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'Jeopardy' contestant's ultimate prank on Ken Jennings brings back 'bad memories' for the host

Jennings had a record-setting winning streak as a contestant before he became the host.
PUBLISHED JUL 14, 2025
Screenshots showing Ken Jennings' and the player's reaction to the prank (Cover image source: YouTube/Jeopardy!)
Screenshots showing Ken Jennings' and the player's reaction to the prank (Cover image source: YouTube/Jeopardy!)

"Jeopardy!" contestants impress the audience with their trivia knowledge and quick thinking, but sometimes they even flaunt their sense of humor on the show. The host, Ken Jennings, is not only known for his witty comments, but he is also a good sport when a player makes fans laugh at his expense. This happened when former champion Brian Chang opted to troll Jennings during Final Jeopardy! before winning big. When Chang got a question he didn't know the answer to, he chose to write down, "What is H&R Block?" This was the answer to the question that ended Jennings' 74-game winning streak on the show. While the perfectly timed joke cracked everyone up, Jennings handled it well.

Screenshot showing Ken Jennings' reaction to the prank (Image source: YouTube/Jeopardy!)
Screenshot showing Ken Jennings' reaction to the prank (Image source: YouTube/Jeopardy!)

Back in 2021, Chang kicked off his win streak with a runaway game where the other two contestants couldn't win enough money to wager and take the championship away from him. Thus, during Final Jeopardy!, Chang had plenty of cushion to play around and have some fun on before the episode ended. Jennings read out the final clue, “Adjusted for inflation, the nightly rate this company put in its name in 1962 is now $51."

Screenshot showing Chang writing down his answer (Image source: YouTube/Jeopardy!)
Screenshot showing Chang writing down his answer (Image source: YouTube/Jeopardy!)

After taking their time, all three players wrote down their answers, and Jennings started with the day's returning champion, Donesh, who wrote down the correct answer, “What is Motel 6?” He then went to the runner-up of the day, Lisa Garner, who also got it correct. Jennings then moved to Chang and painfully read his answer, “What is H&R Block?” They burst into laughter as Jennings let out a big "Oooohh". 

Screenshots showing Chang pulling the prank and Jennings' reaction (Image source: YouTube/Jeopardy!)
Screenshots showing Chang pulling the prank and Jennings' reaction (Image source: YouTube/Jeopardy!)

In 2004, Jennings managed to set a record of 74 consecutive wins on "Jeopardy!" during his time as a contestant on the show. He finally lost his streak to Nancy Zerg, who beat the great champion by just $1 on a question under the "Business & Industry" category. When former host Alex Trebek read the clue, "Most of this firm’s 70,000 seasonal white-collar employees work only four months a year," Jennings seemed to be at a complete loss. While he wrote down "What is FedEx?" as his guess, Zerg got the correct answer, "What is H&R Block?"

Thus, Chang writing down the same as his answer was the ultimate prank on Jennings. Despite being trolled, Jennings handled the situation as a gracious host. “I know from experience, H&R Block is sometimes the right answer, but not today," the host said. "Even though you brought back some bad memories for me, you’re still going to go home with $13,201," he added as Chang grinned.

"Jeopardy!" fans loved the savage move by Chang, and many took to the comments on YouTube. "My man Bryan just paid $3799 to troll Ken," wrote one fan, @caleb6705. "I bet Bryan probably knew the answer, but wanted to troll Ken because it was a business question," added @RT88414.  

More on Market Realist:

'Jeopardy' fans call out host Ken Jennings for making an ‘awkward’ joke at returning champion

Former 'Jeopardy' players spill secrets about the warning given backstage: 'We needed to...'

'Jeopardy' player impresses Ken Jennings but fans can’t stop comparing him to famous TV character

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