Sage’s Top 15 Romantic Comedies

Happy Endings I love rom-coms

Posted by Sage

Romantic Comedies – TRUE romantic comedies – are a lost genre. But, there are enough gems in the years of their existence (let’s say 1934-2004) to make choosing and ranking a Top 15 a completely maddening exercise.

As Kim mentioned in yesterday’s post, we are dipping a toe in the world of podcasting along with fellow likers of liking things, Jenn and Jaime. There’ve been brutal cuts and last minute re-categorizations, but, in the end, each one of us all has finalized a list of our favorite rom coms. (Kim’s list and Jenn’s list are up, Jaime’s is coming soon.) These lists will give us the meat for our first discussion. The process alone has sparked much debate on Twitter. What qualifies a film as a rom com? Can it be an ensemble? How dark can a movie go before it’s labeled a romantic drama or just pure romance? We all have different definitions and, thanks to a 15-year (yikes) age range, emotional connections to different films. Check out my list below and stay tuned for more information on our first episode!

15) Much Ado About Nothing (1993)

Much Ado a stuffed man

Benedick: I do love nothing in the world so well as you. Is not that strange?

Some might consider it sacrilege to classify Shakespeare in this way, but the defiant, sparring lovers Beatrice and Benedick are the mother and father of every rom com couple that came after. What movie on my list doesn’t owe a debt to B&B’s sexually-charged bickering or the plot their budinski friends concoct to get them together?

As the dearly departed Roger Ebert said in his review of the 2012 adaptation, “Beatrice and Benedick steal the show, though, in this version and in every version I’ve seen, on film or on stage. Nobody has informed the two of them that they are not the leads, that their romance is the subplot….Any rom com we see today is haunted by the arguing defensive love-mad ghosts of Beatrice and Benedick. The two are so equally matched, so dazzlingly verbal, so witty, so ‘self-endeared’ (as Hero calls Beatrice), and totally obsessed with each other that, frankly, who else could put up with either of them?”

The three pairs of actors I most relate to these roles all had some prior relationship with each other before taking them on. And it MUST be more fun to play one of these classic characters opposite someone close to you. For David Tennant/Catherine Tate and Alexis Denisof/Amy Acker, it was a friendly, working relationship. And for Kenneth Branagh and Emma Thompson, my ULTIMATE Benedick and Beatrice, it was a marriage. And they were perfect. Like Kim, I’m still a little devastated that they broke up, but feel lucky to have gotten these performances out of them before they did.

14) Brown Sugar (2002)

Brown Sugar she was old school

Chris: I’m not the Humphrey Bogart in this. I’m the Peter Lorre. I’m the sidekick character. You the Humphrey Bogart. You had your opening. You know what I’m saying? She wanted you to stop her from marrying the old dude, but you let it ride, you know? Same thing Bogey did, man. You’re the same dude.

Dre: Man, don’t be dissin’ Humphrey Bogart, man.

Chris: Why not?

Dre: ‘Cause he’s Humphrey Bogart. He’s the man. Yo, he was fightin’ a war. That’s what they did back then.

Chris: You know what he needed to do back then? He needed to stop fine-ass Ingrid Bergman from gettin’ on the plane with the corny dude. And then, he gonna walk off in the fog with some other dude. Come on, man. With another dude, in the fog? Come on.

Sydney and Dre are childhood friends who grew up in the formative years of hip hop. As adults, he strikes out from a sell-out record label to start his own and find the “real deal,” while she takes on an editor position at a music magazine. Also, they’re completely in love with each other and very, very shoddily pretending to still be just friends. Taye Diggs are Sanaa Lathan have amazing chemistry, and good god, they’re both terribly attractive. Their sidekicks are Mos Def and Queen Latifah, respectively – two of my favorite rom com wingmen. The killer soundtrack is packed with old-school hip hop and the film cleverly parallels Syd and Dre’s love affair with that art form to their relationship with each other. It’s equal amounts sweet and sexy, a proportion that few films get right.

13) Friends with Kids (2011)

Friends With Kids let me fuck the shit

Jason: You think that we don’t love each other? You know, I have loved this girl for nineteen years, Ben. That is fully half my life. I know everything there is to know about her. I know the mood she’s in when she wakes up in the morning – always happy, ready for the day. Can you imagine? I know that she is honest; she won’t even take the little shampoo bottles from the hotel room, or sneak into the movie theater for a double feature. She always buys a second ticket. Always. I know that we have the same values, we have the same taste, we have the same sense of humor. I know that we both think that organized religion is completely full of shit. I know that if she is ever paralyzed from the neck down, she would like me to unplug her – and I will. I know her position on just about everything, and I am on board. I am on board with everything about her, so you tell me, Ben. What better woman could I have picked to be the mother of my child?

There was some discussion on Twitter about whether or not this film qualifies as a romantic comedy. I say yes, and not just because my list was seriously lacking films made post-2004. Firstly: it IS an ensemble piece (with an EXCEPTIONAL cast), but Jason (Adam Scott) and Julie (Jennifer Westfeldt) and their evolving relationship are absolutely the main focus. Secondly, there is an element of drama with the crumbling marriage of Ben (Jon Hamm) and Missy (Kristen Wiig), but the movie is primarily a comedy about sex, love, and raising babies. Friends with Kids, I deem thee a rom com.

Jason and Julie are platonic besties who both have ticking biological clocks (yes, he has one too – this is why I love this movie) and no life partners but each other. They decide to just go ahead and have the kid together, which of course brings deeper feelings and confusion about those feelings to the surface. Friends with Kids is hilariously funny, but also perceptive. Watch how having children can either bring a couple closer together (as with Maya Rudolph and Chris O’Dowd) or magnify all the problems that are already there. Jason and Julie think they’re too clever to let their kid entangle them, but they can’t outrun themselves.

Other perks of this film include the changing seasons of New York City as a backdrop and Head Over Feels favorite Adam Scott as a romantic lead who just wants to fuck the shit out of you. What’s not to love?

12) My Best Friend’s Wedding (1997)

My Best Friend's Wedding he's just so wonderful

George: It’s amazing the clarity that comes with psychotic jealousy.

It’s been almost 20 years, so it’s easy to forget just how special this movie is. Because of the ending, I almost considered not including in the romantic comedy pantheon. But truly, My Best Friend’s Wedding is what happens when all the elements of a classic rom com are there: the guy, the girl, the scheme, the best friend, and the rival, but the timing is off. What if you just got there too late?

I’ve never liked Julia Roberts more than as jealous, manic Julianne, chain smoking cigarettes in her tortoiseshell sunglasses and oversized suits. “I’ve got exactly four days to break up a wedding, steal the bride’s fella and I haven’t one clue how to do it. He was in love with everyday for nine godddamn years. Me!” She’s single-minded and ruthless, but we fall for her anyway. And I have no doubt in my mind, that had Rupert Everett been a straight actor playing standout romantic comedy best friend George, he would have gotten an Oscar nomination. (For some reason, the Academy doesn’t consider gay thespians playing gay characters to be actually ACTING.) Dermot Mulroney’s Michael is a little dreamy, but he’s also kind of a putz. We start to realize halfway through the film that he might not have enough imagination to be a real partner to Julianne. The cheerful, people-pleasing Kimmie (Cameron Diaz) is more his speed. I do have some feminist complaints about how Kimmie (dear, candy-covered, chocolate-coated Kimmie) was forced to drop out of school to follow Michael around and vilified when she showed some reluctance, but it’s not even as distressing as Michael and Jules’s pact to marry each other if they’re still single at 28. TWENTY-EIGHT.

My Best Friend’s Wedding is slightly old-fashioned and just a bit zany. We don’t have enough musical numbers in non-musical movies these days. It’s got the most well-used instance of the single f-bomb allowed in PG-13 films. (“He just came in for a few hours to, uh, fuck me!” “Huh. Takes a few hours.”) And in what could be a depressing ending, the girl who didn’t get the guy is swept off her feet by her GBF, who reminds her that, “There may not be marriage. There may not be sex. But by god, they’ll be DANCING.” Words to live by.

11) Love Actually (2003)

Love Actually it's my favorite time of day

Mark’s posters: But for now, let me say …Without hope or agenda…Just because it’s Christmas…And at Christmas you tell the truth…To me, you are perfect…And my wasted heart will love you…Until you look like this…Merry Christmas.

My fellow fans of this movie know the feeling. You might wake up one morning or come home one night and just know – it’s a Love Actually day, and nothing else will do. Again, the categorization of this one might be put into question by the ensemble structure or the more heartbreaking storylines, but Love Actually must be on this list simply because of how it makes me FEEL. It’s like a mug of hot chocolate (with extra marshmallows) for my soul. Even in its darkest moments, Love Actually is full of hope, which is how I can watch Emma Thompson cry in her bedroom to Joni Mitchell before wiping her tears and taking her family to the school play over and over again without offing myself.

10) While You Were Sleeping (1995)

While You Were Sleeping kiss

Peter: I’m making a clean start with Lucy. She is – She is – She…What is she? She’s…

Jack: I’d say that she gets under your skin as soon as you meet her. She drives you so nuts you don’t know whether to hug her or, or just really arm wrestle her. She would go all the way to Europe just to get a stamp in her passport. I don’t know if that amounts to insanity, or just being really, really… likable.

Peter: …no, that’s not it.

The modern rom com died a slow and painful death at the hands of cynicism and mean-spiritedness. While You Were Sleeping doesn’t even acknowledge cynicism as a concept. Even self-centered Peter has a good heart. (“You give up your seat every day on the train.” “That’s not heroic.” “It is to the person that sits in it.”) It’s just lovely. And can I get an amen for a romantic comedy heroine who doesn’t run a magazine or head up a corporation or work in a gallery? (I don’t know anyone who works in a gallery, but Hollywood would have you believe that every other New Yorker does.) Lucy Eleanor Moderatz takes tokens at the L, lives in a shitty apartment, and wear thrift shop sweaters. WYWS is as much about an achingly lonely girl finding a family as it is about two people falling in love. Baby Sandy Bullock (her voice is so YOUNG in this movie) is just heartbreaking in this role, especially when she confesses the truth to the family, essentially giving them up. Bill Pullman is swoon-inducing as stand-up guy Jack. (Take a second and remember how he says the word “likeable” in the dialogue above….I KNOW.) He reminds me a little of Jimmy Stewart – no higher praise. Every member of the Callahan family hits the mark and they’re especially endearing in the group scenes where they’re perpetually talking over each other. And if all these reasons aren’t enough to prove that While You Were Sleeping belongs on this list, I’ve got two words for you: Joe Jr.

9) 13 Going on 30 (2004)

13 Going on 30 I've always loved you

Jenna: You want to know a secret?

Matt: Yeah.

Jenna: You’re the sweetest guy I’ve ever known.

Jennifer Garner has some serious range and I would never suggest she limit herself. But 13 Going on 30 proves that she can do screwball comedienne with an emotional center. I want to see her in a role like this again soon. This movie wouldn’t work without her performance. In the hands of another actress, a 30-year-old woman acting like a teenager could get really old, REALLY quickly. But Jenna Rink is as bright and cheerful as her bubblegum wardrobe. (“Who’s your daddy?” “Wayne Rink!”) Mark Ruffalo is another formidable actor, and I’m delighted that occasionally takes on fluffy parts like this one. And as usual, Judy Greer is comic genius as lifelong mean girl Lucy. 13 Going on 30‘s other pros include one of my favorite rom com montages and a super-fun “Thriller” dance number. It also introduced me to Razzles, which are both a candy and a gum.

8) Only You (1994)

Only You fainting

Faith: How could you do this to me?

Peter: Because I’m in love with you!

Faith: Ha! What kind of an excuse is that?

I remember watching Only You over and over again with my mom and being struck by the magic of it all. At 11 years old, Faith Corvatch gets the name of her soulmate from a Ouija board. 14 years later and 10 days before her wedding to a boring podiatrist, the mythical Damon Bradley calls. Faith drags her sister-in-law Kate (Bonnie Hunt, quintessential rom com best friend) to Italy to track him down. Traveling shoe salesman Peter Wright overhears a conversation and pretends to be Damon for long enough to get Faith to fall for him. He confesses the truth and joins the search, hoping that she’ll eventually come to her senses and see her destiny right in front of her.

This movie has STYLE, which is so rare these days. EVERYTHING about Marisa Tomei’s Faith is to-die-for, from her pixie cut to her show-stopping wardrobe and classic accessories. And while Robert Downey Jr. only gets better with age, there’s something to be said for baby RDJ, who is in full cute effect here. Put them against the backdrop of the Italian countryside and you’ve got all the ingredients for an uber-romantic movie about fate, soulmates, and how to find them.

7) The Cutting Edge (1992)

The Cutting Edge toepick

Kate: You are an immature asshole of the lowest order.

Doug: If it was forty below and that button meant the difference between a long satisfying life and a cold horrible death from hypothermia, I still wouldn’t give you the satisfaction. Skate.

Full disclosure: The Cutting Edge has a special place in my cold, dead heart, because I spent much of my young life in an ice rink. I was nine years old when I joined a group of my skating friends and their moms to see this in theaters. I didn’t get any of the “foreplay” jokes, but I did fall immediately in love with Kate, Doug, and the Pamchenko.

This film has one of the FINEST rom-com screenplays you’ll find outside of the Ephron canon. It was writer Tony Gilroy’s first feature, and he went on to pen Michael Clayton and the Bourne series, among others. It’s forever quotable (“Toepick!), and never talks down to its audience. I come back to it over and over again, and the bits are still solid. (“I been doin’ a little figure skating.” “…finger paintin’?”) And though Kate Mosely (Moira Kelly) is prickly, she’s not your average movie shrew. Kate’s bitchiness is vulnerable, defensive, and real. It’s what’s keeping her from success AND what’s gotten her as far as she’s come. And while it frustrates Doug (D.B. Sweeney) to a degree, he also respects her drive as a fellow athlete. He’s the perfect foil for her – just as determined, but less rigid. They spar like Beatrice and Benedick, but, as they always do, tequila shots draw out the truth. All they needed was a little flip.

6) Bridget Jones’s Diary (2001)

Bridget Jones the most incredible shit

Bridget: Did I really run round your lawn naked?

Mark: Oh, yes. You were four and I was eight.

Bridget: Well, that’s a pretty big age difference. It’s quite pervy really.

Mark: Yes, I like to think so.

To call Pride and Prejudice a romantic comedy would be a mistake. It’s a comedy of manners, as much about family, property, and class as it is about romance. But in the hands of Helen Fielding, Lizzie Bennet becomes Bridget Jones, wanton sex goddess with a very bad man between her thighs, and here we are. We’re used to seeing the schlubby dude getting the out-of-his-league hot lady, but the romance between spectacularly flawed Bridget and buttoned-up dreamboat Mark Darcy gives us all hope. Renee Zellweger committed so strongly to this part. There’s zero vanity in her performance, and I’m not referring to the extra weight she put on for it. She happily makes a fool out of herself at every turn. Hugh Grant has been outed very publicly as a bit of a cad, and his Daniel Cleaver is deliciously corrupt. And siiiiiigh…Colin Firth. I love that he took on a part that was based on his performance as Fitzwilliam Darcy who in turn was the inspiration for THIS character (#metametametametaaaa). Who among us has not dreamt of Mark Darcy telling us that he likes us, just as we are?

5) The Apartment (1960)

The Apartment shut up and deal

C.C. Baxter: Miss Kubelik, one doesn’t get to be a second administrative assistant around here unless he’s a pretty good judge of character, and as far as I’m concerned you’re tops. I mean, decency-wise and otherwise-wise.

Last year, I attended the only New York edition of director Jason Reitman’s classic movie “Live Read” series, and now I am desperate for Emma Stone to star in a remake of this film. She and Paul Rudd played the roles originated by Shirley McLaine and Jack Lemmon. Paul was great, as usual, but Emma was a revelation. Billy Wilder’s The Apartment inspired Jerry Maguire, another one of my favorite films, and Broadway musical Promises Promises. The material’s pretty risque for a classic film: office drone C.C. Baxter climbs the rungs of his company by lending his apartment to his cheating bosses and their mistresses. One of those mistresses is elevator operator Fran Kubelik, who tries to kill herself there when Mr. Sheldrake (Fred MacMurray at his most heartless) backs off of his promise to leave his wife for her. Baxter nurses her back to health, and guiltily realizes how easy he’s made it for the suits to take advantage of these women. Most of the climax of the film takes place within the apartment and there’s no grand gesture beyond a confession during a game of gin rummy, which is then followed by one of the most classic final lines in movie history.

“Did you hear that, Miss Kubelik? I said that I absolutely adore you.”

“Shut up and deal.”

4) Return to Me (2000)

Return to Me poster

Bob: Elizabeth and I were married by the time we were twenty and we’d been going out since we were fifteen so this may sound a bit juvenile but…can I hold your hand?

Had this screenplay (co-written by co-star Bonnie Hunt) been shopped around in 2013, it never, ever would have been made. And that would have been a major loss to the rom com canon. Return to Me is guileless and unapologetically sentimental. Bob (David Duchovny, forever in my Top 5) loses his wife in a car accident. Meanwhile, Grace (Minnie Driver) waits on the transplant list for a healthy heart to be available. You can guess where it goes from there.

The schmaltzy plot is elevated by endearing characters and sweetly clever dialogue. (“Think of riding a bike, and going to Italy, and dating REALLY handsome men. THAT, I know, has to happen for one of us.” “I’m getting a new heart, not a new ass.”) Bob’s grief for Elizabeth is brutal, and without that gut punch, his re-entry into life wouldn’t be as affecting. The elements are simple but perfectly rationed, from the soundtrack of standards to the precious greek chorus of adorable oldsters. A new classic, all around.

3) Sleepless in Seattle (1993)

Sleepless in Seattle hands

Annie: Now that was when people KNEW how to be in love. They knew it! Time, distance… nothing could separate them because they knew. It was right. It was real. It was…

Becky: A movie! That’s your problem! You don’t want to be in love. You want to be in love in a movie.

Where is my generation’s Tom Hanks? Or young Meg Ryan? Or, most egregiously missing, Nora Ephron? The truth is, none of them can ever be duplicated or replaced. Thank goodness we have You’ve Got Mail and my #3 pick, Sleepless in Seattle, to keep coming back to. I’ve talked a lot about my favorite rom com heroines in this list, but may I submit Sam Baldwin for favorite rom com hero? Sure, he’s sweet as pie, and that monologue about how he fell in love with his wife is as moving a speech that’s ever been on film. But Sam is also realistic and wary. His relationship with Jonah is an unlikely father-son movie dynamic. He talks to his kid like an adult, probably because he needs an equal partner to help him deal with his loss. Doesn’t make it any less hilarious. (“Didn’t you see Fatal Attraction?” “You wouldn’t let me!” “Well I saw it, and it scared the shit out of me! It scared the shit out of every man in America!”) Sleepless is a fairytale, but it’s also funny as hell. That was Nora’s genius.

And if we ever do a list of favorite rom com SCENES, you better believe I will be including Tom Hanks and Victor Garber tearfully describing The Dirty Dozen.

2) Bringing Up Baby (1938)

Bringing Up Baby let's play a game

David: Now it isn’t that I don’t like you, Susan, because, after all, in moments of quiet, I’m strangely drawn toward you, but – well, there haven’t been any quiet moments.

I’m a total Cary Grant fangirl. There’s plenty of Cary to choose from in the romantic comedy genre, but my favorite is this screwball romance co-starring the irrepressible Katherine Hepburn. He plays dorky paleontologist David Huxley, who’s engaged to – and kept on a short leash by – his assistant, Alice Swallow. In pursuit of a grant, he gets caught up in the life of flighty heiress Susan Vance and her pet leopard, Baby. Needless to say, hijinks ensue. Describing those hijinks will do it no justice, so, if you’re never seen this film, just trust me and seek it out now.

1) When Harry Met Sally (1989)

When Harry Met Sally 12 years and 3 months

Sally: Well, if you must know, it was because he was very jealous, and I had these days of the week underpants.

Harry: Ehhhh. I’m sorry. I need the judges ruling on this. “Days of the weeks underpants”?

Sally: Yes. They had the days of the week on them, and I thought they were sort of funny. And then one day Sheldon says to me, “You never wear Sunday.” It was all suspicious. Where was Sunday? Where had I left Sunday? And I told him, and he didn’t believe me.

Harry: What?

Sally: They don’t make Sunday.

Harry: Why not?

Sally: Because of God.

Picking up the mic that Kim dropped, I’ll elaborate on why When Harry Met Sally is the greatest romantic comedy ever to be created. Every aspect of this film is perfection. Casting: Billy Crystal, Meg Ryan, Carrie Fisher, and Bruno Kirby (RIP). Direction: Rob Reiner. Flawless screenplay: Nora Ephron. Setting: New York. Music: Marc Shaiman and Harry Connick Jr. All the pieces are there, but it’s that ineffable magic that ties all of it together. It’s the perfect storm of charm. Ranking the rest of this list wasn’t an easy task, but there was never a doubt in my mind that When Harry Met Sally would be #1. My only problem was choosing which piece of dialogue would be my favorite line! There isn’t an unnecessary WORD in this script. (Certainly not “baby fish mouth,” which did sort of sweep the nation.) It’s masterful. I could watch this movie every day for the rest of my life and never be sick of it. Maybe I just will.

What do you think, readers? Did Kim and I miss any of your favorite rom coms? Would you argue that the genre IS still alive in our times? Get your comments in now so we can address them in our still nameless podcast series!

Liked it? Take a second to support HeadOverFeels on Patreon!

21 thoughts on “Sage’s Top 15 Romantic Comedies

  1. I’d say the genre is alive but you have to look harder for the good ones. Like Warm Bodies from this year is straight up rom-com with a bit of action in the climax and it was freaking delightful as hell.

    • HeadOverFeels says:

      I’m a huge fan of Warm Bodies, and I do think it’s to some degree INSPIRED by these movies. But it seems like the only way a rom com can get made these days is if it’s also genre. –S

  2. KatR says:

    You know one that I love and just came to mind? Serendipity, with John Cusack and Kate Beckinsale.

  3. I’m sorry … I think you had some listed past No. 9, but GARNER CRYING PITIFULLY GIF please for the love of puppies SOMEBODY HELP THAT POOR CHILD

  4. These lists make me want a rom com marathon right now at this exact second of this day. Once again reminding me that Brown Sugar is in fact a movie and I didn’t dream it up. I need to rewatch this ASAP. I love all of these movies. WYWS and Sleepless in Seattle have the same non cynical heart which is why I love them both SO MUCH. I would definitely include Someone like you in my personal list. I know that movie is what made me fall in love with Hugh Jackman. These are all just random thoughts I came up with while reading this. I wish the world wasn’t as cynic today for rom coms to make a comeback.

    • HeadOverFeels says:

      I tried watching Someone Like You recently and had to stop cause the “old cow” storyline with Ray depressed the HELL OUT OF ME. -K

  5. KatR says:

    I wanted to say that I read Jenn’s list and then realized I had forgotten about THE PRINCESS EFFING BRIDE, and have fallen into a shame spiral from which I may never recover.

    • HeadOverFeels says:

      Sage and I both had debates about the proper genre placement of that one. It’s tricky!! -K

  6. Oh so happy to see Bringing Up Baby and The Apartment here, but You’ve Got Mail and Amelie’ are my two sick day rom coms. I saw The Cutting Edge approximately 8000 times before I was 18 and I couldn’t agree more about 13 Going on 30.

  7. I love how unexpected your list was but I have to say that you completely won me over with your inclusion of Brown Sugar. OMG that movie was so underrated and so incredibly good. Sanaa Lathan and Taye Diggs had crazy good chemistry. In fact Sanaa Lathan has had 3 of my all time fave rom coms including this, Love & Basketball and Something New (what are your thoughts on that one?) Loved reading this, adding shit to my Netflix queue.

  8. Late to the party, ladies, but in the spirit of ‘I never met a Meg Ryan romantic comedy I didn’t like’: What are your thoughts on French Kiss (my favorite) and/or Kate & Leopold (Classic Jackman, sans troubling elements in “Someone Like You”, and bonus Brad Whitford)?

    • HeadOverFeels says:

      LOVE Kate and Leopold. i don’t really have a strong opinion on French Kiss? It’s definitely one I need to revisit. — Kim

Comments are closed.