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Longmont resident wins big on the Jeopardy stage

Stephen Webb spent a quarter century watching the game show before it was his turn to shine
Jeopardy Productions, Inc.

Stephen Webb watched Jeopardy for twenty-five years but he never imagined that he’d be on the other side of the television. An episode that aired on Feb. 15 featured Webb as one of the contestants.

The Longmont data scientist took the Anytime Test — the Jeopardy qualifier exam — in the spring of 2020 after his wife pointed out his potential. 

“My wife and I started watching Jeopardy every night and you know, she noticed that I kind of knew all of the answers and after a month of her saying ‘you should take that online test to try and get on the show’ … I propped up a laptop and took the Anytime Test,” Webb said. 

Doing well on the test didn’t guarantee Webb a spot on the show, however. He went through rounds of interviews and Zoom meetings before he was granted the opportunity to step foot on the stage almost three years later. 

Webb jumped on a plane to Culver City, Los Angeles with a mind full of trivia answers and excitement. In the studio, he met his opponents and quickly connected with them through their love for the game show. 

“Watching jeopardy with a bunch of other Jeopardy super fans, with people you just met playing Jeopardy, is crazy. It’s so much fun,” Webb said.

When the taping began, the pressure was on. Jeopardy presents reversed questions, with the answer given first and the question guessed by the contestants. Webb’s wife has quizzed him nightly in preparation for the show and he even purchased an Advanced Placement Exam test prep book in hopes of refreshing his high school memory.

Webb faced a food service employee and psychologist, leading with the most points for the majority of the episode. The tensions were high until the winner was announced at the final minute of the show.

Stephen Webb had won it all. His correctly answered questions had racked up $38,401 and the Longmont data scientist said he would do it all again in a heartbeat.

“If they told me to be down there next week … I’d be on a plane next week,”  Webb said.

If others are attempting to jump on the game show stage and answer trivia questions for a chance to win big, their best bet is to read widely, Webb said. He notes that knowing a little bit about everything is the key to doing well. 

Webb encourages potential contestants to stick with the process, even if it seems daunting.

“Life is a lot better when you just say yes to possibilities,” Webb said. 


Ivonne Olivas

About the Author: Ivonne Olivas

I’m from a small town in eastern Colorado and currently a journalism student at CU Boulder.
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