THERE'S AN EPISODE of Cheers—I'm sure it's on Netflixin which Jeopardy!, for reasons unexplained, decides to tape a show in Boston. An expedited tryout process follows and somehow, thanks to another dose of TV magic, Cliff Claven—Cheers' lovebly creepy know-it-all—soon finds himself face-to-face with Alex Trebek and standing beside two rival contestants with far more impressive credentials.

Cliff, of course, is a mailman, and totally out of his league. Then the categories are revealed. For Cliff, they're a dream come true (civil servants, bar trivia, celibacy, etc.), and suddenly he's riding into Final Jeopardy on an untouchable pile of cash. He's going to win. Until he bets it all on a wrong answer—and finishes an irate, angry, bitter third.

As sitcom episodes go, it's great. Trebek even hits the bar later, in a cameo that shows off his unheralded comedic chops.

What does any of this have to do with me? Just that Cliff Claven's story is my story. We're both schlubs. We're both annoying. And we both made it, improbably, onto the most respectable game show humankind has ever conceived. Except for one major difference.

My story ends way better.

PEOPLE KEPT ASKING, after they heard I'd been called for a tryout on Jeopardy!, whether I'd been studying. I hadn't been. Nor did I cram after the tryout, when I got the call (on a Wednesday spent covering Portland City Council for this paper) that the producers wanted me to fly to Los Angeles for a taping.

I was cocky. And I was lucky. Trying out is not for the faint of heart. The questions are hard—much harder than what you'll ever see on the show. You're up against thousands of people way smarter than you, and most of those people have been at it for years, trying time and time again but never making it onto the show. They read guidebooks. They employ strategy. Not me. Like I said... lucky.

It started almost a year ago. My long-suffering wife—who would leave the room when I'd watch Jeopardy! reruns because I'd shout answers and swear loudly at contestants who balked at "making it a true Daily Double"—finally had enough and signed me up for an online test.

I stayed late after work one night to take it—50 questions of impossible depth ticking past at an impossible speed. I was pretty convinced I failed. I'm good at geography and presidents (most of the time), but not so much with Shakespeare, and I'm lousy with classical music. These topics made up much of the quiz's chief lingua franca.

But apparently not enough of it, because I got an email in the fall—miraculously—telling me I should fly down to San Francisco for a tryout in front of two contestant coordinators.

This time, I felt pretty good. They snapped headshots, and I had a good smile. We played an ersatz game, and I was on the ball. They fed us 50 more questions—and on one of those 50, I wrote an answer that I'm sure made Jeopardy! history: "clusterfuck." They wanted personality, and they got it.

Because the quizzes get reused, I won't say what the question was—but I will say the answer was infamous enough that it was mentioned to other hopefuls.

Whatever the reason, on the last day in January, I was flying over the Borg cube known as Los Angeles and checking in for a nervous night at the Radisson in Culver City.

THAT FIRST MORNING, the contestants all gather in the lobby of the Radisson. There's a shuttle bus that takes you to the studio, and if you miss it, you're screwed. Among the faces I remember were a handful of lawyers, a New York Times copy editor, a public radio producer from New England, and a martial artist/drummer from my hometown, Chicago. And there I was, your friendly neighborhood Mercury hack.

We're all neatly dressed, some more dorkily than others. We're also clutching hangers draped with changes of clothing—in case we, you know, manage to win. While we wait I choke down a dry bagel and some coffee. We're all sizing each other up, asking what you studied, what you didn't, but it's pretty cordial, and soon we're off.

The contestant coordinators meet us just inside the gates and hustle us into the green room. There's a modest spread of fruit, more bagels, drinks, and a couple of bathrooms to deposit it all. We sit at a long table where the coordinators give us the rundown on how the day's going to go. Names are called, and two-by-two we file into an anteroom where two pleasant assistants paint our faces and necks matte orange.

It's a long morning. And there are only so many pineapple rings you can eat before you tempt fate and dribble juice on your jacket.

Then, finally, mercifully, it all becomes REAL.

We're ushered onto the set—the actual set where Alex Trebek makes his living—and we're turned loose to start playing mock games. This is important. It shakes out the jitters. It gets us used to the rhythm of the buzzer; you have to wait until three lights come on at the side of the game board, after the clue is read, or else you're briefly locked out. And it teaches us to avoid tripping on the platform that separates the players' lecterns from the rest of the stage.

It also gives us a glimpse into the machinery of the show. Sometimes a square on the board wouldn't light up and the pretend game would stop while the crew fussed with it. This would happen during the real games, too, except that Alex would have to record what's called a "pickup," or a second take, so that the editors could seamlessly weave together the show.

(This isn't just for technical difficulties. There's a reason you've never seen Alex say "steen" when he was supposed to say "stine.")

Eventually, they decide we've had enough. The studio audience arrives, and the first two of us are sent in to take on the returning champ. There are five tapings on any given day, and my name wasn't drawn until the third.

IT'S FUNNY. I remember the meal I ate the night before the taping better than the taping itself: two fried chicken breasts (the specialty at Dinah's, the diner across from my hotel), a waffle drowned in syrup, sweet potato fries, and three glasses of strawberry lemonade.

But when you're in the throes of Jeopardy!, you don't have time to obsess over slipups or celebrate triumphs. There's always another clue. And another. And everyone knows the answer, so you have to time the buzzer right. And you have to call the next clue quickly, because there's no greater sin in Jeopardy! than leaving squares uncovered.

Some responses stick out. "What is convection?" "What is Gravity's Rainbow?" But trying to conjure any more memories is like persuading the Hubble telescope to peek through the background radiation obscuring the Big Bang. It can't be done.

I do remember that it took me awhile to get going. I was already trailing by the first break in play, when Alex comes around to talk to the contestants.

That segment is a surprisingly big deal for the producers. Weeks before the taping, contestants must submit a long list of suitably wacky anecdotes. A coordinator then helps winnow the list down to the three per contestant that wind up on Alex's note cards. He can pick any of the three, so you have to be ready for all of them.

When it was my turn, Alex asked about my collection of TV theme songs. I mumbled something about having several hundred and griped that sitcom themes aren't what they used to be. We also chatted warmly about my name—a conversation that actually started during the break, in my best high-school French, before taping resumed. My dad's Canadian, Alex is Canadian, and, well, pretty soon he was calling me "Duh-NEE."

THINGS DIDN'T CLICK, not really, until Double Jeopardy. I started stuck in third place, stomped by the four-time defending champ standing placidly to my right. And then I made friends with the buzzer. Again and again and again.

I came close to sweeping a science-themed category. I feasted on high-dollar clues. I hewed to my cardinal rule: Don't guess. Ever. Then, once I seized the lead, I kept it by nibbling on the cheap clues, so even if somebody else rang in before me, it'd be hard to regain ground.

By the end of the action, once Alex was ready to reveal the Final Jeopardy category, I had managed to claw my way so far ahead—à la Cliff Claven—that there was nothing the other contestants could do to catch me. As long as I didn't get greedy.

And that, it turned out, was easier said than done. The audience gasped audibly when Alex did the unveiling: TV Theme Songs. They remembered my little story. This was my fucking category.

Even Alex reacted, doing something I've never seen in all my years watching the show: taking a few seconds to reassure viewers that this really was random—a twist of circumstance.

Not that I had long to savor it. The lights went down and it was time to wager. I could bet it all, and lose my ass on a clue that came out of left field. Or I could bet nothing, know the answer, and hate myself.

I had more than double the next player's total, but not by much, so I took up the paper and pen stashed in my lectern and did some sweaty, hasty math. How much could I bet without risking defeat? $199. I checked my work one last time and wrote it down.

And... of course, I knew the answer. The clue mentioned something about "all my rowdy friends... coming over tonight." It was Monday Night Football. So I was out $18,801. But you know what? I still won $19,199.

AFTER THE CHEERING, and the small talk with Alex while the credits roll, I'm told to stay on stage for a testimonial about what it feels like to win.

Then they send you back to the green room first, so you get first crack at the toilet. You get to go first in the makeup chair. People hold the door for you. And you don't know how long it'll last.

I'm on again as this issue hits the streets, on Thursday, April 28's show [KATU, Channel 2, 7pm]. I can't tell you how I did. But in some ways, it doesn't matter. Because whether I lose immediately, or go on to win the next 20 games, there's a painful koan that no Jeopardy! contestant will ever escape.

Not me. Not the guy who won 74 games. And not the guy who won $3.5 million. It's this: Every Jeopardy! winner will, one day, also be a Jeopardy! loser. (Of course, some will be a little richer than the others.)