On ‘Jeopardy!’ 15 Years Ago, IBM’s Supercomputer Watson Beat Ken Jennings & Brad Rutter

Before he was the host of Jeopardy!, Ken Jennings set a record for most consecutive games won on the game show, lasting 74 games in 2004. Jennings also won the Jeopardy! Greatest of All Time tournament in 2020 against James Holzhauer and Brad Rutter, the latter of whom still holds the record for all-time Jeopardy! winnings with his nearly $5 million in prize money. But 15 years ago, both Jennings and Rutter were trounced on the game show by an IBM supercomputer called Watson.

Nowadays, artificial-intelligence technology can easily answer questions posed in everyday human speech, as Jeopardy! clues are. In 2010, however, it was a rare achievement for a computer to respond to a “natural language” question with a correct answer. “Technologists have long regarded this sort of artificial intelligence as a holy grail, because it would allow machines to converse more naturally with people, letting us ask questions instead of typing keywords,” The New York Times’ Clive Thompson wrote in a June 2010 article about IBM’s preparations for Watson’s moment in the Jeopardy! spotlight.

At the time, the computer company wanted to prove its technology’s question-answering mettle by quizzing Watson on national TV, prompting it with clues cleverly worded by Jeopardy! writers, and pitting it against two of the game show’s best players. And Watson, then in development for three years, wasn’t even connected to the Internet. Like human Jeopardy! players, Watson had to rely on its memory — in its case, the stored contents of millions of documents.

And in point of fact, it was Jeopardy! and Jennings that inspired Watson. An IBM employee conceived the supercomputer after noticing bar patrons watching Jennings’ 74-game streak, according to the Pittsburgh Post-Gazette.

In the run-up to Watson’s game-show debut, IBM set up a mock Jeopardy! set in a conference room and enlisted former contestants from the show to play against the computer. As Thompson reported in the Times, humans started to anthropomorphize Watson — “He plays to win!” said contestant Samantha Boardman — and even compared Watson to the humanity-destroying Skynet computer system from the Terminator movies.) “My husband and I talked about what my role in this was,” Boardman said. “Was I the thing that was going to help the AI become aware of itself?”)

By that point, Watson had gotten much more competitive: At the end of 2008, the computer was responding to about 70 percent of clues and getting about 70 percent of those correct, but it would sometimes take up to two hours to offer a response, according to the Post-Gazette. As development continued, however, Watson was beating former Jeopardy! champions about 65 percent of the time.

In December 2010, the stage for the televised challenge was set: Jeopardy! producers announced that Watson had passed the game show’s contestant test and would battle Jennings and Rutter for a $1 million prize in three episodes airing February 14–16, 2011.

For Jeopardy! producers, the special episodes were just as much a showcase of their gameplay as AI intelligence.“We’re thrilled that Jeopardy! is considered a benchmark of ultimate knowledge,” said then-EP Harry Friedman, per The New York Times.

Jennings and Rutter played against Watson the following month at IBM’s T. J. Watson Research Laboratory in Yorktown Heights, New York, with then-host Alex Trebek emceeing. And the action kicked off on TV on February 14, 2011, with the broadcast of the first game’s Jeopardy round.

At the end of that first episode, Rutter and Watson were tied at $5,000, with Jennings trailing with a score of $2,000, J-Archive shows. The next night, viewers saw Rutter briefly take the lead in the Double! Jeopardy round before Watson started dominating the gameboard, finding and correctly responding to both of the round’s Daily Doubles.

At the end of the Double Jeopardy round, Watson was up by more than $30,000. It whiffed the Final Jeopardy challenge, responding with “Toronto?????” after Trebek asked for a U.S. city whose two largest airports are named after a World War II hero and a World War II battle. But it still emerged victorious with a score of $35,734, compared to Rutter’s $10,400 and Jennings’ $4,800.

In the second game of the challenge, broadcast on February 16, Jennings led the pack for most of the game with Watson close on his heels. It was not a runaway game by the time all three competitors provided the correct response to the Final Jeopardy round, naming Bram Stoker as the 19th-century novelist whose most famous novel was inspired by William Wilkinson’s An Account of the Principalities of Wallachia and Moldavia.

However, Watson made a huge wager on its Stoker response, while Jennings only bet $1,000. (“I, for one, welcome our new computer overlords,” Jennings added in his response, riffing on a quote from The Simpsons.)

After both games, Rutter had a cumulative score of $21,600, and he took home $100,000 and earned $100k for the Lancaster County Community Foundation. Jennings had a cumulative score of $24,000, and he took home $150,000 and earned $150k for the nonprofit VillageReach. Watson’s grand total, meanwhile, was $77,147, and with its victory, the supercomputer earned $500,000 apiece for the charities World Vision and World Community Grid.

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Watson did not prove a game-changer for AI — IBM made missteps in the years after the Jeopardy! challenge and got outstripped by Amazon, Microsoft, and Google, as The New York Times reported in 2021 — but the supercomputer did impress Jeopardy! viewers and at least two superchamps from the show.

“My past Jeopardy! experiences have been great, but they weren’t really weighty with this kind of technological, philosophical importance,” Jennings said in an IBM video recapping the man-versus-machine showdown. “I think we saw something important today.”

Added Rutter, “I would have thought that technology like this was years away, but it’s here now. I have the bruised ego to prove it.”

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