We make Ken Jennings relive the worst moment of his life
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In this episode of Wait Wait... Don't Tell Me!, host Peter Sagal welcomes back Ken Jennings, the legendary Jeopardy! champion and current host, for a humorous and nostalgic deep dive into his most infamous moment: losing his record-breaking streak to a question about H&R Block. The segment, titled 'What is H&R Block?', turns the tables as Jennings is quizzed on the tax firm’s history, surprising revenue streams, and a scandal involving their own tax filings. The episode also features lighthearted segments on absurd beach incidents—like a D-Day reenactment interrupting a yoga class and a swimmer accidentally modeling in a fashion show—alongside a 'Bluff the Listener' game and a 'Lightning Fill-in-the-Blank' round with rapid-fire trivia. The show balances satire with affection, celebrating pop culture absurdities while spotlighting Jennings’ resilience and humor in facing his personal trivia nemesis.
Ken Jennings, despite his Jeopardy! dominance, was famously defeated by a question about H&R Block—now a source of playful torment.
The show uses humor to explore real-world absurdities, from over-communicative restaurant texts to accidental fashion modeling.
A recurring theme is the irony of modern life: even elite institutions like Jeopardy! and D-Day reenactments can be disrupted by the unexpected.
The episode celebrates the joy of trivia, imperfection, and the shared human experience of awkward moments.
Ken Jennings’ self-deprecating humor and charm make him a perfect fit for the show’s blend of intelligence and levity.
Welcome to the Show and Listener Quiz
The episode opens with a promotional segment for Pop Culture Happy Hour, followed by the traditional Wait Wait... Don't Tell Me! intro. Host Peter Sagal welcomes listener Veronica Brooks-We, who plays the 'Who's Bill' game with three news-related quotes, including a cruise passenger’s ironic text from quarantine, Trump’s plan to paint the reflecting pool blue, and the New York Times’ announcement of a Wordle TV show.
Bluff the Listener: Beach Chaos
“A swimmer goes to the beach in Australia and ends up in the middle of a fashion show.”
Ken Jennings Returns: The H&R Block Redemption
“After all these years I'm finally back to 500. But you know I think of them every time I drive past a strip mall. You see that little green square?”
Celebrity Jeopardy and Modern Dating Advice
The panel discusses Celebrity Jeopardy, arguing that celebrities are more skilled than commonly assumed. They also explore the controversial advice to discuss prenups on the third date, and the annoyance of restaurants sending endless text confirmations and check-ins.
Limericks and Lightning Fill-in-the-Blank
The episode concludes with a limerick challenge involving a stinky molten planet and dating in running clubs, followed by a fast-paced 'Lightning Fill-in-the-Blank' round. The panel competes on topics ranging from international politics to bizarre tourist mishaps, with Tom Bodette emerging as the winner.
“After all these years I'm finally back to 500. But you know I think of them every time I drive past a strip mall. You see that little green square?”
“The ocean is full of sulfur, meaning that the planet is just an enormous rotten egg laid by a galactic chicken.”
“If you believe in a god, in an original creator, then that creator dealt it. True, that's true. God's whoopee cushion right out there.”
Host
Guest
Ken Jennings
person
Peter Sagal
person
Jeopardy!
media
Joyelle Nicole Johnson
person
H&R Block
organization
Tom Bodette
person
Faith Saley
person
NPR
organization
Wordle
media
Studebaker Theater
other
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