Every year, journalists, politicians, authors and newsmakers from our Pacific Northwest community and around the nation come together at the Crosscut Ideas Festival to take a hard look at the people, policies and events that shape our lives. The 2023 Crosscut Ideas Festival will take place in a hybrid in-person and virtual format. (Intrigued? Get tickets.)

Jennings rose to unexpected fame in 2004 with his 74-game winning streak on the quiz show Jeopardy! In 2020, he won the Jeopardy! “Greatest of All Time” championship, and in July 2022 was named co-host, with Mayim Bialik, following the passing of longtime host Alex Trebek. He is the co-creator of the Omnibus podcast and the author of 13 books, including New York Times bestsellers Brainiac and Maphead.

Before joining us this year, Jennings took the time to participate in a Crosscut Q&A. Or should we say A&Q? Here’s what he had to say about Jeopardy!, ChatGPT v. Watson, life in Seattle and more.  

This interview has been edited and condensed.

What would be your dream Jeopardy! category?

1980s pro wrestling.

AfterJeopardy!, we aren’t surprised that you know a lot … about a lot of topics. And you’ve written books about humor (Planet Funny), geography (Maphead), trivia (Brainiac) and more. What are some ways that you recommend we all keep learning? Or, how do you stay sharp?

Just pay attention to the world around you. The contestants you see on Jeopardy! every night aren't savants who sit around at home memorizing the encyclopedia. They learn about stuff the same way everybody does: doing a crossword puzzle, listening to a podcast, reading the ingredients list on the backs of cereal boxes.

Probably the easiest change you can make is to be more curious in conversation. If someone mentions a place or a subject or a career you know nothing about, don't tune out! That's when I really perk up. A new thing! I'm like a dog with a bone. Take an interest, pepper them with follow-up questions. They won't even register what might feel to you like a weird, unwarranted level of interest. They will be flattered!

Who would win on Jeopardy!, Watson or ChatGPT? In all seriousness, I know you have given a lot of thought to the case for good old-fashioned human knowledge. Any thoughts on ChatGPT?

Watson walked so that ChatGPT could run. And when I say "run," I mean, "tear down the already-crumbling remains of Western civilization around our heads."

Jeopardy! is known as a smart show for a smart audience. Seattle has a reputation for being a literary and innovative city. What’s a Jeopardy! champion’s take on calling Seattle home?

I was born here, so I'm not really sure. I assume it's the weather? Lots of long, dark, rainy days of my childhood spent sitting at home watching game shows. Bill Gates was writing MS-DOS and I was watching Match Game.

Join Ken Jennings and more personalities at the Crosscut Ideas Festival. Get your tickets now.

Deepak Chopra, Michael Barbaro, Susan Glasser, and Andrew Yang are currently slated to appear, with more guests to be added in the coming weeks.


Sessions will cover predictions about the future of political parties; the promise and peril of artificial intelligence; spiritual approaches to the mental health crisis; how CRISPR gene therapy is transforming medicine; and the next wave of Supreme Court decisions poised to further reshape American life.  

This year’s festival will also include live tapings of popular podcasts from news organizations around the country, hosted by some of the most insightful journalists working today.

Our tech-savvy attendees will love The Vergecast podcast's take on the most important industry news. Political junkies will have their plates full with The Assignment featuring CNN’s Audie Cornish, plus The Political Scene from The New Yorker and The Weeds from Vox. Supreme Court watchers know Slate’s Amicus podcast with Dahlia Lithwick is one of our most popular sessions every year. And last but not least, Rachel Belle returns for a live edition of her James Beard Award-winning food podcast, Your Last Meal.

Learn more about the Crosscut Ideas Festival or buy tickets now at Crosscut.com/Festival.  

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