Jon Stewart has no qualms about naming names when it comes to his least favorite “Daily Show” interviews. In a new episode of “After the Cut” released on “The Daily Show’s” YouTube channel Thursday morning, Stewart not only named names, but also explained why.
“After the Cut” is a web exclusive in which the hosts of “The Daily Show” take questions from the audience. In this particular episode, an audience member wanted to know who Stewart’s favorite and least favorite interviews have been over the years. And the host had his answer very much at the ready.
“Rumsfeld comes to mind. Donald Rumsfeld, at the time. was the architect of the Iraq War,” he revealed. “Judith Miller comes to mind, who was the New York Times reporter that they fed stories to that helped gin up that. People that were architects of that war that I had to interview.”
Stewart then circled back to Rumsfeld in particular, recalling how he stayed up extra late the night before the interview, reading Rumsfeld’s book and setting a perfect “logic trap” for the man. But, when the time came, Stewart got a bit derailed.
“I was going to win the interview,” Stewart recalled. “And, like, one minute into it, I’m like, ‘You know, when you guys were selling the war,’ and he’s like, ‘Well, making the case.’ And I go, ‘selling.’ ‘Making the case.’ ‘Well, you only told the good parts, so that’s selling, not making the case.’”
“And I, stupidly, was like, oh wait, no, that’s not my opening. Let me go into my trap, but the truth is, that whole interview lived in the space between selling and making a case,” he continued.
Stewart admitted that he was “so in my head” about the interview that it didn’t feel like a good interaction in the end, “and it tortured.”
“Like literally, couldn’t sleep,” he said. “And I realized — this is when it gets ugly sometimes, when you think about, like, impactful moments — I lost more sleep over that interview than he lost over the entire war. That’s who I was dealing with.”
Stewart added that Rumsfeld then twisted the knife by sending him a note afterward saying he really enjoyed the interview.
You can watch Jon Stewart’s full answer in the video above.
