If trivia were an Olympic sport, Tony Hightower would be on Team USA. He won a quarter of a million bucks on Who Wants to Be a Millionaire last year, is a Jeopardy! champion, has won on Cash Cab, and serves as the executive director of Quizzing North America. He has also hosted trivia nights for over a decade, and emcees the Trivia Championships of North America in Las Vegas. Hightower knows a lot generally and, more specifically, he know pretty much everything there is to know about training for an unpredictable quiz.

According to Hightower, trivia night competitors don’t need to have naturally great recall to win those free rounds. He says it’s about understanding how questions are asked, what questions will be asked, and how to make intelligent guesses at speed.

Inverse asked Hightower to play Yoda to our Luke and teach us the ways of the trivial and obscure. He gave us just enough strategic guidance that we’ll have no one to blame but ourselves the next time we lose.

With Hightower's help, you, too, can have fun playing trivia.
With Hightower's help, you, too, can have fun playing trivia.

Were you always into learning random facts or did you develop that passion later in life?

As a kid, I used to watch game shows. I watched Jeopardy! and a high school quiz-bowl-type show called Reach for the Top in the ‘70s. But I got away from that once I got into high school. I got into a band, discovered girls, did all that stuff. As an adult, I wrote for a while, sang in a band for a while, and then gradually came back to it. I started going to quiz nights. I got asked to host my first quiz night in February of 2006. I haven’t looked back.

Let’s get into the strategy. Is it helpful to have a broad understanding of a number of different knowledge areas or do you ultimately just need to know facts?

The people I know who are really, really good at trivia are people who are voracious readers, and who process information really quickly. But there’s also a certain dreamer thing that you have to have. You have to let your mind travel down rivers that it doesn’t normally go down, and start thinking, ‘Well, what if this?’ and ‘What if that?’ There’s a lot of crossover between trivia people and people who build crosswords. People who are good at analyzing things and making connections between things will retain information a lot faster than people who just memorize lists of things by rote.

On that note, do you have a go-to memorization method?

I don’t think there’s a right way to remember things. I think it’s just a matter of reading stuff, and staying curious. The more curious you are, the better off you’re going to be. That’s kind of a good lesson in life anyway. Your curiosity is going to lead you someplace, and then, once you get there, you’ll find that something you read this week will connect with something you read last week. Suddenly, it’s no longer a road; it’s an intersection. And that makes it easier to remember.

Reference books are great and I’ve got shelves of them. But they’ll only go so far by themselves. It’s a matter of engaging with the world, and having stuff wash over you from all kinds of different directions.

Are there particular types of obscure facts that tend to come up in trivia?

All questions are hard if you don’t know them, and easy if you do. The stuff you think is obscure, somebody else will look at and think, ‘Well, duh. Of course.’ We all have our esoteric areas of knowledge. I co-write a cocktail blog with my friend Sam, and so I know more about cocktails than your average person. But look at Ken Jennings, for example: He won 74 games in a row on Jeopardy! He’s never tasted alcohol in his life. He doesn’t know a thing about cocktails. If you know it, it’s easy; if you don’t know it, it’s hard. Don’t downplay what you know just because you think nobody knows it. That’s a really important thing to remember. The stuff you know matters.

Okay, I’ll grant that. But what’s the best place to start?

Watch Jeopardy! every day. Watch Millionaire, 500 Questions, and as many game shows as you can. There are places with those transcripts. You can Wikipedia surf — I think Wikipedia surfing is an underrated skill. I wouldn’t lean 100 percent on their facts, but it’s a great place to start. Open up Wikipedia and click on the “Random article” link. Just read stuff. Click on it a bunch of times until something catches your eye.

There are a bunch of great online games you can play. The QuizUp app is really good. Sporcle is a lovely site. And don’t be afraid to go back to trivia nights. Grab a posse and go out to a trivia night, wherever you are. The good thing about a trivia night is that it’s social. It’s a night out with your friends where you’re not talking about your job, or your relationship.

That’s how you get better at trivia: by focusing on it. If you wanted to run a marathon a year from now, what’s the best thing to do? Just go out. Run a mile today, run a mile tomorrow, then, one time next week, run two miles. If you keep doing that, and just pay attention to it — you don’t even have to go super hardcore about it — a year from now, you’re running 26. It’s the same thing with trivia.

Astronaut Scott Kelly watches Jeopardy! in space.
Astronaut Scott Kelly watches Jeopardy! in space.

Given the outrageous amount of information that one could learn, and that could come up in trivia, do you even attempt to limit your research?

It depends on what you want to do. If you want to be good at a trivia night, the secret is to go to your local quiz and see the types of questions they ask. It depends on the host: Some hosts are really into presidential trivia, or into the classics, and they’ll ask a lot of questions about opera, or whatever; and then other ones, they’ll only ask about what was in the gossip pages.

If you want to win at a trivia night, or if you want to get on Jeopardy!, go to where they are and see the types of questions they ask.

Trivia covers everything. It’s impossibly large. You wouldn’t go to a restaurant and order everything on the menu. But start somewhere. The secret is to start with something you like, and then take one step off of the thing you like and into something that you’re not really sure about. That’s the secret to knowing stuff, if there is a secret. Keep being curious, and keep the ground moving under your feet.

Final question: On Jeopardy! and Who Wants to Be a Millionaire, do you walk out with a cashable check?

No, they mail it to you. Usually, it’s about three months or so after the air date. You shake hands, fill out the forms, and then you walk out. You treat everybody who came with you to a really nice dinner and then you wait for the check to arrive. That’s really all you do.

But it’s in full, the check, when it does arrive?

They pay you in full. They don’t take anything out. I won $250,000 on Millionaire, and three months later I got a check that literally said two, five, zero, zero, zero, zero on it.

I have never been so afraid walking to a bank in my life.

Photos via Flickr / Josef Jerabek, Wikimedia Commons, Flickr / Steve Jurvetson

Joe is a writer from Vermont who lives in Brooklyn. He has written for PopSci and McSweeney’s Internet Tendency and spent a year playing with words and other writers’ dreams at Tin House in Portland, Oregon.