Best Romantic Comedies, or “My Whole Life Looks Like a Picture of a Sunny Day”

Brandon brought up the excellent idea of making lists of the best romantic comedies for Film Club. One reason this is an excellent idea is because most of the Film Clubbers revile romantic comedies. Every last one of them is younger than me, and I’m a widow besides. I don’t know what’s made them so cynical, other than the fact that there are a lot of terrible romantic comedies. I haven’t seen Friends with Benefits (because it looks bad), but I love that moment in the trailer when Mila Kunis shouts at a movie poster, “Shut up, Katherine Heigl, you stupid liar.” Who hasn’t felt that?

A good romantic comedy is a confection built around emotional truth. It may have some things to say about how to navigate romantic relationships, but the primary focus should be the wonder of falling in love, something that reminds the viewer of how amazing it is to have this dear friend you also get to sleep with. In the dailiness and difficulties of life, sometimes that reminder can be a hope and comfort. Nothing wrong with that. Also, I’m going to draw a line between movies like this and something like Breakfast at Tiffany’s, which is about falling in love and has some humor but is just overall more serious in tone. I think of a romantic comedy as having a sense of playfulness and fantasy.

So here’s my list. Per usual, I will look at this in two days and want to change something about it. Perhaps the whole thing.

10. Crazy, Stupid, Love
A bunch of Film Clubbers hate this movie, and I don’t want to get them all riled up, but this movie charmed me. I still like you haters.

9. Sixteen Candles
A few films in my top ten are about teenagers, and I think that’s because these are movies about first love, which is a lot more purely funny and awkward and wondrous. If you’ve never been in love before, you aren’t thinking, “Oh, no, here’s another person who’s going to die.” (This may be a fairly specific concern, but if you’ve gotten through your early 20s, you’ve probably found a substitute worry of your very own.) This movie is, admittedly, a nostalgic favorite, but I think Molly Ringwald is winning as a girl trying to connect with her crush in a world that is spiraling out of her control. This captures elements of being a teenager, but they’re human elements, too–loving and being exasperated by family and friends, feeling forgotten, continuing to try even though your every effort seems futile.

8. Nick and Norah’s Infinite Playlist
The book is so much better, but Michael Cera and Kat Dennings are sweet in this film, and the soundtrack is a favorite of mine. Parts of the film are hilarious (that girl with the gum!), but then there are moments when it captures what it is to begin to fall in love with someone, the simultaneous resistance and surrender. The film also has a great energy and spirit of fun.

7. The 40 Year Old Virgin
I love Judd Apatow’s work, and I enjoyed the heck out of this romantic comedy from a man’s perspective. This film made me laugh so hard I thought I’d stop breathing, but it made me tear up, too. The whole thing’s crazy, of course–much more comedy than romance–but this character’s extreme concern about not being good enough to love taps into fears most of us have about maybe not being good enough.

6. Some Like It Hot
This is a sentimental favorite of mine, a favorite of my aunt’s that I’ve watched with her more than once. Truly, it’s very funny, and I think a lot of films have tried to copy what this film did so effortlessly.

5. Reality Bites
One of my all-time favorites, about friends who have a little trouble sorting out their lives and the fact that they’re in love. My favorite moment is Ethan Hawke answering the phone, “Welcome to the winter of our discontent.” I think about answering the phone at the library that way all the time, although I’ve never done it. What I love about this movie is how it captures a growing awareness of how complicated the world is, how easy it is to get lost, and what friendship is really about.

4. Bridget Jones’s Diary
Best opening credits scene ever. Tells you everything you need to know about Bridget, and it is recognizable and funny at the same time. I am a huge Bridget Jones fan (one of the encyclopedia entries I submitted yesterday is on Bridget Jones), and it’s for moments like these. Zellweger, Firth, and Grant are all just brilliant together, and the Pride and Prejudice plot satisfies my Jane Austen fanaticism.

3. Clueless
Speaking of Jane, here’s the plot of Emma translated to a modern-day high school. I don’t have much in common with Alicia Silverstone’s Cher, but I completely relate to her desire to improve the world, the messes she gets herself into, and her failure to see what’s right in front of her. Charming and witty. Young Paul Rudd is great, too.

2. Chasing Amy
Another one from a male perspective, and the only one on the list in which the main characters don’t wind up together. (Does this make it not a romantic comedy? Discuss.) Kevin Smith has disappointed me in almost every film he’s made since this one, as here he shows such promise, giving us this hilarious, sharp, profanity-laden dialog that has a lot to say about the worth and complexity of friendship, sex, and love. I’ve always had the sense, too, that even though Holden and Alyssa’s story seems over at the end, that maybe it might really not be. That last scene is so well-played by Ben Affleck and Joey Lauren Adams. A lot is going on there that isn’t spoken, unusual in a Kevin Smith film.

1. When Harry Met Sally
I saw this movie in the theater when it came out in 1989. I was in high school, and even then I responded to this story about best friends who take a long and winding path to each other. I’ve seen it a bunch of times since, and every time I am hit by the film’s depiction of friendship and love, of what it is to truly see another person, to have that person see you, and to choose to keep looking and being seen. The film’s funny, of course, and I love the New York setting. I love Harry Connick, Jr. singing all those standards on the soundtrack, giving this the feel of something timeless. The interviews with elderly couples interspersed throughout the film are a thing of beauty, too, reminding us why love is worth a little trouble. Filmmakers keep trying to remake this movie, but no one’s managed it, and that’s fine. This is a movie I’m always happy to watch again.

Other films I considered for this list but ultimately decided were more something besides a romantic comedy: Breakfast at Tiffany’s, The Princess Bride, Juno, Groundhog Day, and My Best Friend’s Wedding. I feel like there were a few more, but I didn’t write them down, and now I’ve forgotten them.

The romantic comedy I hate the most: Pretty Woman.



  1. olivia
    Posted April 10, 2012 at 10:49 am | Permalink

    Apparently there are a ton of romantic comedies that I haven’t seen. But I do love Fever Pitch. And Music and Lyrics. And Notting Hill. And Runaway Bride. And Pretty Woman, in spite of the overall message/situation of the film.

    Ok, maybe it’s that I love Drew Barrymore and Julia Roberts.

  2. adrienne
    Posted April 10, 2012 at 11:12 am | Permalink

    Notting Hill and Fever Pitch were both on my list of potentials. I haven’t seen Music and Lyrics. I’ll have to add it to my Netflix queue.

  3. olivia
    Posted April 10, 2012 at 11:15 am | Permalink

    We own Music and Lyrics. You’re welcome to borrow it, with no pressure on returning it. It isn’t Downton Abbey, after all. :)

  4. Stephanie
    Posted April 10, 2012 at 12:02 pm | Permalink

    I am embarrassed to admit that I can’t resist a romantic comedy, so I can’t pick a favorite.

    I’m delighted to see you have Some Like it Hot, I had never really thought of it as a romantic comedy, but it certainly works as one.

    If you haven’t seen the rom-coms of the late 1950s and early 1960s, check them out…for the fashion alone–particularly Doris Day/Rock Hudson gems like Pillow Talk and Kate Hepburn/Spencer Tracy movies like Desk Set…yup, I’m old.

  5. adrienne
    Posted April 10, 2012 at 8:53 pm | Permalink

    Thanks, O. I can get it from Netflix at some point. I have a mile-long list of films to watch right now. Film Club and all that.

    Stephanie, Tammy loves Desk Set and keeps telling me to watch it. I’m going to have to move that one up in my queue, too, I suppose.

    And there’s nothing wrong with liking romantic comedies. Nothing at all.

  6. annette
    Posted April 11, 2012 at 11:25 am | Permalink

    _desk set_ is one of the best librarian movies ever! brilliant writing and such great performances. hepburn doing fifteen things at once while reciting a poem? gorgeous.
    do you think _harold and maude_ is a romantic comedy?

  7. Xandi
    Posted April 11, 2012 at 1:01 pm | Permalink

    I love Spencer Tracy and Hepburn in so many romantic comedies…also for a while I considered Arsenic & Old Lace to be a romantic comedy, despite the deranged murderer, Peter Lorre being creepy, and the two aunts cheerfully euthanising their elderly friends. Apparently, this is considered to be “dark” – not romantic.

  8. adrienne
    Posted April 11, 2012 at 2:41 pm | Permalink

    Annette, I haven’t seen Harold and Maude. That’s another one I’ll have to add to my list.

    Xandi, And also Arsenic and Old Lace, and I’m sure if you say it’s romantic, it must be so.

  9. annette
    Posted April 12, 2012 at 11:02 am | Permalink

    _harold and maude_ is my all-time favorite. good for what ails me in almost any situation…
    and i agree that, in my little world, AandOL *is* a romantic comedy, same as HandM…the romantic black comedy, perhaps?

  10. Posted April 12, 2012 at 9:02 pm | Permalink

    A Room With a View is not a romantic comedy, but it does have moments of humor. As movie romances go, it is one of my favorites, even though it is more about the necessity of nourishing the soul (not squelching it) than getting the two romantic leads together in the end. Clueless is up there, too– it’s the best Jane Austen adaptation out there!

  11. adrienne
    Posted April 12, 2012 at 9:36 pm | Permalink

    I have to put A Room with A View in my list, too. I’ll have to post about some of that the other Film Clubbers had to say: they’ve been making me reconsider my list (I knew they would!), and they’ve been adding even more titles to my list.

  12. Xandi
    Posted April 14, 2012 at 11:21 am | Permalink

    Your list has NO John Cusack movies…what kind of child of the 80s forgets John Cusack?!?

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