On the afternoon of Jan. 4, Dillon Hupp accepted a job offer from Syracuse University as its new associate director of development in the College of Visual and Performing Arts (VPA).
On the evening of Jan. 4, Hupp received a phone call from the producers of the nationally syndicated weeknight favorite “Jeopardy!,” inviting him to be a contestant on an upcoming episode.
Hupp with “Jeopardy!” host and legendary former contestant Ken Jennings (Photo courtesy of Hupp)
“I immediately called my HR representative from Syracuse and asked how big of a deal it would be if I took three vacation days the week after I started to compete on ‘Jeopardy!’” Hupp says, as one does if they are a lifelong quiz bowl and trivia nerd whose presence has been requested at the mecca—the Alex Trebek Stage at Sony Pictures Studios in Culver City, California.
Last week, Hupp’s appearance aired and viewers across the country watched him swiftly defeat his opponents on the Monday, April 24, episode and win a final take-home prize of $21,999. He was a returning champion on the episode airing Tuesday, April 25—but ultimately fell victim to some tough competition and a high-risk wager on Final Jeopardy, ending the night with $0 after a clue about ’80s television in the category TV History wound up being a “triple stumper,” meaning all three contestants got the question wrong.
Sporting a blue and orange striped tie in one episode and an Orange Block S pin on the second episode, Hupp proudly represented Syracuse during his two-day run on the popular quiz show. “I went in it without any expectations about winning or what the experience was going to be like. I was just thrilled for the chance to be on the show and wanted to have some fun,” says Hupp, who relocated from Little Rock, Arkansas, to Syracuse earlier this year to join the VPA team and be closer to family.
Surprisingly, Hupp is not a lifelong “Jeopardy!” aficionado—he actually didn’t watch the program regularly before he found out he was going to be a contestant. Instead, he cut his trivia teeth as the captain of his elementary, middle and high school quiz bowl teams, at quiz bowl camp and playing bar trivia.
“My senior year we won the Arkansas Quiz Bowl State Championship, the first in my school’s history, and went on to nationals,” Hupp says. “Since then, I’ve also played enough bar trivia to pay for a few drinks with my winnings over the years. So even though I wasn’t really into ‘Jeopardy!,’ people had of course been telling me my whole life that I ought to try out for the show.”
He eventually did and after taking the Anytime Test, several rounds of Zoom auditions and screen testing, Hupp got the call to be on the show on that fateful day in January.
“Once you get notified that you are in the pool [of contestants], you have 12 months to be called to be on the show—or not,” Hupp says. “If you aren’t called in those 12 months, you have to start the whole process over, beginning with the Anytime Test.”
Hupp
He says in conversing with others who were filming with him in California, he realized most “Jeopardy!” contestants had been trying to get on the show for years, sometimes decades. “I could sense they were kind of seething behind the eyes when they found out I got on the show on the first try,” he jokes. “But ultimately the other contestants helped make it such a blast. We got to hang out on the day of filming and rehearse together and see all the bells and whistles at the studio. It was one of the most amazing experiences of my life.”
Leading up to and since his appearance, Hupp has become a huge fan of the show. To prepare for his appearance, he even downloaded the PlutoTV app, which has a 24/7 “Jeopardy!” channel.
“I thought from a knowledge standpoint that I knew what I knew at that point—sports, geography, history, things like that. I knew I wasn’t going to become an expert in French authors overnight, so I didn’t try to do any rote memorization,” he says. “But I did watch ‘Jeopardy!’ reruns in every bit of free time I had in the month between when I knew I was going to be on the show and when my episode filmed.” Watching old episodes helped him get a sense of the rhythm of the show, how clues are phrased and strategies for how to play.
Although his diligent preparation did not protect him from being defeated in the second game, Hupp says he is pleased with his performance. “I won some cash, I didn’t totally embarrass myself with any of my responses, and I got to spend some time in February in California where it was 75 and sunny rather than being in gray and snowy Syracuse,” he says. “I have zero regrets about the entire thing—except wishing that I had any conception of what the TV show ‘Hawaii Five-O’ was.”
