Whether you’re celebrating Valentine’s Day with your partner, having fun with friends or celebrating yourself, watching a romantic comedy is a great way to spend Valentine’s Day. So here are eight classic rom-coms ranked, so you can know which ones are worth checking out.
8. “She’s All That” (1999)
This high school rom-com follows Zach (Freddie Prinze Jr.) who makes a bet with his friends to turn the school outcast, Laney (Rachael Leigh Cook) into the next prom queen. While this movie had some fun moments, it rubs me the wrong way. It’s the classic makeover story where the most popular guy in school takes off the nerdy girl’s glasses and suddenly falls in love with her. I found it to be somewhat boring and honestly, I felt bad that Laney had to put up with Zach and his annoying friends. But hey, if you want to hear “Kiss Me” by Sixpence None The Richer, this is the movie for you.
7. “How to Lose a Guy in 10 Days” (2003)
In one of the most well known rom-coms, Andie (Kate Hudson), a journalist, sets out to write a piece about how to get a guy to break up with you in ten days, while Ben (Matthew McConaughey) makes a bet with his friends that he can make a woman fall in love with him in ten days. Despite its popularity, this movie annoyed me. The main couple was so incredibly toxic that it was almost painful to watch their interactions. And at the end, Andie gives up her dream of becoming a “serious” journalist to be with Ben, someone who she didn’t even seem to like up until that point. While I know it’s supposed to be fun, their relationship is just something I can’t get behind.
6. “10 Things I Hate About You” (1999)
In this classic high school rom-com, the school loner, Patrick (Heath Ledger), gets paid to date Kat (Julia Stiles). While this is many people’s favorite rom-com, it just didn’t really do it for me. My main issue with the film is that I feel like the main couple didn’t have that much chemistry, so when Kat gives her big iconic monologue at the end of the film, it felt like it came out of nowhere. Personally, I would rather watch the higher ranked movies on this list over this one, but as evident by its massive fanbase, the movie might simply not be for me. I would still give it a shot if you’re looking for something fun and classic to watch.
5. “When Harry Met Sally…” (1989)
This beloved film follows the long-time friendship between Harry (Billy Crystal) and Sally (Meg Ryan) as they slowly fall in love. This movie is funny, sweet and does a good job of showing a slow-burn friends to lovers trope. My main gripe with it is Harry’s character. I know that people probably enjoy this movie so much because the main characters’ personalities are so distinct, but Harry consistently gave me the ick and didn’t seem like a great person. But if you’re in the mood for a heartwarming love story, this would be a good movie for you.
4. “But I’m a Cheerleader” (1999)
In this coming of age rom-com, Megan (Natasha Lyonne) gets sent to True Directions, a boot-camp style “conversion therapy” center, after her parents suspect her to be a lesbian. This is a hilarious film that actually has a pretty strong main couple. While it is a silly film, it also has some moments of seriousness that are really important and give the film its true heart. If you’re looking for a classic queer rom-coms and a good time, this movie would be perfect for you.
3. “She’s the Man” (2006)
Inspired by Shakespeare’s “Twelfth Night,” this film follows Viola (Amanda Bynes) as she disguises herself as her twin brother so she can play soccer at his all-boys prep school after the girl’s team at her school is cut. This film is fun, entertaining and includes a pretty cute couple. I didn’t put it higher because I feel like this film is a little problematic given that the premise of it is inherently queer, and yet the film steers very clear from the idea of queerness. I think if the producers had leaned into the queer side of this film, it could have added depth to the movie and would have made it feel more authentic. If you are looking for a distinctive and fun concept, this would be a good choice.
2. “27 Dresses” (2008)
After being a bridesmaid 27 times, Jane (Katherine Heigl) must now face the ultimate challenge of being her sister’s bridesmaid while she marries the man Jane is secretly in love with. I feel like when people talk about classic rom-coms, this movie often gets overshadowed, but I love this film. I think the main couple is one of the strongest ones out of this list and I found Jane’s journey to be touching. If you haven’t seen this film yet, I highly recommend watching it.
1. “13 Going on 30” (2004)
In this 2000s rom-com, Jenna (Jennifer Garner) makes a wish on her 13th birthday to be 30, but when she wakes up as a 30-year-old, she finds that her life isn’t what she thought it would be. This is one of my favorite films of all time. It’s such a perfect, funny, feel-good movie that also has real depth to it. It explores the power of youthful joy and why we shouldn’t lose it as we age. I also love the couple in this film (though some people argue that it’s creepy because Jenna is still technically 13 while she falls in love with an actual thirty-year-old) and I appreciate that they don’t make unreasonable sacrifices for each other. If you’re looking for a fun yet deep rom-com, this would be perfect for you.
