Seven Underrated Romantic Comedies

For at least ten years, I’ve been reading about the demise of the romantic comedy (aka the rom-com). I even blogged about how there don’t seem to be many rom-coms in theaters and how many recent attempts are, well, not very good. Katherine Heigl made a living for a while playing up-tight career women who could only find love once they’d been humbled in films like The Ugly Truth and 27 Dresses (and even Amy Adams and Jennifer Lopez got in on the act in Leap Year and The Back-Up Plan, respectively).

The past 20 years of film have seen rom-coms that are pretty but in which the romance isn’t compelling (Letters to Juliet), comedic movies in which the romance is compelling but not the focus (Pitch Perfect, Easy A, Bridesmaids, Monsoon Wedding), dramatic films with happy ending romances (The Young Victoria and a host of other biopics), and romance-focused flicks without happy endings (Bright Star, Once, (500) Days of Summer, In the Mood for Love, Moulin Rouge). I started my Fine Romance Friday posts in response to the trend, but not all of the movies I’ve written about are rom-coms and many are older films made before the mid 1990s.

So in that spirit, I want to provide a list of what I see as the most underrated rom-coms of the last 20 years or so. I wouldn’t argue that these are very best rom-coms made in that period, but everyone knows about Amelie and The American President (right?). I’m not going to do full write ups, but I’ll drop in the trailer, link to IMDB, and write a paragraph about why you should check it out. I organized these chronologically. Let me know what I’ve missed in the comments!

One Fine Day (1996)

This is the movie that inspired this post. The premise is that single parents George Clooney and Michelle Pfeiffer are forced to spend the day together with their kids when they’re both late dropping them off for a school field trip. I caught part of it on TV the other day and remembered again how funny, honest, and sexy it is. If anything, I appreciated it more now as a parent than I did as a high schooler when it released. While everyone knows about Clooney’s sexy romance with Jennifer Lopez Out of Sight (1998) and while more people should know about Pfeiffer’s romantic turn in Frankie and Johnny (1991), One Fine Day remains my favorite rom-com featuring these two ubiquitous actors.

But I’m a Cheerleader (1999)

This movie is sarcastic, snarky, and subversive. But it’s also surprisingly sweet and I have no idea why more people haven’t seen it. Natasha Lyon (the titular cheerleader) comes out to her parents who don’t take the news well, going so far as to pack her off to a camp intended to “fix” her. Things don’t go quite as planned when she falls for Clea DuVall. This one is only recommended if you like camp in the John Waters style. If you do, however, this is lesbian romance you’ve been looking for.

Keeping the Faith (2000)

I wrote about this one before, so all I’ll say here is that it’s a luminous love triangle featuring a priest, a rabbi, and their childhood friend wonderfully grounded in late 90s New York City. It’s funny, smart, and modern–and almost no one has seen it.

Casanova (2005)

The obvious Heath Ledger movie for this list would be 10 Things I Hate About You (1999), but I think that one is too well known, so I’m going with this. It’s pretty obviously an attempt to capture in a bottle again the spirit of Shakespeare in Love (1998)–a film I really like and that is easily the most critically acclaimed rom-com of the period–but Casanova is also fun in its own right. The basic plot: the doge issues an edict that the notorious seducer must marry or face expulsion from Venice. Meanwhile, a young bluestocking agitates for women’s rights in disguise as a man. They come together with explosive results. The film’s a silly, charming love letter to Venice. And it’s tons of fun.

Forgetting Sarah Marshall (2008)

When I saw this in theaters on opening day, I had no idea that it begins with one of the funniest and most explicit scenes of male nudity in mainstream American film. And it’s freaking hilarious. The basic premise is that sad-sack composer Jason Segel gets dumped by his famous actress girlfriend (Kristen Bell). He goes to Hawaii to nurse his broken heart where he meets hotel employee Mila Kunis; they have a fling, but could it be something more? No ground gets broken here, but the performances are very funny and Hawaii looks gorgeous.

Going the Distance (2010)

Drew Barrymore has made a fair number of romantic comedies and most of them are pretty good. (And Ever After is GREAT.) But in trying to choose one of her rom-coms that’s lesser known, I’m going with the long-distance relationship romance Barrymore made with then-boyfriend Justin Long. The set-up: Barrymore and Long meet-cute at a NYC bar. She’s a grad student in town doing a newspaper internship; he’s a peon at a record label. They have a six-week fling and then impetuously decide to try to maintain their relationship when she returns to San Francisco. When I first saw it I laughed hard (particularly at Christina Applegate who plays Barrymore’s sister) but I was struck also by how well it captured the here-and-now and how honest it feels about the good and bad things about millennials in love. I almost went with Barrymore’s duet with Hugh Grant (Music and Lyrics) or the roller derby romance she produced (Whip It; it’s good!), but in the end, I’m sticking with Going the Distance.

Beyond the Lights (2014)

I keep going back and forth between director Gina Prince-Bythwood’s Love & Basketball (2000) and Beyond the Lights, but the more recent film won out. (You should probably see them both.) More than any recent release, Beyond the Lights feels like a romance novel on screen to me: Gugu Mbatha-Raw is a young singer on the rise with a controlling mom and an image she doesn’t love. Then she falls for an off-the-charts sexy cop Nate Parker. It’s a lovely story of self-actualization with a nice political dimension. And the music is wonderful. See it.

15 thoughts on “Seven Underrated Romantic Comedies

  1. There is something to the demise of the rom-com, isn’t there? I have barely seen a movie in the last five years (since I had my son and started writing in earnest). The odd time I sit down to browse Netflix or iTunes (and I’m almost always looking for a rom-com…what can I say, I’m predictable), I think to myself, well the upside of never going to the movies means I’ll have tons to choose from. Yet I can never seem to find anything that grabs me. I have been told by others that there are some great Bollywood films on Netflix that are basically category romances, so I want to check those out too. Anyway, long rambly paragraph here, but thanks for the post!

    1. I’m definitely in the same boat. We see about three movies a year in theaters and everything else is after the fact. And television definitely seems more compelling for my limited viewing hours (and making a commitment to an hour-long episode is easier than to a 2.5 hour long movie). Add in that if you like rom-coms, there just aren’t that many of them and most of what’s out there is mediocre.

      I probably should have put this in my original post, but the films that I see as being the canonical rom-coms of the past 20 years are Shakespeare in Love, Notting Hill, You’ve Got Mail, 10 Things I Hate About You, Love Actually, Something’s Gotta Give, and Ever After (ETA: oh, and probably Amelie, The American President, and Sweet Home Alabama too). These films seem to be on cable TV repeats frequently, most Americans who like rom-coms have seen them, etc. I don’t love all of these movies, but I can see how/why they’ve earned cultural currency–and it’s interesting that they’re pretty much all from 1995-2005, with very little in the past decade.

      So yeah, the decline of the rom-com seems real to me. And since women are fronting big blockbusters in ways they didn’t in the past (Twilight, The Hunger Games, 50 Shades of Grey, etc.), it’s also pretty strange. We need more and better rom-coms, Hollywood!

      1. Thanks for this great list, Emma! I’ve seen the canonical rom-coms but not the ones on your list and had basically given up on the genre (too many disappointments), so I’ll be checking them out for sure.

  2. Clarissa: thanks! If you watch any of them, let me know. This is a pretty idiosyncratic list and so it’s possible my taste is just strange. ; )

  3. I’ve only seen one of these movies but I love One Fine Day and never get tired of talking about it. It must be the fantasy?
    That your horrible day can turn into magic. That you get to fall in love with George Clooney or Michelle Pfeiffer. And that it can all happen in one day.
    Films like this keep us breathing, keep us hoping. And Michelle Pfeiffer has never been more gorgeous. I am so in love with her in this film. It’s a great movie, a gift to the heart.

    1. Rom-coms are inherently fantasy, but I think what older rom-coms tend to have going for them is that the fantasy seems accessible and they aren’t as cynical about emotions. Whenever I watch movies from the 70s, 80s, and early 90s, I’m always surprised how “normal” the characters’ jobs are (though of course there were many fantastically rich people in Hollywood golden age cinema). In many of today’s movies, the life style is already so nice, it seems very disconnected from how I at least live. Add in the meet-cute and the perfect love and it’s basically fairy tale.

      Also, there’s definitely been a rise in gross-out comedies and one of these (Forgetting Sarah Marshall) definitely has elements of that. Now gross-out comedies can have sweet cores–the romance between Steve Carell and Catherine Keener in The 40-Year-Old Virgin, for example–but it’s a pretty jaded genre. This just doesn’t make for good romance. We’re going to have to get less skeptical as a culture for the rom-com to come back.

  4. I absolutely recommend CHASING LIBERTY, with Mandy Moore and Matthew Goode. It’s funny, sweet and a total fave. Also WHAT’S YOUR NUMBER, which features Anna Faris and a frequently naked and adorable Chris Evans. And I was surprised by how much I enjoyed Justin Timberlake and Mila Kunis in FRIENDS WITH BENEFITS.

    1. Chasing Liberty looks great. I love political romance and Matthew Goode is such an appealing actor but I strongly disliked Leap Year. (If only because it gets Irish geography so, so wrong.) I’ll have to check all of these out!

  5. Fun list, Emma, and I’ve only seen a couple of these myself. I also loved What’s Your Number, as Suleikha suggested, as well as She’s Out Of My League (I think Jay Baruchel is adorable). I also highly recommend The Switch. Its questionably disturbing premise aside, it’s a really sweet romcom that’s almost more about Jason Bateman’s relationship with Jennifer Aniston’s son, than with Aniston herself. It’s really touching. Both of these movies threaten to go to really embarrassing, humiliating places, but end up being not as cringe-worthy as you think.

    1. Me too! I feel like Beyond the Lights has gained more viewers since it’s been on Netflix for a while, but I wish more people had seen Going the Distance.

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