Rom-com bracket: vote on the Sweet 16

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 Sweet 16 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. (12) My Big Fat Greek Wedding

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The Matchup: A woman trying to escape the streets versus a woman trying to escape the Greeks.

Our thoughts:

JS: My Big Fat Greek Wedding is a pleasant film. It doesn’t deserve to be here, and it definitely doesn’t deserve to make the Elite 8. Pretty Woman has its problems, primarily founded in the power dynamic of a romance between a wealthy man and a prostitute. But it’s Julia Roberts’s virtuoso performance, and she’s completely beguiling in every scene. From the bathtub to the piano to the ending, Pretty Woman has delivered many of the most iconic moments in rom-com history, and it should move on for that.

ZR: My Big Fat Greek Wedding is the type of movie you watch on a Wednesday night three months into dating someone. It is relaxing. It is predictable. It doesn’t take any brain power to enjoy it. We’ve outlined many of the issues with Pretty Woman in prior rounds, so I won’t repeat them again here. But Jake is right that Robert’s performance has enough star power and charisma to push it into the Elite 8. Side note: For a movie about transcending status symbols, the movie sure is built around materialism and status symbols. Food for thought.

YOUR VOTE:

(8) Pretty Woman vs. (12) My Big Fat Greek Wedding

(10) Sleepless in Seattle vs. (6) Forgetting Sarah Marshall

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The Matchup: Two people trying to get away from someone in their past by traveling to a far-off location: one to New York, the other to Hawaii.

Our thoughts:

JS: I’ve said it before and I’ll say it again: Meg Ryan and Tom Hanks are pure magic together, which is why it’s such a shame that they only get to spend a few minutes together in Sleepless in Seattle. For many people this slow burn works, and that’s fine, but to me it just makes for a mostly boring film. My vote goes to Forgetting Sarah Marshall. I recently learned that when Jason Segel was writing the script for the movie, Judd Apatow told him to write it as a drama first, and then they would make it funny later. It’s shocking for a movie that ranks up there among the laugh-out-loud funniest in the Apatow universe, but it also makes sense: there are real emotional stakes in Forgetting Sarah Marshall, and it makes Segel’s character arc much more rewarding. There are few scenes in the annals of rom-com history that combine sadness and humor quite like Segel being broken up with while completely naked.

ZR: Now is when the decision-making actually gets tough. As much as it pains me, I’m voting for Forgetting Sarah Marshall over Sleepless in Seattle. Before y’all come after me, I’d like to reiterate my co-reviewer’s point that Tom Hanks and Meg Ryan spend almost the entire film apart. Sure, it builds the tension and the final scene continues to drive couples to the top of the Empire State Building, but it is also kind of a movie glorifying stalking. Plus, watching someone move across a country is nothing compared to the emotional roller coaster of watching someone trying to mentally move on from an ex. Because of that, I feel so much more invested in Segel and Kunis as a couple and, as Jake once told me, if I want to watch Hanks and Ryan actually be together I can always pop in You’ve Got Mail.

YOUR VOTE:

(10) Sleepless in Seattle vs. (6) Forgetting Sarah Marshall

The Sugar Kowalczyk region

(16) 13 Going on 30 VS. (4) The Big Sick

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The Matchup: A woman becomes an adult to find love; a couple must overcome adult issues to find love.

Our thoughts:

JS: I didn’t get a chance to re-watch either of these movies before diving into the bracket, so I made this decision by watching clips from key scenes on YouTube. Here’s what I learned: Jennifer Garner is unbelievable in 13 Going on 30…and the movie is just pretty good beyond that. But re-watching moments from The Big Sick secured it as my pick for this round. It’s also well-rounded: the moments between Nanjiani and Kazan are charming, but so are all the moments between Nanjiani and her parents (Ray Romano and Holly Hunter) as well. The Big Sick hasn’t had to play against a seed higher than 12 so far, so I’m not sure that it’s one of the eight best rom-coms, but it deserves to move forward again.

ZR: I may seem like the world’s biggest flip-flopper on The Big Sick, but everything is relative right? While acknowledging that the couple ends up happily together in real life, we can also be critical of the fact that a) he only truly recognizes his feelings once Kazan is DYING, b) Kazan spends the vast majority of the movie in a coma, and c) this is a movie about a man coming to terms with what it means to exist between two cultures. Which brings us to the point that 13 Going on 30 deserves to move forward. The movie embodies everything we’ve come to associate with the early 2000s rom-com including, but not limited to, a fantastic Judy Greer performance, a magazine that’s about to go under, and some nice white people falling in love. It’s not perfect, but it has my vote.

YOUR VOTE:

(16) 13 Going on 30 vs. (4) The Big Sick

(7) The 40-Year-Old Virgin vs. (3) Love Actually

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The Matchup: A movie about a man who’s never experienced sexual pleasure vs. a movie that makes me feel the opposite of pleasure while watching it.

Our thoughts:

JS: Love Actually took down my beloved Set It Up in the first round, and I’m still not over it. I won’t even entertain any actual discussion about its merits, which, if I have to get into it at all, Love Actually stinks. The 40-Year-Old Virgin is an innovative addition to the genre, it’s hilarious, it’s cute, and it has my vote.

ZR: Jake is being a petty idiot. Love Actually has defined the genre since it came out. It features not just one, but ten stories demonstrating the multi-faceted nature of love. If I could give it 10 votes I would. The 40-Year-Old Virgin is an innovative addition to the genre, but features some pretty raunchy and vulgar humor that doesn’t age as well as people think.

YOUR VOTE:

(7) The 40-Year-Old Virgin vs. (3) Love Actually

The Princess Ann Region

(1) Amelie vs. (13) You’ve Got Mail

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The Matchup: The quintessential whimsical French rom-com versus the quintessential Nora Ephron-directed American rom-com.

Our thoughts:

JS: I’m truly baffled by all the Amelie love! I know it’s highly rated on IMDb, but on re-watch I found it pretty dull, and I also didn’t know this many people actually saw the French film. You’ve Got Mail is ridiculously under-seeded, and it’s the superior Hanks-Ryan rom-com remaining in this bracket. Their banter is unbeatable, and I want to see it advance to the Elite 8.

ZR: It’s You’ve Got Mail. This is a dumb matchup.

YOUR VOTE:

(1) Amelie vs. (13) You've Got Mail

(2) (500) days of Summer vs. (11) Bridget Jones’s Diary

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The Matchup: A man falls for a woman who might not be right for him; a woman falls for two men who might not be right for her.

Our thoughts:

JS: Yeah, yeah, I get that Bridget Jones’s Diary is a “classic,” or whatever. but honestly, it’s a real snoozer for me, and there’s a better Renée Zellweger movie remaining in this bracket. (500) Days of Summer deconstructs the rom-com idea of “The One,” and, side note, it features one of the all-time great rom-com soundtracks, which we haven’t discussed enough. It has my vote.

ZR: Another brutal matchup for me. While Bridget Jones’s Diary is cemented as a genre staple, when it comes down to the line I’m not sure how much it actually adds to the rom-com canon as a whole. Sure it flips the script on the classic trope of an average guy ending up with the beautiful woman, but I’m not sure what else it offers in terms of novelty outside of that. Furthermore, I’ve watched probably watched that movie about a thousand times, and I can’t pick out a single iconic line. For these reasons, I have to hand it to (500) Days of Summer, which not only subverts our traditional “nice guy” narrative (or at least aims to) but also has more than enough iconic scenes ranging from the heartwarming (a flashmob featuring its very own Disney songbirds) to the heart-wrenching (the misalignment of expectations and reality).

YOUR VOTE:

(2) (500) Days of Summer vs. (11) Bridget Jones's Diary

The Princess Bride Region

(1) Groundhog Day vs. (5) Jerry Maguire

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The Matchup: Two men who must grind through their day-to-day lives before they can realize that the love of their life has been right in front of them the whole time.

Our thoughts:

JS: Ok, so: Groundhog Day is one of my all-time favorite movies, and I could re-watch it endlessly. But it’s missing an essential component required of the movies I’m voting to advance to the Elite 8: a fullness of character development for both romantic leads. It’s primarily a film about Phil’s (Bill Murray) transformation; Rita (Andie MacDowell) is a static foil, a tool to allow Phil to change. Last week I called out the diner scene, in which Phil tells Rita that in the snow she looks like an angel. But as Roger Ebert said in his review of the film, “The point is not that he has come to love Rita. It is that he has learned to see the angel.” Jerry Maguire, meanwhile, is the opposite sort of romantic arc, and the better sort: Jerry (Tom Cruise) and Dorothy (Renée Zellweger) are both flawed individuals who are allowed to develop over the course of the movie, and become better people through love. For that, Maguire takes my vote.

ZR: I think there’s an excellent point in Jake’s review that we’ve overlooked up until this point: both romantic leads deserve character development. That being said, I’m not sure that you can make that point while not calling out (500) Days of Summer for using Zooey Deschanel in the Andie McDowell role. Anyways, I’m losing focus. I too love Groundhog Day, but I too will be voting for Jerry Maguire. Not because I truly believe that Zellweger and Cruise become better people, but because Jerry Maguire features THE most iconic rom-com writing of all time. I love Jerry Maguire for the romantic comedy it wants to be despite its sports drama wrapper.

YOUR VOTE:

(1) Groundhog Day vs. (5) Jerry Maguire

(7) Notting Hill vs. (3) Silver Linings Playbook

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The Matchup: A couple that might be too different from one another to make it work versus a couple that might be too similar to make it work.

Our thoughts:

JS: Silver Linings Playbook is a better movie than it is a rom-com: it’s full of great performances, very good writing, and a decent romance. Notting Hill features an idiosyncratic, self-aware romance featuring the top two rom-com stars at the height of their game. Hugh Grant’s stammering charisma and Roberts’s mile-wide smile have never been used more effectively, and it has my vote to move on.

ZR: Notting Hill really gives You’ve Got Mail a run for best rom-com pairing. Grant and Roberts play off each other in a way that emphasizes the breezy wit we seek in our romantic partners today. Silver Linings Playbook is a great movie, but I’m not convinced it’s a quality rom-com. It’s not that funny nor is it honestly that romantic. I hope its run ends in the Sweet 16.

YOUR VOTE:

(7) Notting Hill vs. (3) Silver Linings Playbook
Jacob SkubishComment