How Jessica Williams' 'First Real Boss' Jon Stewart Inspired Her: 'I Wanted to Be a Kind Boss Like Him' (Exclusive)

Mar. 15, 2025

Jon Stewart and Jessica Williams.Photo:John Nacion/Variety via Getty; Taylor Hill/FilmMagic

John Nacion/Variety via Getty; Taylor Hill/FilmMagic

Jessica Williamsis thankful to her “first real boss”:Jon StewartatThe Daily Show.

TheDaily Showalum, 35, tells PEOPLE that famed comedian Stewart, 61, was especially kind to her during her first entertainment job. Williams was 22 and still in college at Cal State Long Beach when she auditioned for the Comedy Central show.

Reflecting on those days, Williams, who served as a senior correspondent on the series from 2012 to 2016, says Stewart was “present” with her from the start.

Along with learning key comedy skills, Williams also drew deeper inspiration from Stewart: “I wanted to be a kind boss like him,” she says. “I got to just watch him be a performer who kept his values straight."

Jessica Williams and Jon Stewary on April 28, 2012 in New York City.Theo Wargo/Getty

Theo Wargo/Getty

Williams adds that Stewart knew the importance of prioritizing time to “go raise his family."

“He really influenced and imprinted me in that way. And I realized that when I went back to the show,” she notes.

Williams returned toTheDaily Showtwice this year. She made appearances alongside Stewart, whoreturned to host the showonce a week in February 2024 followingTrevor Noah’s departure in 2022. Most recently,Williams reunited with her former bossthe week before the2024 presidential election.

“It was really amazing. It was like coming home to, like, my little family,” she recalls.

Williams also reveals that the production team said they would send her a calendar in hopes of her making future appearances. “It’s a joy, and it’s wonderful to do stuff with him.”

TheShrinkingactress explains that she feels “really lucky” to be “a working actor on a show and still be able to doDaily Showcorrespondent bits.”

“I’m just so grateful to be able to go back, and I’m grateful for other people that work there and write there, and for Jon.”

Jordan Klepper, Jessica Williams and Hasan Minhaj on “The Daily Show with Jon Stewart"on August 6, 2015 in New York City.Brad Barket/Getty

Brad Barket/Getty

Williams explains that because “The Daily Showcame first,” she was able to learn about timing, rhythm, rewriting and rephrasing jokes.

Williams stars alongsideJason Segel,Harrison Ford,Michael Urie,Ted McGinleyand Christa Miller in the sitcom. Segel stars as Jimmy Laird, a single dad grieving the sudden loss of his wife, raising his teenage daughter and navigating his friendships.

ThoughThe Daily Showgave her her start, she says that acting with Segel gives her “permission… to be free.”

“I can be as physical if I want to. I can not be. I can be more subtle. I could be louder, and he’s just always game and ready to meet me wherever I’m at. And vice versa,” she says, adding he’s “always listening and ready.”

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source: people.com