By Mashable | Created at 2026-08-14 11:15:16 | Updated at 2026-08-14 13:48:38
4 hours ago
"Like literally, couldn't sleep."
By
Sam Haysom is the General Assignment Editor, UK, for Mashable. He covers entertainment and online culture, and writes horror fiction in his spare time.
on August 14, 2026
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."
Want more film and TV news and reviews delivered straight to your inbox? Sign up for Mashable’s Top Stories newsletter or get Mashable push alerts today.
Sam Haysom is the General Assignment Editor, UK, for Mashable. He covers entertainment and online culture, and writes horror fiction in his spare time.
These newsletters may contain advertising, deals, or affiliate links. By clicking Subscribe, you confirm you are 16+ and agree to our Terms of Use and Privacy Policy.
