Best Rom Coms of All Time

Romantic comedies as a film genre is maybe the hardest one to get right. If you do, you create timeless classics that are watched as each generation moves on. Get it wrong though, it ends up buried on the actor’s IMDb page and maybe making an appearance on one of the many streaming services. All this to say, it doesn’t really get the appreciation it deserves much anymore; instead of recreating Shakespearean comedies in a modern format or exploring complex relationships in a light-hearted setting, it often now follows a repetitive formula to mild box office success. 

That doesn’t mean the genre doesn’t have its gems, and in this article, we’ll be listing the best rom coms of all time to watch this Valentine’s Day. We’re getting romantic over here at Nerdy Nook, and honestly, who doesn’t need a little light nowadays?

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When Harry Met Sally

Image by Columbia Pictures

Kicking off with perhaps one of the most well-known romantic comedies in the genre, When Harry Met Sally has had a lasting legacy a lot of films could only wish to have. One of Nora Ephron’s best films and one that launched her career, it has become a quintessential comfort movie with legendary scenes that even if you haven’t seen the movie itself, you would know at least one moment from it (especially now as they’ve re-created one of those pivotal scenes for a Super Bowl commercial). 

Starring Billy Crystal and Meg Ryan (a role which earned Ryan her first Golden Globe nomination), When Harry Met Sally brings to us the question – can men and women ever be friends? While that’s an outdated idea nowadays, it was the crux of the entire movie, so we’re going to let that slide. Over a period of twelve years, we watch the titular characters grow from enemies to close friends and then eventually to lovers. We watch them lovingly (and not so-lovingly) argue with one another. We watch as the world keeps bringing them together, until the final scene, where maybe a split second later and that ending wouldn’t have happened. Spliced with scenes from actors re-enacting real love stories, there is something so delightfully heart-warming about this movie, with a bright spark of hope amongst it all. There’s a reason why up to her death, Nora received so many letters about this movie. It became the blueprint for modern rom-coms, but none could pull it off quite as well as this.

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High Fidelity

Image by Walt Disney Studios

The first on our list that might not fall under the ‘typical’ rom-com umbrella, High Fidelity is a film based on a book of the same name. John Cusack stars as main character Rob Gordon, and you may be thinking “why this John Cusack film?”, especially when you remember the recognisable and often imitated boombox scene from Say Anything. Well, sometimes rom coms need a sprinkling of pessimism and ultimately, I find John Cusack so weirdly charming in this film, as his character begins to reflect and grow. 

After a break up from recent long-term girlfriend Laura, Rob Gordon begins to think back on his relationship history, from his very first kiss to his latest crush on a music journalist. Throughout the film, he pines for Laura, experiencing bouts of insecurity about her new boyfriend. Ultimately, after Laura experiences a loss within her family, Rob comes to the realisation that he didn’t commit fully to their relationship, and that jumping from one idealisation to another isn’t what he wants anymore. That other women are a fantasy and she is his reality, someone who he never grows tired of. It’s subtle but clear character growth, as we begin the film with Rob essentially blaming his school girlfriend for his future romantic failings. To contemplate his past romantic relationships, and understand that what’s easy and new isn’t necessarily what’s best, turns the cynical heart of the story into optimistic but realistic. Cusack plays the role perfectly, and if you get tired of the relationship reflections, Jack Black also pops up every now and again.

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10 Things I Hate About You

Image by Walt Disney Studios

There was a brief but impactful period in the 90s where classic literature received modern adaptations. Clueless was based on Jane Austen’s Emma. She’s All That was based on the George Bernard Shaw play, Pygmalion (which also was the basis for My Fair Lady). 10 Things I Hate About You followed this trend, creating a retelling of Shakespeare’s The Taming of the Shrew. Stacked with a stellar cast, and launching the career of Heath Ledger (who had only taken a couple of small roles up until that point), the teenage romantic comedy has carved its way into millennial hearts. 

Following the complicated romantic relationships of the group of friends (complicated for teenagers anyway), 10 Things I Hate About You begins with new student Cameron falling for beautiful and popular Bianca. Though her and her sister’s, Kat, father forbid them from dating, he allows Bianca to date but only if Kat is dating too. Wanting desperately to date Bianca, Cameron pays school “bad boy” Patrick to take out Kat, but what starts off as a simple transaction, quickly becomes unexpected, deep feelings of love between the two stoic characters. The naiveties of the characters brings a level of sweetness to the film, but there is perhaps nothing more heart wrenching than watching Julia Stiles’ character confess her consistent love through tears. Incredible acting performances that have become nothing short of iconic.

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Notting Hill

Image by Universal Pictures

I don’t think it’s possible to write a list like this without Julia Roberts or Hugh Grant’s names being dropped at least once. While both have since moved on from the genre (with Hugh making a brief re-appearance this year for the new Bridget Jones sequel), for a while, it was what their respective careers thrived on. So it was only a matter of time before the stars aligned, and we would find the two of them in a film together. It didn’t hurt that it was written by British rom com royalty, Richard Curtis. 

Notting Hill follows the unlikely romance between Hollywood star Anna Scott and bookshop owner William Thacker (a plot that has since become a fanfiction trope to end all fanfiction tropes). Though they care deeply for one another, Anna finding quiet with William and William finding adventure with Anna, there are moments where it feels as though the differences in their respective lifestyles feel too grand to move past. Through a series of miscommunications and mishaps, the two never feel quite on the same page as each other, until they both realise how much they love each other. Though it may seem quite generic on the surface, there’s something to be said about the chemistry between the two main characters and the British humour that runs deep through its scenes. At its core, it’s a love story overcoming all odds, the (handsome and charming) underdog earning the heart of the woman he adores. It’s sweet.

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500 Days of Summer

Image by Searchlight Pictures

(500) Days of Summer is perhaps a less obvious choice for a rom com, especially given the narrator sets you up for an imperfect ending at the very start of the film, but it has cemented itself as the darling of the genre and has had a lasting impact that has grown since its release. Casting a pre-Inception Joseph Gordon-Levitt and Zooey Deschanel at the height of her twee, the film tackles a different side of the When Harry Met Sally coin, and asks a different question – what happens when perception doesn’t meet reality? 

Told in a non-linear perspective, the film follows the thread of Tom and Summer’s relationship, from the first day they met (or rather, Summer’s first day at work), to their final moments on a park bench, watching the city move beneath them. Though we mainly see it from Tom’s perspective, hearing from his friends and sister as they try to help him navigate the love and loss he feels with Summer, he doesn’t appear to be an unreliable narrator – rather, Summer seems incredibly honest about what she wants and her feelings towards him throughout the whole movie. While the ending isn’t the typical happy ending you would see in other romantic comedies, (and so therefore, might not fit the bill of what a rom-com is, but you know what it’s my list), it doesn’t automatically make it an unhappy ending. Tom and Summer still end up happy – just not in the way you expect them to.

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Crazy, Stupid, Love

Image by Warner Bros.

Though released only a couple of years after our last entry, there’s something that feels a bit more modern about Crazy, Stupid, Love. It may be because while the cast for 500 Days of Summer feels like it had popular actors for that year, the cast for this film have gone on to bigger and grander things since. Emma Stone has won two Oscars, Julianne Moore won her first Oscar, Steve Carrell has made a lasting career of comedy and drama, earning his own Oscar nomination and Ryan Gosling is just – well, I’m sure you know how that sentence ends. With so many huge names (though maybe they weren’t as big at the time), it may seem like a film where the cast holds more weight than the writing, but honestly, it remains a wonderful rom com. 

After his wife Emily asks for a divorce at dinner, Cal begins to frequent a bar in order to drink his sorrows away. There, he meets Jacob, who takes pity on the middle-aged future divorced dad and helps him meet women by changing his look and his attitude. Jacob meanwhile begins to date Hannah, a young woman who he met at the bar and who also happens to be Cal and Emily’s older daughter. A complex weave of relationships and how everyone is connected can often make a film quite fraught, however it only drives the comedy factor of the movie. It seems that the actors used the film as an opportunity to expand their horizons – Gosling is unexpectedly funny, given that at the time he had made a series of serious movies such as The Notebook and Half-Nelson, and Carrell at this point had made a career from awkward comedy, that he was able to shine in the dramatic moments of the film. Ultimately, the romance is a backdrop to what is a story about new experiences and living through them. Rekindling fires that take work to keep lighting, and letting yourself fall in love, even if the person you’re falling in love with is the person you’ve been married to for a few decades.

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Palm Springs

Image by Neon

A slight but necessary detour into the near science-fiction realm, we take a visit to Palm Springs. An updated and bloodier version of other rom com classic Groundhog Day, Andy Samberg and Cristin Milioti as our unlikely couple, as the two are forced to relive the same day over and over again – a wedding day no less. It’s a fairly new film, released in 2020 (which feels apt given a lot of people probably felt they were reliving the same day over and over again), but it already has the makings of becoming a cult classic. 

Nyles is trapped reliving the same day over and over again. He’s at a wedding with his girlfriend, and while there, he connects with the bride’s depressed sister, Sarah. When the pair sneak off from the festivities, Nyles is shot with an arrow by an unknown assailant, and crawls into a cave. Despite being warned not to, Sarah follows and ends up back at the beginning of the wedding day again. Knowing they were essentially trapped in a time-loop together, with no real chance of a way out, the two begin to do whatever they want, adopting careless and reckless lives. There is a lot more to the film that I don’t really want to spoil, but I have to admit I was expecting very little when I first watched it – maybe something to pass a couple of hours. I didn’t expect it to stay with me like it did. Samberg brings a lot of comedy to the role, as does Milioti who proves consistently she’s exceptionally talented, but there’s a lot of bittersweetness to it. Feelings of nihilism and despondence often plague the main characters, something they have to experience and face together to get through to the end. There’s an insane amount of chemistry between the two, and I don’t think the film would hit as well as it does without the two lead actors.

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The Apartment

Image by United Artists

Ending on a classic in the literal sense, The Apartment has grown to become one of the best loved films in the genre. Starring some of the bigger names of the 60s, The Apartment has that old Hollywood charm, and while there are aspects and moments of it that make it feel quite dated, it’s rise as one of the all time classic rom coms can’t be overstated. Its impact on not only the genre, but the film industry itself, goes without saying. Selected for preservation by the National Film Registry, to this day the film still finds itself hitting ‘Best Films of All Time’ lists, with directors, writers and actors alike constantly finding inspiration amongst it. 

Lonely office worker Bud wants to climb the corporate ladder and does in an unusual way – he offers his apartment out to his managers, saying they can have their extra-marital affairs in a secure location. Eventually, this leads to his personnel director, Jeff Sheldrake using it with the woman of Bud’s would-be affections – elevator operator Fran. After constant promises from Jeff he’ll leave his wife for her, but constantly falling short of doing so, Fran feels despair, a feeling Bud knows all too well, and the two become closer with a shared pain of unrequited romance. Bud consistently protects Fran throughout the film, and while the film has its dark moments, it’s also utterly heart-warming. Though its initial release saw critics dismiss the film entirely, since then modern audiences have become enamoured with the bittersweet tale. The tragic undertones are uplifted by the comedic writing, the intricate and sentimental relationship between Bud and Fran feels natural as they move from colleagues to friends to lovers. While our first film may be the blueprint for modern rom-coms, our last movie is the original (darker) blueprint for that. Even their final scenes are set on the same holiday – New Year’s Eve. Nothing more romantic than a fresh start.

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Conclusion

Though the genre is flooded with mediocre attempts of creating something meaningful, there are plenty of wonderful rom coms out there. With writer’s getting more creative in recent years, I’m sure there’s some films I’ve missed from the more recent years. Let me know in the comments if I missed off one of your favourites!

See also: Most Anticipated Movies of 2025

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