Jon Stewart has encountered a number of figures throughout his time with The Daily Show. Recently, he opened up about one interview that ended up really taking its toll on him. However, Stewart’s story ended on a surprisingly positive note.
Jon Stewart First Became Part Of The Daily Show In 1999
Stewart is a comedian, commentator, actor, and media personality. From 1999 to 2015, he became known for hosting The Daily Show for Comedy Central.
Stewart would return to hosting the series part-time in 2024. In addition, he also hosted The Problem with Jon Stewart for Apple TV+ from 2021 to 2023.
Having been part of the show for years, Stewart has encountered a number of guests. During a recent fan Q&A, he was recently asked who was his favorite and least favorite of these guests.
For his part, Stewart didn’t divulge who his favorite guest was. However, he shared another guest who put some strain on him, especially as he prepared for the interview.
Stewart shared that Donald Rumsfeld, who served as the United States Secretary of Defense from 2001 to 2006, “came to mind” when thinking of his least favorite. As he noted, “He was the architect of the Iraq War at the time.”
Stewart continued, “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.”
Despite The Stress, Stewart Noted That Rumsfeld Actually Gave Him A Nice Note After The Fact
Preparing for the interview, Stewart shared, “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.”
However, things still proved to be challenging. Stewart shared, “That whole interview lived in between the trap of selling and making a case. 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.” He continued, “I lost more sleep over that interview than he lost over the entire war. That’s who I was dealing with.”
Despite this, Stewart shared that Rumsfeld actually sent him a nice note after the interview, which took place in early 2011. Stewart noted that it read, “’Jon, really enjoyed the interview. I wish I had known you when we were younger. I bet we would have been friends.’”
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John Witiw has been a writer since at least 2015. He’s covered a variety of topics, especially when it comes to film and television.