Jon Stewart revealed his least favorite guest he’s had on The Daily Show in his 17 years behind the desk.
Stewart, 63, interviewed Donald Rumsfeld, the Secretary of Defense under George W. Bush, in 2011. Stewart was an early critic of Bush and the war in Iraq, for which Rumsfeld served as chief architect. Rumsfeld, who died at 88 in 2021, was promoting his political memoir, Known and Unknown, and Stewart hoped to hold him accountable.
“He wrote a book about [Iraq], and I stayed up—I’m telling you, man, talk about cramming for an exam—like, read through that book, dog-leafed it, highlighter, did all the things,” Stewart said in a behind-the-scenes clip from The Daily Show. “I worked out a logic trap that was a labyrinth, and I was going to draw him into my trap, and then I was going to spring it. I was going to win the Iraq War. I was going to win the interview.”
Stewart began the interview with a joke: “I think I know why you’re here. And let me just deflate the tension right off the bat: Apology accepted.” Rumsfeld laughed and didn’t apologize, and the interview turned toward the subject of Iraq.
During the interview, Stewart told Rumsfeld, “You guys were selling the war,” and Rumsfeld attempted to correct his wording, replacing “selling” with “making the case.” Stewart said this threw off his opening and sent the interview veering off course.
“The truth is, that whole interview lived in the space between ‘selling’ and ‘making a case,’” Stewart said. “That’s where the whole thing was. But I was so in my head that I let that opening slip, and I did not, to my feeling, have a satisfying encounter with him. And it tortured me. Like, literally couldn’t sleep.”
“I lost more sleep over that interview than he lost over the entire war,” Stewart continued. “That’s who I was dealing with.”
Stewart went on to lament Rumsfeld’s petty move after their tense interview. The “motherf---er” sent Stewart a slimy note, the contents of which Stewart said were like twisting “the knife.”
“He knew what I was trying,” Stewart said before sharing what Rumsfeld wrote. “He sends me a note afterwards and he goes, ‘Jon, really enjoyed the interview. I wish I had known you when we were younger. I bet we would have been friends.’”
