Confessions of a would-be ‘Jeopardy!’ champion

Seeing women become super-champions convinced classical music critic A.Z. Madonna to try out for the game show

“Jeopardy!” host Ken Jennings and Boston Globe classical music critic A.Z. Madonna.Courtesy A.Z. Madonna

All I could see was blue. Standing on an elevated platform, I stared at the wall opposite the “Jeopardy!” game board on the Alex Trebek Stage at Sony Pictures Studios in Culver City, Calif.

Behind me, host Ken Jennings invited questions from the studio audience while the crew labored to correct whatever had caused a $2,000 question to appear in the $1,200 spot on the game board. I tried to eavesdrop, but two contestant coordinators swooped in to occupy my fellow contestants and me with small talk. Eventually, we were shuffled off stage and offered seats.

“You’re all doing great,” one of the contestant coordinators said once we were back at our podiums. “Remember, Taylor Swift — shake it off, shake it off!” She did a full-body shake as she sped away.

I made my “Jeopardy!” debut on Dec. 8 after taping in October. I’ve always enjoyed trivia and wordplay, and “Jeopardy!” scratches both itches. As an undergrad at Oberlin College, I auditioned for the “Jeopardy!” college championship. I aced the online test, but after the proctor advised me to smile more and talk with my hands less, I knew I wasn’t getting a call back.

My “Jeopardy!” ambitions gradually faded, but after Trebek died in 2020, I followed the search for a new host. Like many viewers, I was disappointed when the show appointed its own executive producer, Mike Richards, as Trebek’s successor over the engaging and groundbreaking former “Reading Rainbow” host, LeVar Burton, who’d done a stint as guest host. Burton later called the snub “a humiliation.”

It was a squandered opportunity for broader representation, made more infuriating when less than a month after getting the job, Richards stepped down as host and was then fired from his executive producer position amid a maelstrom of scandal: unearthed discrimination lawsuits from his time working on “The Price Is Right” and various resurfaced comments disparaging women and praising “the average white-guy host” that he’d made on his old podcast.

Fans rallied behind LeVar Burton, the beloved former “Reading Rainbow” host, to guest-host “Jeopardy!” Carol Kaelson/Jeopardy Productions/Handout

I didn’t care about the show again until super-champion Amy Schneider logged a 40-win streak last winter. As many lawmakers sought to codify discrimination against trans people, she wore a transgender pride flag pin.

“Jeopardy!” host Ken Jennings poses with contestant Amy Schneider. Schneider capped her big year by winning a hard-fought “Jeopardy!” tournament of champions in an episode that aired Nov. 21, 2022.Tyler Golden/Sony Pictures Television/Courtesy of Jeopardy Productions Inc. via AP

A few months later, I tuned in to watch Gen Z’s first super-champ, Mattea Roach, win 23 games while never dialing down her exuberantly nerdy personality or signature style. Her nose rings, choppy mullet, and boxy blazers signaled “one of us” to younger LGBTQ people like me (I’m the B) before she publicly discussed her own queerness.

Mattea Roach, Gen Z “Jeopardy!” champion. Courtesy of Jeopardy Productions Inc.

My image of a “Jeopardy!” champion had always looked more like clean-cut Jennings, who now cohosts with actor Mayim Bialik. Most of the show’s biggest winners have been white men. But watching Roach talk with her hands while sharing her daily anecdotes, I felt a kinship. It didn’t escape me that some commenters on Twitter called her annoying or arrogant: I’ve gotten the same flak from people who’ve doubted my authority as a classical music critic. As I said on the show, I’m usually the youngest person in my row at Symphony Hall. What I didn’t say is how sometimes I feel I don’t belong there. But just as I’ve grown more comfortable in my voice as a critic, I’ve become less self-conscious about the way I express myself in front of others. Roach showed me that I probably wouldn’t have to hide my quirks if I tried out again.

I took the “Anytime Test” on the official “Jeopardy!” website in May. A few weeks later, I was playing a mock game with a small group on Zoom.

The moderator asked everyone what they’d do with a lot of money, adding something to this effect: We know that if you win, you’re going to fix your roof or pay bills. For this question, pretend such obligations don’t exist.

I was prepared. I said I’d open an all-ages, live music venue. But let’s be real: I’ve mostly seen champions gross somewhere between $10,000 and $30,000 per game, and taxes take a big bite. The consolation prizes of $2,000 (second) and $1,000 (third) are barely enough to cover travel for a lot of people, including me: I lost money on the trip.

Considering the show’s generous jackpot budget, I was disappointed. In 2003, the show eliminated its longstanding five-win limit. The next year, Jennings buzzed his way to an astounding 74-game win streak, taking home over $2.5 million. The era of the super-champion had begun.

When I was invited to be on the show with a month’s notice, I decided to train like I would for a sport. With the help of the fan-run database J!Archive, I binge-scrolled my way through years’ worth of game boards. One troublesome category was United States presidents; I combed through websites intended for students preparing for AP US History exams, hoping something would stick.

In my luggage, I packed a garment bag of shirts conforming to the show’s rules — no white, no small prints, nothing tattered. My bright orange hair and side shave were already going to stand out; my usual style, which TikTok knows as “whimsigoth”, wouldn’t cut it, so I bought a green boat-neck blouse. I already knew my age (29) and gender put my appearance up for more scrutiny, and showing any cleavage on national TV would attract attention I didn’t want.

“Jeopardy!” tapes a week’s worth of shows in one day, and most of the contestants were already sitting in silence at plastic tables when I arrived at the meetup spot on the second floor of a parking garage.

My eyes met those of another contestant, a woman with dark purple hair. Knitting needles were visible in her bag. “What are you working on?,” I asked, pulling out my own needles.

After we were escorted to our holding area in the “Wheel of Fortune” studio, which was decorated for taping Christmas episodes, I also met my eventual opponents: Sriram Krishnan, a government contractor who grew up on the South Shore, and Ron Cheung, an economics professor at Oberlin.

We learned the less obvious rules of the game. We would be called in random order. We couldn’t wager certain amounts of money, including (cough) $69 and $420. If we forgot to phrase an answer as a question during the first round, we’d be reminded. During Double Jeopardy, the omission would be automatically ruled incorrect.

“I just can’t get a classical music question wrong,” I half-joked to another contestant. I was pretty confident I could dominate in that category if it came up. But when “A Night at the Opera” was revealed on the board during my first round, I gulped. What if I missed one of those?

By the time I reached the stage, my lipstick had mostly transferred to my studio-provided KN95 mask, and the makeup artist wanted to touch me up with lip gloss. I’ve always hated the feeling of lip gloss, so I asked if the tube of CoverGirl Burnt Red Pepper in my vest pocket could substitute. Luckily, it did.

The buzzer felt harder to press than it had in rehearsal. I assumed either Ron or Sriram would know everything on the board, so I tried to buzz for every clue I thought I might be able to answer and ended up missing a few, including one about a machine for filling bottles of mustard that I guessed was for medicine.

“Medicine for your hot dogs,” Ken joked.

It was time to pull out the ace. I asked for the $1,000 question in category “A Night at the Opera,” and was rewarded with the blaring Daily Double sound effect. I made the maximum wager. It was about Rossini’s “The Barber of Seville,” which I knew instantly.

“I’ve spent a few nights at the opera,” I quipped when Jennings introduced me.

But Sriram was on a hot streak. I clicked my buzzer furiously, hoping to answer $2,000 questions on topics I knew: “The Girl with the Dragon Tattoo,” Japanese internment, the first sentence of “Atlas Shrugged.” Again and again, Sriram’s podium lit up first. Suddenly, the Double Jeopardy round was over, Sriram’s score was more than double Ron’s, and Ron was ahead of me.

We had a quick break to calculate wagers, and everything I’d learned about playing for second evaporated. My head buzzed. I scrawled $627 (for June 27, my partner’s birthday) and tacked a 0 on the end. I was going home; might as well go big.

The clue appeared.

“A cocktail, an island & a WWII venture originally called ‘Development of Substitute Materials’ all bear this name.”

“Cocktail” collided with “island” in my brain and flowered into paper umbrellas and pineapples. I heard the first few notes of “Bali H’ai” in my head and pushed it down as the iconic Final Jeopardy music filled the air. Pacific Theater. Bikini: that’s an atoll, also not a cocktail — is it? Mai Tai? Could it be an acronym? Military Armaments Initiative something something.

I snarled at the thought of my answer coming up blank and wrote MAI TAI.

My answer was revealed first. Wrong. Ron wrote “martini.” Also wrong.

Then it was Sriram’s turn. “What is Mai Tai?” his answer read.

“The cocktail and island are Manhattan,” said Jennings. “And it was the Manhattan Project that had the code name.”

I almost burst out laughing. My mind had zipped west over the South Pacific, toward the pristine, nonexistent shores of Mai Tai Island: half a world away from Manhattan, the island where I was born.

Since Ron and Sriram had also ended up at sea, I wasn’t ashamed. “My mind only went tropical,” Ron told me later. Sriram’s lead had been big enough to wager nothing, which he did, so his wrong answer didn’t matter.

The night the show aired, I offered my friends mai tais and Manhattans while we watched in my living room, and my boss sent me a picture of my face on a newsroom TV with the message, “you’re a star.” I also got some unwanted sexually charged messages, which I blocked.

Overall, the experience was bittersweet. I had nailed the opera category, I had known almost every answer in Double — I had put up a fight.

My parents and my boyfriend had come with me, and my mom wanted a picture of me in front of the Sony lot before we left. I grinned and threw the loser sign on my forehead just as she snapped it.

“No, not like that!” she said, laughing.

We compromised: one graciously smiling picture for her, and one mugging “L” photo for me. Then I threw my arm around my boyfriend’s waist and rolled my suitcase to the bus stop, feeling like a champion.

A.Z. Madonna in front of the Sony Pictures Television lot after taping her episode of “Jeopardy!”courtesy of A.Z. Madonna

A.Z. Madonna can be reached at [email protected]. Follow her @knitandlisten.