Jon Stewart, former host of "The Daily Show," has identified his least favorite guest, describing a particularly difficult 2011 interview with then-Defense Secretary Donald Rumsfeld that he said left him deeply disturbed.

Stewart recounted the interview, conducted to promote Rumsfeld's memoir, on a recent segment. He explained that he had meticulously prepared for the encounter, devising what he called a "logic trap" designed to challenge Rumsfeld's justifications for the 2003 invasion of Iraq. Stewart had studied Rumsfeld's book intensely, aiming to "win the interview."

However, the conversation took an unexpected turn within the first minute. Stewart began by referring to the administration's actions as "selling the war," but Rumsfeld interjected, insisting the term should be "making the case." This linguistic debate, Stewart realized, sidetracked his intended line of questioning.

"That whole interview lived in the space between ‘selling’ and ‘making a case,’" Stewart stated. "That’s where the whole fucking 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."

Stewart described the experience as torturous, stating he lost more sleep over the interview than Rumsfeld reportedly did over the Iraq War itself. The situation was compounded when Rumsfeld, after the show, sent Stewart a note. Stewart mimicked a stabbing motion as he described Rumsfeld writing, "Jon, really enjoyed the interview. I wish I had known you when we were younger. I bet we would have been friends."

Stewart has previously spoken about this interview, calling it "shitty" in 2015. However, he also acknowledged the relative insignificance of his personal regret compared to Rumsfeld's role in the war's repercussions.

Rumsfeld, a key architect of President George W. Bush's foreign policy, died in 2021 at the age of 88. Judith Miller, a former New York Times reporter who also faced scrutiny for her reporting on Iraq, was mentioned by Stewart as another difficult guest whose presence foreshadowed the war.