The Biggest Losers On Jeopardy!

For decades, one of the most popular shows in syndicated TV, and almost certainly one of the most popular games shows of all time, has been "Jeopardy!" Over the course of its nearly seven decades on the air, the show has made thousands of people at least a few hundred dollars richer than they were before they appeared on the show. Some, such as James Holzhauer and Ken Jennings, became millionaires from appearing on the show, as Vulture notes.

However, as Weird Al Yankovic famously noted in his song "I Lost on Jeopardy!" (available via YouTube), it's quite possible to go on the show, make a fool of yourself, and fail miserably. Countless contestants have left the show with their balance in the negative, meaning they took home naught but the consolation prize for finishing in third place. And a few have left the show with a negative balance well into the thousands, marking their places, along with one contestant who let his emotions get the better of him, as the biggest losers to appear on the show.

Matt King couldn't have picked a worse time to appear on "Jeopardy!" Back in November 2021 (when the show ultimately aired, not when it was filmed), as E! Online reported at the time, he had the misfortune of appearing against Amy Schneider, who as of this writing is still the champion and on pace to join Holzhauer and Jennings among the top earners on the show. King, however, won't be joining them. His strategy, which can best be described as "bold," was to go for it as often as possible, even taking guesses on the clues just to be the first to ring in. It worked out well at first, bringing him up to $2,400, but his strategy soon fell apart and, by the time Double Jeopardy ended, he was over $6,000 in the hole.

He didn't get to compete in Final Jeopardy (he'd have lost anyway, since Schneider couldn't be caught), but he became something of a hero on social media, with viewers praising him for taking risks. "Matt went down swinging. I have to respect that," wrote one fan on Twitter.

On March 12, 2015, "Jeopardy!" history was made twice in one game. First, third-place finisher Stephanie Hull finished with a score of -$6,800, a record at the time, as Slate reported. Second, the second-place finisher also ended the game in the red, albeit with a score of "only" -$200, compared to Hull's several thousand. That meant that only one contestant had any money going into the Final Jeopardy round, and Kristin Sausville effectively competed against herself.

In the years since her history-making defeat, Hull later told Slate that she didn't have the heart to rewatch her episode. "I don't particularly want to rewatch my own episode," she said at the time.

As to how she got there, Hull said that after the Daily Doubles were taken off the board by other competitors, she started to panic. Choosing big-money questions at the bottom of the board seemed like the way to get out of the hole, but she "brain-farted," as she described it, on several of them, and it just kept getting worse. "I was really in panic mode at that time. Total sheer panic," she said.

In terms of monetary value, Ryan Bilger's loss in May 2021 wasn't particularly striking; he finished with a score of $16,002, which is respectable in any episode. Unfortunately, Bilger hadn't counted on his Tournament of Champions opponent, Veronica Vichit-Vadakan, also guessing the Final Jeopardy question correctly, and making a winning wager to boot. As host Buzzy Cohen announced that Vichit-Vadakan had won, and while the studio audience and the other contestants congratulated her, Bilger tepidly applauded while looking crestfallen.

His actions didn't go well on social media, as TV Insider would later report, with outraged fans calling him a "sore loser." "Ryan barely clapping for the winner last night was heartbreaking to the decades I have been watching," wrote one disappointed viewer. Another wrote that "Ryan should be embarrassed." Bilger, for his part, later tweeted his congratulations to Vichit-Vadakan and wished her well in the finals.

Few "Jeopardy!" fans are unaware that, for decades, the show had been spoofed on "Saturday Night Live," with Will Ferrell portraying Alex Trebek as exasperated and long-suffering, particularly at the antics of his celebrity contestants. One particularly memorable spoof involved Norm MacDonald playing the role of Burt Reynolds, and telling Trebek/Ferrell that he was to be addressed as "Turd Ferguson" (the sketch is available via YouTube). 

It was a funny, if forgettable joke, and Talia Lavin brought it back when she appeared on the show. Specifically, as The Today Show reports, Lavin, with $600 going into Final Jeopardy, knew she was going to lose, so she decided to make a joke of it. "I knew as soon as I had $600 going into Final Jeopardy that I wanted to make a joke, because I couldn't win," Lavin later said, and indeed, her joke referenced the decade-old Norm MacDonald bit. "What is the love ballad of Turd Ferguson ps hi mom" while giving a cheery grin and a thumbs-up to the camera. The studio audience got a chuckle out of it, but Trebek, for his part, didn't get it. Lavin later said that she explained the joke to the host backstage after the show, and he responded that he hadn't watched his "SNL" spoofs in a while and thus was confused.

Moving back into the realm of "Jeopardy!" contestants who lost money rather than just losing face, the biggest loser on the show, as of this writing, is Patrick Pearce, who finished with a record negative score of -$7,400, per Entertainment Weekly. Much like Matt King, who had the misfortune of competing against champion Amy Schneider, Pearce was a competitor early in the winning streak of Matt Amodio, who would himself go on to rack up an impressively long winning run, with an impressive amount of cash to boot.

Meanwhile, Pearce's poor performance couldn't have come at a worse time for the man who guest-hosted the show that day. LeVar Burton, who had been a fan favorite to take over for Alex Trebek and even had social media campaigns in his favor, made his guest-hosting debut that day, only to have his appearance overshadowed by history-making ineptitude by a contestant.