Rom-com bracket: vote on the championship matchup

By Jake Skubish

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 voting for the championship matchup, catch up on the rest of the bracket:

• Read the rules of the bracket

• View the round one results

• View the round two results

• View the Sweet 16 results

• View the Elite 8 results

• View the Final 4 results

Here’s how this will work: Zoë and I will break down the championship matchup below. There is a voting button for the 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 championship: (8) Pretty Woman vs. (13) You’ve Got Mail

YOUR VOTE:

Our Thoughts on the matchup, and lessons from the bracket:

JS: Well, we’ve finally made it: after weeks of voting and thousands of votes, we have arrived at the championship. In one corner is the quintessential rom-com problematic fave, Pretty Woman. In the other corner is You’ve Got Mail, the rom-com that laid out the formula for what the modern rom-com should be. Zoë, how did we get here? And what jumps out to you about this matchup?

ZR: I’ll start by saying, I’m surprised that these are the two that it boiled down to. Both movies are more than 20 years old, and with the resurgence of the genre I thought we might be seeing The Big Sick or Crazy Rich Asians in the championship. Then again, the 90s nostalgia is strong with millennials and both of these movies play for hours on end on TBS, so maybe it’s purely familiarity?

There were a lot of movies that suffered as a result of our random assignment at the beginning. I am a firm believer that Set It Up, for example, should have made it to at least the Sweet 16. In terms of this match up, I’m 100 percent behind You’ve Got Mail,  which I would argue is only second to When Harry Met Sally in terms of influence in popular culture. Will Pretty Woman remain your prevailing choice again in the championship?

JS: I voted for Pretty Woman last round, but no, it’s going to be You’ve Got Mail for me as well. Now that we’re down to the final two, I’m thinking about it as if the stakes are way higher than they actually are: if we could only save one rom-com from the past 30 years in our memories, Eternal Sunshine-style, which one would we save? Put in those terms it has to be You’ve Got Mail: it has Hanks and Ryan as the essential pairing, New York as the essential setting, and Nora Ephron providing the best writing of the genre.

This is actually pretty easy for me. I re-watched Pretty Woman this weekend for a podcast I’ll be doing on it eventually, and while I enjoyed it again, the transactional nature of their relationship is really noticeable once you’re not looking for the romance. It’s the 2018 Cleveland Cavaliers of rom-coms: one breathtaking star at the center dragging the rest of the talent to the top, but it doesn’t deserve to win.

Why are you voting for You’ve Got Mail? And why are you voting against Pretty Woman?

ZR: I gave it some more thought and I’m not sure that the transactional nature of Pretty Woman is why I don’t like it. Julia Roberts should be compensated for the amount of emotional labor she provides to Richard Gere throughout the course of the movie. For me, Pretty Woman doesn’t deserve the title because the scenes that remain in the public consciousness aren’t about their romantic relationship. We remember Roberts shopping in Beverly Hills, her “streetwalker” outfit, and Gere snapping the necklace box shut. It’s a film driven by consumerism, not by romance.

While some will argue that You’ve Got Mail does the same thing — Hanks does manage to shut down Ryan’s mom-and-pop store after all — the message in the film is so much sweeter. It’s about putting away your preconceived notions about what your “type” should be. Ryan initially feels that she should be with a journalist taking down the capitalist machine. Hanks starts out with someone with a “killer business” instinct, but to what end? You’ve Got Mail wants us to be with someone who appreciates the same little things, like the smell of freshly sharpened pencils in the fall.

Plus, “I wanted it to be you. I wanted it to be you, so badly” in my mind remains one of the most romantic lines ever.

But moving away from this matchup, what did you learn from making this bracket in general?

JS: I do like that idea that You’ve Got Mail is more classically romantic, and it’s a good winner because of its place in rom-com lineage. It’s a remake of the 1940 Jimmy Stewart classic The Shop Around the Corner, and I like the idea that nearly 70 years later our bracket is suggesting that what once worked in romance always works.

A few other random takeaways from the rom-com bracket process:

• The nostalgia factor is real for the romantic comedy genre. Our Elite 8 contained just one movie of the past 10 years ((500) Days of Summer), and I get the sense 13 Going on 30 coasted to the Final 4 largely on the memory of people watching that movie growing up. Some of my favorite movies in this bracket, including Set It Up, About Time, Sing Street, and Two Night Stand, are all from the past few years and didn’t even make it out of the first round. Hopefully they’ll become more appreciated with time.

• The rom-com genre is a ripe one for a game like this, because some of the movies age really well, and some of them age so, so poorly.

• I think the whiteness of the genre is well known, but I didn’t fully realize until embarking on this quest the maleness of the genre. People think rom-coms are “chick flicks,” but they’re mostly about sad white men.

• After watching nearly all of these movies (sorry, I didn’t actually watch The Holiday), my five favorite rom-com leads of the bracket are:

  • Patrick Verona (Heath Ledger) in 10 Things I Hate About You

  • Kathleen Kelly (Meg Ryan) in You’ve Got Mail

  • Vivian Ward (Julia Roberts) in Pretty Woman

  • Jerry Maguire (Tom Cruise) in Jerry Maguire

  • Jenna Hunterson (Keri Russell) in Waitress

Any other lessons learned for you?

ZR: 1. My main takeaway, as you noted, was there are SO many sad white men. Maybe it speaks to the idea that women are looking for someone to fix (also not true. Women are busy and don’t need men to be an extra project), but I was shocked at how many of these movies were fixated on the depressed adolescent male.

2. After many late-night conversations at the office, I think it’s difficult to pin down the rom-com genre. There are movies we think of as rom-coms, but are really more chick flicks (e.g. Legally Blonde). A lot of movies that fit the coming-of-age mold, but that are also lumped into the rom-com genre (re: Clueless). I’m not sure what the bar is for romance and comedy is in general, but I know this was hard for us to pin down.

3. Female stars are often the ones remembered in rom-coms despite them mainly being about sad men. That being said, Sandra Bullock was in so many more romantic comedies than I remembered. Jennifer Aniston, who is often thought of as a rom-com queen, was in fewer. Reese Witherspoon, I think, was only in one movie in our whole bracket!

4. My favorite lines from the billion rom-coms we watched this year, in no particular order:

• “Tom meets Summer on January 8th. He knows almost immediately she is who he has been searching for. This is a story of boy meets girl, but you should know upfront, this is not a love story.” - (500) Days of Summer

• “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?'” - You’ve Got Mail

• “Guys think that they like girls who like sports. What they actually like is a girl in a very tight sports jersey, serving them wings and getting the terminology wrong. Guys like girls who like guys who like sports.” - Set It Up

• “Can you imagine a world in which we end up together?” - The Big Sick

• “Romantic? Hemingway? He was an abusive, alcoholic misogynist who squandered half of his life hanging around Picasso trying to nail his leftovers.” - 10 Things I Hate About You

JS: Well said. And I’m glad we took on this project! I learned some things and watched some great movies I might not have seen otherwise. I look forward to next year, when we do another TBD bracket. Thanks for playing everybody!