Jeopardy! host Ken Jennings got to live out a lifelong dream on Tuesday night (July 1) when he was invited to sing “Take Me Out to the Ball Game” in the 7th inning of the Chicago Cubs v Cleveland Guardians game.

The beloved game show host appeared in the Cubs’ broadcast booth at Wrigley Field to lead the crowd in the iconic sing-along. Dressed in a Cubs jersey, Jennings took the microphone and belted out the words to the classic song, which was first released in 1908 by Jack Norworth and Albert Von Tilzer.

The sing-along has become a tradition in ballparks across North America, but the Cubs take it a step further by inviting celebrity guests to lead the proceedings. Previous guests to preside over the seventh-inning stretch include Michael J. Fox, Bill Murray, Eddie Vedder, Mr. T, Ozzy Osbourne, John Cusack, and more.

Jeopardy! fans took to social media to share their joy over Jennings’ appearance, though some were surprised to see a lifelong Seattle Mariners fan wearing a Cubs jersey.

#Jeopardy host @KenJennings conducts The Stretch on a beautiful night for baseball at Wrigley Field. @Cubs #GoCubsGo @Jeopardy pic.twitter.com/6vpqFrFUIh

— Billy Krumb (@ClubhouseCancer) July 2, 2025

“I was watching the game and as soon as he showed up, I lost my mind a bit,” wrote one fan on the Jeopardy! Reddit forum.

Another user pointed out how Jennings’ jersey was number “74,” a reference to his record-setting Jeopardy! winning streak. “I was listening to this one on the radio and it was a pleasant surprise! Jersey number 74 is a nice touch,” the fan stated.

Former Jeopardy! contestant Nick Coombs added, “Ken and I talked about baseball in the after-show discussion. He loves the game and I imagine that this was likely a bucket-list highlight for him. Great to see it!”

“I thought he was a Mariners fan!” said another. Jennings, who lives in Seattle, has previously shared photos of himself and his son enjoying a Mariners game.

Another responded, “He definitely is [a Mariners fan] but hey when the Cubs call you to do this I think you have to do it. At least they weren’t playing the Mariners…”

“What is Go Cubs? This guy is cool af!” added another.

One commenter quipped, “This will inevitably turn into a baseball category in which the contestants will go 0/5.”

“This was a pleasant surprise to see on my Reddit feed! The custom Cubs jersey with “Jennings 74” is amazing,” said another.

“Just witnessed ken Jennings sing take me out to the ballgame live in person I feel like a changed woman now,” wrote one X user.

Another added, “That version of Take Me Out to the Ballgame by Ken Jennings might be a top 5 performance this season!”

Jennings is currently on a summer break from shooting, but new episodes of Jeopardy! are still airing until July 25.