Rom-com bracket: vote on the Final 4


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 Final 4 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.

(8) Pretty Woman vs. (16) 13 Going on 30


The Matchup: A completely unrealistic, probably impossible romantic setup versus a woman who time travels to find love.

Our thoughts:

JS: The Cinderella of this tournament is still alive! I am, frankly, stunned that 13 Going on 30 is still in this thing; I didn’t know the love for it was that strong. But midnight has struck for this plucky underdog, because the real Cinderella of the tournament deserves to move on to the championship: Pretty Woman.


I haven’t read Zoë’s take before writing this, but I have a pretty good sense of what her criticism will be, and what the criticism of Pretty Woman generally comes down to: it’s a forced romance between a wealthy man and a prostitute, and the grotesque inequality in their power dynamic undermines whatever charm the movie brings. This is fair, although I do think there are some aspects of the film that make it not quite the outdated pariah such a plot description might imply. Pretty Woman comes pretty close to a 50-50 gender split in dialogue, for example, and it has a pretty keen eye for class dynamics that few rom-coms even try to approach.

I won’t try to assemble some flimsy defense of Pretty Woman’s wokeness, though, because what really makes the movie great is how it leans into the cinematic ridiculousness of its premise. Pretty Woman is ludicrous, but it knows this. The films leans hard into the Cinderella parallels, particularly in the climactic romantic gesture. It’s a self-aware ode to why rom-coms are great: they tell us a story we know is far removed from reality but are thrilling to indulge in all the same. Cinderella knows she has to go home at midnight, but loves the dance anyway. I know very well that when Pretty Woman ends I’ll be thrust back into a reality that looks nothing like it, but that doesn’t mean it’s not great cinema. In fact, that transportation might be the essence of what great cinema is.

And at the center of this ridiculous story is the magnificent Julia Roberts. I have a hard time putting into words just how captivating Roberts is in Pretty Woman, but a discussion about her with a friend recently prompted this question: has any actress ever been more charming in the history of movies? For my money, Roberts in Pretty Woman is right on par with Audrey Hepburn in Roman Holiday and Marilyn Monroe in Some Like It Hot. It’s an all-time performance, and I hope you do the right thing and put it through to the championship.

ZR: Like Jake, I am also stunned that 13 Going on 30 made it this far. Let’s make the damn Disney Channel moment happen and let the underdog win.

He’s right that in Pretty Woman, Julia Roberts has never been more luminous, but does that make the movie a better romantic comedy? Absolutely not. No one argues Ocean’s 11 is a better heist movie because George Clooney is at peak Clooney in it. The premise that the performance of the cast should play into whether or not a movie best represents a genre is ludicrous.

More than that, Pretty Woman doesn’t deserve to win because, first and foremost, it’s a movie about consumerism. Gere kicks off his and Roberts’s “meet-cute” by first handing her a $20 in return for some directions. Arguably the most iconic scene in this film is not about Gere and Roberts together, but Roberts getting her shopping revenge on some snooty shop women. If romantic comedies are supposed to end by helping the characters realize some larger worldly truth, what does this one teach Gere (and the audience)? Women are to be consumed. Women are materialistic. Money can buy you love.

However, 13 Going on 30 shouldn’t win on technicalities. It should get your vote because it’s a better representation of the quintessential rom-com. The failing magazine, the right amount of magic glitter, a killer dance scene, even Judy Greer as the “frenemie.” And if we’re going to laud Pretty Woman for having a 50-50 split in dialogue, than we should note that 13 Going on 30 definitely leans more towards 80-20.

But even if it was missing all of these classic early 2000s rom-com tropes, 13 Going on 30 still deserves to win because Ruffalo and Garner give us a romance to root for. Childhood friends who drift apart in adulthood, but who still have lingering unresolved feelings, is very real and very relatable. And the film notes that even when we have the chance to reunite, the timing is not always perfect. What makes the conclusion of this movie so satisfying and so sweet, though, is that we’re given the opportunity to finally live out our “what if it was always you” fantasy when 13-year-old Garner is able to finally plant a kiss on her childhood best friend.

13 Going on 30 is not better cinema. No one is making that case. But it is a better romance (and hands down funnier) and deserves your vote to go to the championship.


(8) Pretty Woman vs. (16) 13 Going on 30

(13) You’ve Got Mail vs. (7) Notting Hill


The Matchup: Two movies whose premises would basically be impossible if social media existed.

Our thoughts:

JS: Rom-coms, as I noted above in my defense of Pretty Woman, are ridiculous. Pretty Woman responds to this ridiculousness by leaning into it, by reveling in the utter absurdity of cinematic romance. Nearly a decade later Julia Roberts would give us Notting Hill, a completely different but even more insightful meta-take on the rom-com genre.

Like Pretty Woman, Notting Hill is a referendum on the impossibility of rom-coms. Hugh Grant plays an English bookkeeper; Julia Roberts plays, well, a version of herself, a mega-popular American actress who impossibly falls for the stammering bookkeeper. It’s magical, surreal, and highly unlikely.

But while Pretty Woman celebrates the surreality of cinematic love, Notting Hill is a case for how the movies can capture the very real, aimless, meandering state of love in real life. Re-watching the film, I was surprised at how slowly it moves, and how quiet and still many of the scenes are between Grant and Roberts. They speak softly and act hesitantly, because they don’t know if it will work out. “The more I think about things, the more I see no rhyme or reason in life,” says Bella (Gina McKee) in the film. “No one know why some things work out and some things don’t.”

This is why that iconic “I’m just a girl…” scene is so affecting: love is a tenuous thing, and Roberts’s character is finally laying it all out there in a vulnerable attempt to grasp at it. Roberts and Grant are incredible together to be sure, but this is above all else why Notting Hill is such a perfect rom-com. In most rom-coms, togetherness is the inevitable ending. In Notting Hill it is a hope, something the characters work towards but have no guarantee of attaining. (Also, Rhys Ifans wears a t-shirt that reads “Fancy a fuck?” Every moment with him is hilarious. Don’t think this movie isn’t funny as well.)

Notting Hill gets at an eternal sense of love like few rom-coms can, and for that, it has my vote. Plus, don’t you want to see an all-Roberts final?

ZR: I thought fewer choices might make these latter rounds easier. I was very wrong. What makes this round so difficult is how similar these films are: both are slushy, both are romantic, and both even feature independent bookstores.

But You’ve Got Mail is the movie jaded millennials need. So much of our dating lives revolve around swiping right while on the bus, in the grocery store, or laying on the couch. The emails back and forth between Hanks and Ryan, which are arguably the strongest part of the movie, are illustrative of the thought-provoking, intimate correspondence we crave. Vulnerability is most easily displayed when you have a backspace key and the anonymity of the internet.

“'What will NY152 say today?' I wonder. I turn on my computer. I wait impatiently as it connects. I go online, and my breath catches in my chest until I hear three little words: 'You've got mail'. I hear nothing. Not even a sound on the streets of New York, just the beat of my own heart. I have mail. From you.”

It’s clear from the emails that Ryan and Hanks are suited for each other on paper. But what’s genius about You’ve Got Mail is how it demonstrates that our perfect pen pal may not always be our ideal partner. Hanks is a liar. Ryan is mean. We watch him destroy her business. And yet, we continue to root for them to get together because we don’t want them to miss out on the person that will bring them so much happiness. The heart wants what the heart wants, and Ephron dictates to us that we shouldn’t let our own or others’ imperfections stand in the way.

“I would have asked for your number, and I wouldn't have been able to wait 24 hours before calling you up and saying, 'Hey, how about – oh, how about some coffee or, you know, drinks or dinner or a movie... for as long as we both shall live?’”

We’ve gotten this far without even noting what may be the most impressive part of You’ve Got Mail, which is its undeniable influence on the romantic comedy genre more than 20 years later. They Came Together is at its core a You’ve Got Mail parody. The Mindy Project is a long drawn out homage to everything Ephron, just with IMs instead of emails. If icon status is a key part of our criteria, then this movie takes it hands down.

You’ve Got Mail changed the game for romantic comedies and it should get your vote. Besides, would a rom-com bracket even be legitimate without an Ephron movie going to the end?


(13) You've Got Mail vs. (7) Notting Hill
Jacob SkubishComment