How much money would it take for you to sass game-show legend Alex Trebek on national television? For Jeopardy! GOAT contestant Ken Jennings, it took a $400 question. Don’t get him wrong; Jennings has spoken to Vulture in the past about how much Trebek means to him, even calling him “the last Cronkite,†but that didn’t stop Jennings from showing off his mastery of Gen Z disses. On Thursday night’s episode of the Jeopardy! “Greatest of All Time†tournament, Jennings leaped at the chance to answer this clue in the “OK†category: “A 2019 New York Times article says this 2-word phrase ‘marks the end of friendly generational relations.’†Jennings, delighted, said, “I get to say it to Alex! What is ‘OK Boomer’?†to which Trebek smiled and said, “thank you.â€
It is no surprise that Jennings won the night for viral moments. Who could forget his brilliant answer to this question on the “Tool Time†category in 2004?
And Jennings did not just win the night on Twitter. He also won the round of the tournament, beating out fellow GOATs James Holzhauer and Brad Rutter. Now that he has won two games, Jennings stands to win the whole thing if he could score a third victory on January 14. After the broadcast, Holzhauer tweeted, “My wife is going to make me roleplay as @KenJennings tonight,†and Jennings’s response, well … let’s just say if he pulled a joke like this on Jeopardy! Trebek would probably give him a stern talking-to.