Rom-com bracket: vote on the Elite 8

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. Before you dive into the Elite 8 voting, catch up on the rest of the bracket:

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

(8) Pretty Woman vs. (6) Forgetting Sarah Marshall


The Matchup: A woman is able to leave behind a life of crime by falling in love; a man tries to move on from the love of his life, the star of a TV show titled Crime Scene: Scene of the Crime.

Our thoughts:

JS: Wait, how did we get here? Forgetting Sarah Marshall is in the Elite 8? And I voted for it all three times? How did this happen?

Forgetting Sarah Marshall is a very, very good movie. But at this point, I feel like we need to more deeply examine its limitations. It’s a bro-tastic type of romance, as Apatow-universe films tend to be, and thus the female characters are pretty well sidelined. Mila Kunis is essentially the sort of “Cool Girl” Amy Dunne would take issue with, a sexy sidekick whose main role is to just be ok with everything Segel’s character does and to help him develop. And aside from all of that, the romance is only mildly compelling; it’s really all about the jokes.

I could watch Segel’s vampire puppet musical scenes endlessly, but Pretty Woman needs to move forward. It is, admittedly, perhaps more deeply problematic than Forgetting Sarah Marshall, but I think it’s low-key aware of some of those pitfalls, which I’ll hopefully be able to write about more next round.

ZR: Wait, how did we get here? Pretty Woman is in the Elite 8? Oh, never mind. We all saw this coming.

Pretty Woman is a very, very good movie. But at this point, I feel like we need to more deeply examine its limitations. For starters, it reinforces the same tired tropes of a damsel in distress saved by her knight in shining armor, but this time with a fun new hyper-transactional twist! Julia Roberts carries the entire movie on her beautiful, curly red locks and this movie would not have nearly as much longevity without her. Aside from that, I’m not even sure that this movie is that funny.

I could watch Robert’s smile, laugh, and try on hats endlessly, but Forgetting Sarah Marshall needs to move forward. It does, admittedly, potentially hit some of the same male-savior notes, but I think overall it hits the main criteria we outlined at the beginning stronger.


(8) Pretty Woman vs. (6) Forgetting Sarah Marshall

The Sugar Kowalczyk region

(16) 13 Going on 30 vs. (3) Love Actually


The Matchup: A woman does well in her love life by aging versus a movie that does not age well.

Our thoughts:

JS: The Cinderella of this tournament dances on! 13 Going on 30, a 16-seed that had to survive a play-in matchup to even make the field of 64, finds itself in the Elite 8 after pulling out a narrow win over The Big Sick. Now it takes on a powerhouse in Love Actually.

What do you people see in Love Actually??? It’s schlocky, outdated nonsense. It’s also an insult to the genre in that there are eight different narratives; if you can’t fully develop a relationship over the course of a movie, you don’t get to be deemed a great romantic film. I’m voting for 13 Going on 30 to continue its surprising run and reach the Final 4.

ZR: Jake is a grouch. Love Actually is schlocky, but I’m not sure you can argue that it’s outdated nonsense (re: Jake just spent two paragraphs justifying Pretty Woman). Love is multifaceted and this movie makes an effort to showcase that through its eight different narratives. Are all particularly successful? No, but you have to give the movie something for both its ambition and the warm toasty feeling you get inside after watching it.


(16) 13 Going on 30 vs. (3) Love Actually

The Princess Ann Region

(13) You’ve Got Mail vs. (2) (500) Days of summer


The Matchup: A movie that’s completely self-aware of modern rom-com tropes versus the movie that perfected many of those tropes.

Our thoughts:

JS: Oof. This is probably the single toughest matchup of the entire tournament thus far for me; it could easily be a championship match. You’ve Got Mail has the queen of rom-coms doing some of her most charming work. Just take a look at the scene in the coffee shop:

In the span of five minutes Meg Ryan is able to go from hopeful to sad, joyful to angry, and defiant to surprised and regretful. It’s a masterful performance in a masterful scene in a movie full of scenes that set the template for how rom-coms would come to operate.

And yet my vote goes to (500) Days of Summer. Thus far (500) Days of Summer has coasted by on what I think were fairly easy matchups, so I think its ingenuity has flown under the radar. It rejects the false narrative that movies like You’ve Got Mail set forth about the nature of love, yet it is still flamboyantly cinematic. I could watch this impromptu musical scene forever, and the truly brilliant part of the movie is what comes right after it.

ZR: I’m almost tempted to not pick a side in this fight, but that would render this exercise moot. I think in this competition we’ve focused too much on the performances. Strong performances and electric chemistry are important components, but it’s the script that truly pushes a rom-com from good to great.

For a movie in which writing is so central to the plot, I actually think You’ve Got Mail is weaker on this front. While the e-mails back and forth between Hanks and Ryan are beautiful and the types of things younger me always wished a future boyfriend would send, I find myself appreciating the minimalism in (500) Days of Summer. Science tells me that the majority of communication is nonverbal and it’s something that (500) Days does so well. The slump of JGL’s disappointed shoulders as he gazes out over the LA sprawl speaks volumes to the bittersweet nature of relationships, more so than the typed rambling paragraphs and confessions in You’ve Got Mail.

(500) Days of Summer shows us what we’re like when we don’t think anyone else is on the other side of the screen. It gives its characters the room to be self-involved, joyous, and tremendously disappointed all without saying a word and thus will be getting my vote.


(13) You've Got Mail vs. (2) (500) Days of Summer

The Princess Bride Region

(1) Groundhog Day vs. (7) Notting Hill


The Matchup: A girl standing in front of a boy versus a man standing in front of a woman over, and over, and over again.

Our thoughts:

JS: I quoted Ebert last round, but it bears repeating: the point of Groundhog Day “is not that [Phil] has come to love Rita. It is that he has learned to see the angel.” Groundhog Day’s plot is founded on the romance, but it is more about Phil’s transformation than anything else. I’m voting for Notting Hill. And, to avoid talking about the “I’m just a girl” scene yet again, I’ll say this about the movie: it captures the ephemeral, transient, uncertain nature of relationships better than just about any rom-com ever. There is no clear path forward for the two leads in this film, which is what helps make that iconic speech work so well.

ZR: I’m just a girl. Typing for the internet. Asking them to vote for Notting Hill. Notting Hill is the type of movie I want to watch with a tub of ice cream and a glass of wine. Notting Hill makes me want to like Hugh Grant. Notting Hill is great as much as it’s slightly forgettable. Notting Hill deserves to take it here because it’s the full fantasy. While Groundhog Day makes the viewer believe that people can change, Notting Hill suspends reality just enough to give the viewer hope that the hot person you make eye contact with on the bus will some day be yours and when they eventually leave, that they will come back.


(1) Groundhog Day vs. (7) Notting Hill
Jacob SkubishComment