What To Know
- Jon Stewart revealed that his least favorite guest on The Daily Show was former Secretary of Defense Donald Rumsfeld, due to Rumsfeld’s role in the Iraq War.
- Stewart admitted he lost sleep over the interview, feeling he failed to effectively challenge Rumsfeld despite extensive preparation.
Jon Stewart is not holding back. The Daily Show host revealed his least favorite guest that he had on his talk show and why he lost sleep over them.
During a fan Q&A, an audience member asked him who his favorite and least favorite guests were. The clip was posted to Instagram on August 13.
The late-night talk show host started out with the negative. He said Donald Rumsfeld “came to mind” when thinking of his least favorite, adding, “He was the architect of the Iraq War at the time.”
“Judith Miller comes to mind, who was the New York Times reporter that they fed stories to that they helped gin up. People that were architects of that war that I had to interview because, in Rumsfeld’s case, he wrote a book about it, and I stayed up, like I was cramming for an exam. I dog-leafed it, used my highlighter, all the things,” he said.
“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,” he continued.
“That whole interview lived in between the trap of selling and making a case,” he 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 shared. “That’s who I was dealing with.”
Stewart told the audience that Rumsfeld sent him a nice note afterwards. It read, “Jon, really enjoyed the interview. I wish I had known you when we were younger. I bet we would have been friends.’”
He did not reveal who his favorite guest was in the clip. Rumsfeld, who died in 2021, was on The Daily Show in February 2011, according to IMDb. He was the United States Secretary of Defense from 2001 to 2006.
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