chemistry between Constance Wu and Henry Golding. Not only that, but you’ll be entranced by the wealth of this family – the wardrobe alone must have made up the entire budget of the film. However, you’ll stay for the sweet yet complex romance. 

Chris Pine and Anne Hathaway doing archery in Princess Diaries 2

(Image credit: Disney)

38. The Princess Diaries 2: Royal Engagement

The original Princess Diaries is delightful as a story about a teen who learns she’s a princess, but it’s the sequel that finds a spot on this particular list. The Princess Diaries 2: Royal Engagement sees Mia (Anne Hathaway), facing an arranged marriage due to a law that says she can’t take the throne without a husband beside her. Romantic sparks fly between Mia and Nicholas (Chris Pine), a man who’s also vying for the throne. Be it the chemistry between Hathaway and Pine, the fantastic cast – including Julie Andrews, Raven-Symoné, Hector Elizondo and more – Garry Marshall’s direction, the screenplay from Shonda Rhimes, or other talents involved, there’s a lot that works, and continues to hold up not only as a charming rom-com, but one for the whole family. 

Emma Stone in Easy A

(Image credit: Sony Pictures)

37. Easy A

While Emma Stone has appeared in several critically-acclaimed movies, like The Favourite, Poor Things or even La La Land (which earned her an Academy Award), one of the stand-out movies has to be Easy A

Telling the story of a teenager who decides to build up a promiscuous reputation to become popular instead of mocked, Easy A is as raunchy as a rom-com can get without diving into the “too much” category. It’s hilarious in its line delivery, comedic timing, and so much more, and there’s nothing quite like watching Emma Stone sing “Pocketful of Sunshine” again and again. 

Amy Schumer in Trainwreck

(Image credit: Universal Pictures)

36. Trainwreck

Eagerly embracing love and commitment isn’t everyone’s cup of tea. In fact, for some people,  it’s extremely difficult, even when presented with the perfect opportunity for romance with a truly great person. Such is the case for Amy Schumer’s character, a writer who reluctantly falls for Bill Hader’s sports doctor character in Judd Apatow’s Trainwreck

The movie is not at all your typical fairytale. Life and love in Trainwreck are messy, but the movie embraces that mess with surprisingly sweet moments and great chemistry from its leads. And this is all complimented with raunchy humor and a fantastic supporting cast, including John Cena, Brie Larson, Vanessa Bayer, LeBron James and Tilda Swinton, among others. 

Dermot Mulroney and Julia Roberts in My Best Friend's Wedding.

(Image credit: Sony Pictures)

35. My Best Friend's Wedding

My Best Friend’s Wedding should not work: Jules Potter’s (Julia Roberts) scheme to sabotage the nuptials of her lifelong friend—and longterm back-up plan—Michael O'Neal (Dermot Mulroney) and his bubbly fiancée Kimmy Wallace (Cameron Diaz) is not only ill-advised, it’s also downright cruel. She messes with Michael’s job, gets Kimmy’s family involved, and even ropes in her gay BFF (a pitch-perfect Rupert Everett) to pretend to be her lover. 

Jules is undoubtedly the villain of her own rom-com and yet the megawatt charm of ’90s-era Julia Roberts is blinding enough that you can’t help but sympathize with her character’s behavior. And she’s so matched by the equally dazzling Diaz that you don’t even mind when the “wrong” girl gets the boy in the end. 

zooey deschanel joseph gordon-levitt 500 days of summer

(Image credit: Fox Searchlight Pictures)

34. 500 Days Of Summer

500 Days of Summer in many ways is an anti-romantic comedy. It shows the delusions that sometimes overtake us when looking for the ideal mate. We want them to be perfect so badly that sometimes we don’t really see them. Nonetheless, 500 Days of Summer uses the genre to tell a story about a man who confuses his idea of love with actual love. 

Joseph Gordon-Levitt and Zooey Deschanel both make their characters layered and human. Their flaws make their love story feel honest and heartbreaking. Romantic comedies are often charming because of their whimsical nature, but movies like 500 Days of Summer show the messiness of love, especially when one refuses to leave the fantasy. 

John Cusack and Ione Skye in Say Anything

(Image credit: Twentieth Century Fox)

33. Say Anything

Cameron Crowe’s Say Anything is one of those movies most famous for a single image, in this case, the shot of John Cusack standing with a boombox held above his head. But what’s better than the image itself is the context and terrific story that leads up to that quintessential ‘80s moment. 

The movie follows the unlikely romance shared by the underachieving Lloyd Dobler (Cusack) and valedictorian Diane Court (Ione Skye) that blossoms the summer following their high school graduation. Though infatuated with one another, the couple faces a series of obstacles over the summer, including being from different social groups, an IRS investigation, and a looming prestigious fellowship in England that could break them apart.

Ben Affleck and Joey Lauren Adams sitting on swings in Chasing Amy.

(Image credit: Miramax)

32. Chasing Amy

Though it’s still one of Kevin Smith’s best movies, Chasing Amy, which stars Ben Affleck, Joey Lauren Adams, Jason Lee, and an appearance by Jay and Silent Bob, definitely feels like a ‘90s movie. What we mean is, some of the concepts, like a lesbian who falls deeply in love with a man, and the insecurity that a male character feels about a female character’s sexual history, seems pretty dated by today’s standard. That said, the emotions in this one are super raw, and by the end of it, you’re left with a very real feeling of what could have been. 

Jack Nicholson in Something's Gotta Give.

(Image credit: Warner Bros./Sony Pictures)

31. Something's Gotta Give

When it comes to Nancy Meyers’ best movies, Something’s Gotta Give has to be at or near the top. This 2003 romantic comedy puts Jack Nicholson and Diane Keaton up against one another as a wealthy womanizer and prolific playwright, respectively, who are forced to spend a few days together in the Hamptons. What starts as a clash of personalities and ideologies slowly turns into an unexpected romance as the pair learn they have more in common than originally thought.

The movie has all the staples of Meyers’ work with incredibly written characters, captivating dialogue, and a kitchen that belongs in a museum. Oh, and the supporting cast, which includes Keanu Reeves and Frances McDormand, adds a nice touch.

Lana Condor in All The Boys I Loved Before

(Image credit: Netflix)

30. To All The Boys I've Loved Before

To All The Boys I’ve Loved Before quite literally resurrected the teen romantic comedy genre and has gone on to be one the most hilarious romantic comedies with Asian-American leads. Based on the best-selling series of the same name, the first movie centers on Lara Jean, a high school student who fantasizes about love but has never been in a relationship. When her secret love letters to past crushes accidentally get mailed, she finds herself in a fake relationship with Peter, the school’s it boy. 

The original movie celebrated its 5th anniversary in 2023, and it still is one of the best according to fans because it shows Lara Jean and Peter falling for each other for real despite their fake arrangement. Their love is magical in the way all first love is, but it’s the chemistry between Lana Condor and Noah Centineo that really seals the deal.

Kumail Nanjiani and Zoe Kazan in The Big Sick

(Image credit: Amazon Studios)

29. The Big Sick

What happens when “in sickness and in health” pops up way earlier than you anticipated? That’s the crux of this 2017 rom-com, which stars Kumail Nanjiani in a story inspired by his own relationship with wife Emily V. Gordon. (The couple co-wrote the film’s script, which earned them an Oscar nomination.) Nanjiani plays an aspiring comedian whose new girlfriend Emily (played by Zoe Kazan) unexpectedly falls into a coma, leaving him to deal with the fallout and, even more worryingly, their families. 

Echoing another rom-com classic—Sandra Bullock’s While You Were Sleeping—Kumail falls for his future-in-laws (Holly Hunter and Ray Romano) as he waits for Emily to wake up, but also has to contend with his own Pakistani parents, who’ve been trying to set him up for an arranged marriage. From cultural differences to chronic illnesses, The Big Sick lovably manages to make seemingly unfunny subjects feel both romantic and comedic. 

Harold and Maude

(Image credit: Paramount Pictures)

28. Harold And Maude

Harold and Maude is a taboo romance that wins over the audience. On paper, a woman in her 70s (near 80s) falling in love with a man in his 20s almost seems criminal, but Hal Ashby — against all odds  — warms you to the pairing. The film is about a lot more than just the friendship turned romance between Harold and Maude, but the romance helps elevate some of the film’s messages. 

One of those messages is to live your life at maximum capacity. Maude doesn’t let her age or societal norms dictate how she lives. She then passes this wisdom on to Harold. Harold and Maude makes it clear that Maude will not be Harold’s only love, but she will likely be his greatest. To experience such a transformative love story is what most aspire to obtain. 

Sandra Bullock and Bill Pullman in While You Were Sleeping

(Image credit: Buena Vista Pictures)

27. While You Were Sleeping

If you want someone to give a relatable, endearing, and earnest romantic comedy performance, you call Sandra Bullock. She is truly one of the stars of the genre. While You Were Sleeping best demonstrates how Bullock can make you fall in love with her, no matter the crazy plot. Bill Pullman isn’t particularly known for his romantic comedy work, which is a shame. He’s undeniably attractive and bewitching in While You Were Sleeping. He oozes sexiness in the most subtle and appealing ways. 

Bullock and Pullman’s chemistry makes it a must-watch romantic comedy, but it's also a heartwarming tale about family. Bullock’s Lucy doesn’t just fall for Jack but the whole Callaghan clan. The themes of family and merriment make While You Were Sleeping a perfect holiday romance movie as well. 

Cristin Milioti and Andy Samberg on a pool in a floaty in Palm Springs

(Image credit: Hulu)

26. Palm Springs

There are probably more gleefully weird rom-coms than Palm Springs, but it’ll likely be difficult for many people to think of one. As one of our rare sci-fi romantic comedies, it sees Andy Samberg’s Nyles and Cristin Milioti’s Sarah as strangers who attend a wedding, then get stuck together in a time loop. We watch as he and Sarah experience the same day together, growing closer as they try to make sense of and have some wackadoo fun with their new, oddball existence.

The film makes the most of the time loop scenario in how it keeps pushing both characters past their breaking point so that they continue to grow through every insane repeat of the day, learn more about themselves, each other, the world at large, and what it really means to love and accept someone despite having witness the results of their dark thoughts and nonsensical behavior.

Annie punching through a heart in Bridesmaids.

(Image credit: Universal Pictures)

25. Bridesmaids

Rom-coms love to talk about love, but it’s usually the typical scenario of pursuing that great romance, with grand gestures and huge lessons. Paul Feig’s Bridesmaids isn’t that sort of movie, or at least isn’t completely focused on the entanglements of the awkward Annie (Kristen Wiig). 

If there was a true love story to follow in this movie, it’s that of Annie and her best friend/bride-to-be Lilian (Maya Rudolph). But besides that, everything you’d want out of a rom-com is present in the script co-written by Wiig and Annie Mumalo; right down to Melissa McCarthy’s Academy Award nominated comic relief. To appreciate Bridesmaids’ brilliance is to realize that this very R-rated comedy isn’t afraid to leave it all in the middle of the street in the name of a laugh. And after over a decade, director Paul Feig’s reasons for why it holds up have aged all the better.

Nicholas Galitzine as Prince Henry and Taylor Zakhar Perez as Alex Claremont-Diaz in Prime Video’s Red, White & Royal Blue

(Image credit: Amazon)

24. Red, White & Royal Blue

Based on the best-selling novel of the same name, Red, White & Royal Blue was one of the biggest new releases of 2023, at least in the streaming world. Though slight changes were made from the book, the movie follows the First Son of the United States Alex, and Prince Henry of Wales as they go from enemies to friends to lovers. Throughout the movie, the two bond over their alienating positions and their desire to make the world a better place. 

When Red, White, & Royal Blue was released, queer fans around the world found the movie super healing. As far as rom-coms, the movie has some pretty amazing quotes that are hard to forget. Above all else though, fans continue to stream it over and over again because Alex and Henry get a happily ever after at the end, which, unfortunately, is all too uncommon for queer love stories. 

Julia Roberts in Notting Hill

(Image credit: Universal Pictures)

23. Notting Hill

“I’m also just a girl, standing in front of a boy, asking him to love her” is without a doubt one of the most iconic and quotable lines in the history of romantic comedies and one of the reasons Notting Hill is such a joy to watch time and time again. Released in 1999, Roger Michell’s rom-com about a travel book store owner (played by Hugh Grant) and a Hollywood star (played by Julia Roberts) falling in love after a chance encounter on the street is nothing short of magical in every way imaginable.

Even after repeated viewings and despite knowing how things end, it’s impossible to not get caught up in the drama and the “will they or won’t they” aspect of the swirling romance at the center of Notting Hill.

Paul Rudd and Alicia Silverstone as Josh and Cher in Clueless

(Image credit: Paramount Pictures)

22. Clueless

Clueless is a brilliant take on the delightfully witty Emma. This modern version of Jane Austen’s popular novel delivers in performance, writing, and romance. It works both as a straightforward comedy and as a classic rom-com. Alicia Silverstone exemplifies on-screen charm as she makes Cher the clueless best friend that everyone wants. 

Over his many decades in Hollywood, Paul Rudd has become the man next door. The charismatic best friend or boyfriend. Clueless helped set Rudd on this trajectory. Silverstone and Rudd’s glorious chemistry makes it impossible to not root for Cher and Josh to end up together, despite the complexity of their enemies to lovers, former-sibling status. Clueless has rightfully earned its place as a comfort movie. A movie that film lovers (especially rom-com fans) can watch time and time again and still experience the same amount of wonder with each viewing. 

Drew Barrymore and Adam Sandler in The Wedding Singer

(Image credit: New Line Cinema)

21. The Wedding Singer

Whoever cast Adam Sandler and Drew Barrymore together in The Wedding Singer should have become a millionaire for that contribution to the film alone. After director Frank Coraci’s 1998 classic hit it big, there was no turning back. A new pair of rom-com legends was born, and repeated team ups were basically a done deal.

As Sandler’s jilted wedding entertainer slowly falls for Barrymore’s limitlessly sweet waitress, the sort of ‘90s comedy hijinx you’d expect out of a Happy Madison movie is definitely present. But at the same time, this picture marked a very important turning point for the SNL veteran. The Wedding Singer wasn’t just a good Adam Sandler comedy, it also gave him a chance to play a romantic lead. And if anyone had any doubts about whether this was a good idea or not, I dare you to watch the man sing “Grow Old With You” and not feel moved.

Audrey Hepburn in Breakfast at Tiffanys

(Image credit: Paramount Pictures)

20. Breakfast At Tiffany's

Audrey Hepburn’s best films include many from her time in Hollywood, but I can’t think of one that is more iconic than Breakfast at Tiffany’s. This film, nominated for five Academy Awards, follows a young woman trying to marry for money, but in the process, falls in love with a struggling writer. 

This film is the perfect example of how you never really know when love is going to hit. You can make plans, but when you meet the one, it doesn’t matter what social status they are – you just want to be with them. Featuring Hepburn in one of her best performances, Breakfast at Tiffany’s not only gave Hollywood one of the most epic love stories out there, but a brilliant move overall – and don’t even get us started on the fashion. Holly is a snazzy dresser.

Julia Roberts and Richard Gere in Pretty Woman

(Image credit: Touchstone Pictures)

19. Pretty Woman

Yes, I know that “Pretty Woman” is for sure stuck in your head right now, and truthfully, it’s the perfect place to be, because everything about Pretty Woman is great. Starring Julia Roberts in one of her best rom-com movies, Pretty Woman tells the story of a Hollywood escort who is hired by a wealthy man to be his date to several social functions over the course of a week. 

As they spend more time together, their business deal turns romantic, and it’s fair to say that in many ways, Pretty Woman was the blueprint for rom-coms for several years after. Featuring undeniable chemistry from Julia Roberts and Richard Gere, and a love story that will make any romantic swoon, Pretty Woman is one of those films that is a must-watch.

Jack Black and Kate Winslet in The Holiday

(Image credit: Sony Pictures Releasing)

18. The Holiday

Who hasn’t dreamed of just jumping on a plane and traveling to a foreign country to get away from it all? That’s the situation Iris (Kate Winslet in one of her best movies) and Amanda (Cameron Diaz) find themselves in in The Holiday, when heartbreak leads the strangers to agree to switch houses for two weeks. It’s funny how running away from their lives leads to them having to confront some hard truths about themselves, and it’s a delight to watch them do so — Iris with the help of a couple of new friends, including Jack Black’s Miles, and Amanda in developing feelings for Iris’ brother, single dad Graham (Jude Law). 

With Nancy Meyers’ direction and Hans Zimmer’s score, The Holiday has become a beloved holiday classic that will leave you inspired to find your gumption, because anything can happen when the Santa Anas blow.

Jennifer Lawrence and Bradley Cooper in Silver Linings Playbook

(Image credit: The Weinstein Company)

17. Silver Linings Playbook

Silver Linings Playbook follows Bradley Cooper’s Pat when he moves back in with his parents (Robert De Niro and Jacki Weaver) after spending time in a mental institution learning how to live with bipolar disorder. While staying there, and attempting to reconnect with his ex, he meets Jennifer Lawrence’s Tiffany, a widow, and they form a connection as they both reconcile with their lives. 

The two end up bonding, and they decide to compete in a dance competition. As they practice they grow closer, and so begins a chaotic and beautiful relationship. Jennifer Lawrence won her Oscar for Silver Linings Playbook, and for good reason. This gorgeous movie about acceptance and love is quick-witted and deeply moving as it tells the story of these two people finding themselves and supporting each other. 

Glen Powell and Zoey Deutch standing next to each other and holding drinks in a press image for Set It Up.

(Image credit: K C Bailey / Netflix)

16. Set It Up

Before Glen Powell was starring opposite Sydney Sweeney in Anyone but You, he was putting his rom-com acting skills to the test in the 2018 Netflix rom-com Set It Up. Zoey Deutch and Powell both play executive assistants whose lives revolve around making their demanding bosses happy. In order to get their own lives back, the two decide to set up their bosses and end up falling for each other along the way. 

There’s something magical about Set It Up and yet it’s one of the most underrated romantic comedies. Brimming with humor and romance, the movie is also a story about the professional and personal woes young twenty-somethings are currently facing in the world. While it’s been several years since its release, fans and the director are still hoping for a sequel that reunites this incredible cast. 

Tom Hanks in Sleepless in Seattle

(Image credit: TriStar Pictures)

15. Sleepless In Seattle

Maybe it’s the soundtrack. Maybe it’s the seemingly effortless charm of its entire cast. Maybe it’s the way the story makes us feel a mixture of warmth and humor and hope and a little bit of sadness as we follow the two leads on their destined paths toward one another. It’s probably a little bit of everything that makes Nora Ephron’s Sleepless in Seattle work so well, and it continues to hold up as one of the best romantic comedies of all time. It doesn’t hurt that Tom Hanks and Meg Ryan are undeniably likable as love interests in this tale of a grieving widower finding love again after tragedy, which continues to be a timeless classic. 

Hugh Grant in Four Weddings and a Funeral

(Image credit: Rank Film Distributors)

14. Four Weddings And A Funeral

Directed by Mike Newell and written by Richard Curtis, the 1994 romantic comedy Four Weddings and a Funeral is one of those romantic comedies that you just have to watch whenever it’s on TV, even if it’s three weddings in by that point. With a blend of side-splitting humor, great romance, and one of the most emotional eulogies you’ll see in any movie, not just comedies, this timeless classic captures the full human experience.

Hugh Grant, with his portrayal of the soon-to-be-married Charles who has second thoughts after meeting Andie MacDowell’s Carrie at a wedding, became a massive star and a staple of the romantic comedy genre upon its release. It’s hard to imagine Grant’s rom-coms like Notting Hill, Two Weeks Notice, and About A Boy happening without Four Weddings and a Funeral.

Tom Hanks and Meg Ryan in You've Got Mail.

(Image credit: Warner Bros.)

13. You've Got Mail

You’ve Got Mail marked the third time Meg Ryan and Tom Hanks worked together and it’s so iconic, that fans are still begging for the two to reunite for another rom-com. The movie follows Kathleen, a struggling children’s bookstore owner, who starts an anonymous online romance with a man. The man in question ends up being Joe Fox, the owner of the corporate bookstore that just moved in, jeopardizing her own shop. 

Not only do Ryan and Hanks have amazing chemistry in the movie, but it was written by the Queen of Rom-Coms, Nora Ephron, and her daughter Delia. It pulls out all the stops from witty banter in the form of an AOL chat room, heartfelt monologues and grand gestures, and of course, it’s the perfect example of the enemies-to-lovers trope.

Eddie Murphy in Coming to America

(Image credit: Paramount Pictures)

12. Coming To America

Sing it with me. “Sheeee’s yoooour queen to beee.” – John Landis’ Coming to America is one of, if not the best Eddie Murphy movies of all time. The story of a prince who is willing to give it all up to find true love, Coming to America is the quintessential ‘80s movie, which is buttressed by both Eddie Murphy and Arsenio Hall taking on multiple roles. From Prince Akeem, to Akeem’s friend, Semmi, to a Jewish barber, to of course, Sexual Chocolate lead singer, Randy Watson, the laughs come fast and furious in this romantic comedy. 

That said, the best thing about this movie is probably the courtship between Prince Akeem and Lisa McDowell, played by Shari Headley. In the end, Coming to America is a simple love story with a lot of laughs, but seriously. What else could you possibly want? 

Heath Ledger and Julia Stiles in 10 Things I Hate About You.

(Image credit: Buena Vista Pictures)

11. 10 Things I Hate About You

Inspired by Shakespeare’s Taming of the Shrew, 10 Things I Hate About You follows Kat (Julie Stiles) as her sister Bianca (Larisa Oleynik) attempts to set her up with a boy so her father will let her date. Enter Patrick, played brilliantly by Heath Ledger, the boy hired to win Kat over. So, begins a tale as old as the great playwright with all the early 2000s energy we absolutely adore.

This film expertly incorporates lines from Shakespeare’s play into a quintessential early ‘00s story filled with shenanigans that include a grand gesture involving the song “Can’t Take My Eyes Off You,” paintball and an iconic house party.Overall, 10 Things I Hate About You is incredibly intelligent and buckets of fun, plus its supporting cast is stacked with the likes of Allison Janney, Joseph Gordon-Levitt and David Krumholtz. And at the center of it is Kat and Patrick’s enemies-to-lovers relationship that bursts with chemistry.  

Punch-Drunk Love

(Image credit: Revolution Studios)

10. Punch-Drunk Love

Punch-Drunk Love is a lot of things, including a bit unusual and occasionally dark, but at its heart is a charming, humorous love story. If there’s one scene alone that secures its spot on this list, it’s the one set to Shelley Duvall’s “He Needs Me” from the Popeye soundtrack, when Barry (Adam Sandler) tracks Lena (Emily Watson) down in Hawaii, and their connection leads to romance, including some twisted and adorably bizarre pillow talk. Sure, he eventually has to confess that it’s not a coincidence that he’s there, but based on her reaction, she’s kind of ok with that.

As is the case with other Paul Thomas Anderson movies, there’s a mounting tension that builds in the movie. Barry Egan is almost constantly on the move in his bright blue suit, whether it’s dealing with work issues, his overbearing sisters or his occasional bouts of rage. And amidst an abandoned harmonium, being blackmailed by people running a phone sex hotline, and a plan that includes a whole lot of pudding, Barry forms a connection with Lena, who seems to see him the way no one else does. 

Jake Lacy and Jenny Slate in Obvious Child

(Image credit: A24)

9. Obvious Child

Jenny Slate has made a run of movies in which she plays very funny characters dealing with some tough subjects, and no I’m not talking about The Secret Life Of Pets, but rather projects like Landline or most memorably Obvious Child. It was in the latter that Slate’s character Donna had an unusual meet cute, followed by an unplanned pregnancy. Yes, this film is very much still a rom-com, and while a story of a new relationship that simultaneously tackles a tough subject like an abortion is not the normal fodder for a popcorn flick, Obvious Child stands out from the pack. 

Gillian Robespierre’s film is witty, thoughtful, sharply written, poignant and a narrative that many women can identify with and relate to, though is rarely normalized on the big screen. Just don’t go into this one expecting a bombastic “I Love You Baby” finale or a boombox-over-the-head ending, because it’s really not that kind of movie.

Jack Nicholson and Helen Hunt in As Good as It Gets

(Image credit: Sony Pictures Entertainment (SPE))

7 (Tied) As Good as it Gets

There are few characters more hilariously unlikeable than Melvin Udall (Jack Nicholson). The successful author is rude, bigoted and generally insensitive, but in As Good As It Gets, we see him take several turns for the better once he’s forced to help his recently assaulted neighbor (Greg Kinnear) as he becomes closer to Carol (Helen Hunt), the only waitress at his favorite restaurant who can stand/handle his horrid behavior. 

One of the many great things about this film is that it shows how two wildly different people can grow to respect, enjoy and even love each other and just how transformative that process can be, all while making us laugh and hope for Carol and Melvin’s Happily Ever After. Hunt and Nicholson have amazing tension that turns into a similar level of great romantic chemistry, and they sparkle so much in their respective roles that both nabbed Oscars for their work. If you haven’t seen this one at all, or in a while, the sweet moments and funny bits still hold up, and you should definitely add one of Jack Nicholson’s best movies to your queue soon.

Audrey Tautou in Amelie

(Image credit: Canal+)

7 (Tied) Amelie

For a lot of people, Amélie was not just the first French film they ever watched, it served as their introduction to the enchanting world of international cinema. Released in 2001, Jean-Pierre Jeunet’s charming, ambitious, and tremendously shot romantic comedy follows a young and beautiful yet incredibly lonely woman named Amélie Poulain (Audrey Tautou) as she explores life, love, and her own imagination in Paris. Putting her own happiness on the back burner, the introverted and quirky waitress spends her days trying to improve the lives of those around her so that at least someone can find love and meaning in the world.

What makes this Paris-set movie so beloved and popular nearly a quarter-century after its release is the way Jeunet takes elements of the traditional rom-com and adds a unique flair and sense of place to it, resulting in a unique and unforgettable experience. It also doesn’t hurt that Tautou is at her best when portraying the whimsical young woman with a bob haircut and hunger for adventure and wonder.

the stars of groundhog day

(Image credit: Columbia Pictures)

6. Groundhog Day

Sure, most people remember Harold Ramis’ Groundhog Day as that Bill Murray movie where he repeats the same day over and over again. And why wouldn’t they remember it as such since it’s probably Bill Murray’s funniest role.. However, what people sometimes tend to forget is that, at its heart, the movie is really a love story between a weatherman and his new producer. The weatherman in question is, of course, Bill Murray, and his new producer is played by Addie MacDowell. 

Day after day, Bill Murray’s character, Phil Connors, learns to at first revel in a life with no consequences, and then despise it. But, the one constant in his time loop is that MacDowell’s character, Rita Hanson, is usually at the center of just what he needs in his life. Throughout the film, Connors goes from being selfish, to learning to care about others, and then finally, to learning to love Rita Hanson. Yes, it’s a very silly movie, but it’s also a beautiful one as well. Plus, you’ll never hear the song, “I Got You Babe” the same way ever again. 

Westley holding Buttercup in The Princess Bride

(Image credit: 20th Century Fox)

5. The Princess Bride

The Princess Bride is a story for someone who doesn’t want to be told a story. As Peter Falk tries to cheer up on-screen grandson Fred Savage while he’s home sick from school, screenwriter William Goldman’s epic love story/adventure/comedy starts with the perfect foundation for a timeless story. Because when someone doesn’t want you to tell them a story, that’s when you pull out all the stops.

Director Rob Reiner’s movie is not only a perfect rom-com, but it also allows both sides of that coin to have moments of pure joy. It even goes above and beyond, giving us everything from Inigo Montoya (Mandy Patinkin) and his quest to avenge his father, to Fezzig (André the Giant) proving that not all massive men want to crush and destroy. What reigns supreme though is the romance between Princess Buttercup (Robin Wright) and Westley (Cary Elwes). You don’t question that romance for a second, and even viewers that aren’t into “the kissing parts” root for these young lovers every step of the way. By the time The Princess Bride concludes, we’re all like Fred Savage’s Grandson character: ready to hear it all over again, the same time tomorrow.

Rachel McAdams and Domhnall Gleeson in About Time.

(Image credit: Universal Pictures)

4. About Time

Time travel has long proven to be a stunning device to center great movies, and in 2013’s About Time, the concept was cleverly woven into the romantic comedy genre in an unforgettable way. Written and directed by Richard Curtis, who famously brought other movies on this list to life like Love Actually, Bridget Jones’s Diary and Notting Hill, About Time tells the story of Tim (Domhnall Gleeson), an unassuming gent who is unlucky in love, and finds out one day he has the ability to travel through time at his whim. 

When Tim meets Mary (Rachel McAdams), he’ll travel as much in time as he can to get things right with her. What starts as a fun rom-com with a science fiction bent, transpires into something more, as About Time explores how precious each moment we get with our loved ones truly is, whether it be with our significant others, family or friends. As the best rom-coms do, the 2013 movie not only is a great commentary on modern romance, with plenty of laughs weaved in, it also feels very honest, and is quite the tearjerker as well.

the stars of the american president

(Image credit: Sony Pictures Releasing)

3. The American President

You might not think a budding relationship between the President of the United States and an environmental lobbyist would make for one of the best romantic comedies of all time, but with the superb writing of Aaron Sorkin and endearing leads like Michael Douglas and Annette Bening, that’s exactly what The American President is. The meet-cute happens when President Andrew Shepherd walks into a meeting just as Sydney Ellen Wade makes a disparaging remark at his expense. Rather than get angry, the widower seems amused, and he ends up asking her out.

But it’s not so easy to be the president and someone’s boyfriend, especially during a re-election year, when fulfilling your duties to the country leads to your girlfriend getting fired. Bening’s scathing parting words — “You just lost my vote.” — are a thing of beauty, and oh what a world where sending a bill through to Congress can be a big romantic gesture. The combination of an idealized universe, one of the all-time best fictional presidents, and two ridiculously compatible characters spouting smart dialogue make this one rom-com you can enjoy over and over.

Woody Allen and Diane Keaton in Annie Hall

(Image credit: United Artists)

2. Annie Hall

Annie Hall isn’t your typical romantic comedy. Those looking for the conventional reassuring structure of meet-cute to courtship to adversity to marriage will be disappointed, but Annie Hall is among the top movies on this list because it has so much to say about relationships. How we choose our partners, how we argue with them, how we decide to move in or not move in with them, how we drift apart, how we break up how we sometimes see the best in lovers and sometimes see the worst— it’s all analyzed and shown here, sometimes in subtle ways that let the viewer draw their own conclusions and sometimes in very overt statements we get from the narration. 

Also, it’s hilarious, sometimes in the exact way you’d expect from Woody Allen, like in a scene where he’s invited over in the middle of the night to kill a particularly large spider– and sometimes in offbeat and unexpected ways like when we got a scene with subtitles of what each character is thinking. It’s all so sharp and clever that it would probably get old or feel preachy if it wasn’t held together by an all-time Diane Keaton performance. Her Oscar-winning turn here is somehow both relatable and full of eccentric and quirky charm and is the biggest single reason why this movie is so fondly remembered decades later.

Meg Ryan and Billy Crystal in When Harry Met Sally....

(Image credit: Columbia Pictures)

1. When Harry Met Sally...

Can two people, who are attracted to each other, really just stay friends? It’s a question many of us have had to ask ourselves time and time again, and the premise of Nora Ephron’s rom-com masterpiece, When Harry Met Sally. The 1989 movie tracks the lives of Meg Ryan’s Sally and Billy Crystal’s Harry through a decade of knowing each other, from first meeting on a ride-share in New York City to an all-time great movie moment with Harry's New Year’s Eve confession at the end, with both sincerity and tons of charm. 

From Ephron’s razor-sharp dialogue, Rob Reiner’s honest direction, the lush autumn New York setting and the magnetic chemistry between Crystal and Ryan, that will have one saying, “I’ll have what they’re having,” we’ll be talking about great rom-coms and When Harry Met Sally in the same sentence for eons to come. We want to spend the rest of our lives revisiting that one, and another rewatch cannot come soon enough. 

As evidenced by the variety of movies above, not all love stories take the easy road, but some of the best ones do it with a bit of humor and a lot of heart.