10 Best Rom-Com Movies of All Time You Should Watch

The best rom-com movies of all time include When Harry Met Sally (1989), Notting Hill (1999), 10 Things I Hate About You (1999), How to Lose a Guy in 10 Days (2003), The Proposal (2009), 500 Days of Summer (2009) and La La Land (2016). They mix humour with real feeling and sharp writing that still works years later.

A good romantic comedy is more than a predictable love story. The best ones have characters you care about, funny dialogue and a few honest moments about love, loss and timing. This list covers ten classics from Hollywood and Europe, with the year, director and lead cast for each, plus a newer hit for your next movie night.

Best rom-com movies of all time: quick facts

Film	Year	Director	Lead cast
When Harry Met Sally	1989	Rob Reiner	Billy Crystal, Meg Ryan
10 Things I Hate About You	1999	Gil Junger	Julia Stiles, Heath Ledger
How to Lose a Guy in 10 Days	2003	Donald Petrie	Kate Hudson, Matthew McConaughey
500 Days of Summer	2009	Marc Webb	Joseph Gordon-Levitt, Zooey Deschanel
The Proposal	2009	Anne Fletcher	Sandra Bullock, Ryan Reynolds
Me Before You	2016	Thea Sharrock	Emilia Clarke, Sam Claflin
La La Land	2016	Damien Chazelle	Ryan Gosling, Emma Stone
Love and Other Drugs	2010	Edward Zwick	Jake Gyllenhaal, Anne Hathaway
Amélie	2001	Jean-Pierre Jeunet	Audrey Tautou
Notting Hill	1999	Roger Michell	Hugh Grant, Julia Roberts

1. When Harry Met Sally (1989)

Rob Reiner’s film, written by Nora Ephron, asks a simple question: can men and women ever be just friends? Billy Crystal and Meg Ryan play Harry and Sally, who keep meeting over more than a decade and slowly change their minds about each other.

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Its natural dialogue and its focus on friendship before romance have kept it at the top of many rom-com lists.

2. 10 Things I Hate About You (1999)

This high-school comedy loosely adapts William Shakespeare’s The Taming of the Shrew. Julia Stiles plays a sharp-tongued teenager, and Heath Ledger plays the rebel who sets out to win her over.

Directed by Gil Junger in his debut, it also features Joseph Gordon-Levitt and Larisa Oleynik. It remains a favourite for its wit and its leads.

3. How to Lose a Guy in 10 Days (2003)

A magazine writer, played by Kate Hudson, sets out to drive a man away within ten days for an article. The man, played by Matthew McConaughey, has made a bet that he can make any woman fall for him. Neither knows the other’s plan.

Donald Petrie’s film works because of the leads’ chemistry and the steady build of comic chaos.

4. 500 Days of Summer (2009)

Marc Webb’s film tells a love story out of order. Joseph Gordon-Levitt plays Tom, who falls for his colleague Summer, played by Zooey Deschanel, while she does not want a serious relationship.

It is less conventional than most rom-coms and captures the pain of a one-sided relationship and a bad breakup with honesty.

5. The Proposal (2009)

Sandra Bullock plays a tough boss who faces deportation. To stay, she pushes her assistant, played by Ryan Reynolds, into a marriage of convenience, and the fake couple slowly becomes a real one.

Directed by Anne Fletcher, it is light, funny and easy to rewatch, with strong comic timing from both leads.

6. Me Before You (2016)

Based on Jojo Moyes’s 2012 novel, this film follows Lou, played by Emilia Clarke, who becomes the caretaker of Will, a paralysed man played by Sam Claflin.

Directed by Thea Sharrock, it starts as a sweet romance but turns emotionally heavy. Be ready for a sad ending.

7. La La Land (2016)

Damien Chazelle wrote and directed this musical romance about Mia and Sebastian, two aspiring artists. Emma Stone and Ryan Gosling play the pair, who must make hard choices between love and their careers.

The film won six Oscars from 14 nominations at the 89th Academy Awards. Its bittersweet ending sets it apart from typical rom-coms.

8. Love and Other Drugs (2010)

Jake Gyllenhaal and Anne Hathaway star in a romance set against the pharmaceutical industry, in which her character lives with Parkinson’s disease. The relationship grows more serious than either of them planned.

Edward Zwick’s film blends comedy with a serious look at illness and commitment.

9. Amélie (2001)

This French film by Jean-Pierre Jeunet follows Amélie, a shy waitress in Paris played by Audrey Tautou. After an unexpected discovery, she starts quietly changing the lives of people around her, and her own life changes too.

Its colourful, dreamy look of Paris and its gentle humour have made it one of the most loved non-English romantic films.

10. Notting Hill (1999)

Hugh Grant plays William, who runs a small bookshop in London. One day, a famous American actress, played by Julia Roberts, walks in, and an unlikely romance begins.

Written by Richard Curtis and directed by Roger Michell, it is a classic British rom-com about fame, privacy and ordinary life.

Newer and bonus picks

• Anyone but You (2023): Sydney Sweeney and Glen Powell star in Will Gluck’s loose take on Shakespeare’s Much Ado About Nothing. It earned about US$220 million worldwide.
• Crazy Rich Asians, Long Shot and I Give It a Year: three more fun choices if you have finished the list above.

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Frequently asked questions

Sources: Wikipedia: When Harry Met Sally, Wikipedia: La La Land, Wikipedia: Notting Hill, Wikipedia: Anyone but You.