Rating the 10 Best Romantic Comedies According to Vanity Fair


As February of 2023, the month of all things love, becomes more and more part of history, I wanted to examine the movie genre most associated with the month. By that I mean romantic comedies, more commonly known as rom-coms. So, I searched the internet for an adequate list to rate. While watching the 42 movies on Vanity Fair’s ultimate rom-com list sounded fun, I had a deadline, so I ultimately decided to do the top 10.

According to Vanity Fair, “every single pick may not contain every element commonly associated with the romantic comedy, [but] they all fit the American Film Institute’s broad definition of a genre in which the development of a romance leads to comic situations.” So, without further ado, here are the ten best romantic comedies according to Vanity Fair – and my takeaways from them.

10. Roman Holiday (1953) – Starring Audrey Hepburn and Gregory Peck, Roman Holiday follows a sheltered princess who escapes her guardians and falls in love with an American reporter in Rome. The movie wasn’t my favorite, mainly because some dialogue feels slow. Something this film does do right? Audrey Hepburn. Her character was energetic and charismatic, an overall great character that made the movie more enjoyable.

9. Love & Basketball (2000) – This was the movie that I had the most fun watching. Following childhood friends Monica and Quincy, who both aspire to be professional basketball players, Love & Basketball shows how the two begin to fall in love over time. Still, their distinct paths to basketball stardom threaten to separate them. Their love was sincere and authentic — those who haven’t seen it must watch immediately. Love and Basketball was one of my sister’s favorite movies, so I’m mad that I haven’t watched it sooner. It has a fantastic love story with an excellent cast and soundtrack, making it one of my favorite movies.

8. Groundhog Day (1993) – This was the movie on the list that surprised me the most. I knew about this movie but never considered it a rom-com. Bill Murray plays narcissist weatherman Phil Connors, who finds himself in a time loop on Groundhog Day. I knew the movie’s overall plot, but I didn’t think there was enough of a romance element for it to be in the top 10 out of all rom-coms. However, this is what makes this movie the perfect rom-com for people who don’t typically like rom-coms.

7. What’s Up, Doc? (1972) – When four identical plaid overnight bags are accidentally mixed up, they result in increasingly bizarre situations. I think that this movie is hilarious. There were multiple instances where I laughed out loud at some of the jokes, and I think the humor holds up very well. The romance aspect, on the other hand, was lacking.

6. 10 Things I Hate About You (1999) – This is one of my favorite rom-coms, maybe even movies, of all time. 10 Things is about a pretty, popular teenager, Bianca, who can only go out on a date once her irritable older sister, Kat, does. I love almost everything about this movie, from the soundtrack to the plot to the fantastic cast, which includes Julia Stiles, Joseph Gordon-Levitt, and the late Heath Ledger. It’s just overall a delightful movie.

5. Phantom Thread (2017) – Reynolds Woodcock is a well-known dressmaker whose meticulous life is disrupted by Alma, a young woman with a strong will who becomes his muse and lover. This one may be my least favorite of all the movies on this list. The tone shift from the other films just threw me off. One thing I did like about this movie is its cinematography – it had some stunning shots in it.

4. Bridget Jones’s Diary (2001) – In a diary she keeps for a year, Bridget Jones is determined to improve herself while she looks for love. There’s not much to say about this movie; it feels like your average rom-com. This movie has a lot of humanity, sincerity, and thoughtfulness mixed in with comedy, which I enjoy.

3. Clueless (1995) – A wealthy, well-known high school student makes friends with a new student, decides to give her a makeover, plays matchmaker for her teachers, and examines her own life. Clueless is a classic that I love very much. However, I do think that it’s a better chick flick than it is a rom-com. It feels like the focus is more on Cher’s life and actions than on her love life.

2. You’ve Got Mail (1998) – In the anonymity of the Internet, independent bookshop owner Kathleen Kelly and book superstore magnate Joe Fox fall in love, blissfully unaware that Fox is attempting to shut Kelly’s store down. The story is lovely if you ignore the fact that Joe shuts down Kathleen’s business and lied about who he was. Because of this lying, their relationship was far from my favorite. While watching this movie, I realized how many rom-coms center around people lying to each other.

1. When Harry Met Sally (1989) – This movie being on the list was no surprise. Harry (Billy Crystal) and Sally (Meg Ryan) are unlikely friends who keep running into each other and eventually develop a unique friendship. Everything about this movie, to me, just screams rom-com. The comedy is full of emotions and romance and gets severe and profound at different points. The characters are charming. The mockumentary-style interviews with couples sprinkled in the movie also make this movie very special.

This list had some hits and misses, but I (mostly) had fun nonetheless. Of all the films on this list, the ones I recommend most are When Harry Met Sally and Love & Basketball. However, all of these movies are worth a watch, and I recommend checking out the whole list – I hope you have as much fun as I did.