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I won on Jeopardy!
Then why do I feel so bad?

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Why was I so miserable?

One evening some weeks back I was in the middle of a pleasant trip to sunny Southern California, a welcome change from frozen Wisconsin. Earlier that day I'd seen a legendary entertainment franchise close up, as a guest at Sony Pictures Studios lot in Culver City. It was a holy-of-holies pilgrimage for a pop-culture obsessive like me. And, oh yeah, I'd won $23,600 in the space of about an hour.

I was a Jeopardy! champion. Or at least I had been, for a brief moment in time.

It was the culmination of a life journey. Since I was a kid, I'd watched the show and played along, thinking to myself, I could do that. I could be one of those nervous, everyday-looking people who, drawing on knowledge of Chaucer or physics or professional wrestling, show off their intellectual prowess and win lots of money. In the years leading up that evening, I had watched for opportunities to try out, taken qualifying exams, traveled to an audition, and waited anxiously to hear whether the producers deemed me Jeopardy!-worthy.

I was even ready to lose. Just the chance to shake Alex Trebek's hand and buzz in with an authentic Jeopardy! signaling device - that alone, I imagined, would make the effort worthwhile.

And, in fact, I didn't lose. I won. I walked with game show giants. Being Jeopardy! champion was one of the great triumphs of my life, as thrilling as any time I've performed on stage, as a singer in a succession of bands.

But that night, as I lay in my king-size bed at the Culver City Radisson, I wasn't thinking about my victory. I was thinking about my mistakes, about questions I answered wrong, about questions I didn't answer at all. I was thinking about how unexpectedly forlorn I'd felt once my two-game run was over. I was thinking about the money I didn't win.

I was sulking. It was an unhealthy feeling, one I knew I needed to get beyond. My life journey with Jeopardy! had not yet reached its end.

How did I get here?

I've been a fan of Jeopardy! since the current, Alex Trebek-hosted version began airing in 1984. I've always admired the fact that, unlike other game shows, Jeopardy tests contestants' knowledge, not their simple luck (although luck does play a role). And in 2004 I watched closely as the software engineer Ken Jennings won a sensational $2,522,700 in 75 games.

Enticed by that wealth and fame, I began earnestly striving to get on the show. I signed up for email alerts about tryouts. I took tests. Finally, last June, I found myself in a hotel conference room in downtown Chicago, joined by 20 or so other would-be contestants, among them lawyers and schoolteachers.

All were dressed as if for job interviews. Some, having tried out before, were chummy with the Jeopardy! staffers, who distributed official Jeopardy! click pens, perfect for practicing buzzer technique.

A producer named Maggie spoke about the audition process and dispensed advice. She punctuated her talk with shticky asides and amusing digressions. Finally we took another exam, played a few mock rounds of the game, and submitted to lighthearted grilling from the staffers. (One asked me, "What will you do with the money if you win?" "Invest prudently," I said. The Dow Jones Industrial Average was then still comfortably above 12,000.)

Wait 18 months, we were told. If you don't hear anything, try out again. Driving back to Wisconsin, I was philosophical. At worst, I reasoned, I had burned a vacation day.

In December, I got a call at work from a Jeopardy! producer. I was invited to appear on the show. Amid the frenzy of work and the holidays, the exchange was surreal. As an entertainment editor I get calls from TV people all the time. When the receptionist told me Jeopardy! was on the line, I thought it might be about an upcoming contestant from Madison. It was. That contestant, it turned out, was me.

Not wanting to jinx myself, I initially only told a few friends and family members. "Granny Hicks would be so proud," my stepmother emailed from Nashville in response to the news. "It was her favorite show."

You mean I'm first?

As my Jeopardy! experience approached, I prepared. I made plane reservations, hotel reservations. I put in for vacation days.

Friends asked if I was studying. I wasn't. I planned to rely on a lifetime of trivial pursuits.

On a cold Monday morning I flew to Los Angeles, where I was greeted by a warm Monday afternoon. I took a shuttle to the hotel, checked in, tried to relax.

The day of my taping, Jan. 20, I was not well rested. Thanks to the excitement and an unfamiliar bed I had not slept well. I gulped down the cup of not-good coffee I brewed in my Radisson bathroom.

It was Inauguration Day, the swearing in of President Barack Obama, but my schedule did not permit time for such distractions. At 7:45 a.m., I went down to the hotel lobby, where I noticed a dozen or so other people sitting stiffly. All were dressed as if for job interviews. Some clutched packets I recognized from my Jeopardy! mailings.

"Jeopardy!?" I asked. There were nods. We waited. No one spoke. Finally we boarded a hotel shuttle and waited more wordless minutes. A driver climbed in and asked, "Jeopardy!?" We nodded. "Not LAX?" he grinned, naming the airport nearby. There was nervous laughter.

After a short drive, we arrived at Sony Pictures Studios. In its earlier incarnation as MGM, the lot is where The Wizard of Oz was filmed, and Gone With the Wind, and Singin' in the Rain. Now I would be taped there, providing answers in the form of questions.

In the green room there were forms to be filled out, makeup to be applied. The producer Maggie, whom I remembered from Chicago, gave another talk filled with shticky asides and amusing digressions. She mentioned Ken Jennings frequently. She also cautioned us not to "get all Sean Connery" - a reference to Saturday Night Live's very funny Jeopardy! parodies, which feature a vulgar Connery berating an impatient Trebek. The parody is, I gather, admired on the Jeopardy! set.

In our short time together I got to know a little about my fellow contestants - the graphic designer, the government economist, the guy who wanted to know if he could wear his hat on camera. (Answer: Yes.) A sleepy-looking lawyer made a brief speech about our rights as contestants, and I thought of Ralph Fiennes in Quiz Show as the disgraced, manipulated game-show casualty Charles Van Doren.

Although Jeopardy! is broadcast each weekday in half-hour installments, a week's worth of episodes are taped in a single day, at a breakneck pace. Lots were drawn to determine the order. My turn came first, along with grad student Jerome and the returning champion, retired librarian Jeanie.

We all filed into the studio, which was smaller than I expected, and then a producer read questions as we played several mock rounds. We practiced writing and buzzing in. Finally it was time to play, and a burly technician put microphones on Jeanie, Jerome and me. We spent a few minutes taping awkward greetings for the show's website and being photographed with a limping, grimacing Trebek, who had injured himself in a home-improvement accident.

Then the music played, announcer Johnny Gilbert did his thing, and the game began.

Over so soon?

I was on fire.

Over the course of two rounds, in some of the most joyful minutes of my life, I answered question after question correctly. In one of my proudest moments I said, "Who is Spears?" I'm a closet Britney Spears fan, and it pleased me to know what to say in response to a clue about her recent hit "Womanizer." I referred to her in Jeopardy! convention by last name only, like a head of state.

I raced through categories. Some played to my strengths: Springsteen songs, Literary Opening Lines. Other categories were baffling. Pigeons?

I answered 25 questions correctly, missing none in the first two rounds. I seemed to hear gasps from the producers and the studio audience. As the "Final Jeopardy" round began, my score was exactly twice that of second-place Jeanie, so I was ideally situated. I did not have to wager any money, because if Jeanie bet everything, answered correctly and tied, we would be co-champions and return, the two of us, for the next game.

I wagered nothing and answered wrong ("What is the Nile?"). Jeanie answered right ("What is the Danube?"), but unfathomably she did not bet everything. I was Jeopardy! champion, with $21,600 to show for it.

Producers rushed over, smiling and congratulating me. At the studio I had already sensed that Jeopardy! staffers very much like phenomenal players like Jennings. They're good for promotions and ratings. And I believe that after my extraordinary first game they hoped I would be another phenomenon. Me too.

The burly technician called me Champ as he removed the microphone. Elated, I hurried to the green room to change clothes. I took my place behind the champion's podium alongside opponents Kelly, an actuary, and Jorge, a contamination-control technician.

And then I played an uninspired round of Jeopardy! I found two Daily Doubles but answered both incorrectly. As I slipped behind I shrugged off Jeopardy! norms and chose high-dollar questions first in what a blogger, describing my play later, called the "high school strategy." Mostly I failed to buzz in before Kelly, who played magnificently. I was in last place as "Final Jeopardy" began, and she was the one to beat.

But she answered wrong ("Who is Fitzgerald?"), and Jorge and I answered right ("Who is Hemingway?"). My total climbed to $17,200, but Jorge edged past me with $18,100 to win. My second-place finish notched a consolation prize of $2,000.

The producers looked sad as they told me goodbye, then rushed on to the next taping. Removing the microphone, the burly technician didn't call me Champ. I quickly signed some papers and was whisked off the set. I joined the audience and watched the next taping. Next to me sat Kelly, who'd come so close to victory, then saw it snatched away. She was weeping.

Afterward, over a late lunch at a Los Angeles diner, I told a college friend how excited my new friends the Jeopardy! staffers had been, and then how disappointed.

He was playfully blunt. "They only like you when you're winning," he said.

What is wrong with me?

And so, alone in my hotel room that night, I was depressed. I had won, yes, but why couldn't I have won more? Why couldn't I have just have answered some of those easy questions? What is Del Monte? What is the violin? What are kites?

I was still reeling from the show's wickedly quick pace, its deceptive intensity, even cruelty. True, the contestants were a pretty mild-mannered lot, but our competition for money and glory was fierce and real. And for all their friendly graciousness, the Jeopardy! employees contributed to the intensity.

"We want you to win a lot of money," we were told. The corollary went unspoken: Many of you are going to lose.

I kept thinking of what might have been. Ken Jennings' $2,522,700 would have been wonderful, of course. But I would have happily accepted the $222,597 brought home by grad student Larissa Kelly after her impressive Jeopardy! run last spring. At idle moments before my Jeopardy! trip I had even used a calculator to compute what a modest rate of investment return would produce on $222,597. After taxes, of course.

Yes, I had whimsically envisioned a life of comfort predicated on a lucrative Jeopardy! run, which in turn would be predicated on having spent years pursuing knowledge for its own sake. The bachelor's degree, the master's degree, all that Marx and Freud and Socrates I'd read in college at the University of Chicago, to say nothing of all those Britney Spears songs I'd listened to - all of it would finally pay off, and not just in the benignly humanist terms usually touted by champions of liberal arts education. It would pay off in the form of money, maybe even a fortune.

Instead, it paid off in, roughly, the amount of a down payment on a house. I was miserable. And I hated myself for being miserable.

I flew home. On the plane to Madison an elderly woman sat next to me. She was very excited when I told her about my Jeopardy! appearance and carefully noted the run date in her calendar.

Weeks passed, and I still was uneasy. So I called George. George is my friend, a very smart guy I sometimes turn to for advice. He was thrilled when he heard of my victory and bemused when I told him I wasn't altogether happy about it. He asked a few questions, then rendered a verdict. "What you're describing," he said, "is greed."

Oh yeah. Greed. One of the Seven Deadly Sins, along with wrath, sloth, gluttony. Sin is a religious notion, of course, and while at this point I wouldn't describe myself as religious, I'm a spiritual enough dude to recognize that sometimes my thoughts and actions are harmful and can get in the way of happiness. That, I think, is the nature of sin. Greed is not good, at least not the kind of greed that had me retroactively grasping for the title of a Salman Rushdie book, to increase my bounty.

I feel ridiculous even telling you this. Of course I should be grateful for my prize, for a fascinating experience and a trip to California and all the rest. I am. I tried to remember that during those dark, greedy moments. And after a while, those moments stopped coming. Mostly.

Is this fun or what?

Nothing prepared me for what happened when my episodes aired. My first appearance was on the Monday between Oscar Sunday and Mardi Gras, and the festival feeling began to kick in days before. That was partly my own doing. As a longtime performer of live music I know the value of Internet promotion, so I used Facebook to alert 406 friends to my Jeopardy! appearance.

As the day approached, greetings trickled onto my wall ("My DVR is ready!"). Then, as the programs aired, congratulations poured in. From grade school friends: "My 9 year old said, 'Mom, your friend is like a computer!'" From high school friends: "OMG!" From college friends: "You did the U of C proud with Socrates and Supply Side!"

People posted pictures of me grinning like a fool on the program. Co-workers stopped by my desk to congratulate me. A friend in Turkey saw the episode early on the Armed Forces Network and wrote a complimentary email about my "crushing of the poor librarian lady."

Members of the press called. My boss mentioned me in his column. Texts came in a flood, and phone messages - from Mom and Dad, my brother in Alabama, screaming friends in New York. My grandfather, recovering from heart surgery, called from Nashville: "You like to give me another heart attack!" The frenzy was remarkable. I forgot all about my dark thoughts.

I celebrated my appearance with people all over, many of whom I haven't seen since I was 14 and younger. That's in part a testimony to the strange and new power of Facebook. It's also a testimony to the strange and enduring power of Jeopardy! This simple quiz show has long been widely watched and widely loved - by my 10-year-old nephew, by the late Granny Hicks.

True, the experience made me face some unpleasant truths. I tend to self-pity. I'd like to have a lot of money I haven't earned. But as a friend recently told me, we drive ourselves crazy when we live in regret.

I did a silly thing. I took an online quiz, appeared on a game show, won a bit of money. But the real result was a celebration in my world that matched the energy of the exultant Bollywood dancing at the end of Slumdog Millionaire, another story about a game-show winner. A colleague at Isthmus told me my appearance boosted staff morale amid the difficult times that our newspaper, like every newspaper, is enduring. I believe her.

And I got to say "Who is Spears?" on Jeopardy! They can't take that away from me.

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