Monday, May 27, 2024

Our 10 Favorite Romantic Comedies Of All Time

We’ve shared Next Best Picture team’s favorite horror movies for HalloweenThanksgiving movies, and Christmas movies, so it felt appropriate to share our favorite romantic comedies in honor of Valentine’s Day. I talked to the team to gather some of our collective favorite romantic comedies (or rom-coms_ and we had a lot of variety. There were (of course) a lot of great ones that didn’t make the list like “You’ve Got Mail,” “Pretty Woman,” and “Love, Simon.” 

Whether you’re in a committed relationship with a partner or just with Letterboxd, here are some great movies to watch on Valentine’s Day weekend. 


​10. “The Philadelphia Story” (1940) 

​“The Philadelphia Story” (1940)

Katharine Hepburn, Cary Grant, and James Stewart star in George Cukor’s “The Philadelphia Story” about a Pennsylvania socialite who, on the eve of her second wedding, is faced with her ex-husband and a charming newspaper reporter who develops feelings for her. This play turned film was nominated for six Academy Awards and won Best Actor for James Stewart and Best Adapted Screenplay. Hepburn, Grant, and Stewart are truly three of the greatest actors in Hollywood history and the screenplay is full of funny quips and more serious ruminations on romance like, “I don’t want to be worshipped; I want to be loved.”

9. “Clueless” (1995) 

“Clueless” (1995)

“As if!” Amy Heckerling wrote and directed this modern adaptation of Jane Austen’s “Emma” set in Beverly Hills. It’s a coming-of-age story about a rich and beautiful but self-centered girl who tries to matchmake for everyone around her, but ends up in many romantic mishaps herself and is shocked to discover her feelings for the last guy she would have expected. It stars a young Alicia Silverstone and Paul Rudd and also boasts some of the most iconic fashion of any movie of the 1990s.

8. “As Good As It Gets” (1997) 

“As Good As It Gets” (1997)

Every rom-com should have an adorable dog in it, right? James L. Brooks’s “As Good as it Gets” stars Jack Nicholson as a romance novelist who hates people, Helen Hunt as a waitress and single mother, and Greg Kinnear as a gay artist recovering from a terrible assault by robbers. The film was nominated for seven Academy Awards and won Best Actor and Best Actress. It’s a unique and touching story, though not everyone is thrilled with its more conventional ending.


​7. “It Happened One Night” (1934) 

​“It Happened One Night” (1934)

The oldest film on our list is Frank Capra’s “It Happened One Night.” This was one of the last pre-Code films, which has elements of classic romance tropes and screwball comedy. It follows a socialite trying to elope who ends up going on a series of adventures and falling in love with a reporter. It stars Clark Gable and Claudette Colbert and even if you’ve not seen it, you might recognize the clip of Gable trying to hail a car and failing and Colbert getting a car to stop for them by sticking out her leg. It is one of only three films to win all five major Oscars: Best Picture, Best Director, Best Actor, Best Actress, and Best (Adapted) Screenplay.

6. “Shakespeare In Love” (1998) 

“Shakespeare In Love” (1998)

John Madden’s “Shakespeare in Love” might be a bit controversial because of its seven Academy Award wins, including Best Picture, but it’s hard to deny that it’s a very enjoyable film. This film imagines a love affair between rising playwright William Shakespeare and the wealthy Viola de Lesseps who would rather be an actor than marry the nobleman her parents have chosen for her. It stars Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush, Colin Firth, Ben Affleck, and Judi Dench. It’s certainly not period accurate, but it is thrilling and rather funny.

5. “Sabrina” (1954) 

“Sabrina” (1954)

Not to be confused with the inferior 1995 remake, Billy Wilder’s “Sabrina” is the story of a young woman who is the daughter of the chauffeur of a wealthy family. She has had a crush on playboy David Larrabee her whole life, but he doesn’t notice her until she comes back from culinary school in Paris, suddenly sophisticated and fashionable. However, she might just end up falling for David’s sensible brother Linus instead. The film stars Audrey Hepburn, Humphrey Bogart, and William Holden, each at their most charming.

4. “Moonstruck” (1987) 

“Moonstruck” (1987)

Norman Jewison’s “Moonstruck” is famously the movie that won Cher her Best Actress Oscar. It is about an Italian-American widow who falls for her fiancé’s estranged younger brother while he’s away in Italy with his dying mother. It stars Cher, Nicholas Cage, and Olympia Dukakis and was nominated for six Oscars, winning three. It’s an iconic New York City movie, with some great scenes at the Lincoln Center, and delightfully funny.


​3. “The Big Sick” (2017)

“The Big Sick” (2017)

The Big Sick,” directed by Michael Showalter, is a semi-autobiographical story written by Kumail Nanjiani and Emily V. Gordon based on their real-life romance. It stars Nanjiani, Zoe Kazan, Ray Romano, and Holly Hunter. When Emily is hospitalized with a serious lung infection and induced into a coma, her ex-boyfriend Kumail is forced to face his feelings for her and grows closer to Emily’s parents. It also explores how Kumail’s Pakistani family doesn’t approve of him being in a relationship with a non-Pakistani girl. This movie is sure to make you laugh, but it also will destroy you emotionally.

2. “Annie Hall” (1977)

“Annie Hall” (1977)

Woody Allen wrote, directed, and starred in this romantic comedy about a comedian who falls in love with a woman named Annie Hall only for it to fall apart. Diane Keaton plays the titular role in this incredibly funny, but also smart film. It won four Oscars, including Best Picture. Allen’s legacy may be (rightfully) tarnished, but this film continues to stand the test of time.

1. “When Harry Met Sally” (1989)

“When Harry Met Sally” (1989)

There was one film that appeared on almost every team member’s ballot and that was the beloved “When Harry Met Sally,” directed by Rob Reiner. Nora Ephron’s witty screenplay shines in this film about two friends who grow together over time only to realize that they’re in love. It’s the ultimate “friends to lovers” story, demonstrated beautifully by Meg Ryan and Billy Crystal. It has so many quotable lines and fantastic supporting performances by Carrie Fisher and Bruno Kirby. I’ll have what she’s having, indeed!

What is your favorite rom-com? Do you agree with our list? Let us know in the comments section below or on our Twitter account. 

You can follow Nicole and hear more of her thoughts on Film and the Oscars on Twitter at @nicoleackman16

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Nicole Ackman
Nicole Ackman
Blogger, YouTube, Broadway World UK writer, University of London postgrad & Elon.

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