Ken Jennings Makes Surprising Comments About ‘Drag Race’ & Taylor Swift

(left) RuPaul on 'Drag Race,' (middle) Ken Jennings on 'Jeopardy!, (right) Taylor Swift at an award show 2025
Jeopardy! Inc./Getty Images/Paramount+

What do Ken Jennings, Taylor Swift, and RuPaul’s Drag Race have in common? Not much, but the Jeopardy! host talked about them in a new video.

In an Instagram Q&A for the new Jeopardy! YouTube spinoff, which premieres on March 31, Jennings answered surprising questions on March 29. YouTube stars Rebecca Black, Brennan Mulligan, and Monet X Change are all competing on the premiere.

With Monet being a prominent Drag Race contestant, Ken Jennings was asked which he thinks is harder — Jeopardy! or Drag Race. “Well, on Jeopardy!, you can dress more comfortably. But, of course, the hardest thing would be to be in your drag persona and to go on YouTube Jeopardy!.

After fans saw his knowledge of the drag community, they begged him to host the show. “Ken Jennings guest judge on Drag Race when?? 💃💅,” a fan asked.

“Need this so bad tbh,” another replied.

“I never realized my life’s dream until now,” a third replied.

“I would cryyyy omg,” another said.

“NEED A DRAG RACE CROSS OVER IMMEDIATELY!!!!!!” a fan commented.

 

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“@rupaulsdragrace can you please get Ken on as a guest judge ASAP,” one last fan said. Others begged for Drag Race contestants to be on the game show.

Taylor Swift is no stranger to the drag community. She had drag queens in her 2019 music video for “You Need To Calm Down,” about acceptance of the LGBTQ+ community. There are also drag brunches, where the pop star is impersonated.

The next question shocked some fans. Jennings was asked, “If you could go on tour with any pop star, who would it be?” The host said that he has wanted only one thing his whole life — to be friends with Taylor Swift. “I think maybe just by putting it out there right now, I’m manifesting it,” he said.

“And here I always thought KJ was an Olivia Rodrigo kinda guy,” one fan said.

“I was shocked his response was TS,” another replied.

“I KNEW HE WAS A SWIFTIE,” a third commented.

“We need this friendship to happen. ✨manifesting✨,” another wrote. Other fans tagged the pop star and asked her to put Jennings in a music video. In 2023, Jennings shared on Jeopardy! that he failed to get tickets to Swift’s The Eras Tour.

He then shared that he falls on the Lawful Neutral side of the Dungeons and Dragons system scale. “But, a Jeopardy! host should be Lawful Good,” Jennings shared. “I’m pretending to be Lawful Good on TV every night.”

About the spinoff, he was asked if watching YouTube helps prepare for the show. “Jeopardy! rewards curiosity. A diverse expression of curiosity is what YouTube is very good at,” he said.

The final question was whether there was anything Jennings watches on YouTube that would surprise people. He shared that because he is middle-aged, he used the platform to watch shows he missed because he is “too sleepy” to watch them when they air.

Were you shocked at Jennings’ responses? Let us know in the comments.

Jeopardy!, Weekdays, check local listings, stream next day on Hulu and Peacock

Jeopardy! YouTube Edition, starting March 31, 9ET/6PT, YouTube