5 ways to get better at trivia, according to a Jeopardy! contestant

About three years ago, I stopped telling people I was on Jeopardy!. This is primarily because it is a very strange way to start a conversation, but also because it does become repetitive answering the same questions (they don’t tell you the categories beforehand, and Alex Trebek was very nice). Recently, the show invited me back to compete in the upcoming High School Reunion Tournament, and as I prepared I found myself cataloging all the techniques I’ve developed over my years of trivia. I’d like to pass on my expertise to everyone who wants to get better.

I’ll be honest, though: some trivia does simply come down to luck—it is a lot easier to name the states bordering Illinois if you live in Chicago, for instance. But there are definitely a few tricks to the trade that will almost immediately help you get better at trivia. So the next time you’re at your local bar playing with some friends or following along with Jeopardy! at home, consider these tips before you finalize your answer.

Every time I hear a trivia question, I break it down into a bulleted list of facts in my head. Take this question I saw last year in the trivia league LearnedLeague: “Kathleen Hanna, co-founder and lead singer of the punk band Bikini Kill, allegedly (and inspirationally) once wrote with a Sharpie on a hotel room wall, ‘Kurt smells like’ what?”

Here’s how I broke it down:

• The answer is a word or phrase that completes the sentence “Kurt smells like…”
• The answer somehow inspired one of Kathleen Hanna’s friends.
• Bikini Kill played punk music, so the answer probably has something to do with rock music.
• Kathleen Hanna knew a guy named Kurt.

You likely only know one musical Kurt (Cobain), and he did play rock music, so it almost certainly has something to do with him. Cobain was the lead singer of Nirvana, so you can start thinking through Nirvana songs. From there, you’re likely to come up with Smells Like Teen Spirit. “Teen Spirit” nicely completes the phrase and is indeed the correct answer.

If you’re asked a question about a movie from the 1940s, for instance, you can immediately begin honing in on your answer based solely on what’s relevant enough for someone to know (think Citizen Kane or It’s a Wonderful Life, not some B movie only five people have watched). While I was in my last year of high school, I appeared on Jeopardy’s Teen Tournament, where I finished as a semifinalist and won $10,000.

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Here’s my breakdown of the final question of that Jeopardy! semifinal (I got the question wrong, in case you were wondering). The category was “the American Revolutionary era”: “She was disowned by the Quakers after marrying an Episcopalian upholsterer in 1773 and later took over his business.”

• The question says she, so we’re looking for a woman.
• This person was a Quaker, but was later disowned.
• This person married an upholsterer.
• This person took over her husband’s business.

There were plenty of women around during the Revolutionary era, but only a few of them are remotely famous. The answer is going to be someone you’ve heard of. It won’t be someone pulled from obscurity. So, I started running through famous revolutionary women—Martha Washington, Abigail Adams, and Dolley Madison were the names I came up with.

Unfortunately, I couldn’t go much further than that. I didn’t know any of the presidents’ religions, and the last clue just didn’t fit at all. In fact, the answer was not a president’s wife, but seamstress and alleged flag designer Betsy Ross. I kicked myself when the answer was revealed, going “Of course! Very famous, very ‘knowable.’”

Don’t be afraid to guess

Sometimes, you’ll have to make educated guesses because it’s impossible to know literally everything. At the bar where my friends and I play trivia every Tuesday, an incorrect answer doesn’t have a penalty, so if we don’t know, we always take a guess. On Jeopardy!, which does penalize incorrect answers, it’s wiser to play a little more cautiously when you’re unsure. But in general, it’s good practice to guess.

Take this other question from my other Jeopardy! Teen Tournament appearance: “The word ‘trombone’ comes from the Italian for this related instrument.”

• The answer is the name of an instrument.
• That instrument is related to the trombone.
• Its name is the origin of the word trombone.

At that point in my life, the last time I’d played a musical instrument was during piano lessons in fifth grade. I did not know the answer to this question, and I did not know the origin of the word trombone. However, I did know that trumpet and tuba are both related instruments that start with “T.” Of the two, “trumpet” shares more letters. My gut instinct said trumpet, so I buzzed in, said “trumpet,” and got the question right.

Watch for wordplay

Trivia writers (Jeopardy! especially) love to throw in little wordplay hints to lead you to the answer. Pay attention to them, because they’re relatively common when the main fact is pretty obscure. Wordplay hints generally won’t get you to 100 percent certainty, but they’ll often get you from knowing nothing to an educated guess.

Here’s another example from LearnedLeague: “The American photographer William Wegman is well-known for his warmly whimsical and witty works which primarily feature dogs of what breed?”

• We’re looking for a dog breed.
• This breed is featured prominently in photographs by William Wegman.

I’d never heard of William Wegman or his photographs, but paying attention to the exact wording of the question led me to tack on this bullet point:

• That’s weird, why do so many of the words in this question start with “W”?

To a trivia writer’s mind, this is probably a hint that the name of the dog breed you’re looking for starts with “W.” So, start going through dog breeds until you happen across the correct answer, “Weimaraner”, and take a shot in the dark. This will never be perfect (you could have thought of the Whippet, for instance), but it is quite useful.

There is one more strategy I have for learning things, although it’s a little more artificial than simply consuming media and remembering. There is a subset of hints that either make excellent trivia facts or uniquely identify an individual, but get overused when writing questions. Jeopardy! enthusiasts refer to these clues as “Pavlovs” and quizbowl players call them “stock” clues.

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For example, the Russian poet Alexander Pushkin, who wrote Eugene Onegin and Boris Gudonov, fought a bunch of people in duels before dying, so he’s often clued as a “duelist” or as a “Russian duelist.” If I hear that turn of phrase in a question, the answer will almost always be Pushkin.

Other Pavlovs include “Iowan painter” for Grant Wood of American Gothic fame, “Artist in Tahiti” for French painter Paul Gaugin, and “King of Swing” for clarinetist Benny Goodman. 

Pavlovs make nice shortcuts, especially when you’re talking about literature and the arts. You can’t read every book, but if you can remember that Nigerian author Chinua Achebe once gave a speech about racism in Joseph Conrad’s Heart of Darkness, you might not need to.