Best Romantic Comedies.

20 Rom-Coms You Must Watch Before You Die

< 20 – 11

10. When Harry Met Sally… (1989)

This is Meg Ryan and Billy Crystal at their best. But let’s not forget the flawless screenplay by Nora Ephron, the master of rom-com writing (also for Sleepless In Seattle). Having already inspired countless movies since 1989, this particular film continued the romantic comedy tradition in Hollywood, paving the way for the 90’s rom-com outburst. We are not only talking about a good film here. We are actually talking about a landmark. Fake orgasm, please?

9. Groundhog Day (1993)

Up until 1993, Bill Murray was a funny person, writer and Saturday Night Live alumni. Groundhog Day made him a great actor. The brilliant script by Harold Ramis and Danny Rubin made a huge impact upon its theatrical release, while the film is regarded as both one of the greatest comedies, as well as one of the best fantasy movies ever made. The rest is history. The rest is history. The rest is history. The rest is history. The rest is history. The rest is history.

8. 500 Days Of Summer (2009)

What makes this film important is the chemistry between Joseph Gordon-Levitt and Zooey Deschanel. And actually, not in a romantic way. The storyline begins by telling you how it will end. It’s about a break-up accompanied by intellectual twists and witty punchlines. A story you never want it to end and when it does, you just cannot stop talking about it. If 500 Days Of Summer would have been released during the last couple of years, it could easily become the most shared film on social media.

7. Bridesmaids (2011)

Kristen Wiig is hilarious. So is Maya Rudolph. And Melissa McCarthy. And Rose Byrne and Ellie Kemper. This female-driven comedy made Wiig an A-list actress and an Oscar nominated writer, while it proved that women in Hollywood can be as funny, gross, fearless and box-office-friendly as men. Mary Elizabeth Williams of Salon called Bridesmaids the “first black president of female-driven comedies”. True that and God bless McCarthy for effortlessly delivering the “I’m glad he’s single, because i’m going to climb that like a tree” line.

6. The Apartment (1960)

Billy Wilder was a genius. You may hear that about a lot of people, but he actually was a genius. One of the most versatile filmmakers of the Hollywood Golden Age of cinema, he also was the first person to win Oscars as a producer, director, and screenwriter for the same film; The Apartment. This is the oldest piece of art on my list, but you need to watch it in order to realise that it’s not. Shirley MacLaine and Jack Lemmon are breathtaking, and as the film itself claims: “Movie-wise, there has never been anything like it – laugh-wise, love-wise, or otherwise-wise!”.

5. Shakespeare In Love (1998)

Yes, Gwyneth again. This is the most awarded production on the list, with 7 Oscars, 3 BAFTAs and 3 Golden Globes. Some people will agree that it’s one of the most overrated films in history. Let’s just state that I’m certainly NOT one of those people. Gwyneth’s charm and beauty, Judi Dench’s incomparable talent, Geoffrey Rush’s wittiness and John Madden’s sensitive and sweet approach in direction make Shakespeare In Love succeed on every level. The only drawback? Harvey Weinstein winning an Oscar as a producer.

4. Four Weddings And A Funeral (1994)

It’s the third Hugh Grant on my rom-com list (out of 4! Take another hint, lad…) and I can’t help but wonder: am I a big fun of his or is it just the genre? I have realised I’ve watched everything he’s done, so this writing procedure, apart from fun, has also served as a catharsis. LOL. Four Weddings And A Funeral is one of the best British films ever made and that’s more than a fact. Nominated for Best Picture and Best Original Screenplay at the Oscars, it’s one of these rare times that a romantic comedy project is regarded as one of the best films within a year. And yes, Hugh Grant is awesome in it.

3. Notting Hill (1999)

The fourth Hugh Grant film, indeed! You’ve probably guessed it though. Not including Notting Hill on a rom-com list is like not dressing up like Cher in a drag show; unacceptable. When you have a Richard Curtis script in your hands (Four Weddings And A Funeral, Love Actually, Bridget Jones’s Diary, About Time), as well as Hugh and Julia Roberts as lead actors in a 90’s project, it’s almost inevitable not to turn it into a big hit. In addition, we are talking about a killer soundtrack album, with songs and covers performed by Elvis Costello, Al Green, Shania Twain, Bill Withers and Ronan Keating. The only thing that’s missing is… I don’t know, Meryl Streep?

2. Amélie (2001)

Voilà, I’m getting emotional. Amélie is on the verge of being a poem, a board game, a painting, a bedtime story or even a utopic dream. She could be your best friend, your mom, your weird neighbour or your version of Tinker Bell. This film is nothing less than a modern masterpiece, while Audrey Tautou is nothing less than a revelation in it. If Amélie cannot make you smile the whole way through like a child, you should really re-evaluate yourself as a human being. De rien.

Honorable mentions:

Love, Simon (2018)

High Fidelity (2000)

Funny Face (1957)

Much Ado About Nothing (1993)

There’s Something About Mary (1998)

About Time (2013)

Legally Blonde (2001)

My Best Friend’s Wedding (1997)

How To Lose A Guy In 10 Days (2003)

Roman Holiday (1953)


1. Breakfast At Tiffany’s (1961)

Prior to Julia Roberts, Meg Ryan and Gwyneth Paltrow, there was Audrey Hepburn; the original rom-com queen. Henry Mancini’s music and George Axelrod’s  adaptation of Truman Capote’s 1958 novella made this film beautiful and smart, but it was Holly Golightly that made it historically significant and aesthetically perfect. Breakfast at Tiffany’s has to offer one of the most memorable opening scenes in film history, Audrey singing Moon River, 1960’s Manhattan at its best, the Little Black Dress by Givenchy, killer lines and some kind of eccentric urban wisdom. It’s the most romantic of the comedies and the funniest of the romances. It’s the perfect combination of sugar and spice. And it’s almost 60 years old. Oh well…

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author avatar
Elias Malassidis

Elias's tendency to storytelling could have been a hereditary thing, but his love for everything urban, for all things modern, and for the answer to the question 'why' all led him to his personal quest for self-fulfillment.

He has been a leading member of the team behind Birthday Wishes Expert, and has served as the chief editor on the website.

He is an avid traveller, a film director, and a recording artist under the moniker El Buho.

(Website | Spotify | Apple Music )