Jon Stewart has named the guest he enjoyed interviewing least across his long run on The Daily Show.
Stewart, 63, did not hesitate before pointing to Donald Rumsfeld, the former secretary of defense who served under President George W. Bush.
Rumsfeld appeared on The Daily Show in February 2011.
‘He was the architect of the Iraq War at the time,’ Stewart recalled during an unaired exchange with an audience member released by the show’s producers on Wednesday.
Stewart said he prepared intensely for the conversation after reading Rumsfeld’s 2011 political memoir, Known and Unknown. ‘[H]e wrote a book about it, and I stayed up, like I was cramming for an exam,’ he said.
‘I dog-leafed it, used my highlighter, all the things,’ Stewart added. ‘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.’
But the plan unraveled once Rumsfeld was in the chair, Stewart admitted, saying he became too caught up ‘in [his] head’ for the strategy to land.
Jon Stewart, 63, was asked who his least favorite guest in Daily Show history is in a new, behind the scenes clip
An audience member asked who had earned the distinction during the show’s 17 years on the air
He remembered how, about one minute in, he let Rumsfeld say he helped ‘make the case’ for the war rather than ‘sold’ it – phrasing Stewart used in his question.
The correction, he said, threw him for a loop.
‘I let that opening slip,’ Stewart recalled. ‘[A]nd I did not, to my feeling, have a satisfying encounter with him [afterwards].
‘And it tortured me. Like, literally couldn’t sleep.’
‘I realized, “this is when it gets ugly sometimes,” when you think about, like, impactful moments,’ Stewart said.
‘I lost more sleep over that interview than he lost over the entire war.
‘That’s who I was dealing with,’ the early Iraq War critic complained.
Rumsfeld died at 88 in 2021. He was remembered by former President Bush as a foreign policy luminary who ‘never paled before tough decisions, and never flinched from responsibility.’
Stewart sat with Donald Rumsfeld for a Daily Show interview in February 2011 – an occasion he said still haunts him to this day
Stewart glossed over the late Republican’s calls to invade Iraq over nonexistent weapons of mass destruction. Rumsfeld – who died at 88 in 2021 – appeared on The Late Show in January 2016 as well
Rumsfeld – a one-time presidential candidate – also played a prominent role in Bush’s decision to invade Afghanistan to hunt down Al-Qaeda.
The US launched a war against Iraq in 2003. No weapons of mass destruction were found, contrary to claims from politicians like Rumsfeld at the time.
Stewart, meanwhile, recently claimed he went easy on Democratic Senator John Fetterman during their interview this week.
‘I think it’s because in the conversation, I did get to a place where I felt bad,’ he said, citing the increasingly conservative senator’s 2022 stroke.
‘I know he’s a senator, I shouldn’t. There’s no amount of having that, you know – but having diminished ability, but having power not be diminished, that’s a scary place for people to be.’
