Rom-com bracket: vote on the field of 32

Image by Zoë Ryan

Image by Zoë Ryan

Welcome to the great rom-com bracket of 2019! In honor of the 30th anniversary of When Harry Met Sally, Zoë Ryan and I are setting out to determine the best romantic comedy of the past 30 years. We’ve previously laid out the rules of the bracket, and you can view the round one results here. Now, we’re down to the final 32.

Here’s how this will work: Zoë and I will break down each of the matchups below. There will be voting buttons with each matchup below that you can use to cast your vote. If you don’t want to scroll through all of our fascinating insights, you can also check out the voting page here: rom-com voting page.

You can track the results and view the full bracket by clicking here: full rom-com bracket.

Let’s get to it.

The Annie Hall Region

(1) Wall-E VS. (8) Pretty Woman


The Matchup: A robot with a singular purpose is thrown off course by love; a man with a singular purpose is thrown off course by prostitution, and then love.

Our thoughts:

JS: I should pick Pretty Woman, right? It’s an all-time iconic rom-com, and Julia Roberts’s smile could end wars, and my co-host doesn’t even think Wall-E is a rom-com at all. But I’ll be damned if the scene below isn’t one of the very best romantic moments in movie history. I’m going with Wall-E.

ZR: I said it once and I’ll say it again: Wall-E is not a rom-com. Regardless, it’d be hard to beat Pretty Woman. Sure it glamorizes prostitution and reinforces the idea of a male savior, but I’d be hard pressed to find a pairing better than Richard Gere and Julia Roberts in this film.


(1) Wall-E vs. (8) Pretty Woman

(4) CRAZY, STUPID, LOVE VS. (12) My Big Fat Greek Wedding


The Matchup: Crazy, stupid love versus very normal love.

Our thoughts:

JS: Crazy, Stupid, Love is, frankly, an awful movie. I love so many people in it, but it’s just terrible. My Big Fat Greek Wedding may be dull, but it’s at least watchable.

ZR: My Big Fat Greek Wedding may hold a special place in my 25 percent Greek heart, but I will concede that Crazy, Stupid, Love is a better rom-com thanks to the ample tension between Ryan Gosling and Emma Stone.


(4) Crazy, Stupid, Love vs. (12) My Big Fat Greek Wedding

(2) As Good As It gets VS. (10) Sleepless in Seattle


The Matchup: The showdown between grumpy men who somehow end up with incredibly caring, kind women.

Our thoughts:

JS: Rom-coms are all about the redemption of a flawed character via love, and I’m all for those transformations. But Nicholson’s Melvin is one step too misogynistic, one step too homophobic, one step too just plain awful for my taste. Sleepless in Seattle may keep Meg Ryan and Tom Hanks apart for most of the film, but the final five minutes alone beats the entirety of As Good As It Gets.

ZR: WHO ARE YOU AS GOOD AS IT GETS VOTERS?!? While this film features an amazing Helen Hunt performance, it was never going to be enough to stand up to the charming duo of Tom Hanks and Meg Ryan. Sleepless in Seattle is the obvious winner and will be getting my vote.


(2) As Good As It Gets vs. (10) Sleepless in Seattle

(3) Love, Simon VS. (6) Forgetting Sarah Marshall


The Matchup: A boy trying to keep his love anonymous versus a man in love with one of the most famous people in the world.

Our thoughts:

JS: I just caught up with Forgetting Sarah Marshall again and…wow is it good. Its only flaw in this bracket might be that it is significantly funnier than it is romantic.

ZR: I did finally watch Love, Simon and I agree with Jake’s point last round that it’s primarily a film about identity. There’s no genre confusion for Forgetting Sarah Marshall and it’s based on a true story, which apparently is important to you guys (re: The Big Sick).


(3) Love, Simon vs. (6) Forgetting Sarah Marshall

The Sugar Kowalczyk region

(16) 13 Going on 30 VS. (8) Crazy rich asians


The Matchup: A woman who finds love by jumping forward in time versus a woman who finds love by jumping forward an income bracket (or seven).

Our thoughts:

JS: Crazy Rich Asians: a very good film! But the romance is one of the least memorable parts about it. That’s honestly a little true for 13 Going on 30 as well; I mostly remember it for just how incredible Jennifer Garner is. But perennial side character Judy Greer has to make the Sweet 16, right?

ZR: Calling it now, I think 13 Going On 30 is the dark horse of the bracket. Why aren’t Mark Ruffalo and Jennifer Garner in more films together now? While Crazy Rich Asians is a beautiful film and Constance Wu is a delight, I still don’t buy that the romance in this movie is that exciting.


(16) 13 Going on 30 vs. (8) Crazy Rich Asians

(4) The Big Sick VS. (12) Friends with benefits


The Matchup: Two movies about people who try, and fail, to be just friends.

Our thoughts:

JS: Friends with Benefits is cookie-cutter rom-com fare; it adds nothing new to the genre. The Big Sick is a modern classic, and because you fools voted out Ruby Sparks last time I need to keep the indelible Zoe Kazan in the field by voting her through here.

ZR: Everything I said last round about The Big Sick should be thrown out the window because now that it’s up against Friends With Benefits, anything goes. Mila Kunis and Justin Timberlake’s chemistry in Friends With Benefits is believable. But I’d rather have a giant stuffed giraffe over a cheesy flash mob number any day.


(4) The Big Sick vs. (12) Friends with Benefits

(15) My Best Friend’s Wedding VS. (7) The 40-Year-Old Virgin


The Matchup: Two people trying to put off events they should have seen coming a long time ago.

Our thoughts:

JS: My Best Friend’s Wedding, without giving too much away, is low-key innovative for how the film wraps up. But The 40-Year-Old Virgin is hilarious and has some really tender moments. It’s an honest expression of societal sexual expectations filtered through crass male humor, otherwise known as a Judd Apatow movie. It deserves to move on.

ZR: As I said last round, The 40-Year Old Virgin is both sweeter and holds up better than one would expect for a sex comedy film that came out in 2005. I really do like My Best Friend’s Wedding. But if we’re picking movies on the basis that they changed the genre, then The 40-Year Old Virgin takes it on concept alone.


(15) My Best Friend's Wedding vs. (7) The 40-Year-Old Virgin

(3) Love Actually VS. (11) While you Were Sleeping


The Matchup: A movie about a man who sleeps the whole time versus a movie I wish I could sleep through the whole time.

Our thoughts:

JS: You buffoons voted Love Actually over Set It Up last round, an unforgivable offense. I’m voting for While You Were Sleeping, and I only think it’s alright. But at this point, it’s about justice. Love Actually is never getting my vote.

ZR: I may have thrown my support behind Set It Up in Round One, but now I’m all in on Love Actually. While You Were Sleeping has one iconic Sandra Bullock monologue, while Love Actually has about a billion moments that have been copied and satirized a thousand times over. So from a numbers standpoint, it should move through to the next round.


(3) Love Actually vs. (11) While You Were Sleeping

The Princess Ann Region

(1) Amelie VS. (8) Knocked Up


The Matchup: An eccentric, delicate French film versus a crude, on-the-nose American comedy.

Our thoughts:

JS: I thought I was going to vote for Amelie, but even though I re-watched it recently I don’t remember much about it. It’s a little too in love with itself, I think. Knocked Up has some Katherine Heigl problems (I’m sorry, she’s not very good) and some we-can’t-talk-about-abortion problems, but the birth scene really gets me.

ZR: I know that Amelie is a better movie, but I had to look up what the romance part was on Wikipedia just so I would have something to write here. I was really banking on y’all pushing through The Five-Year Engagement. I guess I’m voting for Knocked Up, but I’m feeling pretty darn apathetic about this match.


(1) Amelie vs. (8) Knocked Up

(13) You’ve Got Mail VS. (5) 10 Things I Hate About You


The Matchup: Two couples that hate each other, until they don’t.

Our thoughts:

JS: A tough matchup; 10 Things I Hate About You manages to make me care deeply about both of its central couples. But come on, it’s You’ve Got Mail. For all the things You’ve Got Mail has going for it, a recent re-watch got me thinking about just how incredible Meg Ryan’s ability is to express five different emotions all in an instant. She’s an absolute treasure.

ZR: No offense to 10 Things I Hate About You, but You’ve Got Mail is the clear winner here. The film that made us fall in love with independent bookstores, New York City, and the truest of all rom-com pairings, Tom Hanks and Meg Ryan. The line “I would send you a bouquet of newly sharpened pencils if I knew your name and address” in and of itself makes me swoon every single time and cements You’ve Got Mail as an all-time classic.


(13) You've Got Mail vs. (5) 10 Things I Hate About You

(2) (500) days of Summer VS. (7) Four Weddings and a Funeral


The Matchup: The matchup between two men who fall for the wrong person.

Our thoughts:

JS: The difference between these movies is that in Four Weddings and a Funeral Hugh Grant picks the wrong person but the movie thinks it’s the right person, whereas in (500) Days of Summer Joseph Gordon-Levitt picks the wrong person, but that’s kind of the point. (500) Days of Summer is a groundbreaking film, while Four Weddings is just a rough draft of later, better British rom-coms yet to come.

ZR: Part of the appeal of Four Weddings and a Funeral is how effortlessly light and breezy it is. However, its ease is what makes it forgettable. Forgettable is not a word I’d use to describe (500) Days of Summer, which seems charming and easy on the surface but subverts the genre to demonstrate the pitfalls of the “nice guy” complex.


(2) (500) Days of Summer vs. (7) Four Weddings and a Funeral

(14) She’s the Man VS. (11) Bridget Jones’s Diary


The Matchup: Two women try to find their footing in a world full of men, one a bit more literally and the other a bit more literarily.

Our thoughts:

JS: I voted against both of these films last round, so I don’t really want either of them in the Sweet 16. I’ll go with She’s the Man because it’s just a lot more fun.

ZR: It’s Bridget Jones’s Diary. Any other answer is ridiculous and will not be tolerated.


(14) She's the Man vs. (11) Bridget Jones's Diary

The Princess Bride Region

(1) Groundhog Day VS. (9) the Holiday


The Matchup: Two couples need a change of scenery to find love, while a man needs the same scenery every day to find love.

Our thoughts:


Yep. It’s Groundhog Day.

ZR: Groundhog Day is near perfection as a movie, but The Holiday is near perfection as a romantic comedy. Not only is it set during Christmas (the most romantic holiday), but it also features two pairings that you wouldn’t expect to work and isn’t excessively sweet to boot. I think the case could be made that Groundhog Day actually fits the mold of a coming-of-age movie more than a rom-com and thus its run should end in the Top 32.


(1) Groundhog Day vs. (9) The Holiday

(4) Garden State VS. (5) Jerry Maguire


The Matchup: A Manic Pixie Dream Girl helps a man discover that he should enjoy life, while a very real couple sorts through life’s very real problems.

Our thoughts:

JS: “You complete me” and “You had me at hello” are spoken within moments of each other, and that is just incredible. It’s Jerry Maguire, easily. SHOW ME THE SWEET 16!!!

ZR: The manic pixie dream girl is a cornerstone of the rom-com genre (see: Ruby Sparks, Elizabethtown, etc.) and Garden State best epitomizes the trope thanks to a spunky performance from Natalie Portman. However, Jerry Maguire had me at hello and will be getting my support this round.


(4) Garden State vs. (5) Jerry Maguire

(2) Moonrise Kingdom VS. (7) Notting Hill


The Matchup: The matchup between two couples who don’t get to spend very much time together due to outside forces.

Our thoughts:

JS: Aside from the diner orgasm scene and the ending in When Harry Met Sally, Notting Hill might have single most iconic rom-com moment. Moonrise Kingdom is a better movie, but for the collective Wes Anderson experience, not for the romance alone.

ZR: I’m looking forward to seeing if the Moonrise Kingdom support continues in Round 2, but I’m going to have to hand it to Notting Hill. Sure it’s cheesy and a bit too long, but it’s a movie that taught viewers to fall in love with London like how When Harry Met Sally taught viewers to love New York. Plus it truly makes me happy to watch and that should count for something.


(2) Moonrise Kingdom vs. (7) Notting Hill

(3) Silver Linings Playbook VS. (6) To All the Boys I’ve Loved Before


The Matchup: A pair of completely messed up individuals try to find peace, while a pair of perfectly well-adjusted high schoolers fall for each other.

Our thoughts:

JS: I voted for To All the Boys last round, and I voted against Silver Linings Playbook. But Silver Linings Playbook is my pick here, for Jennifer Lawrence’s best performance and for that electric dance scene.

ZR: I think the strongest romantic comedies present us with flawed characters who become better through love. To All The Boys I’ve Loved Before offers us two relatively flat characters who remain flat. For that reason, I will be rooting for the markedly less funny, but much more complex Silver Linings Playbook.


(3) Silver Linings Playbook vs. (6) To All the Boys I've Loved Before
Jacob SkubishComment