‘Jeopardy!’ star Ken Jennings' ‘archrival’ was one of biggest challenges on path to becoming game show host

Jennings, who set the record for longest consecutive winning streak in 'Jeopardy!' history in 2004, turns 50 on May 23

Ken Jennings is celebrating a milestone birthday.

As the "Jeopardy!" champion-turned-game show host turns 50, here is a look back at his journey on the show.

Jennings' record-breaking win

Ken Jennings and Alek Trebek on "Jeopardy!"

Ken Jennings won 74 consecutive games on "Jeopardy!," setting a record which has yet to be broken. (Photo by Jeopardy Productions via Getty Images)

Jennings made his "Jeopardy!" debut in June 2004, going on to appear in 74 episodes and setting a record for the longest consecutive winning streak in the show's history. The record has yet to be broken by another contestant. 

Prior to Jennings appearing on the show, contestants were limited to five consecutive wins, after which they would not be allowed back. While Jennings was not the first to go past five games after the rule was removed, he is the contestant that has gone the farthest.

After earning over $2 million as a contestant, Jennings lost in a November 2004 episode. The clue that took Jennings down was "Most of this firm’s 70,000 seasonal white-collar employees work only four months a year," to which he incorrectly answered "What is FedEx?" with the correct answer being: "What is H&R Block?"

While Jennings set the record for most consecutive wins, he has not earned the most money. Through return appearances in tournaments, Jennings has earned a total of $4,370,700 in winnings, with Brad Rutter beating him with a total of $4,938,436 in winnings.

‘Quiz-show archrival’

Ken Jennings playing "Jeopardy!" against the WATSON computer

Ken Jennings returned to "Jeopardy!" for various tournaments. (Photo by Ben Hider/Getty Images)

Following his record-setting winning streak, Jennings returned to the "Jeopardy!" stage in various tournaments. 

He appeared in the first-ever "Jeopardy! Ultimate Tournament of Champions," and finished in second place, with Rutter coming in first. Unlike the other contestants, Jennings was guaranteed a spot in the finals, and did not need to compete in any other episodes.

In one of "Jeopardy!'s" most memorable competitions, Jennings went up against the IBM Watson computer, finishing the tournament in second place, losing to the computer, but defeating the second human contestant, Rutter. He went on to place second in other tournaments, such as "Jeopardy! Battle of the Decades," and "Jeopardy! All-Star Games." 

"During my 2004 ‘Jeopardy!’ streak, I was accustomed to mowing down players already demoralized at having to play a long-standing winner like me. But against Watson I felt like the underdog, and as a result I started out too aggressively," he wrote in a February 2011 essay for Slate. 

"I tried to keep my chin up, but in the back of my mind, I was already thinking about a possible consolation prize: a second-place finish ahead of the show’s other human contestant and my quiz-show archrival, undefeated ‘Jeopardy!’ phenom Brad Rutter."

‘Greatest of All Time’

Ken Jennings holding the Greatest of All Time trophy after he won

Ken Jennings went on to win the "Greatest of All Time" tournament in 2020. (Eric McCandless/ABC via Getty Images)

In January 2020, Jennings won the game-show's "Greatest of All Time" tournament, marking his first win since his streak in 2004. 

While speaking on "Good Morning America" following his win, Jennings explained he remembered "feeling shock" when he won, joking he had "an amazing talent for finishing second" when it came to "Jeopardy!" tournaments. 

"There’s a little bit of math that goes into wagering on ‘Jeopardy!’" Jennings told the outlet. "And generally, what happens is the person in second should often make a very small wager. You’re counting on the person in first to make a big wager, so it doesn’t matter at that point. If they get it wrong, they’re out. So it doesn’t matter what you wager, you want to risk as little as possible for that eventuality."


The win came with a $1 million prize, bumping Jennings' total winnings from all his appearances up to over $4 million.

Trivia master

Ken Jennings on "The Chase."

Ken Jennings has appeared on various other game shows. (Raymond Liu/ABC via Getty Images)

Due to his many appearances on "Jeopardy!," Jennings became known as a trivia master, landing him a place on various other trivia-related game shows.

From 2008 to 2009, he was featured in "Stump the Master," which gave the at-home audience a chance to win $1,000 by calling in and asking Jennings a question with the hope of stumping him. He was then featured as one of the rotating trivia masters on the show "Best Ever Trivia Show," and its successor, "Master Minds."

Later, he appeared as a contestant on the revival of "The Chase," teaming up with fellow "Jeopardy!" alums, Rutter and James Holzhauer.

‘Jeopardy!' host

Ken Jennings hosting "Celebrity Jeopardy!"

Ken Jennings went on to host "Jeopardy!" and "Celebrity Jeopardy!" following Alex Trebek's death. (Eric McCandless/ABC via Getty Images)


In October 2020, Alex Trebek filmed his last episode of "Jeopardy!" after hosting for 37 seasons. He died one month later, in November 2020, from pancreatic cancer.

After many guest hosts, it was announced in July 2022 that Jennings and "Big Bang Theory" actress Mayim Bialik would be splitting hosting duties. The two took turns hosting the main show, while Bialik took on full-time hosting duties of "Celebrity Jeopardy!"

Things changed, however, when Bialik announced in December 2024 she would no longer be hosting the popular game show, leaving Jennings as the sole host.

"It took me off guard, because I loved working with my Mayim and I’m gonna miss her," Jennings told The Hollywood Reporter when the announcement was made. "I can’t speak to her decision-making process or her opinions about it. But on my end, I’m just a fan of 'Jeopardy!' and I’m always delighted to host when they call upon me. I just feel extremely lucky to have even been considered for this job as a non-broadcaster."


Ken Jennings standing in front of a "Jeopardy!" board

Ken Jennings is now hosting "Jeopardy!," as well as the tournaments and "Celebrity Jeopardy!." (Eric McCandless/ABC via Getty Images)

Jennings now hosts the main show, as well as the tournaments and "Celebrity Jeopardy!"

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