Ken Jennings in an interview with Grant Barrett on a minicast from A Way With Words:

People think trivia questions must come automatically from a book or a computer. It’s a very tight and controlled art form. It’s like writing haiku or a villanelle or something. It’s this very tight, constrained format that really requires a lot more work than people suspect to get the trivia to work right.

I’ve said that trivia questions land halfway between haiku and jokes on the writing spectrum.

I was reading Luke Wroblewski’s blog for my day job and came across this idea:

Will Wright, the creator of the Sims & Spore, has a belief that games should allow people to succeed within the first five seconds.

What does this mean for writing trivia? Quizzes and quiz rounds should start with their easiest question and get harder as they go. Given Wright’s “success in the first five seconds” thought, though, inspires me to go further:

The first question of the quiz is one that everyone should get right, right away. Asked, answered, minor victory achieved.

(The trick: making that question both easy and interesting.)

(Also: Anyone have a straight-from-the-source cite for that Wright quote? Let me know.)

I put together a quiz on Sporcle so you can test yourself.

I got 6 out of 6, but given that I put it together, I don’t consider it much of an achievement.

I’m hosting tonight’s quiz* at the Old Pequliar in Ballard. There’s a requested round on John Irving (and I swear you don’t need any knowledge of Irving to do well).

Want to win a batch of cupcakes from Yellow Leaf Cupcakes you can eat at tonight’s quiz? Tell me what these performers have in common:

• Peter Falk
• Harvey Fierstein
• Morgan Freeman
• Dustin Hoffman
• Elizabeth Montgomery
• Douglas Rain
• Henry Winkler

Email your answer to james at quizquizbangbang dot com by 6pm. You gotta play tonight’s quiz to win the cupcakes.

Haven’t been before? Here’s what you need to know to go:

1. Quiz starts at 8. Seating gets tight earlier.
2. $5 for a team of up to 5 players; $7 for a team of 6.
3. First, second, and third place win cash.

*For posterity’s sake, “tonight” is June 1, 2010. Hello, people of the future.

Audio rounds. So simple. Such a pain in the ass.

Now that I’ve gotten all zen on you, have some fun with the audio round I put together for May’s quiz at the Old Pequliar. Then I’ll explain what I mean.

If I Had a Stammer: Each of these songs repeats a word or phrase in its title.
Can you name the title and performer for each clip?

1. The clip: Question 1
   (Answer.)
2. The clip: Question 2
   (Answer.)
3. The clip: 10May04_Q03_audio_audio
   (Answer.)
4. The clip: 10May04_Q04_audio_audio
   (Answer.)
5. The clip: 10May04_Q05_Audio_Audio
   (Answer.)
6. The clip: 10May04_Q06_audio_audio
   (Answer.)
7. The clip: 10May04_Q07_audio_audio
   (Answer.)
8. The clip: 10May04_Q08_audio_audio
   (Answer.)
9. The clip: 10May04_Q09_audio_audio
   (Answer.)
10. The clip: 10May04_Q10_audio_audio
    (Answer.)
11. The clip: 10May04_Q11_audio_audio
    (Answer.)

Most audio rounds go like this: I play a song clip, and you get a half point for identifying the performer and a half point for identifying the song title.

It’s simple and easy to understand, but each question is basically “Recognize this song from a 20-second clip?” There’s not much room for reasoning it out. You either get “You Get What You Give” by The New Radicals or you don’t.

I’ve mixed up the formula, but “What is this song?” is solid, and doesn’t involve wheel invention. It’s also popular with the pub crowd, which is the most important thing.

That leaves me content and structure to dazzle your brains with rather than clever premises.

Content: Which songs?

Step one: Pick an interesting topic. (Really, do that and you’re halfway home.)

The best audio round topics turn up wayyyyyy more songs than I could possibly use. It kills me to leave out a couple of songs — like “Rush Rush” this time. A broad selection means it’s easier to include a variety of songs. (And lets me bring back the category back in a few months.)

For “If I Had a Stammer,” the “repeating words” idea turned up tons of possibilities, especially once I branched out from my initial idea of titles that were literally one word repeated.

(Side net: Simplenote has made brainstorming and compiling audio rounds much, much simpler. I’ve got five or six active ideas for audio rounds, with a Simplenote file for each one. Whenever I hear or remember a song that fits a category, I can add it to the list at a moment’s notice.)

Once I started putting together the round in earnest, I had a list about 50 songs long. That helps me ensure variety on a lot of fronts: Easy vs. hard to get, multiple decades, multiple genres (pop, rock, country, hip hop), obvious vs. non-obvious candidates, popular stuff vs. music nerd stuff, songs from my own library vs. songs that I don’t know well or listen to.

That last bit’s important: I don’t want the round to become a “guess James’ music tastes” round. Mostly.

(That’s another way Simplenote helps: I can take more time to research songs, so I stray further from my own playlists. I think I underrepresent hip-hop, for example, mostly because I don’t listen to much of it, so I’ve been making a deliberate effort to include more.)

“If I Had a Stammer” includes one song from the ’60s, two from the ’70s, four from the ’80s, one from the ’90s, and three from the ’00s. That’s pretty good, but I could’ve taken one or two away from the ’80s and added one or two to the ’90s, given the demographics of the pub I host at.

I didn’t own eight of the songs (though I happily bought several of those for the round). “Boom Boom Pow” is contemporary and wildly popular; “Hold On, Hold On” and “Take Take Take” are contemporary but niche; “Anything, Anything” is familiar to a lot of people but not really a hit.

And the round had a curveball, a song I knew I had to include the moment I thought of it: “Mahna Mahna.” It’s the Muppets. Iconic Muppets. It came out in the ’70s but kids have rediscovered it for years. It was fun to watch people switch in an instant from concentration to delight, because who (this side of Statler and Waldorf) doesn’t love “Mahna Mahna”?

The structure: How should I put them together?

Ideally, the audio round (like most rounds) is easiest in question 1, hardest in question 10.

Like that ever happens.

Still, it’s what I aim for: Open with a song that no one is going to miss, end with a song you need a music nerd to get. (Or at least an inner music nerd.)

One challenge: It’s really, really hard to find a song that everyone knows. “Bad, Bad Leroy Brown” was a good pick, but one team missed the title and another the artist.

Going by the scoresheets, I should’ve started with “Tonight, Tonight,” which one team missed the title of (though everyone got Smashing Pumpkins). “Boom Boom Pow” was a good second or third track — one team guessed the song was “We Suck Suck Suck.” Four teams got full credit for Neko’s “Hold On, Hold On,” and I wouldn’t have touched that song if I hadn’t known our crowd was a) local and b) rife with KEXP fans.

“Anything, Anything” was just about perfect for its slot. Lots of people were singing along, but only a couple of teams knew both the title and the artist. (Most popular guess for title: “Marry Me, Marry Me.”)

The hardest song turned out to be “Over and Over” by the Dave Clark Five. One team got the full point.

Astute readers will notice that I didn’t address the eleventh song on the list. At the Old Pequliar, thanks to a now-departed host, the audio rounds always go to eleven. And I usually like to use that eleventh spot as a punchline, of sorts. “Mahna Menha” is one example: familiar, fun, something most people know and love.

Sometimes #11 will be a song that everyone knows and is a total blast — “YMCA” and “Faith” have both appeared there. If I hadn’t used “Mahna Mahna” this time, I’d have gone with “Hot Hot Hot” — it’s always good to leave people buttrocking.

On the other hand, I’m happy to sacrifice familiarity for fun: In March I ended with “Rockin’ Pneumonia and the Boogie Woogie Flu,” by Johnny Rivers, which most people knew the title of. When I did a round on artists’ last top 40 hits, the eleventh spot went to Pat Boone’s gloriously kitschy and racist “Speedy Gonzales.” No one got a full point for that one, but the song was transcendently awful.

Regardless, it’s an eleven-point round. I figure it should take a lot of work to actually earn all eleven points.

In conclusion

How I try to do it:

1. Pick an interesting theme.
2. Pull from a broad variety of songs.
3. Try to go from easiest to hardest.
4. End with something fun.

What do we have here? I scrambled the lyrics (minus any mentions of the title) to a well-known song using Wordle. (Wordle is awesome. Have fun.)

Your task: Identify the song.

Added March 26: the answer, in handy music-video format. (Which is probably how you know the song anyway.)

If you’ve been around here for a while, you know the drill. I took the lyrics to a popular song (not necessarily current, mind you), removed any mention of the title, and made them into a word cloud using Wordle.

Your task: Identify the song.

Added March 19: Tired of staring at it? Here’s the answer.

It’s easy to write difficult trivia questions.

It’s easy to write easy trivia questions.

It’s difficult to write challenging trivia questions. So of course, they’re my favorite kind.

(What makes a question “challenging”? You can solve it if you think about it. Or at least make a reasonable guess. It isn’t you-know-it-or-you-don’t, at least not instantly.)

A complete quiz blends all three kinds of questions: Easy ones to keep casual players interested, hard ones to reward dedicated trivia hounds, and challenging ones to keep people intrigued and on their toes. I think a quiz without any challenging questions is not a great quiz.

Something I posted on Twitter the other day:

Good trivia questions are part magic trick and part riddle, seasoned with a little bit of haiku.

No spice or puppy dog tails required. Got it? Good. In my next few posts I’ll talk a little about what I mean by that.

After February’s quiz, Mehal chatted with me for a minute. Then he mentioned that his team (Annyong!) had collapsed in the second half.

It's a pressure cooker! (Get it?)

Yeah, I said. The second half was harder than the first — but that’s how I like it. (OK, truth be told I don’t like teams to collapse.) I think a good quiz should get more difficult as you go along.

“Why’s that?” he asked. Which is a good question.

Apparently some hosts like to lead off with a difficult round. Players haven’t had as much beer, the theory goes, so they’re sharper.

But most games start easier and get harder as they go along — and pub quiz is a game. It’s more satisfying for players to ease in, get comfortable with the rules, and then start spraining their brains.

Compare with game shows: Jeopardy! is easier in the first half than in Double Jeopardy, and Final Jeopardy is in theory the hardest question of the show. Cash Cab starts with easier $25 questions and builds to more difficult $200 questions. And you don’t your shot at becoming a millionaire until you’ve answered 14 easier (but progressively more difficult) questions.

And at pub quiz, the first round should be easier than the last round.

At the Old Pequliar, the first round people see is actually round 4, the first picture round. They get to work on that through the entire first half. And they see round 8, the second picture round, in fifth position, at the second half.

So this is what I shoot for: Round 4 as the easiest round, round 7 (the movie round) as the hardest round, and the ones in between getting more difficult as you go.

In practice, it’s difficult to gauge things that precisely. I can make the movie round the hardest round, no sweat. And I can pull off a pretty easy picture round. But placing the other rounds exactly in order of difficulty? Tricky. (The infamous round 1 poetry round was within the last few months, after all, and that was murder. I’m still learning.) I’ve gotten better at ensuring that the first half is easier than the second half, though.

I also try to do this within individual rounds. Again, look at Jeopardy!: the easiest questions in each round are at the top of the board, and they get harder as you go down. So in an ideal pub quiz round, question 1 should be easier than question 10.

I find this especially important when it’s a high-concept round with unusual rules, like triangulation or “complete the set.” The first one or two questions, being easy, help people understand the concept and build confidence; the last couple of questions make them sweat.

(Side note: This is one of the reasons I wasn’t fond of geography as round 1. For most teams it’s one of the harder rounds.)

Escalating difficulty is less of an issue for regular teams — if you play the quiz at the same pub every week, you get a good sense of what’s asked and how hard it is and how everything works. But I think it’s vital for making sure new teams have as good a time as possible. Make it too hard too quickly and you spur walkouts, or at least inspire people to give up after one round and vow never to return.

And I find that it’s more satisfying to build up players’ confidence before you smash it.