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

Jessica Williams is grateful to her “first real boss”: Jon Stewart Daily show.

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

Looking back on those days, Williams, who was a senior correspondent on the show from 2012 to 2016, says Stewart was “there” with her from the start.

Along with learning key comedic skills, Williams also drew deeper inspiration from Stewart: “I wanted to be a kind boss like him,” she says. “I just have to look at him as a performer who sticks to his values.”

Jessica Williams and Jon Stewary on April 28, 2012 in New York City.

Theo Wargo/Getty

Williams adds that Stewart knew the importance of prioritizing time to “raise a family.”

“He really influenced and left an impression on me in that way. And I realized that when I returned to the show,” she notes.

Williams returned to The Daily show twice this year. She appeared alongside Stewart, who returned to host the show once a week in February 2024 following the departure of Trevor Noah in 2022. Williams recently reunited with her former boss a week before the 2024 presidential election.

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

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

The Shrinkage the actress explains that she feels “really lucky” to “be a working actress on the show and still be able to work Daily show correspondence bits.”

“I’m very grateful to be able to come back, and I’m grateful for the other people who work 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

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Williams explains this because “Daily show was the first”, she managed to learn about time, rhythm, rewriting and reformulating jokes.

“There is no Gaby without Daily show at all,” she says of her role on the AppleTV+ sitcom Shrinkagefor which she was nominated for an Emmy in 2023.

Williams stars alongside Jason Segel, Harrison Ford, Michael Urie, Ted McGinley and Christa Miller in the sitcom. Segel stars as Jimmy Laird, a single father grieving the sudden loss of his wife, raising his teenage daughter and maintaining his friendships.

Jason Segel and Jessica Williams in “Downsizing.”

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Still Daily show gave her a start, she says that acting with Segel gives her “permission … to be free.”

“I can be physical if I want to be. I can’t be. They can be more subtle. I could be louder and he is always in a good mood and ready to meet me wherever I am. And vice versa,” she says, adding that he’s “always listening and ready.”

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New episodes Shrinkage season 2 airs Wednesdays on AppleTV+.

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Source: HIS Education