Olivia Rodrigo Surprises Jimmy Kimmel's Kids On The Way To School

25 Oct 2023

Picking up a hitchhiker is a bad idea, right? Well, maybe not in this case.

The Oct. 24 episode of “Jimmy Kimmel Live!” featured the host and his wife, Molly McNearney, picking up pop sensation Olivia Rodrigo while taking their kids, Billy, 6, and Jane, 9, to school.

Olivia Rodrigo - Figure 1
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“They listen to the music every morning on the way to school, so we thought it’d be fun to surprise them by picking up a very special home-schooled hitchhiker this morning on their way to class,” Kimmel said while introducing the segment.

They spotted her thumbing a ride while driving, and Kimmel says they should pick her up.

“Oh, my God, Billy! That’s Olivia Rodrigo,” Jane says.

A bubbly Rodrigo opens the door and hops in the back seat, asking if she can get a ride, while Jane remains completely stunned by what’s happening.

Rodrigo (center) sings along with a very excited Jane (right), while Billy looks on.YouTube

“I’m Olivia. Do you guys mind if I hitch a ride to school with you guys?” she asks.

Olivia Rodrigo - Figure 2
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“Oh, my God!” Jane says, while keeping her hands over her mouth in disbelief.

Kimmel tells the singer his family listens to her music on the way to school “all the time,” and Jane finally gets in on the conversation when she shares that “Ballad of a Homeschooled Girl” is her favorite song.

Billy is pretty fired up to have a pop star in the car on the way to school.YouTube

Billy, meanwhile, gives an enthusiastic thumbs-up when his dad asks what he thinks of the situation and adds he loves her song “Get Him Back!”

“He wants to get him back for you,” McNearney tells Rodrigo.

Olivia Rodrigo - Figure 3
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“Aw, thanks, Billy!” Rodrigo responds.

“And then what do you want to do when you get him back?” McNearney continues.

“Punch him in the penis,” Billy says, drawing huge laughs.

Billy's plan to "get him back" is kind of aggressive.YouTube

“Am I a bad influence on your children? I’m sorry,” Rodrigo says.

Rodrigo and Jane then sing along to “Ballad of a Homeschooled Girl” before Billy joins them on “Get Him Back!”

Kimmel says Rodrigo sings about kissing, and the kids love when he and McNearney kiss. They smooch, and the kids are grossed out.

“I do this every time,” Jane says, while pretending to vomit. Her parents kiss again, prompting another strong reaction.

Olivia Rodrigo - Figure 4
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Rodrigo bonds with Jane.YouTube

As they arrive at school, the kids hug Rodrigo.

“Have a great day! It’s all downhill from here,” McNearney says.

After the kids get out, Kimmel reminds Rodrigo it’s not safe to hitchhike, and he hopes she doesn’t do it again.

“I’m sorry. I just — I don’t have my driver’s license,” she says, referring to her mammoth 2021 hit “Drivers License.”

It was a ride to school unlike any other with Rodrigo (center) getting to know Jimmy Kimmel and Molly McNearney's kids.YouTube

“I thought you got it last week,” Kimmel says, a nod to a lyric in the song.

“I made it up,” she replies.

Olivia Rodrigo - Figure 5
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“This isn’t 'Carpool Karaoke,'” she says, referencing the famous bit James Corden used to do on his “Late Late Show.”

“Oh, no, we’re going to get sued,” Kimmel jokes before Rodrigo hops out of the car as the bit ends.

Drew Weisholtz

Drew Weisholtz is a reporter for TODAY Digital, focusing on pop culture, nostalgia and trending stories. He has seen every episode of “Saved by the Bell” at least 50 times, longs to perfect the crane kick from “The Karate Kid” and performs stand-up comedy, while also cheering on the New York Yankees and New York Giants. A graduate of Rutgers University, he is the married father of two kids who believe he is ridiculous.

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