19 years ago, Ken Jennings lost on ‘Jeopardy!’ after 74 straight wins. Here are 4 big moments from his legendary run

Ken Jennings had 30 seconds to come up with the answer.

The clue: Most of this firm’s 70,000 seasonal white-collar employees work only four months a year.

Jennings wrote his answer down quickly. His competitor, Nancy Zerg, took a little longer. And then time was up. Zerg, who was in second place with $10,000, revealed her response: H&R Block.

She was correct. Her $4,401 wager put her just a dollar ahead of Jennings. All eyes were now on the reigning champ.

His answer? FedEx.

It was the gasp heard round the world. Sounds of disbelief rang throughout the “Jeopardy!” studio. Even Zerg’s mouth dropped open.

Jennings smiled through it all. He shook Zerg’s hand and the two hugged, marking the end of a “Jeopardy!” era. (Zerg would end up losing her very next game.)

That shocking episode aired 19 years ago. On Nov. 30, 2004, Jennings was dethroned after a 74-game winning streak that earned him $2.52 million — a streak that still remains unmatched.

Nineteen years after H&R Block cost Jennings his 75th victory, the contestant, who now lives in Seattle, remains in the spotlight. In 2020, he beat out fellow “Jeopardy!” greats Brad Rutter and James Holzahuer to claim the Greatest of All time title. And he now serves as the co-host of “Jeopardy!”

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“As a contestant, there’s something really special about being onstage with the greatest player of all time,” Mattea Roach, who won 23 games in 2022, previously told Vulture. “Someone who understands in a very visceral way what it’s like to be in your position.”

Here’s a look back at some highlights from Jennings’ legendary run and what made him so successful.

Remembering Ken Jennings’ legendary ‘Jeopardy!’ run

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Game 1: Jennings’ “Jeopardy” run is even more remarkable when you look at his first game, which aired June 2, 2004. Going into Final Jeopardy, Jennings had $20,000. He bet $17,201 of that amount on the final clue: “She’s the first female track & field athlete to win medals in five different events at a single Olympics.” Jennings responded, “Who is Jones?” referencing Marion Jones.

According to a Ken Jennings timeline, host Alex Trebek said, “We will accept that, in terms of female athletes, there aren’t that many.” But if the response hadn’t been accepted, Jennings would have finished last, and his streak never would have started.

• Game 38: On July 23, 2004, Jennings correctly answered 44 of the 60 clues and set a new single-day winning record of $75,000 — a record Holzhauer has since beat 10 times over. Going into Final Jeopardy, Jennings had $51,400. The Final Jeopardy clue: “2 of the 4 Shakespeare plays in which ghosts appear on stage.”

Jennings responded with “What are ‘Hamlet’ and ‘Richard III’?”

Trebek, knowing Jennings was on the verge of breaking a record, toyed with him: “‘Hamlet’ is correct, ‘Julius Caesar’ is correct, ‘Macbeth’ is correct … and ‘Richard III’ is correct.”

Jennings slapped his desk and with a wide smile said, “You’re killing me, Alex!”

“I know, I know, but you’re killing us!” Trebek said. “Look what you won!”

Jennings’ $75,000 victory that day brought his total winnings to $1,321,660. That game also marked the final episode of season 20.

• Game 59: Until the 20th season premiere in September 2003, “Jeopardy!” had a five-game limit. When the rule changed, Trebek said to his audience, “That could mean perhaps champions leaving us with a quarter million or half a million dollars, who knows? Let’s start finding out.”

On Oct. 25, 2004 — Jennings’ 59th game — Jennings did much more than that, reaching $2 million. He was the first competitor to achieve this milestone. Ironically, the Final Jeopardy category was “Historic Firsts.”

The clue: “The brother of this leader is believed to be the first known European to have died in the Americas.”

Jennings, who already had a substantial lead in this game, was the only one to come up with the correct response — Leif Ericson. The $30,000 Jennings won from this game brought his total to $2,006,300.

• Game 74: Nov. 29, 2004, marked Jennings’ final victory. It was a runaway game going into Final Jeopardy, and Jennings was the only one to get the biblically themed Final Jeopardy clue right. As Trebek said, “He has not missed many questions or clues that have to do with the Bible.”

The clue: Of the Social Security Administration’s Top 10 boys’ names in 2000, the 2, ending in the same letter, on a list of the 12 apostles.

Jennings came up with the right answer — Matthew and Andrew — and brought his total winnings to a grand $2,520,700.

The following day, Jennings would wind up in second place, adding $2,000 to his total and finishing his historic run on the beloved game show.

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Throughout his 75-game run, Jennings, who was then a software engineer in Salt Lake City, improved the show’s ratings by 22%, according to Hollywood Reporter. In 87% of his games, he accumulated more than double the money his closest competitor earned going into Final Jeopardy, securing his victory.

During his run, Jennings correctly answered 2,693 questions. The number of questions he missed was significantly smaller — 263. His average game total was $33,727, and he was quick on the buzzer, beating his competitors to the question 61.5% of the time.