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There’s just one week to go until we announce the winner of our first ever Romance and Comedy Award! To celebrate, we put together lists of our favorite films from each genre… and now it’s the turn of the hybrid rom-com genre!

Once again, this isn’t comprehensive and we don’t necessarily think these are the best comedy films. They’re just our favorites, and we think that there’s lots to learn for writers by watching them…


1. THE BIG SICK
No genre is more plagued with clichés than romantic-comedies, and avoiding them is a big problem for even the most experienced writers. They’re not a problem for THE BIG SICK, however, which somehow manages to tell a story that is both moving and funny without falling back on any of the usual tropes. It helps that it was based on the real-life romance between its writers Emily V. Gordon and Kumail Nanjiani (who also starred in the lead role), but the care and originality of this script always shines through – and was rewarded with a nomination for Best Original Screenplay in 2018.

2. ROMAN HOLIDAY
A classic of the genre, William Wyler’s tale of a princess escaping her guardians and roaming Rome (see what we did there?) with an American reporter has a rare kind of charm. Having Gregory Peck and Audrey Hepburn (in her only Oscar-winning performance) in your cast certainly helps, but the script is a wonderful work of art, winning the Academy Award for Writing in 1953. It wasn’t until 1992 that the real writer was retroactively given his award, though; Dalton Trumbo (brilliantly portrayed by Bryan Cranston in 2015’s TRUMBO) was blacklisted at the time.

3. WHEN HARRY MET SALLY
Another Oscar nominee for Best Original Screenplay! It’s almost like good writing shows… WHEN HARRY MET SALLY is smart, funny, and original, and introduced the world to a lot of new concepts about relationships. If you ever doubt its importance in the canon of romantic-comedies, just go and watch something in the same genre from the 1990s and you’ll find this film’s fingerprints (both Harry’s and Sally’s) all over it; FRIENDS, the biggest sitcom of all time, is a notable example!

4. BREAKFAST AT TIFFANY’S
The second film to star Audrey Hepburn on this list, which just goes to show how she excelled in these kind of roles. This one was adapted from the novella of the same name by Truman Capote, so there was already a great writer behind it before George Axelrod got his hands on it – but strangely enough, the part was originally written and tailored for Marilyn Monroe, who was Capote’s first pick but turned the role down. He apparently hated Hepburn in the part… but we’ll disagree with him there. There’s a difference between writing a novella and a screenplay, and while those differences didn’t make BREAKFAST AT TIFFANY’S the most faithful adaptation, it certainly made it a great film.

5. SHAKESPEARE IN LOVE
This one might prove a bit controversial – although perhaps not quite as controversial as when it beat out SAVING PRIVATE RYAN for the Oscar for Best Picture. Still, it also won Best Original Screenplay for Tom Stoppard and Marc Norman, and with good reason in our opinion. Charming, witty, and romantic, it ticks all the boxes for a rom-com that we can think of. A big plus, of course, is that it’s about the greatest writer in history, and that definitely helps win our approval too.

HONORABLE MENTION: MOST OF HUGH GRANT’S MOVIES
No, this doesn’t include PADDINGTON 2 (although we’re a big fan of that as well). You know what we’re referring to: most of Richard Curtis’ output, with a few others thrown in for good measure, including ABOUT A BOY, NOTTING HILL, FOUR WEDDINGS AND A FUNERAL, and LOVE ACTUALLY. We’d have loved to have included them in the main list above, but unfortunately they all cancelled one another out and it was impossible to choose between them.


So there you have it – our favorite rom-com films that we think every writer should watch. And you can also check out our lists of our favorite romance films here and our favorite comedy films here!

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