I Lost on ‘Pop Culture Jeopardy!’

Now it can be told: My trivia team competed on ‘Pop Culture Jeopardy!’ this summer in Los Angeles. Our episode (Season 1; Episode 14) is streaming now on Amazon Prime. We played a spirited game, and took the lead midway through the second round with a big Daily Double bet. But we were up against a tough opponent who pulled ahead right at the end. And we lost.

I won’t pretend I’m not a little bit sad about this, because, you know, I wanted to win. But it’s also a lot different from the first time I appeared on Jeopardy! in 2013. Back then, I was broke and feeling more than a little shattered from some mid-career disappointments. Winning three games of Jeopardy! transformed my life. Not only did it give me a new hobby and many new friends, but it also helped get my family back on sound financial footing. With the help of my winnings, we bought the house that we still live in today. Becoming a Jeopardy! champion gave me confidence, energy, and something to talk about at parties.

The version of me who appeared on ‘Pop Culture Jeopardy!’ was a decade older and wiser, and less financially desperate. It’s not that I didn’t want to win; I did, and gave it everything I had. But if I didn’t win–which I didn’t–I wasn’t going to let it ruin me. Which it didn’t. After we lost, we remained sequestered in Los Angeles. The show didn’t keep us in our hotel, but told us that if we wanted to fly home early, we’d have to do it at our own expense.

Instead, I spent the small per diem they gave us on going out for Korean food, having a schvitz at a bathhouse in Koreatown, going to the Academy Museum to see their antisemitic exhibit about the birth of Hollywood, and spending a fun night at Quentin Tarantino’s coffeehouse and movie theater in Los Feliz. The next day, I played some poker in Inglewood and visited my sister and her family the Valley. When that was done, my head was clear, and Pop Culture Jeopardy! was just another Cool Thing I Did.

Now that I’ve put everyone at ease as regards my general psycho-intellectual state, I hear the same questions about Jeopardy! over and over again, and some very specific Pop Culture Jeopardy! ones, so I thought I’d answer them here, on the website that I edit, where no one can stop me:

How Do You Get On Pop Culture Jeopardy!?

You have to take an online test. In the case of Pop Culture Jeopardy!, your entire team has to pass an online test. When they first announced the show, there was a lot of scrambling in the trivia community to find teammates. I knew immediately who I was going to ask. I’ve been playing with Kate Reed Hauenstein and Cecily Squier for years in Austin. They’re both former Jeopardy! contestants themselves. Kate has an encyclopedic knowledge of music, and Cecily knows a lot about many arcane pop-culture things. Though neither of them won on Jeopardy!, I considered that an anomaly. Also, I’ve traveled to trivia competitions with them before and know that they like to hang out and eat good food and are cool and fun. So, it was an obvious choice.

And for some reason they wanted to play with me as well, even though I am bossy and annoying in ways you couldn’t possibly imagine. All three of us passed the test. Then there were a series of Zoom auditions where we played sample games and showed that we wouldn’t be terrifying to watch on TV. And then, a few weeks before the taping, while I was in line for an overpriced burger at Johnny Rockets during a dinner break at the World Series of Poker Senior’s Tournament, I got the email: We were in!

How Do You Prepare for Pop Culture Jeopardy!? 

No, they don’t give you the topics beforehand. But in the case of Pop Culture Jeopardy!, the subject matter is somewhat limited. Though Pop Culture is vast, you don’t need to study geography or history or word origins or any of the high-minded stuff that comprises regular Jeopardy!. Maybe you need to know who played Thomas Cromwell in the PBS adaptation of Wolf Hall (Mark Rylance), but you don’t need to know anything beyond that.

I told Kate and Cecily that we might not win (we didn’t win), and we might not know all the answers (we didn’t), but that no one was going to outwork us. So we went through a rigid schedule where we crammed old pop-culture quizzes from an online league I play in, we played pub trivia so we could streamline our team dynamic, we discussed betting strategy, and we drilled with an online Jeopardy! simulator where we used our space bars instead of a buzzer. We made a plan. Even though we didn’t win, we were in it to win. We were definitely ready.

Other aspects of preparation were more slippery. Pop Culture Jeopardy! wanted us to provide a team name. Sometimes one online iteration of our team goes by Austin Powers, because we’re from Austin. I worried, though, that would force me to actually dress like Austin Powers on TV.

No one wanted to see that. Another team name for us, Post-Trivia Stress Disorder, fell into the discard pile because PCJ! felt like it would be triggering to people with actual PTSD. I don’t know about that, but I wasn’t going to argue, because I wanted to be on TV. So we went with The Recruits, because I technically had “recruited” Kate and Cecily to play trivia with me. It was kind of boring, but it stuck. As did our dark, business-casual team attire, which I think looked good on TV. Kate and Cecily, childhood best friends, had a lot of makeup preparation to do that involved at least one trip to Sephora. I stayed as far away from that as possible, though I did get my hair cut and my eyebrows trimmed.

How Is Pop Culture Jeopardy! Different From Regular Jeopardy!?

In many ways, it’s the same game. You have 61 clues, three rounds, and the same number of Daily Doubles, you have to buzz in, and you have to answer in the form of a question.

But there are some interesting differences, some of which are obvious to the audience, and some of which aren’t. First of all, it’s a team game. So instead of three players, there are nine players. But you don’t buzz in as a team, you buzz in as individuals. This means you’re competing with eight other players to get in there first. There’s a reason I only answered six or seven questions the entire show. Most of the players know most of the answers, so it’s kind of a crapshoot.

The buzzer dynamics are different, too. On regular Jeopardy!, your buzzer window begins when a light, invisible to the TV audience, blinks around the game board. If you buzz in before that, you get locked out for a certain fraction of the time. On Pop Culture Jeopardy!, there is no lockout. So you can start slamming that buzzer the second you hear the clue, if you want.

Though the buzzing is individual, and only individuals can answer the questions, it’s still a team game. So if you buzz in first, and miss, your other teammates are disqualified. However, if you hit a Daily Double, you can confer about the answer with your team. You’re also allowed to confer when on Final Jeopardy! There’s a reason why the final scores have been so generally high on Pop Culture Jeopardy! If you have three good trivia players in a huddle, at least one of them will often know the answer.

There’s also the Triple Play, which is a fun new game feature where a question has three answers, or, since this is Jeopardy!, where an answer has three questions. Anyone from your team can buzz in, but there’s no guarantee that the rest of the team will know anything. For instance, in one Triple Play, I had no idea about a Megan Thee Stallion lyric, while on another Triple Play about cold-weather sports movies, I got ‘Cool Runnings,’ but my teammate couldn’t peg either of the two more difficult answers.

Also, PCJ!, unlike most of Jeopardy!, is a tournament. So there are 81 teams. We lost our qualifier, but the team that beat us moved on to the next round. And there were a few more rounds after that. I have no idea what happened in the other games. Whenever the championship airs, I’ll be as surprised as the rest of you. We got $1500 as a team for our trouble.

This doesn’t sound like a lot, and it’s not, but back in the day for Jeopardy!, I had to pay my own airfare and hotel. This time, the show treated us like talk-show guests and paid all our expenses. It may not sound like a big deal, but it was a huge difference for me. I felt like I’d qualified for something fun, instead of engaging in a Running Man-level desperation bid to extract my family from financial straits. Jeopardy! is fun if you win, but can be kind of grim if you lose. Pop Culture Jeopardy! was fun either way. I didn’t see anyone leaving unhappy.

What Was Colin Jost Like? 

This is the most common question, because people just want to know what it’s like to meet a celebrity. Game show hosts do not mingle with contestants before the episodes. That is against federal law thanks to the quiz-show scandals of the 1950s. I saw about as much of Colin Jost as you do watching the show. He is handsome and charming and funny and blessed by God with more good fortune than any human deserves. My episode ran very smoothly and professionally. No notes.

Would You Do It Again? 

Absolutely. The one thing that many Jeopardy! contestants regret after their experience ends is that they’ll never be able to play again. Very few end up elevated to the status where the show asks them to return over and over again to play for increasingly large amounts of money. But with Pop Culture Jeopardy!, and with these new Second Chance and Invitational tournaments, suddenly the window is open a crack again. Kate and Cecily and I got the call again. Five of our other opponents on our day were also previous Jeopardy! contestants. I love being on TV and will be on TV in whatever capacity anyone wants me to be on TV. Put me in, coach.

Ever since my first Jeopardy! appearance, I’ve devoted a large portion of my life to keeping my brain sharp and my body relatively fit in case the opportunity arose again to answer questions for money on TV. It happened in 2021, when I lost to James Holzhauer on The Chase. And it happened again in 2024, when Kate, Cecily, and I lost to “Only Winners In The Building,” an extremely good trivia team, on Pop Culture Jeopardy!

I don’t really want to wait another 13 years to be on Jeopardy! again. If that happens, I’ll be 68 years old. They can also call anytime before, or even after. If I’m still alive, I’ll be ready.