The interview opens with Kamau welcoming Ken Jennings and reflecting on how they first met at a Seattle Bumbershoot festival through comedian Doug Benson's podcast. They bond over the classic era of Twitter, agreeing that their generation of Gen Xers had one social media platform they tolerated before it deteriorated.
Kamau shares his admiration for Jennings as a Jeopardy! host, recalling how smooth and natural Jennings appeared when Bell appeared on Celebrity Jeopardy!. The two discuss how Jeopardy! built itself around Trebek over decades, and Jennings admits he was skeptical the show would survive after Trebek's passing.
Jennings describes the difficult circumstances of stepping into the hosting role, explaining that he was originally scheduled to guest host while Trebek underwent cancer treatment, only to receive a call the morning he was due to rehearse informing him that Trebek had died overnight. Jennings felt compelled to continue because crew members told him he reminded them of Trebek.
The conversation turns to Jeopardy!'s cultural significance, its loyal multigenerational audience, and its role as a rare steady long-term job in show business. Jennings discusses his hosting philosophy of receding into the background, following Trebek's ethos that the show should be about the players and clues.
The interview then addresses Jennings speaking out politically on issues including immigration enforcement, trans rights, and reproductive rights, with Jennings framing this as a matter of personal conviction rooted in his Latter-day Saints upbringing. Donate to World Central Kitchen at and support Scarecrow Video at .
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Who's With Me is produced by Rabbit Grin Productions. Music by Chris Dowd.
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