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

Jessica Williams is thankful to her "first real boss": Jon Stewart at The Daily Show.

The Daily Show alum, 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."

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 to The Daily Show twice this year. She made appearances alongside Stewart, who returned to host the show once a week in February 2024 following Trevor Noah's departure in 2022. Most recently, Williams reunited with her former boss the week before the 2024 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.”

The Shrinking actress explains that she feels “really lucky” to be “a working actor on a show and still be able to do Daily Show correspondent 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.”

Williams explains that because "The Daily Show came first," she was able to learn about timing, rhythm, rewriting and rephrasing jokes.

“There's no Gaby without The Daily Show at all,” she says of her role in the AppleTV+ sitcom Shrinking, for which she was nominated for an 2023 Emmy.

Williams stars alongside Jason Segel, Harrison Ford, Michael Urie, Ted McGinley and 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.

Though The Daily Show gave 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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New episodes of Shrinking season 2 are released on Wednesdays on AppleTV+.