Jon Stewart reveals his worst ever Daily Show interview guest

A man holding a microphone stands on a talk show stage. The caption at the bottom reads,

The Daily Show hosts sometimes take audience questions between segments, and Jon Stewart was posed a great one by a recent attendee: Who’s his least favourite interview guest?

The answer? Donald Rumsfeld, who was U.S. Secretary of Defense during the Iraq war. In the clip above, Stewart says he concocted a trap for Rumsfeld that he thought would allow him to “win the interview”, but then got so focused on it that he missed something he felt undermined his argument.

“I did not, to my feeling, have a satisfying encounter with him. And it tortured me. Like literally, couldn’t sleep,” says Stewart. “I lost more sleep over that interview than he lost over the entire war.”

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