My Top 10 Favorite Romantic Comedies

I love a good romantic comedy. It’s one of my favorite film genres, even to the point that I’ve written a script. When they’re done well–that is, characters do things that make sense, they’re not filled with tropes, and there is both heartwarming romance and laugh-out-loud comedy–they make me incredibly happy.

After discussing some favorite rom coms with friends the other day, I decided to make my own top 10 list. As I did, I realized that I needed a key construct to help me define a romantic comedy, and I stumbled upon it in this old blog entry: In addition to making me laugh, a rom com must make me want to fall in love or appreciate the love I have. That’s the separating factor between many of the honorable mentions and those in the top 10 list.

Honorable mentions: What If, Midnight in Paris, Warm Bodies, High Fidelity, When Harry Met Sally, There’s Something About Mary, Knocked Up, Silver Linings Playbook, Hitch

10. Friends With Benefits: This is one of two similarly themed movies that came out at the same time, and I’m pretty sure this is the one I liked more.

9. When We First Met: One of several movies on the list with a time travel hook and a great twist.

8. The Proposal: I was quite surprised by how much I enjoyed this Ryan Reynolds/Sandra Bullock film.

7. What’s Your Number?: This was another big surprise. It’s funny, it’s sweet, it’s sexy, and it’s fun to watch Chris Evans and Anna Faris have a good time together.

6. My Big Fat Greek Wedding: This teeters on the edge of more comedy than romance, but in the end, it just works.

5. Notting Hill: Hugh Grant and Julia Roberts, plus a hilarious supporting cast? There are a few tropes in this one, but the comedy holds it together.

4. You’ve Got Mail: I really need to rewatch this to confirm that it belongs, but I felt that Tom Hanks and Meg Ryan needed to be on the list somewhere. I don’t think Sleepless in Seattle holds up to dissection, but I’m pretty sure this one does.

3. Sleeping With Other People: There’s something very modern about this movie that pushes it onto the top of the list. It’s really good, and it’s on Netflix–check it out.

2. Groundhog Day: Does this belong on a romantic comedy list? Maybe not. But romance and comedy are central points of the movie, and I love it, so it’s here.

1. Definitely, Maybe: I absolutely love this movie. It’s funny, it’s heartwarming, it’s real, it’s pretty to look at…I highly, highly recommend it.

Listing these movies makes me want to watch all of them, and I haven’t seen several of them in years. That’s one of the great things about romantic comedies, in my opinion: There’s a certain level of comfort to them that I really enjoy.

What are your favorite romantic comedies?

PS. If you want to know why Love Actually isn’t on the list, I have reasons.


19 Responses to “My Top 10 Favorite Romantic Comedies”

  1. My favorite go-to is The Holiday. Also Mamma Mia gives me warm fuzzies despite the questionable vocal talent of a couple actors.

  2. dmvp says:

    One of my daughter’s favorite rom coms is called, “About Time”. I’m curious as to if you’ve watched it, and if so what you thought of it.

  3. Ray B says:

    This is a bit self serving, but back when I was actually a film critic one of the pieces I was most proud of was a 6 part series on what I considered the greatest Romance movies of all time (this was a decade ago). Now this isn’t just romantic comedies…it’s just Romances in general, but I still think it’s a great list for people to check out:

    25. A Room With a View (1985)
    24. Pillow Talk (1959) and its spiritual modern successor Down With Love (2003)
    23. Chasing Amy (1997)
    22. Roman Holiday (1953)
    21. Punch-Drunk Love (2002)
    20. Sweet and Lowdown (1999)
    19. Out of Africa (1985)
    18. Sabrina (1954 and 1995 versions are both great)
    17. Forget Paris (1995)
    16. When Harry Met Sally (1989)
    15. Secretary (2002)
    14. Amelie (2001)
    13. From Here to Eternity (1953)
    12. Pillow Book (1996)
    11. The American President (1995)
    10. The Princess Bride (1987)
    9. Lost in Translation (2003)
    8. Breakfast at Tiffany’s (1961)
    7. Edward Scissorhands (1990)
    6. Vertigo (1958)
    5. Eternal Sunshine of the Spotless Mind (2004)
    4. The King and I (1956)
    3. The Diary of Anne Frank (1959)
    2. Moulin Rouge! (2001)
    1. and of course, Casablanca (1942)

    Some of those might seem like really weird choices but I stand by them to this day. I guess if anyone were interested in said explanations you could see them here! (https://drive.google.com/file/d/1niBqTl38mxHSD6WoGMp3oU8druiKXlP1/view?usp=sharing)

  4. Candy Mercer says:

    Must watch The Big Sick! I love the genre, but it is really hard to do something fresh, with twists you do not see coming. Bonus points as it takes place in the comedy world. Just amazing though. I bet you will cry! Have Biddy close for emotional support!

    • Jamey Stegmaier says:

      Oh yes, I’ve seen The Big Sick! It’s an interesting movie because it’s not really a romance–it’s much more about the relationship between the man and the girl’s parents. I’d call it more of a dramatic comedy than a romantic comedy.

  5. Neilan Naicker says:

    Great list! Have you seen About Time? Seems like it’d be right up your alley.

  6. Brad Wilson says:

    Though it’s not as funny as some of these I have always loved the movie Serendipity. It has whimsy, charm, and is believable. That makes it a winner for me!

  7. Jay Wilde says:

    I’m not a big fan of Romantic Comedies, but my favourite is Keeping the Faith (Jenna Elfman, Ben Stiller, Edward Norton, Directed by Norton). Next on the list would be Fools Rush In. Third is a crossover with your list is My Big Fat Greek Wedding. Part of what the last two have in common is the theme of very different families integrating. And I find the characters experiencing the their partner’s family the best part.
    Also, you point out that MBFGW is on the edge of just comedy, and that is probably why I like Keeping the Faith. It is Ben Stiller at his best, and it shows the Norton can do comedy as well as the more serious movies that I think he was best known for in his early career (but then again he was in Death to Smoochy).
    I love Groundhog Day, and would not have thought of putting it on a list like this. But if it goes on the list, its probably second best, just as in your list.

  8. Charles Dionne says:

    Not my favorite genre but here’s a few I enjoyed that haven’t been mentioned:
    – 500 Days of Summer
    – Forgetting Sarah Marshall
    – 10 Things I Hate About You
    – The Wedding Singer
    – Once (more of a romantic musical than comedy but I love it)

    and +1 for Amelie. Fantastic movie!

    • Jamey Stegmaier says:

      Thanks for sharing, Charles! Of those, I think I’ve seen Forgetting Sarah Marshall the most. I like 500 days of Summer, particularly some of the non-traditional cinematography. I need to rewatch 10 Things I Hate About You.

  9. Cierra Edwards says:

    How to Lose a Guy in 10 Days and 10 Things I Hate About You are a couple of my favorites.

    • Jamey Stegmaier says:

      As I created this list, I looked at other lists on the internet, and many of them mentioned How to Lose a Guy in 10 Days. I haven’t watched it in a while, so I need to give it another try.

  10. […] I really, really love this movie. If you like romantic comedies so much that you nitpick about the tropes in them, I truly think you’ll enjoy Isn’t It Romantic?. I think it may have moved into the #2 spot on my list of top 10 favorite rom coms. […]

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