From One Trivia Buff To Another: ‘How Did You Know That?’


It was the trivia world that got me my first 15 minutes of fame, and though I don’t have much time to play pub quizzes anymore I still feel an obligation to give back. Tony Hightower, the executive director of TCONA – Trivia Championships of North America, the only trivia convention by trivia buffs for trivia buffs.

TCONA has it all, a Vegas hotel stuffed with geeks for an entire weekend from August 7-9, 2015, with every form of trivia imaginable available. There’s the esoteric Quiz Bowl and Learned League championships, pub quizzes, Kno’dgeball, a game invented at TCONA combining trivia with rubber-inflicted violence, and versions of American standards like Wheel of Fortune, The Amazing Race and, yes, Jeopardy!

Not to mention quiz-themed podcasts and presentations — this year’s keynote being David Wallechinsky, the author of The Book Of Lists, which is like the Bible for trivia nerds.

Ken Jennings, Brad Rutter and other trivia luminaries make it there every year. Unfortunately, I have already done so much traveling this year that it feels like I’ve slept a total of three days in all of 2015, and had to decline my invitation to go.

In lieu of attending I told Tony I’d be happy to do an interview with him and try to get it published somewhere in order to shamelessly shill for TCONA. One thing that I learned from our conversation is that, unfair as it sounded at the time when people called my Jeopardy! run joyless, I have gotten kind of burned out on the trivia scene over the years, probably because I’m a fiercely competitive jerk who takes everything too seriously.

I’d love to take the chance to reignite my love of playing trivia just for the fun of playing trivia rather than to make hundreds of thousands of dollars to spite jerks on Twitter. Maybe next year…sigh.

To any of my fans or friends out there who have a few hundred bucks and a weekend to spare, there are few better ways you could use them than attending TCONA 5. Go give ’em hell for me.

Below, here’s a rundown of my conversation with Tony on life, the universe and trivia.

Arthur Chu: How did you get involved in the world of trivia and how did you get the idea to make trivia into an event unto itself? Was there any particular trivia franchise — Jeopardy, Millionaire, Quizbowl — that pulled you in?

Tony Hightower: I was always a bookish kid growing up, and I was one of those kids that loved game shows of all kinds. I watched plenty of Jeopardy growing up, but my earliest childhood memories were of growing up in Toronto watching Reach For The Top, the local high school Quiz Bowl variant, and thinking that knowing stuff was cool. I did get to be on it myself (my high school won a North American championship against a team from DC before I quit), but really, I’ve never been far from playing with facts and looking for connections between random things.

I toured with a band for much of my 20s, which brought me to New York, where my band quit on me, and I realized a few things: I had a good speaking voice, I could handle drunk people fairly well, and I was still a little nerdy. So I started hosting my first trivia night in early 2006, and, well, here we are.

AC: What do you think about the evolution of the idea of “trivia” and “trivia mastery” in today’s world? A lot of people have said that with a program like Watson that can hold the entirety of Wikipedia in its memory, the “skill” of trivia recall is obsolete — certainly it’s become much easier for anyone to “know” any fact by grabbing their phone and Googling it as soon as the question is asked.

Pete Holmes did a bit in his stand-up about how we’ve lost the “experience of not knowing things”, the nagging sense of not knowing where to look up the answer to some question and the excitement of running into someone who just happens to know the answer — meeting the one dude from Florida who just happens to know that that’s the state Tom Petty is from.

Do you agree that there’s been some loss of the sense of “wonder” in trivia now that we have a wealth of trivia at our fingertips at all times?

TH: The short answer is no, I don’t agree. People still play chess since Deep Blue beat Garry Kasparov. People still watch Jeopardy! after Watson; it didn’t (and won’t) destroy trivia. Sure, it’s easier to outsource your knowledge of the world to the cloud brain, but I think people mostly understand the danger of that. Maybe it’s just the people I tend to know.

Relying on the Memory Hole and the hive mind might be easier than actually knowing things, but it also removes some of what makes you a unique individual. The point of trivia as a discipline isn’t to know a ton of stuff. That’s a just a byproduct. The real upside is being able to carry on a conversation with (pretty much) anyone about (pretty much) anything.

Every decent bar trivia night will drop a few dozen conversation topics on the table, and if two or three of them “take” over the course of the night, then you’ve had a night out with your friends where you’re talking about something brand new, not your crap job or someone’s relationship issues or the same boring stuff you talk about all day. Someone went to Versailles as a teenager. Someone else watched a documentary about Nikola Tesla. Someone else went to an XFL game once in the 1990s. Someone else used to work at a bowling alley and knows all the terminology. Everyone gets to share.

My favorite question for me to overhear at trivia events, the one that starts a million conversations, is “How did you know that?”

All that said: is constant internet access changing the way we access information? Of course. The technological revolution is changing the way our brains are wired, and when you have quick, easy access to the sum total of human knowledge at any time, day or night, you have to change how you find wonder in the world. But people still do.

AC:  I know that a lot of people’s love of shows like Jeopardy! comes from the Slumdog Millionaire effect — the excitement that comes from knowing some particular bit of trivia because you have a personal story connected to it, like Joseph Gordon-Levitt shouting out on Celebrity Jeopardy! that Catcher in the Rye is “my favorite book”!

For me the problem with being a trivia expert is that you get fewer and fewer of those idiosyncratic stories the more stuff you learn through intentional studying and memorization. Do you find that some of that early joy of playing trivia games gets lost the more steeped you get in the trivia world?

TH: Absolutely not. I’m with the British quiz-show producer John Lloyd on this: Every fact in the universe is interesting if you look at it right.

There’s always another wave to catch, another mountain to climb, another interesting thing you don’t know about yet, another book or play or movie or branch of science, or meme, or new world leader or interesting quote from someone, or new development in world news, that casts something that happened before in a whole new light. 20 years from now, Joseph Gordon-Levitt’s daughter is going to be on Celebrity Jeopardy!, saying “Aww, yessss! What is ‘The Fault In Our Stars!’ ”

I’ve been into trivia on some level my whole life, and actively hosting it as a hobby (and later a profession) for the last decade, and I’m not bored by learning new stuff yet. The world is an infinitely large and intricate jigsaw puzzle, and I find great joy in collecting pieces and trying to build as big a picture in my mind out of it as I can. Memorizing lists by itself is boring, but the magic happens when one list overlaps with another, which is where brute-force memorization turns into a tiny piece of actual knowledge.

Maybe it’s because I never went to college, but I never felt the need to specialize. I might be really into music and literature, but I find science and philosophy just as interesting. There’s a running joke at one of my nights that I never go a month without asking at least one epistemology question. I don’t even mean to. It just happens. Everything is interesting if you look at it right.

AC:  I heard you just taped Millionaire last week. Was that your first experience on a “real” trivia show for real money? One of the paradoxes of the trivia world that I remember vividly from Quizbowl is that the more “into” trivia you are, the lower the monetary stakes are likely to be — Quizbowl tournaments organized by trivia buffs for trivia buffs often have no prize other than, say, your pick of a stack of new books, whereas everyone jokes about how game shows like Jeopardy! and Millionaire are geared toward the amateur “lay” audience. Did you feel any of that tension going into playing Millionaire?

TH: I did! It wasn’t my first game show experience (I was on Jeopardy! In 2011, winning just 10 fewer games than you did, and I did get to be Ken Jennings’ Plus-One lifeline on Millionaire last year), but the only pressure I felt was professional, not personal. When I was on Jeopardy!, I had a joke-that-wasn’t-a-joke that if I pulled a Wolf Blitzer (finishing deep in the red), I’d have to quit trivia and become a karaoke host. But as far as the game itself? I wasn’t too concerned. Being on TV is fun, the same way Tuesday night bar trivia or a quiz bowl tournament in some high school classroom somewhere is fun. They’re just questions. You either know them or you don’t. The fun is in the asking, the competition, and the picking up new facts. Prizes are nice (especially cash), but that’s not the point.

One thing being on game shows has given me was a sense of having proved myself. Could I have done better on Jeopardy? Probably. It’s a whirlwind, as you know, and I made a bit of a human-judgement error on FJ on Day 2. But once you realize you’re not going to poop on the floor on national TV, suddenly… it’s okay. And then serving as the MC of TCONA the last couple of years, meeting and making friends with all these game show and trivia legends, as well as having spoken with thousands of quiz fans and players from literally all over the world, has given me what feels like a bit of perspective about all of this. As long as you’re interested in learning new stuff, then you get to stay in the game, regardless of your skill level.

AC: What do you think about how the word “trivia” is defined? I’ve always thought the interesting thing about trivia games is that they’re really a test of what we consider to be “common knowledge,” that they’re a sort of statement about what our culture considers to be important. What do you think about how the way trivia questions work tends to uphold a “canon” of, say, books and writers that you’re “supposed” to know?

This is especially relevant since we’re seeing more and more complaints about shows like Jeopardy! switching their content to be more pop-culture focused rather than focusing on “classical” trivia. I remember the endless bickering in College Bowl about whether the content of a given question was tournament-worthy or was pop-culture “trash”. Do you think there’s a real standard for what makes something “worthy” content for trivia or is it all arbitrary?

TH: I never had a lot of patience for this argument.

Everything matters. What good is thinking (let’s say) Eleanor of Aquitaine is more worthy of being known about than (let’s say) Spongebob Squarepants, if it means you can’t have a conversation with the lady at the deli?

Trivia is just the art of turning the learning of facts into a game. What the actual facts in any given game are is not relevant to the game, whatever it is. The Kardashians & Kant both fit into any quiz if you ask about them right.

Knowledge is supposed to build bridges between people. What the old-schoolers call “classical knowledge” is the foundation that has brought humanity to where we are, and it’s crucial to understanding the bigger picture. But without paying attention to modern “trash” culture (I hate these terms, but I don’t have better ones) as well, then all that knowledge stays trapped inside your head, doesn’t advance humanity, and doesn’t give you anything to talk about with anyone outside your immediate cloistered group. Great trivia works both ends of that street, giving us both the ability to share what we know, and some perspective about what it all means, and turning it into a fun game for the whole family. (Seriously. Epistemology questions. That is, quite literally, what I’m talking about.)

Keeping that balance is a tough, inexact science, and Jeopardy is a national institution that has advertisers they need to satisfy, so I understand the occasional forays into modern junk culture. The real problem isn’t with Jeopardy, though. You can’t ask them to be all things to all people. The problem is that shows like College Bowl aren’t on TV anymore. I’d love to see that again, or an American version of the weightier British shows like Mastermind or Eggheads, just to balance off the lighter-themed shows out there, and leaving Jeopardy free to maintain the middle ground. That would be wonderful.