True Story: I Won Jeopardy Five Times

won jeopardy
This True Story interview comes to us via my brother-in-law Mike! #coolerbyassociation

Tell us a bit about yourself!
I am 45, raised in and live in Minneapolis, I have three kids, and I am an IT consultant/manager. Reading this sentence makes me hang my head in shame because it can’t possibly get more boring. I’m also the president of my son’s baseball association. No, this doesn’t do much to get me out of middle-America dullard territory.

I am a heavy-duty business traveler and have become quite the beer geek lately, which puts me in two of the most whiny, miserable, self-loathing, and entitled subcultures there are.

When did you realize that you had a gift for retaining trivia and facts?
Honestly, pretty damn early. In kindergarten, I knew all 50 states. I also knew their rank by size. In second grade, we had a “recite all the facts you know in these topics” type contest. Everyone assumed I’d win, but I spent so much time helping a friend with his answers (well, not a friend, just an 8-year old crafty enough to know that if he ingratiated himself to me he could suck out all my knowledge when it mattered) that I forgot to take my own entry seriously, and my friend beat me.

My teacher and my mom both chewed me out for underachieving. This was all foreshadowing for my atrocious academic performance in high school and college.

What made you audition for Jeopardy?
I watched Jeopardy in college with my roommates, rather than studying or even showing up for class. I was only 20 and often drunk or stoned, but I was plenty competitive with the contestants and usually nailed a few questions they left unanswered. I contemplated trying out then, but it required getting to LA on my own dime. I could barely afford ramen then, so that wasn’t gonna happen. But I did hold on to the desire to try out someday.

In 1999, I no longer watched the show regularly, but sometimes watched with my mother-in-law, who recorded the show and got caught up on the weekend. When she learned Jeopardy was doing an audition at the Mall of America, she encouraged me to try out. I hedged initially because I don’t handle rejection well at all, but ultimately I decided to go for it.

Tell us about the audition/application process.
Because thousands showed up for the Mall of America cattle call, there was a weeding-out test before the real test, and a huge wait just to take the weeding-out test. I had heard you needed a perfect score (unconfirmed) and one question was iffy, so I thought it was over before it began. I guess I had my game face on because the assistant grading my test told me “relax, will you? You passed.”

Next, I took the standard contestant quiz. In the 90’s I took a mock quiz in a book about the show (“books” are the paper-based forerunner of the Internet), found it pretty tough and narrowly passed. Taking it for real was probably a similarly close call. While our tests were being graded, the contestants congregated and we went over the answers weren’t sure about.

In my little question klatch was a loud, confident woman who was loudly and confidently certain about all the answers I was iffy on. Listening to her, I was pretty sure I was going to come up short. I passed. She did not.

Those who survived stuck around to compete in a mock game. The mock game is all about personality, and the contestant coordinators answering a critical question: “Can we make this awkward putz acceptable to a TV audience in a short timeframe?” Waiting my turn, I realized that while plenty of contestants were perfectly normal, for others, the answer was “hell no!”

Stage fright, slovenliness, and pomposity were among the red flags. I also noticed that interview responses were pretty bland. For example, when asked what they would do if they won big, nearly everybody said they would spend the money on family and travel. When it was my turn, I made sure to have fun in the mock game, and when asked how I would spend the money, I said I would buy a big green pimp hat with a big green pimp feather.

I knew I’d done well in the screening process, but after a few days of neurotic optimism I forgot about it. When a staffer from the show called me six weeks later, I had no clue what she was talking about and figured she was from the Jeopardy telemarketing group and wanted to sell me gold-plated silverware.

How did you prepare to compete on the show?
I bought a PC version of the Jeopardy game (useless), and resumed watching the show. Mostly, I worked out. I figured in a month I couldn’t close the gaps in my knowledge base much, but anything I could do to appear less dumpy and geeky on TV was worth a try.

How did you feel when it actually came time to compete?
Terrified. Like I’d swallowed a live ferret.

What if I was the worst player ever? Additionally, I am mildly paranoid and believe good things never happen to me, so right up to the end I feared this was all an evil, elaborate hoax. First I thought it was a variation on Nigerian money scams. At the studio, I’d get jumped, robbed, and left for dead. Even when that didn’t happen my paranoia didn’t fully go away.

Right before my first game, the makeup girl came by and put some more gunky what-not (cosmetics is not one of my better categories) on my face, and I asked one of the other contestants if she had just slathered me in blue smurf makeup.

Walk us through the days you actually played and filmed.
Jeopardy records a week’s worth of episodes in a day. Until your name is called, you sit in the audience, but you are fully sequestered from the outside world. The first day I didn’t get on until the Friday game, so there was a lot of sitting and alternately getting bored, anxious, and nervous.

I was a wreck for the first game, totally mortified to see myself on screen and hear my voice on microphone. I was marinating in sweat and had epic dry-mouth. My first attempted response was moronic and a few minutes later something even dumber came out. Despite all that, I settled down, got friendly categories late in the game when it mattered most and won. I gave Alex Trebek a sopping wet handshake when the game was over.

After the studio let us go, I went out to celebrate with my brother, who had accompanied me (my pregnant, puking wife wasn’t getting on any plane). My brother was really excited and complimentary of my play, but he also carpet-bombed me with all the stuff he felt I was deficient in. For some reason, this included the books of Studs Terkel. He knew all of them but one. Amazingly, Studs Terkel came up in my third game….and it was the book my brother didn’t know.

The next day I had to play four games and it was exhausting. In between games you change clothes, get hair styled, get face spackled and have a little time to banter with other contestants. The games really come rapid-fire. They are over in a hurry and they come one on top of another.

With each game, I found myself getting less nervous. By game three, the nerves were gone, and I was mildly and narcissistically amused to see myself on the jumbotrons in the studio. But I also found myself getting progressively more tired. Because your adrenaline flows so strong during the game, once it’s over, there’s a massive headache and a massive crash.

We had lunch before my final game and I fell asleep at the table. I played my best in my last game, but I look like I’m on the brink of toppling over from fatigue, which I was.

You won Jeopardy five times!  What did you do with your winnings?  How did your Jeopardy experience affect the other aspects of your life?
You know how I ridiculed people who said they’d spend their winnings on family and travel? Well, that’s exactly how I spent mine. No green hat. It also sped up getting a down payment on a house.

I met some interesting people on the show, some of whom I still keep in touch with and consider friends. The experience certainly gives me something to talk about, but I’m usually pretty slow bringing it up, whereas right after my appearance it was usually the first thing out of my mouth. The people who hear about the experience think it’s pretty cool, which it is. Some people refuse to believe it, which makes me think, “Really? Am I making that shitty of an impression on you?”

They also think it qualifies me as a genius. Flattering, but I don’t agree. Trivia knowledge is fun to have, but it’s also the most useless application of intelligence there is. And sadly, it’s most of what I’ve got. When the zombie apocalypse comes, some can contribute to the survival effort by hunting, some by strategizing, some with what they can build with their hands. Me? I can contribute to the collective by reminding everyone what all the Super Bowl scores were.

Regardless, going on the show was the coolest and most interesting thing I’ve ever done. I’m glad I did it because, without it, I shudder to think what would be the most interesting thing I’ve done instead.

Thanks so much for sharing your story, Mike! Do you guys have any questions for him?

P.S. Life has big plans for you


Executive Sweatpants

Sure! When you have only one discernible asset, might as well extract all the value you can from it, right? Actually, I’d play Jeopardy for charity. It was a blast. And the year after, in 2001, I went on an ESPN show called 2-Minute Drill. Went to Manhattan for taping. Played fantastic. Lost. Wandered around the Lower East Side under an angry black cloud, hoping some bum would panhandle me so I could kick him in the balls. Not to be one of those people who always whines about getting screwed by fate but I got screwed by fate .

Long-time Reader, Seldom Commenter!

This was probably the funniest and best written “True Story” I’ve read to date. Mike, you should consider blogging – or at least turn your experience into a longer column and/or memoir. If anything, Sarah, you should exploit his good nature a bit more regularly on Yes and Yes. Hilarious!

Sarah Von Bargen

So funny, right?! The first time I read it, I was in public and I was laughing so much I had to close my laptop.

Sarah M

This guy was hilarious…”Nigerian money scams”….HAH! If you found your day job boring, you could always try to live off those earnings and become a comedian…
Sarah M

Robyn Petrik

This was a super entertaining and funny True Story. I agree – Mike should consider blogging or writing a longer piece about this experience if he feels so inclined. I laughed a ton over my lunch break with this one. Thanks Sarah and Mike!


Really enjoyed reading this! I’ve been a life-long Jeopardy! fan, so this inside look was fascinating. I took the online quiz a few years ago, but must not have passed since I never heard back. Not surprising though- the questions were really hard!


Mike – you’re extremely funny! This was indeed entertaining to read! I subscribe to the “More Mike” request above!


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