How Firewatch Designer Chris Remo Started an Experimental Crossword YouTube Series

There's an unexpected connection between game design and crosswords.

For a majority of my life, the world of crosswords is one that has been shrouded in mystery. I understand the puzzle at its most basic level; there are black-and-white squares, the latter of which you have to fill in with letters making up words both down and across the grid. You’re provided with clues in order to figure out which letters go where. So far, this all sounds relatively straight forward. And then, I learnt about the rebus.

Do you know what a rebus is? I’ll give you some time to have a guess if you’ve not heard of it before. I certainly hadn’t until recently. Have you done a quick Google search? I’ll explain it anyway. According to Will Shortz, famed editor of The New York Times crossword puzzle, “a ‘rebus’ in a crossword is anything that gets entered in a square that’s not a single letter of the alphabet. Typically, rebuses are parts of themes.” They’re also, perhaps unsurprisingly, a pain in the ass to understand at first. 

You might be wondering, ‘where does one learn about this horrible-sounding aspect of crosswords that I just didn’t know existed?’ I’m sure there are detailed guides somewhere out there, but I had the pleasure of first hearing of the concept from Firewatch game designer and composer, podcaster, and now crossword-solver Chris Remo.

“I don’t know, I think that probably says more about maybe my neuroses than my intelligence or aptitude that I’ve kept this streak going that long,” Remo says, ruminating on whether he’s now a specialist with a nearing 900-day streak in The New York Times crossword app. 

In July, Remo decided to try an experiment. Solving crosswords had been a part of his daily routine for a while, and he missed putting something out regularly like in his podcasting days. So he uploaded a video where he completed the crossword from Monday, July 5th, uncertain of whether anyone would even care or not. 

“I did tell myself, if it doesn’t seem like it’s going anywhere, I don’t think I can stick with it,” he says. “But it’s grown enough… even though it doesn’t necessarily make sort of financial sense for me to be doing it. It’s just nice to see that people are enjoying it.”

We’re now two months into this experiment of his, and like many others, I also quite enjoy it. Before being introduced to The Daily Solve, I had zero interest in crosswords. I’m not good at classic puzzles like that (if you ask me to do a sudoku, I will cry), and I generally think the knowledge I’ve acquired over my short time on earth is too niche for most crosswords. But through Remo’s show, I’ve gained a newfound appreciation for them, even if I’m still not very good at them.

The episode that really made crosswords click for me as an interesting pastime to engage in was the Thursday, August 19th puzzle, by Oliver Roeder and, in Remo’s own words, “edited as always by Will Shortz.” Remember our old friend the rebus, and how it’s usually part of a theme? In this particular episode, the theme for the crossword was “oat.” In a number of the answers, one of the tiles had to be filled with all three letters, and I’m not being hyperbolic when I say this blew my mind. ‘Excuse me?’ I said to myself. ‘Is this allowed?’ It turned out that yes, it was allowed, and that I had never completed a particularly complicated crossword in my life.

“I can tell, because of the comments on the channel when those videos go up, that a lot of the people watching are utterly flabbergasted by this kind of thing,” Remo says about the rebus. He is very clearly aware of the fact that doing this for an audience instead of for himself means he has to approach the crossword differently — he has to walk us through his process. 

“I have to really put some thought into trying to explain what my thought process is that leads me to suspect there might be a Rebus in this puzzle… when you’re doing this for [other] people, even though they’re not here with me, and even though I call it a live solve that’s not actually live, it feels like there are people around me doing it with me.”

The task of solving the crossword alongside Remo feels collaborative, even though it actually isn’t. I’ll sit there watching an episode of The Daily Solve, feeling great on the odd occasion I figure something out before he does. The whole web series almost feels like a tutorial for how crosswords work. I want to be clear: I’m still not good at them. Yet, like how a video game might slowly introduce concepts, The Daily Solve does, too.

“I think I sort of approach it almost more as an educator,” says Remo, speaking specifically about what it’s like to tackle crosswords as a game designer. “I’m almost trying to put myself in the mind of one of my audience members… the videos are not so much for my solving enjoyment — it’s for the benefit of the people watching.”

Game design is an incredibly complicated thing to figure out, and so are crosswords; Remo understands both these things. “The comparison I draw there to game design is, in some ways, it’s sort of the art and craft of applied empathy. You’ve got all of this context, as the person making the thing, you understand where your decisions came from, you understand how you arrived at this particular design. And so it’s easy to fall into a trap of thinking it should be so obvious for the person on the other end of this.”

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Crosswords feel like they make many assumptions of its players, with all of the archaic and sometimes nonsensical rules they harbor. Another such ‘hidden’ rule of crossword design is that, when a clue has an abbreviation, the answer will always be abbreviated. To be fair to this rule, with a little bit of thought, you might be able to figure it out. It could almost function in the same way as an axe embedded in a tree in The Legend of Zelda: Breath of the Wild; there’s an implication something more might be happening here, but you’re not directly being told what.

I think that’s what I’ve found to be so fun about crosswords, even if at times they can be a little obtuse. They’re surprising and clever, and sometimes have themes around the word “oat.” Even if nothing particularly funny or fun is happening, I’d catch myself smiling just because of something unexpected; it’s the same joy I get from playing a video game that does something unpredictable. Remo hones in on this feeling best when he says: “I think that’s really what you should strive for, ideally, in interactive design. You should look for ways to surprise people and subvert their expectations, but not in a way that’s fundamentally unfair.”