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We're Launching a Crossword Puzzle About the Internet

Solve the Internet is a new weekly mini crossword puzzle for the extremely online.

We are bombarded every day with snippets of information—tweets, Facebook posts, facts, quips and asides in podcasts, advertisements, cable TV shows, rap beefs, and memes. Most of it ends up in our brains somewhere: ready to deploy in casual conversation, in our own tweets, or in arguments with our families. We’re hoping to give you a healthier outlet for all the trivia you’ve accumulated: Our brand new crossword puzzle, Solve the Internet.


Solve the Internet comes to you on Motherboard via Caleb Madison and Marley Randazzo, who are longtime puzzle enthusiasts and generally Very Online people. The long and short of it is that we’ll be bringing you a brand new internet-themed mini crossword puzzle every Wednesday. We’d be stoked if you play it, and tell your friends about it.

If you wanna skip the introductions, you can solve our first puzzle here.

But I figured we might as well introduce Caleb and Marley, so I sat down with them to talk about the new endeavor (actually, we Skyped.)

MOTHERBOARD: As far as I know, there’s the New York Times crossword puzzle (which I love), a couple newspaper crossword puzzles, and not much else. Am I totally wrong here? What else is out there?
Caleb Madison: There are a lot of non- New York Times crossword. I got into crosswords around 10 years ago, when social media culture was forming, and there was this crop of indie crosswords that were all different and had unique voices and were unconstrained by the institutional oversight of something like the Times and could be a little more familiar with their solvers. That’s what got me into puzzles in the first place.

One of the things I don’t like is the exclusivity of the language of crosswords sometimes. When I ask people if they like crosswords, they say, “I could never do this, or I could never do that.” The language can keep you on the outside a little bit. I’m excited to be able to tone down that formality and try to make it as casual an experience as possible with the clues, because I think that’s fun and that’s what I like to solve—when it feels like there’s another person on the other side.

I do think it sometimes feels like crossword puzzle clues come from the sky or something—there’s rarely a sense of who is making it. I remember growing up and watching my dad doing crossword puzzles and I could never do them. Now I feel like I can just because I’m older. But if you don’t know a bunch of trivia it can be hard to get into them.
Marley Randazzo: The New York Times is quizzing you on what you can remember about the world—it’s things that are solidified in canon. They only reference certain things in puzzles. What we want to do is make something that can be solved if you’re paying attention to what’s going on in the world right now. It’s more of a test, more of a game. And it can be a form of journalism for sure.

Madison: There’s a quote—I think from [legendary crossword editor] Will Shortz—that people enjoy a crossword because it’s a different way of using all the vocabulary and knowledge that’s in the rest of the newspaper. It’s made abstract and turned into a pattern. The internet is infinite so there’s a lot more opportunity to make puzzles around ephemeral events—memes are perfect for this.

We’re held hostage at the mercy of a billion pieces of useless trivia every day, so why use old trivia when you can maybe recycle one of the facts that has been part of the news cycle?

Is there a generational divide between crossword solvers and makers? Is there a perception that young people don’t like crosswords?
Randazzo: That’s the main question we’re trying to figure out. We recognized there’s this antiquated medium that exists but also this intense demand to continue to do it by young people. People enjoy solving. Look no further than all the quiz games like Sporcle—the puzzle gaming experience is totally universal and spans generations. There’s that nostalgia you mentioned, I think we all have some kind of experience with a crossword in our lives whether it’s a family member or a friend’s parent. I think adapting this old medium into a new way and changing the voice a little bit so it’s a little more recognizable and internet native—it can be really fun.