I'm starting a new series of articles collecting a list of recommendations if you're stuck for a film to watch. Look out for my lists for comedies, dramas and action films coming up too.
For this post, I've put together a list of 20 rom-coms - a genre that's deceptively tough to get right. In fact the last ten years have been relatively sparse in terms of great romantic comedies, but that makes the few great ones even more special.
Last updated: September 2023
10 Things I Hate About You (1999)
First on the list is a '90s retelling of Shakespeare's The Taming of the Shrew starring Heath Ledger, Julia Stiles and Joseph-Gordon Levitt. 10 Things I Hate About You is an absolute teen romantic-comedy classic. Ledger and Stiles bring so much charisma to their roles, and the movie is endlessly rewatchable.
Watch this if you enjoy: Heath Ledger being incredibly charming, Julia Stiles being an absolute '90s icon
500 Days of Summer (2009)
A quirky romantic comedy that subverts the genre by focusing on a break up, and pokes fun at some of the the tropes of the genre (including a whole musical dance sequence). Joseph Gordon Levitt plays Tom, a man who believes in love and happily ever after's, and who falls in love with Summer (Zooey Deschanel) who doesn’t believe in love or destiny. As their relationship progresses, Levitt starts to question his idea of love and relationships.
Watch this if you enjoy: New Girl, quirky or cute movies, Ikea
About Time (2013)
About Time is so many things: a great romantic comedy, a touching family drama, and a brilliant time travel film. It's to be expected from the king of the British rom-com, Richard Curtis. Domhnall Gleeson and Rachel McAdams are such likable leads, but it's Bill Nighy as Gleeson's kind and warm father who steals the film.
Watch this if you enjoy: the most British movies ever, father/son stories, time travel, hopeful and uplifting messages
The Apartment (1960)
One of the wittiest scripts of the list comes from Billy Wilder's 1960 classic, The Apartment. The plot follows CC Baxter (Jack Lemmon) a clerk at an insurance company who lends his apartment to his bosses to conduct their extra-marital affairs. Things get complicated when he falls for Fran (Shirley MacLaine), his boss' mistress.
Watch this if you enjoy: classic movies, office-based comedy, unrequited love
As Good As It Gets (1997)
As Good As It Gets is about an ill-mannered man called Melvin, who also happens to have obsessive compulsive disorder. Coming out of his lonely life as a writer, he reluctantly befriends his gay neighbour and a single mother, learning to be a nicer human being along the way. It's a little more of an odd-beat rom-com, but the performances won Helen Hunt and Jack Nicholson Academy Awards for their performances.
Watch it if you enjoy: mean protagonists on the verge of being problematic, road-trip movies
Bridget Jones's Diary (2001)
Based on the hit novel of the same name, Bridget Jones's Diary is a beloved British comedy starring Renee Zellweger. It's an irreverent, modern take on Jane Austen's Pride and Prejudice complete with Mr Darcy himself, Colin Firth. Though it's thoroughly 2000's, the idea of the 'imperfect', awkward female protagonist is still as fun as ever (if you can survive a bit of cringe comedy that is).
Watch this if you enjoy: the feeling of realising that someone else has it worse than you
Crazy Rich Asians (2018)
Aside from being a landmark movie for Asian representation in a major Hollywood production, Crazy Rich Asians is also a solid rom-com. Constance Wu plays Rachel who flies to Singapore to meet her boyfriend's insanely rich friends and family, and has to navigate their resentment and jealousy.
Watch this if you enjoy: watching lavish weddings, Michelle Yeoh, travel programs
Crazy, Stupid, Love (2011)
To get over his divorce, Cal (Steve Carrell) starts picking up women at a bar on the insistence of his new-found friend, Jacob (Ryan Gosling). Written by Dan Fogelman (the writer/creator of This is Us), the film's worth watching if only for its hilarious ending.
Watch this if you enjoy: Ryan Gosling and Emma Stone, comedy based on misunderstandings
Enchanted (2007)
Enchanted is one of the best Disney live action films, poking fun at the cliches of classic fairytale stories. Thrust into the not-animated, ‘real’ land of New York City, Giselle (Amy Adams) quickly discovers that the world is a lot more complicated than the (literal) fairytale she's been living. Amy Adams is wonderful in the lead role, emulating the mannerisms and naivety of a Disney princess flawlessly. James Marsden is similarly hilarious and charming as the dopey Prince Edward (and the Ken before Gosling's Ken).
Watch this if you enjoy: Amy Adams, fairytales and Disney, James Marsden
The Holiday (2006)
The Holiday is a Christmas favourite starring Cameron Diaz, Kate Winslet, Jude Law and Jack Black. It's one of the best holiday movies, but it's also a great feel good romantic comedy.
Watch it if you enjoy: festive vibes, travel programs, Jack Black being charming
Love Actually (2003)
Another Christmas staple! Starring possibly all of Britain and written/directed by Richard Curtis, Love Actually is undoubtedly one of the most popular romantic movies ever made. Though it's known for being sentimental, the real stand out storylines are about Liam Neeson and Thomas Brodie-Sangster's father-son bond, and Emma Thompson and Alan Rickman's troubled marriage.
Watch this if you enjoy: the idea of Hugh Grant being the prime minister
The Map of Tiny Perfect Things (2021)
The second of three time related movies on this list. The Map of Tiny Perfect Things is more of a feel-good, sentimental drama than romantic-comedy but still has plenty of the familiar comedic elements you might expect from two Gen-Z's stuck in a timeloop together.
Watch this if you enjoy: timeloop movies
Palm Springs (2020)
Stuck in a time loop, two wedding guests encounter one another (again and again) unable to move on from the same day. The film stars Brooklyn-99's Andy Samberg and Black Mirror's Cristina Milioti, and definitely veers into wacky comedy territory but still retains its charm.
Watch this if you enjoy: timeloop movies (... wait I said that before!)
Plus One (2019)
If you're feeling like a familiar romantic comedy while still wanting to watch something fresh, Plus One is a good time. Jack Quaid and Maya Erskine play two long time friends who agree to be one another's plus one during one busy summer of weddings.
Watch this if you enjoy: wedding based rom-coms
The Princess Diaries 2: A Royal Engagement (2004)
Look, you might think this is my childhood nostalgia talking but Princess Diaries 2 has Anne Hathaway and Chris Pine as royal enemies to lovers, Julie Andrews singing and is basically all set in a palace. So, it's basically the best thing ever?
Watch this if you enjoy: Disney, Julie Andrews, scenes where a girl gets a walk-in wardrobe
Rye Lane (2023)
Rye Lane is one of the best modern rom-coms, and criminally underrated. Considering it's director Raine Allen-Miller's feature debut, it's surprising just how full of heart, humour and style (which verges on an Edgar Wright-like aesthetic) this film is. Set in South London, the plot is about two young people recently getting over break-ups who bump into each other one eventful day.
Watch it if you enjoy: seeing London romanticised, stylish editing, 'walk and talk' romance
Set it Up (2018)
Glen Powell and Zoey Deutch play two overworked assistants who come up with a scheme to set their bosses up. Powell and Deutch's chemistry, and the refreshing simplicity of the plot, sets this film apart from other rom-coms of the past few years and is definitely one to check out if you love rom-coms.
Watch it if you enjoy: actually good chemistry, office-based comedy
To All the Boys I've Loved Before (2018)
A Gen Z addition to the historic staple of the rom-com genre which is the 'fake dating to real relationship' trope. Watch this one for Lana Condor and Noah Centineo's charming chemistry, and the film's cute valentine's aesthetic.
Watch it if you enjoy: the Gen-Z instagram aesthetic, high school romance, the fake dating trope
When Harry Met Sally (1989)
Billy Crystal and Meg Ryan play Harry and Sally who keep crossing paths with each other over the course of many years. Though they initially hate each other, the two characters begin to warm towards one another, forming a friendship and then perhaps something more. When Harry Met Sally is possibly *the ultimate* romantic comedy.
Watch this if you enjoy: any rom-coms!
You've Got Mail (1998)
Tom Hanks and Meg Ryan play rival bookstore owners who unknowingly write to one another as penpals on the internet. Featuring enemies to lovers, old-fashioned internet culture, a romanticised version of New York and lots of books.... so what more do you want?
Watch this if you enjoy: the idea of owning your own bookstore and living in New York
Thank you for reading this article; leave your recommendations in the comments below...
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