It was confirmed in July that Jennings and Mayim Bialik—who shared Jeopardy! hosting duties throughout most of Season 38—had signed contracts to solidify their roles, bringing an end to a long-running side-plot in the show’s story.

The announcement came after a revolving door of celebrities tried out to become the syndicated quiz show’s new presenter throughout much of Season 37, following the November 2020 death of beloved host Alex Trebek.

With Jennings going from all-time Jeopardy! champ to official host, fans of the show dug up a video of his appearance on CBS’ the Late Show with David Letterman back in 2004, during which he shared 10 ways to irritate Trebek.

Before Jennings stepped out into the studio to take part in the show’s popular countdown segment, Letterman listed the budding TV star’s stats, stating that he had clocked up 29 consecutive Jeopardy! wins and earned more than $900,000.

A youthful Jennings then read out a list officially titled: “Top Ten Ways to Irritate Alex Trebek.”

Raising laughs from the audience, Jennings shared a list that read as follows:

10: Ask him on air, ‘So who did your Botox?’ 9. Instead of responding, get his attention by throwing nickels at his hand. 8. Buzz in without using your hands. 7. Give Courtney Love directions to his house. 6. Whenever he says the word “potpourri,” you mumble, “woman.” 5. Tell him he is no Wink Martindale. 4. Remind him that although he’s a naturalized citizen, he’ll always be a product of the evil Canadian empire. 3. Complain that he’s not nearly as Trebek-y in person. 2. You’re only response: ‘Who gives a rat’s ass?’ 1. Insist on buying a vowel.

On Monday, a YouTube clip of the segment was shared on a Reddit Jeopardy! fan page, where members showered Jennings with praise for his smooth delivery.

“Ken is so fantastic,” wrote one fan. “His voice and mannerisms have changed quite a bit from 2004 to now.”

“Shows he was a natural at delivering a great one-liner even before he stepped into the hosting role,” said another in response.

“I’m sure Ken wouldn’t agree with me but I would call him a comedian” opined another. “After reading [Jennings’ book] Planet Funny you can tell he’s been a student of comedy for his entire life… but more importantly, he’s just naturally funny.”

One fan gave a nod to how successful Jennings went on to be during his Jeopardy! stint, securing 74 consecutive wins—the show’s longest win streak—and a $2,520,700 cash prize. To date, he remains the most successful regular season play contestant of all time.

In an apparent reference to the fact that the show is regularly recorded weeks in advance, the fan commented: “Ken had that sly smile as Dave was reading his winning streak and money and I’m sure thinking ‘I’m way past that now dude!’”

Jennings paid tribute to Trebek in late July, after his new role at Jeopardy! had been confirmed by the popular show’s producers.

A message from the verified Jeopardy! Twitter account read that the team “couldn’t be more thrilled” to welcome Jennings and Bialik as co-hosts, prompting Jennings to respond: “It’s official! There is white smoke over Culver City. @missmayim and I are your Jeopardy! hosts next season.

“Jeopardy! has been a big part of my life since I was a kid, and I take the show and its legacy very seriously,” added Jennings. “It’s been a singular honor to be associated with the talented staff and crew there for the past 18 (!) years.”

He then turned his attention to Trebek, who famously helmed the long-running show for 37 seasons from 1984 until he passed away.

“I’m not a professional broadcaster, obviously,” Jennings wrote. “I still get nerves out there every single show. But I was lucky enough to watch Alex host Jeopardy! for decades—about as well as the job could possibly be done. I hope a drop of that Trebekian perfection slips through sometimes.”