The Top 5 Greatest Romantic Comedies

Ash Walker • 11 Feb 2025 Features

Roses are red, violets are blue, have we got some movie recommendations for you!

Valentine’s Day is almost here! It’s the lovey-doviest time of the year, and there’s nothing guaranteed to give you the warm-and-fuzzies like settling down in front of a good romantic comedy.

Join us as we look back through the history of love and laughs on screen, and pick out the absolute best rom-coms ever made.

5. Groundhog Day (1998)

Credit: GROUNDHOG DAY - Official Trailer (Sony Pictures Entertainment, YouTube)

While it’s generally considered a classic, it’s easy to focus on the ‘comedy’ part of Groundhog Day, forgetting all about its ‘romantic’ side. But romantic it certainly is.

Curmudgeonly weatherman Phil Connors (Bill Murray at his most sardonic) is sent to the small town of Punxsutawney, PA, to cover the annual Groundhog Day festivities - a celebration in which the town elders turn to a prognosticating rodent to predict if winter will continue for another six weeks.

A real thing, by the way.

After something of a breakdown, Phil wakes to find that he must live Groundhog Day over and over again… forever. Unless, that is, he can somehow change his ways and find love with Andie MacDowell.

A wonderful film and one of the all-time Bill Murray performances. Deserves to be watched again and again. And again. And again. And again.

4. Notting Hill (1999)

Credit: Notting Hill Official Trailer #1 - (1999) HD (Movieclips, YouTube)

“I’m just a girl, standing in front of a boy, asking him to love her.”

The best of the Richard Curtis rom-coms - facing stiff competition from Four Weddings and a Funeral, Love, Actually and About Time - Notting Hill just about edges it with a killer hook and a pair of winning performances from genre mainstays Hugh Grant and Julia Roberts.

The film follows the blossoming romance between a London bookshop owner (Grant) and the superstar American actress who wanders into his store one day (Roberts). Will their love survive, or will it be squashed by the challenges of fame and public scrutiny?

Of course they end up together! This is a romantic comedy, after all…

If nothing else, watch it for Rhys Ifans’ absolutely chaotic performance as scummy Welsh flatmate Spike.

3. 10 Things I Hate About You (1999)

Credit: 10 Things I Hate About You -Official Trailer #1 (1999) (Rotten Tomatoes Classic Trailers, YouTube)

Forget Nora Ephron - William Shakespeare is the OG rom-com maestro. Just take a look at 10 Things I Hate About You, adapted from the Bard’s Taming of the Shrew, which isn’t just one of the best high school movies ever made, but one of the best romantic comedies.

One of the funniest, too. Like many of the pantheon of ‘90s teen classics (see Clueless, etc.), this is absolutely jam-packed with snark and witty one-liners (“What is it, Asshole Day?”), not to mention the comedy inherent in Shakespeare’s premise.

New kid Cameron (Joseph Gordon-Levitt) immediately falls for the beautiful, popular Bianca Stratford (Larisa Oleynik). The only problem? Her overprotective dad won’t let her date until her antisocial older sister Kat (Julia Stiles) does.

So, in a classic case of Shakespearean scheming, Cameron hires bad boy Patrick Verona (Heath Ledger) to seduce her. And wouldn’t you know it, the mismatched pair end up falling madly in love.

2. The Wedding Singer (1998)

Credit: The Wedding Singer (1998) Trailer #1 (Rotten Tomatoes Classic Trailers, YouTube)

Whatever your feelings on Adam Sandler, nobody can deny the sheer poptastic power of The Wedding Singer.

Set in a brightly-coloured, nostalgic version of the mid-’80s, this is the story of Robbie Hart (Sandler), a successful wedding singer who longs for nothing more than to get married himself. Unfortunately his fiancee feels differently, and Robbie’s life falls apart when she stands him up at the altar.

Of course, before long he falls for waitress Julia (Drew Barrymore), who is in a problematic relationship of her own. The chemistry between Sandler and Barrymore is off the charts - chemistry they took advantage of twice more, in 50 First Dates and Blended.

Add in some genuinely hilarious jokes, an incredible jukebox soundtrack of ‘80s bangers and an incredible cameo from Billy Idol, and you’ve got one of the all-time great rom-coms. Plus, there’s a pair of genuinely brilliant original songs, performed by Sandler himself, in the hilariously angry ‘Somebody Kill Me’ and the beautifully heartfelt ‘Grow Old With You’.

Sweet, funny and endlessly romantic.

1. When Harry Met Sally (1989)

Credit: When Harry Met Sally (1989) - Official Trailer (HD) (Shout! Studios, YouTube)

An absolute masterpiece of a romantic comedy, from director Rob Reiner (The Princess Bride) and writer Nora Ephron (Sleepless in Seattle). This is the big one. The one that changed the game and set the tone for decades to come.

You can feel its DNA in pretty much every modern rom-com, from the meet-cute to the quirky sidekicks to the third act break-up, all the way through to the last-minute race to reconciliation - which might take place at a New Year’s party rather than an airport, but is no less classic for that.

Buoyed by a pair of brilliantly natural, charming lead performances in Billy Crystal (Harry) and Meg Ryan (Sally), you instantly know that these two characters are destined to be together - even if they don’t themselves - and you can’t help but root for them.

The movie’s endlessly quotable too. It doesn’t get much more iconic than the diner scene (“I’ll have what she’s having”) or that aforementioned New Year’s party (“When you realize you want to spend the rest of your life with someone, you want the rest of your life to start as soon as possible”)

But arguably the film’s masterstroke is its series of interviews with elderly couples, randomly peppered throughout, where seemingly ordinary people tell the story of how they got together, and how long they’ve been married.

These skits are all sweet and funny, but the whole thing pays off beautifully at the very end, when we get the final interview - Harry and Sally themselves, revealing that they have (so far) lived happily ever after.

Honourable Mentions

There are a lot of rom-coms out there - like, a lot - and not all of them are good, but there are a few undeniable gems that didn’t quite make our Top 5. Check them out if you need more love in your life.

Roman Holiday (1953) - A princess goes incognito for a day in Rome, alongside a charming reporter who secretly wants her story.
The Princess Bride (1987) - Fantasy comedy starring Cary Elwes, Robin Wright and… Andre The Giant!
Pretty Woman (1990) - My Fair Lady with a sex worker.
Sleepless in Seattle (1993) - Tom Hanks and Meg Ryan find each other through a talk radio show.
Four Weddings and a Funeral (1994) - Quintessential British rom-com with Hugh Grant and Andie MacDowell.
Before Sunrise (1995) - Two young people meet on a train and spend the night hanging out.
Bridget Jones’ Diary (2001) - A loose, modern day adaptation of Pride & Prejudice, starring Renée Zellweger, Colin Firth and Hugh Grant.
Hitch (2005) - Will Smith plays a relationship expert who’s bad at relationships.
(500) Days of Summer (2009) - Anti-rom-com about a relationship from beginning to a very definitive end.
The Proposal (2009) - An ambitious career woman enters into a marriage with her employee for a Green Card.
The Big Sick (2017) - A budding relationship is thrown a curveball when one of the couple becomes seriously ill. Based on a true story.