Since winning 75 consecutive games of Jeopardy! in 2004, Ken Jennings has staved off becoming a pop cultural flash in the pan by keeping busy. He's written four books (two on trivia, one about maps, and one debunking old wives' tales) and branched out into children's lit with his Junior Genius Guide series (the latest installmentU.S. Presidents—hits stores today). On a weekly basis, he puts together separate quizzes for Slate, Parade, and his email newsletter. He's also amassed 159,000 Twitter followers, as one of the most consistently funny tweeters out there (let's see IBM's Watson make orthoepic/syllabic Pedro the Lion jokes).

This week, Jennings returns to showcase his trivia wizardry as part of Jeopardy!'s "Battle of the Decades" competition finals. Unsurprisingly, he thumped his peers from the 2000s during the preliminary round. Jennings continues his quest for supremacy on this Thursday's episode (May 8). If he continues winning, the "Battle of the Decades" championship round airs on May 16. As if that wasn't enough, this Thursday Jennings also has the honor of announcing Bumbershoot 2014's musical lineup as the host of the Pink and Purple Pickwick Party at Neumos.

For our latest Fiendish Conversation, we chatted with Jennings about returning to Jeopardy!, society's elevation of comedy, and Gwen Stefani songs.

So how was it entering back into the Jeopardy! world for the “Battle of the Decades” shows?

I was worried that I was gonna be a little rusty, because it’s been 10 years. And I don’t think anybody is as sharp at 40 as they were at 30, and I was really wondering, “Can I still even do this?” And then I just got behind the podium and it was just like getting back on a bike. There’s this weird sense of, “Oh yeah, this. I can do this,” and feeling very much at home. So it was a great experience. It’s sort of weird that this is a thing I really am good at and I like to do, and I never get to do it. Contractually, Jeopardy! is one to a customer. It’s not like a pro golfer who can play 30 weekends a year or whatever. So it was a treat to get to go back.

One of the best things about watching your first “Battle of the Decades” show was the visual frustration you showed at a couple points getting back into the flow of buzzing in. My favorite was when you got out buzzed and gave a really dejected look for being denied the chance to answer, “What is ‘Hollaback Girl?’”

How often do you get to say “Hollaback Girl” to Alex Trebek? (Laughs) Not very often.

What do you expect your role will be at the Bumbershoot party?

From what I can tell, my role seems to be guy who got asked to do it and did not say no. (Laughs) I feel like I’m breaking new ground as a game show champion hosting a rock lineup party, I don’t think this has ever been done. So I very much invent the form. I have this idea that we should actually play a game show, that when people go to the rock show what they want between sets is a game show. So maybe we’ll get people up on stage and make them answer in the form of a question and give away some Bumbershoot passes. That’s my idea right now.

You’re also part of the words and ideas lineup at this year’s Bumbershoot. What do you and George Meyer plan to do at your Needle Party?

George called me—you know, George is a comedy legend largely responsible for the comic sensibility of The Simpsons, which means he’s really shaped how every person in America has thought about funniness and jokes for the last 20 years—and when he called me and said, “Hey, we should do something for Bumbershoot,” I was not going to say no. We’ve been talking a lot about it. There’s not going to be any actual needles, it’s a reference to the Space Needle. Just so your readers know, I don’t want people to be expecting more heroin than is actually in the act. We’re talking about it as the lighter side of comedy. It’s not the comedy stage, but we want to be funny and do something unexpected. And George is really a genius at that sort of fast paced thing where you never know what’s going to happen next.

Do you have a favorite Bumbershoot moment?

I’m a huge Bumbershoot guy. I guess a very formative Bumbershoot moment for me was in the late 90s, opening day of Bumbershoot, seeing R.E.M. play the stadium. They had been my favorite band for so long, and for whatever reason I had never seen them live. And in the intermeaning decade, they’d become everybody’s favorite band. I remember getting there early enough to hear the sound check, we were one of the first people in the stadium, so we were right up front. It was just a great show. I don’t think anybody’s idea of a high point in R.E.M.’s career, but they were still so great live, and obviously had been playing together for well over a decade and sounded amazing. It was not a letdown at all.

How would you describe your series of kid’s books?

They’re amazing fact books, the kind I loved when I was a kid. The idea is to make normal kids weird and weird kids even weirder. They’re just for a certain type of smart kid that’s just a sponge for facts from the Guinness Book of World Records or whatever. I always liked that as a kid, I had this procession of obsessions. So the books are written with that 4th grade brain in mind. There’s a book about geography, and one about Greek mythology, and presidents and space. I’m working on Egypt now, and dinosaurs. Hopefully, the books can trick kids into thinking learning about this stuff is actually fun. If you go about it the right way, it doesn’t have to be as boring as school.

Do you have any new books target at adults on the horizon?

I’m pitching a couple other—I guess I can’t say “adult books,” because that’s something else—but I’m pitching a couple books for grownups. I have an idea for a book that’s about the modern sense of humor, and the mystery of where our modern sense of humor comes from; sort of a cultural history of funny. And then I have an idea for another book about weird foreign words. So those are two ideas that I’m actually pitching to publishers this month, so that’s the next thing once I’m freed from my kiddie lit dungeon.

I hope it’s not an actual, literal dungeon.

No, they’re very nice on the kiddy lit floor. It’s a lot of nice white women with offices full of board books about potty training and teddy bears.

Speaking of comedy, you’re one of my favorite people to follow on Twitter. What’s your approach to Twitter since you mainly work in a comedic realm but aren’t a person people necessarily expect to be funny?

Twitter’s actually been pretty huge for me in thinking that there’s a book in this. I love Twitter. I waste way too much of my day on Twitter, but it just seems perfect for my short attention span and this idea that you can interact with people in an unmediated way. Like, “Well you weren’t funny on Jeopardy!.” Well of course, nobody’s funny on Jeopardy!. That’s not what Jeopardy! is for. And I do benefit from that low bar of, “Wow, he’s funnier than we thought.” Which was zero. That’s something you couldn’t do 10 years ago, like find out which which people on TV were actually funny. That’s a very cool part of the age we live in, especially since we now weirdly sort of worship funny above all.

Yeah, I read something recently that said young people now define themselves more by their favorite comedians instead of by their favorite music. Do you have any ideas on why that shift to comedy worship is occurring?

I was on a plane the other day and the safety video—it used to be just some laminated cards showing what you would do in the loss of cabin pressure, this terrible, dire sort of first aid kind of thing—was a full on comedy video with dance numbers and jokes about mullets. At the end there a Kareem (Abdul-Jabbar) cameo because he was in Airplane. And I just realized that this is what it has become, everything has to be funny now. The question on why that happened is interesting. There’s definitely a lot going on. The book is sort of the archaeology of that. I don’t have some one-sentence pitch as to what’s different now versus 20 years ago. I feel like the boilerplate answer is always “the Internet.” Technology made that possible. It’s okay to be a geek about things now. One of the only things the Internet does really well is to let people share jokes and have little community in-jokes. There are just more platforms now than there used to be for stuff that makes you laugh.

Pink and Purple Pickwick Party (Hosted by Ken Jennings)
May 8 at 9, Neumos, $15