In Jeopardy

The final Jeopardy category: Phrase Origins. My wager: $6,999—all I had. The clue: “This two-word adjective for going against accepted speech or conduct first appeared in a 1933 translation from Izvestia.”

It wasn’t exactly my best subject—I would have felt more confident in, say, “The Beatles”—but phrase origins are the kind of English-major trivia on which “Jeopardy!,” the king of TV quiz shows, has thrived for nearly 50 years. And this was my shot.

Plastered with makeup, dazzled by studio lighting, and gripping my signaling device with a clammy hand, I’d achieved a long-term ambition. After several decades of yelling out answers—er, questions—from my own couch, I was standing in a freezing cold Sony studio in Burbank, Calif., as a contestant on the show that aired Dec. 3, 2012

With its unpredictable mix of categories, Daily Double bonanzas, and fiendish final questions, “Jeopardy!” is to me the perfect 30-minute balance of scattershot knowledge and luck. The wonkfest’s been on the air since 1964, so you probably don’t need much explanation of the format: 30 clues in six categories, with three contestants, for two rounds, with one chance to return as a champion. Humming along with the show’s music (penned by show creator Merv Griffin) is mandatory, even if you don’t watch

But you do. Twenty-five million couch potatoes tune in each week, usually, as the show’s contestant coordinator Maggie Speak cracks, “in a recliner with a beer.” And like me, most convince themselves that they too could compete on camera—if they got the chance. How do you vault from one in 25 million viewers to one of 500 annual contestants? Practice, practice, practice (and remember that beer)

While I didn’t need to be as smart as Watson (the IBM computer who won a two-part match in 2011), I did aim to be as successful as its human opponents, Brad Rutter and Ken Jennings, who with combined winnings of nearly $6 million, are “Jeopardy!” icons. So did the 10 other hopefuls who walked into the studio for our August taping. They looked smart. And nervous. And Alex Trebek was nowhere in sight

I’d previously qualified to be a contestant back in 1995. Entering a “Jeopardy!” tryout while on a business trip to Kansas City, I aced enough of 50 written questions to nab an informal audition on the spot. Although in the official contestant pool for a year, I’d never gotten an invitation to appear.

As the qualifying test moved online, I weighed in annually. At 8 p.m. on Feb. 8, 2011, I logged in once again for the real-time test. Spewing one-word answers without categories, I kept typing and hitting enter at top speed. An inscrutable final screen thanked me for playing, without announcing a score. While I’d known most questions, I had no idea what constituted a winning performance; 100,000 people take the test each year

Fast forward three months: In April, an email invited me to an in-person audition for the show, to be held at a Washington, D.C., hotel. No promises, and no travel money. No problem. I was there

From this point on, I had a mentor. At my urging, my twin sister had previously taken the online test, and ended up as a contestant in 2010. So I knew that the scouts would group the 30 of us into trios for a loose, casual version of the show. I knew, too, that there was no way to study hundreds of possible categories, or to envision the Before and After answers, in which clues overlap, like this: Singer of “Superfreak” and licensed to kill; Who is Rick James Bond?

How to characterize the competition? In a word, young. A handful were teachers. Others, like me, were writers. And a surprisingly large proportion were medical students, their brains presumably honed to a razor edge. Led by the indomitable Maggie, the show’s staffers applauded, shouted and cajoled us to laugh, take a guess and above all, speak very loudly. After an hour, our group of 30 was dismissed. I was back in the contestant pool—this time for 15 months. “Don’t wait by the phone,” warned Maggie bluntly

I didn’t. But 15 months later, my caller ID displayed the magic phrase SONY CORP. Could I come to Los Angeles Aug. 28, when “Jeopardy!” would tape a week’s worth of shows? Again, no travel reimbursement. But I knew that even a third-place finish would earn me $1,000, enough to cover a flight and hotel room. I doubled up, recording extra shows and standing up to play along (pretty well) with the two-week Tournament of Champions, using my souvenir “Jeopardy!” ballpoint pen as a clicker. I dipped into “Jeopardy!” advice websites and databases, which revealed a level of shared obsession that terrified even me. I recited the list of U.S. presidents in order dozens of times as I drove through West Virginia on assignment. I made a mental note of recent pop music hits, often dropped into the show. And I thought of all the things I didn’t know. Please God, not the Bible

On Aug. 28, I walked into the Sony studio lot with 10 other contestants. In a small conference room, we signed bulky contracts, taped “Hometown Howdies” to promote our appearance on local network affiliates, and polished our player introductions. (My fun fact: My twin was a “Jeopardy!” champion in 2010). We visited the set to practice buzzing in.

Ah, the buzzer. Unseen by viewers at home, each “Jeopardy!” clue is framed in a band of light. Players may buzz in only when Alex Trebek finishes reading the clue and after the frame lights up. Signal prematurely, and you’re locked out from responding for a crucial quarter-second; too early is as bad as too late. One by one, we emerged from the makeup room as more glamorous versions of ourselves. Finally, we chose numbers to select playing order. I’d be first up, against returning champion Jason Shore from Texas and Basia Piuoro from Grand Cayman.

Both were in their twenties. Worse, Jason was a third-year medical student who’d already won $67,800. Miked and positioned between my opponents, I heard the bass-thumping theme song swelling up behind Johnny Gilbert’s booming announcement. “This is Jeopardy!” Despite the nerves, I broke out in a huge grin. Alex Trebek, impeccably tailored and tan, finally swept onto the set and announced the categories. From then on, the game—conducted in real time—blurred. In the first round, I answered correctly twice, identifying Mother Hubbard’s Monopoly token as the shoe, and recognizing Elsinore as the first scene setting in “Hamlet.” But Jason, a fast hand on the buzzer, forged ahead in Six-Letter Words and a big Shakespearean daily double bet, and Basia did well on Vegas Hotels—a place, alas, I’ve never been. With a few wrong answers, I ended the round with -$200. Jason? He already had $8,800. But I would get first choice in the Double Jeopardy round

The second-round categories seemed promising: Painted Ladies, Sometime a Great “Otion,” Military Mite, Pop Quiz, Bubble Up, and Mountain DO. A Pop Quiz clue made sense: ” ‘Miss Independent’ and ‘Stronger’ were hits for this idol.” I buzzed: “Who is Kanye West?”

“No,” replied Trebek, though I could hear West’s song playing in my head. “Who is Alicia Keys?,” Jason leapt in confidently

At the next commercial, the judges huddled, and reversed the ruling. Because the clue didn’t specify original hits, and Kanye had covered both Keys songs, I added $800 to my score. A series of correct answers about short soldiers, bubbles and the perpetual motion machine quickly dug me out of the hole. Jason beat me to the buzzer on the $1,600 pop music clue: “Supermodel Paulina Porizkova, who married Ric Ocasek of this group, appeared in their video for “Drive.” Of course I knew it was The Cars—I’d even met the couple a few years back! Practically family!—but once again Jason signaled first. I jumped back in for a geezer music clue: “This band made its top 40 debut in 1967 with ‘Happy Jack.’ ” After “Who is The Who?,” I’d notched $8,600. By the end of Double Jeopardy, after a wrong guess on a second country for the Carpathian Mountains (in Slovakia and Romania, not the Czech Republic), I’d totaled $7,000.

I knew Jason would be almost unbeatable in Final Jeopardy. I could bet only $6,999. That meant that if I answered correctly, Jason would have to bet and lose at least a third of his $21,200 total on a wrong guess. Basia, with $4,700, was less of a threat. But the biggest threat to all three of us was the Phrase Origin clue. As the music played, I knew the question would refer somehow to Communist Russia. Russia and grain… against the… against the… I scribbled “against the grain” as the music ended, knowing a three-word response was incorrect

As it turned out, “incorrect” was part of the correct response. However, all three of us failed to ask, “What is ‘politically incorrect’?” But Jason had bet a conservative $3,800, easily adding to his winnings, finishing with a tuition-paying $85,200 four-day total. In 28 minutes, it was over, and I was a second-place finisher. As the credits rolled, we had our one and only conversation with Trebek, in which Basia kept moaning, “I blew it.”

As I staggered back into the L.A. sunshine, I was $2,000 richer—minus California tax, but a better hourly wage than I’m used to. “Way to represent hip-hop AND perpetual motion machines!” my son texted happily.

I’m putting my winnings toward a family trip, rather than the early Ken Jennings-style celebrity retirement I’d envisioned. But my big prize can still be phrased in the form of a question:

What is living the dream?