Ken Jennings Trivia
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50 free Ken Jennings trivia questions with answers — entertainment quiz, new questions added Aug 2026.
Ken Jennings went from software engineer to 74 straight Jeopardy! wins, lost to a tax-prep clue, welcomed our computer overlords, beat Brad Rutter and James Holzhauer for the Greatest of All Time title, and then inherited Alex Trebek's lectern. This Ken Jennings trivia covers the streak, the tournaments, the books and the podcast. Every answer is sourced, with a short explanation so you learn something even when you miss.
30 of 50 questions with answers and explanations. Play the quiz
Q 01How many consecutive Jeopardy! games did Ken Jennings win in 2004?
74
74 wins is still the show's record, but not quite the longest quiz run on television. Britain's Ian Lygo won 75 straight on the game show 100% in 1998, until its producers asked him to step down.
Q 02Roughly how much did Ken Jennings win during his record Jeopardy! streak?
$2.5 million
$2.5 million, or $2,522,700 to the dollar, came from a run that opened with a $37,201 first game. Even the defeat that ended it paid: second place was worth $2,000.
Q 03Ken Jennings was born just outside which city, where he has settled?
Seattle
Seattle is home: he was born in the suburb of Edmonds and moved back after his Utah years. Hosting lets him stay, because the show tapes several episodes a day and needs him only a few days a month.
Q 04Ken Jennings grew up overseas while his family lived in which two Asian countries?
South Korea and Singapore
South Korea and Singapore were the family's homes while his father practised law abroad. In Seoul the only English-language channel was a US military network, and he watched Jeopardy! on it after school every day.
Q 05Ken Jennings served a two-year Mormon mission in which city?
Madrid
Madrid was his home for two years in the mid-1990s. He went partway through college, breaking off his studies at the University of Washington and finishing his degree elsewhere after he came back.
Q 06From which university did Ken Jennings graduate in 2000?
Brigham Young University
Brigham Young University is where a flyer for the quiz bowl team changed his life. He went on to captain the side, and came to see the college circuit as a farm team for Jeopardy!.
Q 07Ken Jennings won his first Jeopardy! game with a final response giving only the surname of which Olympic sprinter?
Marion Jones
Marion Jones was the answer to a clue about five medals at one Olympics, and he wrote only "Who is Jones?". Alex Trebek let it stand, saying there weren't that many women athletes it could be.
Q 08What was Ken Jennings's job before his Jeopardy! run?
Software engineer
Software engineer was his day job at a health-care staffing firm in Salt Lake City. A book deal after the streak let him give up programming to write, and he has published more than a dozen books since.
Q 09Before 2003, how many consecutive wins were Jeopardy! contestants limited to?
Five
Five wins once meant retiring undefeated. The show scrapped the cap in 2003, and within a year Jennings had begun his record run.
Q 10What did Ken Jennings use as a practice buzzer while preparing at home?
His child's toy
His child's toy, a Fisher-Price ring stacker, was about the size of the real buzzer. His wife drilled him with flash cards, including a set on cocktail ingredients because he doesn't drink.
Q 11Which TV journalist put Ken Jennings in her 2004 year-end special?
Barbara Walters
Barbara Walters named him one of her ten most fascinating people of 2004. By then his two-year-old son was calling him "Ken Jennings" rather than Daddy, because that was what the television said every night.
Q 12How many Jeopardy! episodes had Ken Jennings taped before his first one aired?
48
48 shows were already recorded, because a week of episodes is taped in one afternoon and his first game sat on the shelf from February to June. He had to keep every trip to Los Angeles, and every result, secret.
Q 13Who ended Ken Jennings's Jeopardy! winning streak in November 2004?
Nancy Zerg
Q 21Narrating Alex Trebek's memoir earned Ken Jennings a nomination for which award?
A Grammy
A Grammy nomination for best spoken word album came for his reading of The Answer Is..., the memoir Trebek published months before his death in 2020. Jennings went from voicing Trebek's words to doing his job.
Q 22What did Ken Jennings add to his final response against Watson?
"I for one welcome our new computer overlords"
"I for one welcome our new computer overlords" riffs on a Simpsons newsreader who greets what he thinks are invading giant ants. Jennings added it once the match was lost, beneath a correct response about Bram Stoker.
Q 23In 2011 IBM's Watson answered a Jeopardy! clue about U.S. cities with which city?
Nancy Zerg wagered $4,401 to lead him by a single dollar before his wrong answer was revealed. Alex Trebek called her a giant killer, and she finished third in her very next game.
Q 14Which company did Ken Jennings wrongly name in the final response that ended his Jeopardy! streak?
FedEx
FedEx was his guess for a firm whose seasonal staff work four months a year; the answer was H&R Block. His excuse was that he does his own taxes, and both companies later hired him for publicity.
Q 15What did H&R Block offer Ken Jennings after a clue about the firm ended his streak?
Free tax planning for life
Free tax planning for life was the firm's way of cashing in on the clue. Its press release went out the day the episode aired, with an executive joking that the offer meant no Final Jeopardy for Jennings.
Q 16Ken Jennings says which two senators urged him to run for the Senate from Utah?
Chuck Schumer and Harry Reid
Chuck Schumer and Harry Reid each phoned him in 2004, by his own account, hoping he would take on Orrin Hatch. He said no, and joked that the calls showed how much trouble the Democrats were in.
Q 17Why did Ken Jennings sit out the 2004 Tournament of Champions, held in the middle of his streak?
Only defeated players qualify
Only defeated players qualify, and he was still winning when the tournament interrupted his run. The following year he was waved straight into the final of a far bigger tournament without playing a qualifying game.
Q 18How much did Ken Jennings collect for second place in the 2005 Ultimate Tournament of Champions?
$500,000
$500,000 went to Jennings as runner-up. Brad Rutter took the $2 million first prize, and with it Jennings's place as the biggest money winner in game-show history.
Q 19Ken Jennings's 2023 book is a tongue-in-cheek travel guide to which destination?
The afterlife
The afterlife gets the guidebook treatment in 100 Places to See After You Die, with travel tips for heavens and hells from ancient Egypt to The Good Place. Jennings calls it a bucket-list book for after you kick the bucket.
Q 20With which actor did Ken Jennings win $1 million for charity on Who Wants to Be a Millionaire in 2025?
Matt Damon
Matt Damon was playing for Water.org, the clean-water charity he champions. Jennings had left the show with $100,000 on his own in 2014, and joked that Damon turned out to be worth an extra $900,000.
Toronto
Toronto, followed by five question marks: Watson doubted its own answer to a clue about Chicago's airports and had bet only $947. It still won the match with more than three times Jennings's total.
Q 24IBM named its Jeopardy! machine Watson not after Sherlock Holmes's sidekick but after whom?
The company's first chief executive
The company's first chief executive, Thomas J. Watson, gave a maker of tabulating machines the name International Business Machines in 1924. The echo of Holmes's sidekick was a welcome bonus.
Q 25Ken Jennings won the Greatest of All Time tournament on which network in January 2020?
ABC
ABC gave the match a prime-time slot, a rarity for a quiz that is normally sold station by station in syndication. The gamble paid off: the hour-long nights drew enormous ratings.
Q 26What prize did Ken Jennings win with Jeopardy!'s Greatest of All Time title?
$1,000,000
$1,000,000 went to the first player to win three nights. Jennings later said he had fully expected to lose, and entered mainly to share a stage with Alex Trebek one more time.
Q 27Where did Brad Rutter finish in the Greatest of All Time tournament?
Third
Third, behind Jennings and James Holzhauer. Until that week Rutter had never lost a Jeopardy! match to a human opponent, through two decades of regular play and tournaments.
Q 28James Holzhauer fell $58,484 short of which Ken Jennings record?
Regular-season winnings
Regular-season winnings: in 2019 Holzhauer got that close in only 32 wins by hunting for Daily Doubles and betting huge sums. He lost with the record in sight.
Q 29What was Ken Jennings's nickname as a chaser on the quiz show The Chase?
The Professor
The Professor was his billing, beside James Holzhauer's High Roller and Brad Rutter's Buzzsaw. For once the three rivals were on the same side, taking turns to chase down contestants' prize money.
Q 30Who co-hosted the Omnibus podcast with Ken Jennings?
John Roderick
John Roderick, who fronts the indie-rock band The Long Winters, joined him in explaining odd corners of history and culture that they feared would be lost to posterity.