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

Jessica Williams expresses gratitude towards her "first real boss," Jon Stewart, known for his work on The Daily Show. She highlights his kindness during her initial steps in the entertainment industry. At just 22 years old, while attending Cal State Long Beach, she auditioned for the show on Comedy Central.

Reflecting on her early career, Williams served as a senior correspondent on "The Daily Show" from 2012 to 2016. She recalls how Stewart was genuinely "present" with her during those formative years. Beyond mastering critical comedy skills, his approach greatly inspired her: "I wanted to be a kind boss like him," Williams revealed. She observed how he consistently maintained his values as a performer.

According to Williams, Stewart understood the importance of balancing work and family life. He prioritized time for his family, which had a lasting impact on her perspective. "He really influenced and imprinted me in that way," she stated, recognizing this effect upon her return to the show.

This year, Williams made two appearances on The Daily Show, reuniting with Stewart. He returned as host each week in February 2024 after Trevor Noah's departure in 2022. She reflected on their reunion ahead of the 2024 presidential election, describing it as "coming home to my little family."

Williams mentioned that the production team even offered her a calendar to assist in planning future guest spots, expressing her joy at collaborating with Stewart again. "It's a joy, and it's wonderful to do stuff with him," she said.

The actress emphasized how fortunate she feels to be a working actor while still participating in The Daily Show segments. "I'm just so grateful to be able to go back," she commented, acknowledging her appreciation for Jon and the rest of the team.

Williams attributes much of her learning experience to her time on The Daily Show, detailing how she honed timing, rhythm, and the art of joke crafting. She stated, "There's no Gaby without The Daily Show at all," referencing her role in the AppleTV+ sitcom, Shrinking, where she was nominated for a 2023 Emmy.

In Shrinking, Williams stars alongside Jason Segel, Harrison Ford, Michael Urie, Ted McGinley, and Christa Miller. Segel portrays Jimmy Laird, a widowed single father navigating life challenges while raising his teenager. Though her career started with The Daily Show, acting with Segel grants her "permission... to be free."

She elaborated on the creative dynamics they share, stating, "I can be as physical if I want to... I can be louder, and he's just always game." Williams appreciates how Segel continuously listens and matches her energy in performances.

New episodes of Shrinking season 2 are available on Wednesdays on AppleTV+.

Earlier, SSP wrote that Taylor Swift expressed gratitude for TTPD support and Grammy nominations.