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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.
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Q 01How many consecutive Jeopardy! games did Ken Jennings win in 2004?
74
It remains the longest streak in the show's history, though Britain's Ian Lygo won 75 games of 100% in 1998.
Q 02How much did Jennings win over his original 75-day Jeopardy! run?
$2,522,700
That includes the $2,000 consolation prize for finishing second in game 75.
Q 03In which Washington town was Ken Jennings born?
Edmonds
It sits just outside Seattle, where he still lives, flying to Los Angeles twice a month for tapings.
Q 04Jennings spent much of his childhood in which two Asian countries?
South Korea and Singapore
His father was an international lawyer; Ken graduated from the Seoul Foreign School.
Q 05Jennings served a two-year LDS mission in which city?
Madrid
He has called his faith central to his grounding while publicly criticising some church policies.
Q 06Where did Jennings graduate from in 2000?
Brigham Young University
He captained the quizbowl team and met his wife Mindy there.
Q 07Jennings double-majored in English and which other subject?
Computer science
The degree led to a software engineering job at a healthcare placement firm in Utah.
Q 08What was Jennings's job before his Jeopardy! run?
Software engineer
He worked for CHG Healthcare Services in Holladay, Utah, and left after landing a book deal.
Q 09Before 2003, how many consecutive wins were Jeopardy! contestants limited to?
Five
Lifting the cap the season before Jennings arrived made his streak possible.
Q 10What did Jennings use as a practice buzzer while preparing at home?
His child's toy
He used the couch as a lectern while his wife read flashcards and kept score.
Q 11Jennings's first Jeopardy! win aired on June 2 of which year?
2004
He unseated two-time champion Jerry Harvey in the show's 20th season and kept going into the 21st.
Q 12How many episodes had Jennings taped before his first one aired?
48
Jeopardy! tapes five shows a day, so his fame arrived months after the games were played.
Q 13Who finally defeated Jennings in his 75th game?
Nancy Zerg
She wagered $4,401 to edge him by a single dollar, then lost her own next game.
Q 14Which company was the correct response that ended Jennings's streak?
Q 21Which company built the machine that beat Jennings and Rutter on Jeopardy! in 2011?
IBM
It was the first man-versus-machine contest in the show's history, and the machine's $1 million went to charity.
Q 22What did Jennings write under his Final Jeopardy! response against Watson?
"I for one welcome our new computer overlords"
The Simpsons reference became the most-quoted moment of the match.
Q 23How much did Watson finish with in the 2011 IBM Challenge?
$77,147
Jennings had $24,000 and Rutter $21,600; Jennings collected $300,000 for second place.
H&R Block
The clue was about a firm whose 70,000 seasonal white-collar employees work only four months a year.
Q 15What did H&R Block offer Jennings after his loss?
Free tax planning for life
A company executive estimated he owed around $1.04 million in taxes on his winnings.
Q 16Which two senators asked Jennings to run for the Senate from Utah in 2004?
Chuck Schumer and Harry Reid
He revealed the Democratic approach in a 2011 Reddit AMA and declined.
Q 17Why was Jennings never invited to a regular Tournament of Champions?
Only defeated players qualify
Invitations go to champions with four or more wins once they lose; by then his streak had its own tournaments.
Q 18How much did Jennings collect for second place in the 2005 Ultimate Tournament of Champions?
$500,000
Jennings took the $500,000 runner-up prize; Rutter briefly overtook him as game shows' top money winner.
Q 19Brad Rutter worked at a record store in which Pennsylvania city before Jeopardy!?
Lancaster
He retired as an undefeated five-day champion in 2000 with $55,102 and then dominated tournaments for two decades.
Q 20Until 2020, Brad Rutter had never lost a Jeopardy! match to what kind of opponent?
A human
His only defeat before the GOAT tournament came against IBM's Watson computer.
Q 24The IBM machine that beat Jennings was named after whom?
IBM's founder and first CEO
The system came out of IBM's DeepQA project led by David Ferrucci.
Q 25Jennings won the Greatest of All Time tournament on which network in January 2020?
ABC
The prime-time event pitted him against Brad Rutter and James Holzhauer.
Q 26What prize came with the Greatest of All Time title?
$1,000,000
It pushed his lifetime Jeopardy! winnings to $3,522,700 at the time.
Q 27Where did Brad Rutter finish in the Greatest of All Time tournament?
Third
It was his first overall defeat and only the second time he finished behind a human.
Q 28How many games did James Holzhauer win during his 2019 streak?
32
The professional sports gambler also holds all top ten single-game winnings records, topped by $131,127.
Q 29What was Jennings's nickname as a chaser on ABC's The Chase?
The Professor
Rutter and Holzhauer were the other original chasers; Mark Labbett joined in season two.
Q 30Who co-hosted the Omnibus podcast with Jennings?
John Roderick
Roderick fronts the indie-rock band The Long Winters; the show ran from 2017 until a final live episode in Seattle in 2025.