It’s not every day that your morning school run turns into a late-night television bit — but that’s exactly what happened to Jimmy Kimmel’s children, Jane and Billy, this week when they unexpectedly picked up a very unusual “hitchhiker.”

Back in October, Kimmel and his wife, Molly McNearney, orchestrated a heartwarming surprise for their kids by picking up pop sensation Olivia Rodrigo on the way to school. That moment, immortalized on Jimmy Kimmel Live!, became a cherished family story.

This time, however, Kimmel decided to pull off the prank again — only with a twist. Instead of another chart-topping teen idol, they “rescued” a man their children had never heard of: comedy legend and Daily Show host Jon Stewart.

“They love Olivia Rodrigo,” Kimmel explained on the show. “This time… my kids have no idea who this person is. But they do now.”

A Surprised and Confused Carpool

In a clip shown to the Jimmy Kimmel Live! audience, the family is seen driving along when Stewart appears on the roadside. With mock hesitation, Kimmel’s kids agree to pick him up. The comedian clumsily squeezes into the car, joking about the tight fit, before asking where they’re headed.

“What’s so funny?” Stewart asked as Jane and Billy giggled. “Do you guys know who this is?” Kimmel teased — only to reveal the truth later.

Stewart gamely tried to win them over by claiming, “I’m in a band,” and even offering to play some of his “songs” on Kimmel’s phone. Soon, the car was filled with the sound of music — and confused laughter.

From Raisins to Nerds

When Stewart finally introduced himself, he did it with a dose of self-deprecating humor.
“My name is Jon Stewart… but I only work on Mondays because I’m very old,” he said, explaining that aging turns you from “a grape into a raisin.”

The conversation soon drifted into hilarious territory — from lunchbox inspections (“You put Nerds in their lunch? That’s like putting cocaine in their lunch!”) to Stewart joking about “diarrhea factories” and Kimmel’s love for Arby’s.

At one point, Stewart praised Jane as “the nicest person I’ve ever met,” even offering to hire her to “taunt my enemies.”

An Awkward Olivia Rodrigo Finale

Before Stewart hopped out, Kimmel suggested they listen to one Olivia Rodrigo track “for old time’s sake.” Stewart played along — awkwardly filling in “bad words” when needed — before finally exiting the car.

As the kids waved goodbye, Kimmel asked, “Who was that?” to which they honestly replied, “I have no idea.”

From School Runs to Studio Laughs

Back in the Jimmy Kimmel Live! studio, Kimmel introduced Stewart to the audience properly, along with other guests Mike Birbiglia, Trenny, and musical guest Incubus.

It was a perfect blend of family fun, celebrity comedy, and just the right amount of absurdity — proof that sometimes the best late-night moments happen far from the desk, right in the family minivan.