Answers in the Form of Questions

In January 2020, the five most important figures in the history of modern Jeopardy! took the stage in a ballroom of the sprawling Langham Huntington resort in Pasadena.

The complex, with acres of manicured gardens, has served as a historic getaway for the entertainment industry’s elite, and it drips with Hollywood history. The pilot episode of Remington Steele was filmed on the grounds, the building’s exterior served as a playground for Lindsay Lohan’s mischievous twins in 1998’s The Parent Trap, and HBO’s Westworld converted the hotel’s lawn into a British Raj–styled theme park.

But few ever to visit the hotel can rival the iconic status of the group who made their way to a tightly packed row of gray director’s chairs that winter afternoon.

On one end of the stage, James Holzhauer—who had just thrilled the nation with a thirty-two-game winning streak that saw him shatter record after record en route to becoming the fastest player in the history of the show to win $1 million—sported one of his signature V-neck sweaters and tight smiles. To his left sat Ken Jennings, with the ease and confidence that come with owning the all-time record for Jeopardy! victories thanks to a dominant seventy-four-game winning streak in 2004. They were joined by Brad Rutter—wearing a checked plaid suit purchased earlier after an ABC wardrobe consultant insisted on an emergency Nordstrom run for all three—a former record-store clerk who now holds the record for the highest overall Jeopardy! winnings.

The trio had gathered in the room of television critics to promote their prime-time showdown—billed as the Greatest of All Time tournament—under the eye of the other two men on the stage, longtime host Alex Trebek and executive producer Harry Friedman. Having had some practice with the unusually high seats, both casually crossed their legs while the younger men dangled their feet awkwardly.

Friedman—just the third executive producer in modern Jeopardy!’s history—single-handedly dragged the show into the twenty-first century, pioneering a slew of major innovations, from doubling the prize money in 2001 to lifting the five-day cap for returning champions, which fundamentally changed the way the game was played. And with his long-planned exit from Jeopardy! just months away, the GOAT tournament would serve as a crowning achievement for a showrunner whose more than two decades on the job had been a persistent fight to broaden its pop-culture appeal while nurturing the bookish DNA that endeared the show to generations of nerds.

But the center of gravity—as it has been for the thirty-six years since he began hosting the show—was Trebek.

People might not have originally expected a smooth-talking, lightly sardonic Canadian to capture the hearts of American television audiences, but Trebek did just that with decades of knowing winks and gentle—okay, sometimes less than gentle—corrections of mispronunciations. For the show, Trebek has been a constant unlike any other—a sometimes mustachioed, sometimes prickly, always steady presence, the keeper of a finite blue-purple world where the passage of time could be counted both in operatic ephemera and, maybe, the number of different living rooms where you found yourself watching over the years.

The assembled crowd engaged in a cursory discussion of the contest, asking how Jennings, who had won the previous night’s opening round, and Rutter, who in twenty years of Jeopardy! competition had never lost to a human opponent, intended to counter the newcomer Holzhauer, who had scandalized some viewers of the show with an aggressive playing style and betting strategy. The veteran contestants—who in reality had taped the competition a month earlier—talked about the ways they might tweak their strategies, noting that selecting from the middle of a category, rather than the top, improves your chance of hitting a Daily Double.

But the concern looming over the showcase—in fact, the reason it probably existed in the first place—was evident from a mere glance at the group.

Attached to the lapels of Holzhauer, Jennings, and Rutter was a purple ribbon—intended to promote pancreatic cancer research and a gesture of solidarity after Trebek’s announcement a year earlier that he had been diagnosed with Stage 4 of the disease.

Trebek, then seventy-nine, was asked about the outpouring of support he had experienced in the wake of his announcement, and responded with trademark self-deprecation. He wrote off tributes to his decades of hosting as the type of recognition that anyone who had, like him, spent “more than half my life” hosting a program would receive. And he waved off accolades as a reaction to his illness.

“The pity factor is out there,” Trebek said. “I’m not unaware of that.”

His eye-rolling continued as critics asked the contestants to reflect on his role as host.

“Brad, James, and Ken,” one reporter began. “The answer is: ‘The thing you admire most about Alex.’” They would have to answer in the form of a question.

“Oh dear,” quipped Trebek.

The panel concluded with more laughter, with Holzhauer commending the longtime host on navigating decades in Hollywood without embroiling himself in scandal.

“There’s still time,” Trebek responded.

But those gathered in the Pasadena ballroom—and millions of faithful Jeopardy! viewers across the nation—have been asking themselves how much more time there might be before a show known as a beacon of television stability changes forever. As much as this was a moment of celebration for the show, it was also, perhaps, the end of an era.

Jeopardy! has achieved a rare omnipresence in American culture—befitting for the show that holds the trademark for “America’s Favorite Quiz Show.”

It’s not merely its frequent appearances through cameos and spoofs on other television programs, though there have been many: from the Celebrity Jeopardy! and Black Jeopardy! sketches on Saturday Night Live, to Golden Girls, Baywatch, The X-Files, and The Simpsons, to the 2014 finale of The Colbert Report, in which Stephen Colbert rode off in a farewell sleigh alongside the foremost arbiters of American public life—Abraham Lincoln, Santa Claus, and Trebek.

With more than eight thousand episodes under its belt, the show has become a byword for brainy gumption: When 2020 presidential candidate Amy Klobuchar blanked on the name of Mexican president Andrés Manuel López Obrador, she later defended herself in a debate by saying, “This isn’t like a game of Jeopardy!”

Indeed, no less than former Chief Justice of the Supreme Court Warren Burger once sent Jeopardy! a letter requesting that the show spotlight the Bill of Rights in a category in the upcoming season in honor of the document’s 1991 bicentennial. Burger concluded his handwritten letter, “P.S. Jeopardy! is the only quiz show allowed in our home. It is truly a fine educational piece. Long ago Mrs. Burger and I were teachers.” (The writers obliged the judge.)

Nearly four decades into its present incarnation, Jeopardy! has gained the patina of an immovable cultural artifact. At the 2015 Emmys, the comedian John Oliver joked, as he introduced an award for limited series, “Every show on television will go off the air eventually, with the sole exception of Jeopardy!”

Oliver continued, “And I’ll tell you what: The sun could burn out, humanity could flee to another galaxy, time as we know it could cease to exist, but Alex Trebek will still be there scolding librarians from Ames, Iowa, to answer in the form of a question and passive-aggressively insulting their hobbies.”

If it’s felt like Jeopardy! has always been there, that’s partly by design. “We came on the air very quietly, without any great fanfare,” Trebek said in 2004. “There were no fireworks, no bright lights, no wild and crazy music. We were just an easy show to get used to, an easygoing rhythm.”

But change is coming all the same.

Friedman, the EP, departed at the end of 2019–2020’s Season 36 after a quarter century at the helm of Jeopardy! and fellow Merv Griffin creation Wheel of Fortune. Maggie Speak, the longtime head of Jeopardy!’s contestant department, also retired in 2020. A singular presence in the history of the show, Speak—who handpicked the contestants who appeared on each episode—did as much as anyone to shape the show millions of Americans watch every night.

At the time of writing, Trebek and his offscreen counterpart, announcer Johnny Gilbert, were well on their way to completing their fourth decade with Jeopardy!

But Trebek has been vocal about his grueling rounds of chemotherapy even as he continued to host. And in July, as the show wrapped its season, Gilbert turned ninety-six. It’s reasonable to think that someday, perhaps even someday soon, the pair will hang up their signature blazer and bomber jacket.

A lot of change, in short, is due for a show Trebek himself once equated to “this nice warm bath.”

“It is not known as a wild up and down show,” Trebek has said of the program. “There aren't these great highs and great lows. We just cruise along smoothly.”

One thing, at least, is unlikely to change: the contestants.

Many fans are surprised to learn just how sportlike Jeopardy! can be. It has many of the hallmarks that we associate with sports: a prospect pipeline, rigorous physical (and, yes, mental) preparation, a hall of fame, and strategic innovators revered decades later for their additions to the game, who sometimes go on to assume the role of coaches.

The show’s viewers, too, can take on a dedication rarely seen outside the confines of sporting fandoms. That’s the way it is in the home of actor Michael McKean, where he and his family gather every night at 7:00 to watch the night’s episode and play along, culminating in a nightly Final Jeopardy! showdown.

“There’s only one rule—you don’t talk about Jeopardy! club,” he jokes.

No—it’s something far more serious. Everyone stays silent through the first chorus of music during Final Jeopardy!, before counting down from three during the latter half and shouting their answers at once. (He insists that no one keeps track of their scores after the fact.)

McKean is admittedly no normal Jeopardy! fan: He’s won Celebrity Jeopardy! on three occasions, and is, thanks to nabbing the grand prize in the 2010 Million Dollar Celebrity Invitational, one of just four Jeopardy! contestants ever to win a million-dollar tournament prize. (The others: Rutter, Jennings, and Watson, the IBM supercomputer.)

The premise of Jeopardy! is simple enough: two grids of thirty questions, a preliminary Single Jeopardy! round with a single hidden Daily Double betting opportunity and then the trickier Double Jeopardy! with two Daily Doubles, with difficulty and dollar value increasing downward. This is followed by one last question—Final Jeopardy!—on which players have the option to wager everything they have.

By the time a contestant makes it to the Jeopardy! stage, the odds are good that he or she has long been training in some form to compete on the show. Many players spend years working their way up through a series of nontelevised (and mostly nonpaying) circuits, a kind of Triple-A league for Jeopardy! hopefuls. Even casual viewers might be aware of the rise of advanced statistics on Jeopardy!, whose complex lessons about defensive gameplay, Daily Double and Final Jeopardy! wagering, buzzer advantage, and other metrics and tactics have fueled the rise of recent champions like Holzhauer.

A great Jeopardy! player is likely concerned with far more than just presidents, state birds, and the corresponding flash cards. That player may also have immersed himself or herself in everything from game theory to thumb reflex and grip strength training and even, in some cases, scouting of other players ahead of time. On TV, you see a scant twenty-two minutes of action; for the contestants, those minutes may have been months or years in the making.

Before we get into it, some disclaimers. Most of this book will be concerned with the era that began with the show’s revival in 1984 with Trebek and Gilbert. But today’s Jeopardy! would not exist without the show’s original incarnation on NBC, with actor Art Fleming as host and Don Pardo—later the legendary voice of Saturday Night Live—as announcer.

The original version premiered in 1964 and lasted (counting a one-year revival in 1978) twelve years. Unlike the modern edition, it aired during the middle of the day, making it and its lead-in Hollywood Squares a favorite of college students and workers on their lunch breaks.

The original Jeopardy! also was a hit, albeit of a different kind—at one point in its network-TV-heyday run, it captured a baffling 38 percent of the viewing audience—and one with some critical rule differences that we’ll dig into later on. When Trebek first took over Jeopardy!, it was years before audiences were won over, and there still exist die-hards who refuse to watch the modern edition out of lingering loyalty to Fleming.

Without the success of the Fleming-and-Pardo Jeopardy!, there would never have been a Trebek-and-Gilbert Jeopardy! The show’s endurance through the years is a testament both to Griffin’s game as well as to the team that first wooed audiences into making it a daily routine.

My focus here will also be largely on the flagship Jeopardy! show, though the number of spin-offs it has spawned—including VH1’s four seasons of Rock & Roll Jeopardy! with future Survivor host Jeff Probst, a sports-themed game hosted by former ESPN anchor Dan Patrick, and a children’s version known as Jep!—is proof of the show’s seminal place in television history. That’s true even outside the borders of North America: In 1996, 1997, and 2001, English-speaking champions from different nations’ Jeopardy! franchises faced off in an International Tournament. (The winners: Sweden, Canada, and the United States.)

Another disclaimer: I am not a Jeopardy! contestant, former or, alas, future. I grew up, as so many have, watching the show with my parents, in awe of how the players (and—ugh—my parents) knew all this stuff. When I got an apartment (and a cable subscription, a few apartments later) of my own, recording Jeopardy! and shouting out the answers each night from the couch became one of my first traditions with my now-husband.

I started writing a column about the show as a fan—one largely unaware of how much goes on just beneath its surface. In time, I’ve come to know a bit about the depths of strategy and the world of contestants, both alumni and aspiring. My hope is to share some of that with you, so that wherever you count yourself within the Jeopardy! world—alum, future champion, or nightly shouter of answers from your own couch—you’ll learn a little more about how the show works and what has made it such a unique corner of television.

As for my odds: I am a thoroughly lousy trivia player—a mediocre pub quiz participant at best. Even if I had the stomach for hand-to-hand, or brain-to-brain, buzzer battles on national TV—I emphatically do not—I know for a fact, as you will read in the coming chapters, that I won’t be competing on the Jeopardy! stage anytime soon.

One additional technicality. Jeopardy! tapes most episodes approximately two months before they appear on TV; unless otherwise noted, episodes are referred to by their air date, not their tape dates.

With that: Let’s meet today’s contestants.