If Bruce Springsteen is in the house, there’s a good chance Jon Stewart isn’t far behind. Stewart crashed Jimmy Kimmel‘s fourth night of shows in Brooklyn by biking through the audience mid-monologue—with Guillermo’s Grubhub order in hand.
“What is happening here? Why are you delivering food?” Kimmel asked, after recognizing Stewart.
“I’m delivering food,” Stewart deadpanned. “On Thursdays I deliver for Grubhub… among other things. I’ve got some side hustles.” He then launched into a full breakdown of his week: Mondays, he said, he hosts The Daily Show. Tuesdays, he’s a manny. Wednesdays, he’s hawking “those nuts in the cart that smell so [bleep] good.” Thursdays, he’s on Grubhub duty. And Fridays? “I am a New York City police horse.”
When Kimmel pressed him on why he needed so many jobs, Stewart leaned into the punchline. “In case you haven’t heard, late night talk show hosts—the job security is not really there right now.”
From there, the two fell easily into familiar rhythms, commiserating over the Mets’ eternal heartbreak before turning their attention to Guillermo’s creative pronunciation of the word “yenta” and the promise of Springsteen waiting in the wings. When Stewart asked if he could stick around for The Boss, Kimmel agreed—but only if Stewart swore not to get too handsy.
Finally, when Kimmel told Stewart he had to get back to his monologue, Stewart cut him off with a mock scolding: “I’m sorry, Mr. Free Speech. Free speech is only for Mr. Free Speech.”
It wasn’t Stewart’s first drop-in with Kimmel. In 2024, he memorably hitched a ride with Kimmel, his wife Molly McNearney, and their unsuspecting kids. Earlier this year, he popped up again, crashing a bit Kimmel was taping outside his studio on Hollywood Boulevard.
