A Complete List Of The Best Romantic Comedies Ever

callmesyedfarman@gmail.com July 22, 2025 0

The Princess Bride

1987’s The Princess Bride follows the story of a farmhand, Westley, who sets out to save his true love Princess Buttercup from the vile Prince Humperdinck. Along the way, Westley meets plenty of dubious characters who join in on the quest and help him retrieve the princess. The movie itself is based on a novel of the same name by William Goldman and faithfully follows its metafictional narrative style. Although The Princess Bride enjoyed only moderate success upon its release, it soon became a classic cult movie because of its off-kilter humor, a fresh take on romance, and, of course, quotability.

10 Things I Hate About You

A modernization of Shakespeare’s late-16th-century comedy The Taming Of The Shrew, 10 Things I Hate About You blessed us with breakthrough roles for Heath Ledger and Joseph Gordon-Levitt. Together with Julia Stiles, it makes up for a very naturally-charming cast that elevates this movie to new heights. Centered, of course, around a high school setting, this movie’s full of teenage drama and love.

Clueless

There are many cases when a book-based movie turns sour, but Clueless is a stellar example of how such a movie should look and feel, I daresay. Loosely based on Jane Austen’s 1815 novel Emma, Clueless is considered one of the greatest romantic comedies ever made. The film’s success propelled young Alicia Silverstone’s career, had us all swooning for Paul Rudd, adopting the “As if!” and wishing for the dazzling outfits from Cher’s and Dionne’s closets.

The Proposal

The Proposal, a 2009 romantic comedy, centers around the story of a Canadian executive (Sandra Bullock) facing deportation from the U.S. because of her expired visa. And what’s the thing that makes the most sense in this scenario? Well, fake marriage, of course. So, she convinces her assistant (Ryan Reynolds) to play-act her fiance, and although he’s quite reluctant at first, you know how it all ends. And if The Proposal cannot boast of its original plot, then the fresh and undeniable chemistry between Bullock and Reynolds makes it all up.

Pretty Woman

This list just wouldn’t be complete without Pretty Woman. Though it is filled with slick humor and charisma supplied by Julia Roberts and Richard Gere, the critics weren’t too enthralled about Pretty Woman’s premise, and the reviews were quite average. Average or not, the movie resonated with audiences and saw the highest ticket sales for a romantic comedy ever.

When Harry Met Sally

When Harry Met Sally is a 1989 romantic comedy directed by Rob Reiner and written by Nora Ephron, and once you see her iconic name in the credits, there’s no doubt the movie will be as sweet as honey. The same goes for When Harry Met Sally – here, Harry (Billy Crystal) and Sally (Meg Ryan) play a cat-and-mouse game through twelve years of chance encounters in New York City, but will they actually become a couple; you’ll have to see for yourself. However, When Harry Met Sally is not just some soapy romance, but also one of the greatest comedy movies of the time. Double the entertainment and double the fans!

Legally Blonde

There’s probably no other romantic comedy as iconic as Legally Blonde and all because of the charms of Reese Witherspoon as Elle Woods. Here’s a movie that shows us all the blonde girl stereotypes and triumphantly crushes them, all the while keeping a sunshine-y and witty atmosphere. And if you’ve missed Elle, Legally Blonde 3 is scheduled for a release this year!

How To Lose A Guy In 10 Days

Remember the days of pre-Rustin Cohle Matthew McConaughey? Well, how could one forget the most charming, charismatic romantic comedy lead ever? And where he truly shines in this kind of a role is in How To Lose A Guy In Ten Days when paired with Kate Hudson. The story of this 2003 comedy is quite an original one – a journalist (Kate Hudson) is given a task to write a ‘How To’ column for a magazine, and her topic is that of the movie’s title. The guy in question is an advertising executive Ben, whom she initially charms and then tries to ward off with all the classic tricks in her book. Do we need to tell you how it all ends?

You’ve Got Mail

1998’s You’ve Got Mail is the third time we get to see Tom Hanks and Meg Ryan paired in a romantic comedy and the second when it’s written by Nora Ephron. Here the story follows an online romance between Joe Fox (Tom Hanks) and Kathleen Kelly (Meg Ryan), who are unaware of each other’s identities and the fact that they are real-life business rivals. Will love prevail against the ruthless world of business? I guess you know the answer, but You’ve Got Mail is still so very worthy of watching for its swooning romance, amazing on-screen chemistry, and relatable comedic situations.

#10

While You Were Sleeping

While You Were Sleeping is a 1995 romantic comedy starring Sandra Bullock and Bill Pullman. And where else do you get to see a Chicago Transit Authority token collector suddenly entangled in a romantic story if not in this heartwarming, beautifully made movie? A fare collector, Lucy, is secretly in love with one of the commuters whose life she so bravely saves from muggers. And here’s where the miscommunication starts, and Lucy is deemed his fiancee, despite having never even conversed with him. Although the movie follows some well-known tropes, they are all very skillfully arranged, and Sandra Bullock’s performance is worth the praise of the highest class.

#11

Love Actually

Love Actually is a 2003 Christmas-themed romantic comedy starring predominantly British actors. It is set five weeks before Christmas and each week coming to Christmas, we get to meet different pairs and see how they are experiencing love. All of their stories are linked in one way or another, and it is truly fun to try and decipher all of the connections—a beautiful, heartwarming, and most importantly, Christmassy romance that will swoop you away.

#12

Sweet Home Alabama

Sweet Home Alabama, a 2002 romantic comedy, follows the story of a New York fashion designer Melanie (Reese Witherspoon) and her estranged husband, Jake (Josh Lucas). Hailing from the South, Melanie hides her roots and the fact that she is still married to Jake fiercely as it is so unfitting with her New York persona. But, as we all know, the fake facade glimmers into oblivion when true feelings are discovered, and so too in Sweet Home Alabama. This flick is a truly beautiful fantasy elevated by Reese’s charms that will always keep its title as a classic romantic comedy.

#13

Sleepless In Seattle

Sleepless In Seattle, a 1993 Nora Ephron flick, is a classic will-they-won’t-they story, even if the main characters spend most of the movie separately. It’s a story of a single father’s (Tom Hanks) and a reporter’s (Meg Ryan) roads to true love that they, incidentally, find in each other. And, although the critics weren’t too excited about the plot, they spared no praises for Sleepless In Seattle’s warmth, chemistry, and innocence.

#14

Overboard

2018’s Overboard is a remake of the original 1987 romantic comedy with one catch, and it’s reversing the lead character role. And if you’d ask us, it truly works! Here we meet Kate Sullivan (Anna Faris), a struggling, middle-class single mother who successfully convinces a rich playboy with amnesia (Eugenio Derbez) that they are married. Needless to say, they do fall in love with each other, and there’s a gloriously sweet happy ending. Some critics scolded the director for churning out yet another remake, but such criticism fades entirely compared to Anna Faris’ superb comedic performance.

#15

My Big Fat Greek Wedding

My Big Fat Greek Wedding, a 2002 romantic comedy, proved to be one of the greatest sleeper hits of the decade, becoming one of the highest-grossing romantic movies ever, despite never reaching the number one position in the box office. The story is simple yet heartwarming, proving that love knows no boundaries and that family, however erratic and loud, is always there to support you. Fotoula and Ian’s story will not disappoint you and leave you with that warm feeling after it has ended.

#16

The Princess Diaries

How do you amp up a regular Ugly Duckling story? Why, by making said duckling an heiress to a European kingdom! And that’s precisely what we get to see in The Princess Diaries – a regular, clumsy, and unkempt American teenager transforming into a beautiful princess, fit to rule a country. Besides having the most iconic makeover sequence (which Anne Hathaway later repeated in several other movies), The Princess Diaries also gave us love, enjoyable humor, and awesomely played characters.

#17

50 First Dates

If Adam Sandler seems an odd choice for a romantic comedy, let him disprove your prejudice by watching 50 First Dates, where he co-stars alongside Drew Barrymore. The story is simple – Sandler is a womanizing marine veteran who falls in love with an art teacher. Here’s the catch – the art teacher is suffering from a fictitious ‘Goldfield’s Syndrome’ that is very similar to short-term memory loss. Entertaining and loveable, this movie has proudly made its place on our list.

#18

The Wedding Singer

Surprisingly romantic, sweet, and beguiling, The Wedding Singer is consistently named one of the best Adam Sandler comedies. And you know what, we might just agree – everything’s better with a bit of romance and an awesome soundtrack in it. It’s also one of the few movies on our list that got a Broadway remake, and though it wasn’t a massive success, The Wedding Singer musical has become popular with community theaters and high schools.

#19

Crazy Stupid Love

Crazy Stupid Love, a 2011 romantic comedy, might have the most charming cast ever assembled, consisting of Steve Carrell, Ryan Gosling, Julianne Moore, Emma Stone, Marisa Tomei, and Kevin Bacon. The story it follows, one of a recently separated man in search of his manhood, is equally funny, charming, and heartwarming. And how could it not be with such actors lending their talents to making this original plot come to life? Even if you’re not really into the whole romantic comedy vibe, you’ll find this movie highly entertaining and just simply good.

#20

13 Going On 30

Though it’s a bit unclear if this movie was meant to be for the thirteen-year-olds who at heart are at the age of thirty or vice versa, 13 Going On 30 is a thoroughly entertaining, magically nostalgic romantic comedy. The movie’s protagonist Jenna, played by the charming Jennifer Garner, wakes up one morning at the age of thirty instead of thirteen and gets into a whole lot of funny misunderstandings figuring it out. Besides being quite a funny film, it also carries a strong and important message; though you’ll have to watch the movie to know what it is!

#21