Winona Ryder and Jon Stewart in The Larry Sanders Show (1992)

Jon Stewart and Austan Goolsbee in The Daily Show (1996)

Sigourney Weaver and Jon Stewart in The Daily Show (1996)

Joseph Gordon-Levitt and Jon Stewart in The Daily Show (1996)

Jon Stewart, Trevor Noah, and Kenny Specht in The Daily Show (1996)

Jon Stewart, The Kid Mero, and Desus Nice in It Be Your Own Mans (2020)

Jon Stewart and Don Dahler in The Daily Show (1996)

Jon Stewart in Saturday Night Live (1975)

Jon Stewart and Mitch McConnell in The Daily Show (1996)

Jon Stewart and Marcus Goddard in Batman v Superman: Dawn of Justice (2016)

Conan O'Brien and Jon Stewart in Conan (2010)

Jon Stewart in The 43rd Annual Grammy Awards (2001)

Elijah Wood and Jon Stewart in The Faculty (1998)

Denis Leary and Jon Stewart in The Daily Show (1996)

Drew Barrymore, Jennifer Beals, James Le Gros, and Jon Stewart in Wishful Thinking (1997)

Gillian Anderson, Sean Connery, Ryan Phillippe, Madeleine Stowe, Angelina Jolie, Gena Rowlands, and Jon Stewart in Playing by Heart (1998)

Stephen Colbert, Jon Stewart, and Samantha Bee in The Daily Show (1996)