There are tons of Top 20 lists of the best romantic comedies.
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I’ve seen them all, and they never get boring to me. I could watch them over and over again and always be entertained.
I’ve seen plenty of older romantic comedies that are excellent, but this list is going to focus on the best ones that came out while I was growing up.
I couldn’t pick one favorite, so I’m putting them in release date order. Let me know your thoughts and if you agree with my list.
The Top 20 Romantic Comedies
1. When Harry Met Sally (1989)
This movie brings up the age-old question: “Can men and women be just friends?” The well-written screenplay beautifully shows the progression of Harry’s and Sally’s relationship. There are plenty of classic moments in this movie, like the famous restaurant scene, so this is a perfect romantic comedy for my list.
2. While You Were Sleeping (1995)
I watched this movie A LOT growing up. The misunderstanding that arises because of Sandra Bullock’s crush on a man she has never spoken to is comedy gold. Will she fall for the guy who’s in a coma? You’ll have to watch to find out.
3. Clueless (1995)
This is such a fun movie to watch. I love how they portray wealthy Beverly Hills students, and Alicia Silverstone playing a ditzy girl who cares so much about helping others is sweet and uplifting.
4. The Truth About Cats & Dogs (1996)
This is a really cute movie about honesty and self-respect. With Janeane Garofalo’s engaging personality and Uma Thurman’s natural beauty, will this unlikely pair become friends?
5. My Best Friend’s Wedding (1997)
This classic wedding story is perfect from start to finish. Julia Roberts and Cameron Diaz are both relatable and beautiful, and their opposite personalities bounce off of each other well.
6. The Wedding Singer (1998)
This is the first movie Drew Barrymore and Adam Sandler star in together, and it’s my favorite from that duo. Adam Sandler’s outrageous behavior mixed with Drew Barrymore’s sweet innocence create a funny character dynamic. The song played at the end of the movie is very catchy and romantic, too.
7. Can’t Hardly Wait (1998)
This movie has a variety of characters showing different high school cliques. All the plots intertwine flawlessly to create a funny and heart-warming movie. It even shows where the characters end up years after graduation, which gives it a satisfying conclusion.
8. There’s Something About Mary (1998)
The Farrelly Brothers definitely know how to write and direct an excellent movie. The plot is so intricate, and it all weaves together seamlessly. Which oddball character will win over Mary’s heart? You’ll have to watch it to find out.
9. 10 Things I Hate About You (1999)
Any movie starring Heath Ledger and Joseph Gordon-Levitt is bound to make my list. I’m personally not a Shakespeare fan, but I like the fact that this movie is a modern version of “The Taming of the Shrew.”
10. Never Been Kissed (1999)
Drew Barrymore knows how to pick the right screenplays for her audience, and I am always drawn to movies she’s in. All the typical high school cliques are represented with over-the-top and comical scenes that occur.
11. American Pie (1999)
This movie has a great ensemble cast of hilarious characters. Everyone can relate to someone or something that happens. Even parents can identify with the awkward talks Eugene Levy has with his son. The four main friends have unique personalities that attract different types of women, and all the lead-up to prom night is pure entertainment.
12. Bridget Jones’s Diary (2001)
Renee Zellweger does an exemplary job portraying a disheveled, slightly awkward woman in her 30s. No matter what she faces, her loving friends stick by her and help her through the bumpy road of life. The opening scene with the song “All By Myself” starts the movie off in the right direction.
13. Hitch (2005)
Watching a dating coach help lonely men find love is really inspiring! Will Smith is the ideal actor for this role, and Kevin James’s awkwardness with women is entertaining. The two main romantic relationships complement each other nicely to create an enjoyable experience for all romantic comedy fans.
14. Wedding Crashers (2005)
The combination of the four main actors is magnificent, and all the character personalities mesh so well together. I did background work at the time, and I’m in one of the wedding scenes. Let me know if you find me!
15. The 40-Year-Old Virgin (2005)
The title says it all. How can a movie with this name not be funny? This was also filmed during my time doing background work, so I’m in a few scenes. This movie gets me every time with its ridiculous humor and hysterical characters.
16. Just Friends (2005)
Based on the title, it’s pretty obvious that this is another movie that delves into the topic of men and women being just friends. Will Ryan Reynolds and Amy Smart be in the friend zone forever? You’ll have to watch to find out.
17. Forgetting Sarah Marshall (2008)
Jason Segel wrote an impressive screenplay, and he incorporated some real life events into the plot, including a full frontal breakup at the start of the movie. The combination of characters mixed with the humorous scenes are not to be missed.
18. My Best Friend’s Girl (2008)
This movie didn’t get as much praise as it deserves. I never see it on a list of the best romantic comedies, but it should be. The interactions between Kate Hudson and Dane Cook are amazing, and Alec Baldwin as a womanizing father is also hilarious to watch.
19. Crazy, Stupid, Love (2011)
This movie has a lot going for it, including a top-notch cast, a phenomenal screenwriter, and a heart-warming plot. Writer Dan Fogelman knows how to incorporate many different storylines into one flawless movie.
20. What’s Your Number? (2011)
Here’s another movie that I never see on any list of the best romantic comedies, but it really should be. The plot is spot on for any modern woman who still hasn’t found “the one.” This movie makes you question whether you should try to date ex-boyfriends again. Will Anna Faris find love with one of her old boyfriends?
If you’re interested in other romantic movies, check out my blog entitled Romantic Time Travel and Alternate Reality Movies. Another extensive list is by Rotten Tomatoes, which highlights the top 200 romantic comedies of all time. There are lots to watch, and they will all warm your heart and teach you a lesson about love as well.
This is a great list! I’ve seen most of them but not all and can’t wait to finish the list!
Let me know if you have other favorites to recommend!