Special Topics In Gameology is an in-depth look at a specific corner of the gaming world, in miniseries form. For this edition of the feature—Funny People—Anthony John Agnello interviews a few icons of video game comedy. The series debuted last week with Leisure Suit Larry creator Al Lowe. This week: You Don’t Know Jack head writer Steve Heinrich.

You Don’t Know Jack was weirdly prophetic. The series of trivia video games styled as interactive live TV shows was a phenomenon before the rebirth of the primetime game show or the Wii boom. It was a popular multiplayer game years before online PC gaming became ubiquitous. For all its prescience, though, Jack didn’t kick off a trend of hilarious game design. Few games have matched or even aspired to the brand of antagonistic humor that developer Jellyvision executed so deftly in the 1990s Jack CD-ROM games.

The series went into hibernation after You Don’t Know Jack Volume 6: “The Lost Gold” was published in 2003. After an eight-year hiatus, Jack returned last year as a going concern on PCs and consoles, and this May, Jellyvision launched a Facebook version. Lead writer Steve Heinrich talked with The Gameological Society about the challenge of writing a perfect question and the enduring appeal of his game.

The Gameological Society: Walk me through the process of writing a You Don’t Know Jack game.

Steve Heinrich: First, we decide who the host is. For this most recent version, we went with Cookie Masterson, who has been the host since You Don’t Know Jack Volume 3 way back on the PC. He’s one of the fan favorites. Now you know who you’re building around. Then you develop a stable of characters. You’ve got your director, your interns, whoever you decide are the people to include in questions.

Once you have that framework, You Don’t Know Jack is all about the questions themselves. Writing a You Don’t Know Jack question is very different from writing a Jeopardy! or Who Wants To Be A Millionaire question. Where writing a regular trivia question might take 10 minutes, we allow two hours to write any given You Don’t Know Jack question. That’s the baseline we give our writers.

It’s this hodgepodge, mixing a pop-culture reference, a high-culture reference, then writing dialogue for each wrong answer, so no matter what a player picks, they get a specific response. Sourcing it, crafting it, working the characters in, giving the host suggestions on how to read things, nutty sound effects. Everything in our game is supported by the questions. And, of course, our host. Tom Gottlieb [who plays Cookie] is brilliant, and we can’t overstate how important he is to the writing process.

Gameological: How has that process changed between Volume 6, which came out in 2003, and the revival in 2011?

Heinrich: It’s stayed remarkably the same. We write the questions and of course the host—Cookie, in this case—he’s more than welcome to suggest, “Hey, what if we did it this way?” It’s very much a mutual, back-and-forth process. With this most recent game, we had a lot of people still here from when the game first started. There’s been a lot of continuity. We’ve also brought in some fresh, young writers from the Chicago improv scene.

Gameological: What’s the first challenge in writing comedy that requires audience interaction? How do you make sure something’s funny when you need people to press buttons and pay close attention for the jokes to even work?

Heinrich: For this most recent You Don’t Know Jack, we were under a real crunch to get it done. We didn’t have as much time as we usually have for audience feedback and play-through sessions, so we just ended up hoping that all of it would work. A lot of it does, some of it doesn’t. That’s the nature of comedy.

Luckily for us, the most consistent from of comedy comes from somebody getting something wrong. You can take any little snippet of a wrong answer about, say, root beer, and you can turn it around. “Looks like you’ve been drinking too much regular beer!” Being wrong is a consistent well of humor. That’s why it’s such a great party game, because people love to see their friends put down by what’s basically an inanimate object.

Gameological: Why did it take the better part of a decade for You Don’t Know Jack to come back?

Heinrich: Number one was probably the lack of people offering us money to do it.

Gameological: That would do it.

Heinrich: What happened with the original series was that the PC market started to die down. We had 12 different versions of the game, including the teen version of the game called Headrush, an online version, and of course the TV show with Paul Reubens as the host that lasted for six weeks. We had the tabletop version of the game. A couple of books. The first answer is that the series needed a break.

Being wrong is a consistent well of humor.

The second answer is that the PC market was overrun by the console market. We didn’t have much expertise in that field. We had one attempt, You Don’t Know Jack Mach 2 on Playstation 2, and, well—we weren’t prepared as a company to take advantage of the console gaming market. So we took a break, and the company went in a different direction. Now there are two sides of the company: Jellyvision Labs, who creates interactive conversation technology for businesses, and then a devoted game company our side. There were definitely people here from the old gaming days and we were pining for it. We’re happy it’s back.

Gameological: What about the audience has changed that made this the right time for You Don’t Know Jack to re-emerge?

Heinrich: For one thing, Wii was popular. We were reading studies about how more women were using the Wii than any other console. Families were using it. Back in the day, when, You Don’t Know Jack was on PC, you would get multiple people huddled around the keyboard looking at a little 13-inch monitor. Looking at a TV while sitting on a couch is really the ideal scenario for this game.

The previous versions were so successful, but there were so many things that could have been improved. Here we are now, and we’re able to present it with proper stereo speakers, giant TVs, and people on the couch. The market was there, particularly on the Wii, with more people were spending time together doing things in front of the TV. The other factor is that pop culture is really prevalent in the news today. Back in the ’90s, pop culture was pop culture. These days, you turn on the nightly news and it’s all about Brangelina or whatever.

Gameological: So much of the game is reliant on topical humor and humor that references pop culture within the last 20 years or so. You’re as likely to have a Seinfeld gag as a Brangelina gag. How much a consideration is longevity?

Heinrich: When we started this, I had to ask: “Which way are we going to go?” In 1996, when the original came out, there were references to Gilligan’s Island and The Brady Bunch, late ’60s and early ’70s stuff, and that original game was played by 20- and 30-somethings remembering their childhood. There was more of a nostalgia factor.

Time’s progressed between 1995 and 2010; things move a lot faster now. Something can be popular, and then six weeks later it’s dated. There was a conscious decision to not go that far back again, no Brady Bunch, because even though those people who are now in their late-30s and 40s will play it because they love it, we want stuff that everybody knows about that’s happened in the past 10 to 15 years.

Seinfeld’s a great example. That’s the show I point to with the staff. Seinfeld is in, but something like Mad About You is right out. On the other hand, you don’t want to ask a question about something that’s happening today because it could blow over and be gone.

Gameological: How long do you want a You Don’t Know Jack episode to endure?

Heinrich: People should think it’s funny the first time the play it. If they play it a second time, they should be playing it because they thought it was funny that first time. Trivia is consumable. If you play World Of Warcraft, it goes on forever. You’ll never be done with it. Even a Mario game invites replaying. But with You Don’t Know Jack, if you played that question, you know the answer. We do have jokes waiting if you go back and get a different wrong answer, but we don’t concern ourselves with replay-ability because people probably aren’t going to want to consume it again.

Gameological: What stressed you out more than anything else in making this new version?

Heinrich: Aside from how fast we were moving, the issue for us was: Who is going to play the game? Is it going to be a bunch of 19-year-old boys? Is it going to be people in their early forties who remember the game from back in the day? Or is it going to be a combination of everyone in between? That meant we had to write for everybody. When you write for everybody, you worry whether or not it will appeal to any audience at all. So we just kept the same style and sensibilities that we had before, because it worked, and we hoped it would stand up. I feel like we’ve succeeded so far.

Gameological: I promised my girlfriend I’d ask this: What is the genesis of a Dis Or Dat question? How do you come up with two totally unrelated things in the writer’s room and then build the question from there?

Heinrich: Oh man. Dis Or Dats are by far the hardest questions to write. They’re hard for the reasons you’re hinting at, but they’re hard now because we’ve done so many of them that, I kid you not, we are just about out of “groups of things.” If I could tell you exactly how you come up with one, that would be a million-dollar idea.

We strive to tell the player, “You are not in control of this situation.”

What often happens is a writer decides, okay, I’m going to look up different species of snakes. Then you see three or four in there that sound like, say, a Las Vegas casino name or something. That moment hits, and you’re like, OK! I just did one where I was looking at the names of a bunch of children’s board games, and they were called things like “Don’t Spill the Beans,” “Don’t Tip the Waiter”—they all start with the word “don’t.” They all sounded like pieces of advice. So I look up Dr. Phil and, lo and behold, he has a book that’s all about advice for a first date. You can’t plan for that. You just have to get in there.

Gameological: There’s a lot of humor in the game that’s separate from the trivia. The little interstitial animations of the numbers dancing around between questions for example. How do you make it so that people won’t get sick of them after watching them over and over again?

Heinrich: There are two paths you can take for those question segues. One is that you can create five or six different segues for every single questions so you rarely see the same one over and over again. The second tact you can take is to make them so they get stuck in people’s heads, so they remember it, then maybe that one becomes their favorite, and they find themselves singing the song in their head all day. That’s the tactic we took, but you still want to keep it varied. On the console version, when you play multiple episode sessions, say in Question Four when they’re singing, “Everybody cuatro! Everybody cuatro!” sometimes one of the number fours will get shot. Then the police come in. Then there’s a crime scene. Then at the end of the game, you see “4” getting buried in his grave.

Gameological: The first time the number six turned to the camera during that question segue and said, “I love you,” I just lost it. My girlfriend and I could barely breathe. There’s a ton of humor like that in the game, though—humor that requires patience, little things that happen totally outside of the game, like the audio commercial spoofs that play over the credits. How do you decide what to actually write and include when there’s no guarantee the audience will pay attention?

Heinrich: Since it was invented, You Don’t Know Jack, for whatever reason, just works. What we’ve found is that a lot of trivia games allow the player to skip through things. There’s obviously validity in allowing them to do that. We strive to tell the player, “You are not in control of this situation.” You are on a live trivia game show that is being run by Cookie and everyone else, and you are going to play at their pace. That’s the best way to do it. If we created another game, we may decide that it’s going to be super-fast, super-quick, but what people say inevitably is that even though Jack has these moments that force you to pay attention, it seems like such a fast moving game. You have to constantly make it feel like it’s moving forward. Give room for the characters to grow, for things like the commercials to play out and it ends up as a magical stew.

Gameological: Why do you think the live-action version of You Don’t Know Jack failed?

Heinrich: That’s the million-dollar question. I actually went out to work on it.

Gameological: You weren’t the head writer, though?

Heinrich: There were actually two writing staffs, which was one of the issues. There were so many issues, it would take too long to list them all. I went out there to write questions with Tom Gottlieb, one other question writer, and then the head question writer who was a veteran of a few TV game shows. Then there was the larger stable of writers who were in charge of the comedy, sketch, and sitcom elements of the show. The idea was to make a cross between a sitcom and a game show. So we had these two staffs who rarely—way too rarely, really—integrated with each other.

The other issue was Paul Reubens as the host. I grew up loving Pee-wee Herman. Who doesn’t love Pee-wee Herman? It’s a genius, genius character. But we had a variety of different hosts in our games, and there were only a couple that the audience responded to. There was the first one, our founder Harry Gottlieb as Nate, and now his brother Tom Gottlieb as Cookie. It’s really hard to get that exact tone that makes a You Don’t Know Jack question work. The host needs to be likable but also able to put down the player in the same breath. I just think Paul was brought in late in the game and there wasn’t enough time to really immerse him in it.

To be frank, the answer might be that You Don’t Know Jack just plain doesn’t work live. It may never work live. It just might be something that exists in the player’s mind and that space we’ve created for them will never be as exciting on a real TV as it is in your head.

Gameological: Why aren’t most video games funny?

The host needs to be likable but also able to put down the player in the same breath.

Heinrich: Let me tell you: It’s hard. You don’t want to spend too much time on the comedy because people want to play the game. You don’t want to spend all your time on the game because the comedy is what makes it work. We’re in Chicago, and that gives us access to a lot of comedy-writing talent. We brought a lot of those people in over the years. We actually hold auditions when we begin making a game, and we have them come in and write samples. We look at which ones we like, then bring them in and say, “Now write some You Don’t Know Jack questions.” No matter how much we try to explain it to them, you end up going from having 400 really funny people to that one person who kind of gets it. I can’t speak for other games, but for You Don’t Know Jack, it’s difficult, and only a few people so far have been able to do it really well.

Gameological: If Jellyvision were going to make a comedy game that wasn’t You Don’t Know Jack, what would it be?

Heinrich: Stay tuned. What I can tell you is that you’re not going to find us making a first-person shooter. We had a meeting the other day to try and figure out how we define ourselves. We define ourselves by being funny and by having accessible, word-based games. It’s not all going to be trivia, it’s not always going to be an interactive television show, but the core of what we do is always going to be casual. It’s always going to be funny.

Illustrations by Richard Hofmeier.