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The best rom-coms of all time

Here are the best rom-coms of all time, from the teen classics 10 Things I Hate About You and Clueless, to the Oscar-winning Moonstruck.

The best rom-coms: Alicia Silverstone in Clueless

What are the best rom-com movies? Beginning with the first staged comedies in Ancient Greece, romantic comedies have been delighting viewers for more than two millennia. However, books and plays aside, these movies are especially enjoyable, bringing funny one-liners and light-hearted depictions of true love to the big screen. They make us laugh, cry, and believe in corny meet-cutes, as well as happily-ever-afters.

But, let’s be honest, this cinematic sub-genre is overflowing with choices, and it’s easy to drown in the ocean of sentimental romance movies out there. Be it musicals, modern-day fairy tales, or black-and-white lovelorn classics – sometimes there are just too many fish in the sea to choose from. Being spoiled for choice, you may be left wondering which rom-com is truly your perfect match come movie night. Well, fear not, we’ve got you covered.

The Digital Fix has put its matchmaker hat on and rounded up a list of the very best rom-coms which everyone can enjoy – no matter your romantic preferences. From quality love stories, rewatchable scenes, or laugh-out-loud titles – we’ve banged out a list that even the most sceptical of our readers can’t help but fall in love with. So sit back, and crack out the wine and popcorn: here are the best rom-com movies of all time.

What are the best rom-coms of all time?

  • 10 Things I Hate About You
  • Moonstruck
  • It Happened One Night
  • When Harry Met Sally
  • How to Lose a Guy in 10 Days
  • The Princess Bride
  • Clueless
  • The Big Sick
  • Roman Holiday
  • Guys and Dolls
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10 Things I Hate About You (1999)

Who knew that adapting Shakespeare for a ’90s movie would look so good? Directed by Gil Junger and starring Julia Stiles and heartthrob Heath Ledger, 10 Things I Hate About You is a teen rom-com classic. A modernisation of William Shakespeare’s play The Taming of the Shrew, this high-school flick tells the story of bad boy Patrick (Ledger), who is paid to take out the unapproachable Kat (Stiles), while two other boys fight for her sister’s attention.

However, things get complicated once dear old Patrick starts catching real feelings, and Kat opens up about her past. 10 Things I Hate About You ticks all the romantic comedy boxes. It has a banging soundtrack, relatable teens hating the world and each other, and a cute love story born out of an elaborate scheme – what more could you want?

Best rom-coms: Cher and Nicolas Cage as Loretta and Ronny in Moonstruck

Moonstruck (1987)

If you didn’t think Moonstruck would make this list, well, in the wise words of Cher, “Snap out of it!” Heavy on the wit, and featuring Nicolas Cage and Cher giving two of the best performances in their careers, Moonstruck is a rom-com movie that every genre fan needs to see at least once.

An Italian-American widow named Loretta Castorini (Cher) gets engaged again, but soon falls in love with her fiancé’s hot-headed and handless (yes, you read right, handless) younger brother (Cage).

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The movie received six nominations at the 60th Academy Awards, winning three Oscars, including Best Actress, Best Supporting Actress, and Best Original Screenplay, for its clever and engaging story. If, for some reason, you aren’t sold on Moonstruck yet, seeing a young Cage in a sweaty tank top is also a sight to behold, trust us.

Best rom-coms: Clark Gable and Claudette Colbert as Peter and Ellie in It Happened One Night

It Happened One Night (1934)

We can’t talk about the best rom-coms without mentioning the cinematic original, It Happened One Night. Directed by Frank Capra and written by Robert Riskin, the ’30s flick centres around Heiress Ellie (Claudette Colbert), who escapes her controlling father to reunite with her new husband in New York.

While on the run, she meets the out-of-work reporter Peter (Clark Gable) – who agrees to help her in exchange for publishing her story. However, the two end up falling in love instead. Despite a slow start on its initial release, the film would later become a box-office hit and the first of the only three films (the other two being One Flew Over the Cuckoo’s Nest and The Silence of the Lambs) to win all five major Oscars.

It Happened One Night, at its heart, is screwball comedy at its finest, satirising the traditional love story formula by dismantling social class structures in relationships – making the film stand as revolutionary for its time.

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When Harry Met Sally (1989)

One of the funniest romantic comedies around, When Harry Met Sally, is iconic. Launching the career of rom-com juggernaut writer Nora Ephron (Sleepless in Seattle, You’ve Got Mail, and more), as well as solidifying Meg Ryan’s spot as the rom-com queen for years to come, When Harry Met Sally is an important flick for the entire sub-genre. The film revolves around the classic rom-com question that Hollywood would try desperately to replicate for decades: can straight men and women really ever be just friends?

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That’s right, kids, it’s a scenario we’ve seen played out countless times since the film hit theatres, but no other friends-to-lovers rom-com has ever managed to top When Harry Met Sally. From its charming script to stellar performances from Billy Crystal and Ryan to intercuts of the interviews with older couples telling hilarious stories as the movie unfolds, this rom-com is a masterful feel-good watch.

Best rom-coms: Kate Hudson and Matthew McConaughey as Andie and Benjamin in How to Lose a Guy in 10 Days

How to Lose a Guy in 10 Days (2003)

Misunderstandings and the ‘I won’t fall in love’ trope are rom-com’s bread and butter, so it makes sense that we’d include the 2003 comedy movie How to Lose a Guy in 10 Days on our list. Based on the short comic book of the same name by Michele Alexander and Jeannie Long, How to Lose a Guy in 10 Days is a hilarious love story that all begins with a mountain of lies.

The 2000s movie follows a reporter (Kate Hudson) who enters a relationship with advertising executive Benjamin (Matthew McConaughey) with plans to make him break up with her in 10 days for a new story she is writing.

However, there’s a problem –Benjamin has made a deal for a new campaign where he has to prove that he can make a woman fall in love with him. So a relationship stand-off from hell ensues. The movie is silly, delightfully predictable, and just plain fun.

Best rom-coms: Robin Wright and Carey Elwes as Buttercup and Westley in The Princess Bride

The Princess Bride (1987)

What romance fan doesn’t love the idea of prince charming? Well, how about a devilishly sarcastic farmer boy turned pirate? Adapted from William Goldman’s 1973 novel, The Princess Bride is hilarious, rewatchable, and puts a meta spin on the typical damsel in distress and fantasy movie tropes. In 2016 the film was also inducted into the National Film Registry, being recognised as “culturally, historically or aesthetically significant,” cementing its place on our list. (We view it as one of the best movies of all time, in fact.)

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Telling the story of separated lovers destined to struggle to be together, Buttercup and the farm boy Westley must embark on a dangerous journey through the kingdom of Florin. Battling kidnappers, giant rats, and crashing weddings, the heroes fight to save their lives, get their happy ending, and escape from Buttercup’s fiancé Prince Humperdinck.

As you can probably gather from everything we’ve just said, it is all very romantic, the humour in the script genuinely smart and funny, and the entire story is exciting as well as fantastical.

Best rom-coms: Stacey Dash and Alicia Silverstone as Dionne and Cher in Clueless

Clueless (1995)

Based on Jane Austen’s novel Emma, Clueless is one of the most quotable rom-coms you can find, as well as the most stylish. Gathering a cult following since its release in the ’90s, the film follows Bronson Alcott High’s rich and fabulous teen matchmaker Cher (Alicia Silverstone). Desperate to continue setting up couples for her school, Cher sets her sights on new girl Tai Frasier (Brittany Murphy) – but soon realises that you can’t plan or control love during her new matchmaking scheme.

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As a protagonist, Cher is delightfully romantic and delusional, making her super entertaining to watch as she is made to face the reality of relationships and her matchmaking abilities – sometimes, it just doesn’t work out. Also, Paul Rudd plays the snarky yet adorable love interest whose love/hate dynamic with Cher gives us one of the cutest relationship build-ups seen in a high school movie, period.

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The Big Sick (2017)

What happens when two cultures clash in a relationship? Written by real-life couple Emily V. Gordon and Kumail Nanjiani, The Big Sick, avoids all the clichés you’d come to expect from a film dealing with relationships struggling due to cultural differences while also giving us a heartfelt and hilarious romantic comedy in the process that ticks all the right boxes.

Kumail Nanjiani plays himself while Zoe Kazan plays the part of Emily in a love story about a Pakistani-American culture shock. The movie follows the typical rom-com beats until the second act, when Emily is struck with a serious illness, and Kumail must face anxiety, tear-jerking hospital trips, and anxious parents. Few flicks feel as authentic or bittersweet, will leave you laughing in stitches, and hit as hard as this modern masterpiece.

Best rom-coms: Audrey Hepburn and Gregory Peck as Princess Anne and Joe in Roman Holiday

Roman Holiday (1953)

No rom-com list would be complete without mentioning the actor Audrey Hepburn. So it makes sense that we’d pick the charming flick that saw her win the Oscar for Best Actress as our top choice, right? The film follows Princess Ann (Hepburn), who is wrapping up her royal European tour in Rome; however, the strict rules and life as a princess have begun to take a toll on the young gal.

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Deciding to run away from her royal duties, Ann meets Joe (Gregory Peck), an American interviewer who secretly humours her in order to get a sneaky exclusive. But in rom-com fashion, the two bond, and feelings begin to bloom.

While the love story is great, this film also feels enchanting as we witness Ann experience freedom for the first time in the beautiful city of Rome. Roman Holiday is smile-inducing. From its cinematography to the enduring lead performances, this movie will never fail to warm your heart.

Best rom-coms: Marlon Brando as Sky Masterson in Guys and Dolls

Guys and Dolls (1955)

After a romantic comedy that is a musical? How about one that also stars big Hollywood names like Frank Sinatra and Marlon Brando as its leading men? Well, look no further because the foot-tapping ’50 hit Guys and Dolls has got you covered.

Based on the 1950s Broadway musical of the same name, Guys and Dolls tells the story of a gambler (Sinatra) who bets another high roller named Sky (Brando) that he can’t convince a religious woman, Sarah (Gene Simmons), to go out with him.

Sky strikes a deal with Sarah – getting her to agree to a date in exchange for his help to recruit more people for her religious mission. However, as you can probably guess, the ‘bet’ turns into so much more. All in all, Guys and Dolls is a home run on the romantic comedy front. The writing is exciting and light-hearted, the production design feels grand, and the singing (Brando aside – sorry) is downright fantastic.

And there you have it! The best rom-coms of all time. Here is our guide to the best family movies if you are after more feel-good stories. Or if new releases are more of your thing, here are all the new movies coming out in 2023.