The Wait Wait 2026 summer spectacular, part 2!

This episode of Wait Wait… Don’t Tell Me! features a compilation of memorable segments from earlier in the year, including interviews with Ken Jennings, Olivia Munn, Father James Martin, and Bobby Lopez. The hosts, Peter Sagal and Bill Curtis, along with panelists Alonzo Bodden, Negin Farsad, Paula Poundstone, and Luke Burbank, revisit some of the most entertaining and insightful moments.

Ken Jennings on Jeopardy! and H&R Block

Peter Sagal welcomes Ken Jennings, the legendary Jeopardy! champion and now host, to the show. Sagal asks Jennings about his experience transitioning from contestant to host, and whether he agrees with Alex Trebek's assertion that it's the “hardest job in show business.” Jennings emphatically agrees, noting that many experienced broadcasters who guest-hosted after Trebek’s passing were surprised by the show's fast pace. “This game moves really fast,” Jennings recalls them saying.

Sagal then inquires about the existence of Jeopardy! host training. Jennings reveals that there is indeed a “Jeopardy! boot camp” where writers impersonate contestants. Initially, they act as well-behaved contestants, but as the difficulty increases, they portray “unruly and disobedient” contestants to prepare the host for challenging situations. These simulations include contestants stopping mid-response, correcting answers late, or calling out categories without prompting. Jennings admits he was made for this role, having spent his life trying to get out of conversations with people after 20 seconds.

Sagal brings up Jennings’ famous Jeopardy! loss, which ended his 74-game winning streak with a question about H&R Block. Jennings confirms that he ran out of interesting anecdotes about himself very early on in his run, resorting to making up stories. He jokingly adds that nobody fact-checks these stories, suggesting that if you claim to be a birthday clown, they won't look it up.

The segment culminates in a game where Jennings is asked three questions about H&R Block. He correctly answers that H&R Block’s surprising source of revenue is owning the copyright for GIFs, having acquired CompuServe, which patented the GIF format. He also correctly identifies that H&R Block got into trouble in 2005 for making significant errors when filing their own corporate tax returns.