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10 Most Devastating Jon Stewart Interviews


Jon Stewart is famous for interviewing everyone from Barack Obama to Miss Piggy on The Daily Show. He is best known for his brilliant mockery of American political trends, but politicians and businessmen expecting an easy ride from this comedian are often shocked by just how penetrating Stewart’s questions can be. Here are 10 of his most devastating interviews ever.

10. Paul Begala and Tucker Carlson, October 15 2004

Comedians from The Daily Show have a habit of being invited to places where they really shouldn’t be; Colbert’s appearance at the White House during the Bush administration is good evidence of that. Arguably Stewart’s most famous interview wasn’t part of his own show; it was his legendary 2004 appearance on CNN talk show Crossfire. Stewart arrived seething with pent-up rage at the entire news establishment and, without even attempting to play along with the show, proceeded to rip apart the entire format of Crossfire live on air, calling host Tucker Carlson a “dick” and accusing him and fellow host Paul Begala of being “partisan hacks” and “bad for America.” The audience could do nothing but laugh nervously and wonder if they’d wandered into an Andy Kaufman sketch. His appearance more or less single-handedly got the show pulled from the network, and it was off the air three months later.

9. President Barack Obama, October 27 2010

Probably the last thing the President of the US expected on the liberal-leaning Daily Show was a grilling. Still annoyed, perhaps, by accusations that he went easy on former Democrat presidential candidate John Kerry, Stewart proceeded to batter Obama in front of a delighted audience by calling his attempts at reform “timid” and accusing him of doing little more than papering over corruption in Washington in the name of pragmatism. He grilled him particularly strongly about his hiring of Larry Summers, saying: “I remember you said we can’t expect different results from the same people. When you hired Larry Summers, I remember thinking ‘that sounds like the exact same person.'” Obama kept his cool under questioning but conceded that “Yes we can” may have been a bad slogan for his administration and that “Yes we can but it’s not going to happen overnight” would have been better.

8. Christopher Wallace, June 19 2011


There have been many, but one of Stewart’s most memorable falling-outs with Fox News happened when he was interviewed by Chris Wallace on Fox News Sunday. Stewart came prepared and still full of cold anger towards mainstream news establishments; Wallace asked him on arrival at the studio, “How does it feel to be in the belly of the beast?” Stewart’s response: “This is the belly? I thought this was a slightly lower appendage here.” The level of dialogue didn’t rise much further, with Stewart accusing Wallace of being “insane” for referring to his parody of Sarah Palin’s bus tour as a political statement. He also described Fox viewers as being “the most consistently misinformed” when it came to the actual facts in the news.

7. Jim Cramer, March 12 2009

In 2008 Jim Cramer of CNBC’s Mad Money had some serious egg on his face after repeatedly recommending investors leave their money in Bear Stearns only a week before the entire company went under. His appearance on The Daily Show is a classic example of an interviewer annihilating his interviewee, with Cramer reduced to a sweating man-child after Stewart called him on knowing what the banks were doing but still touting the stocks for months beforehand. At least Cramer apologized… sort of: “The market was going up for a long time and our real sin was believing it would continue to go up a lot” in the face of borrowing and further shenanigans. In another clip played later in the show, however, Cramer admitted to creating activity to drive the futures of his hedge fund when he needed extra money. The way Stewart nails him both coming and going almost makes you feel sorry for Cramer.

6. Tony Blair, September 18 2008

George Bush Jr had understandably declined to appear on The Daily Show to talk about the Iraq war during his presidency, but in 2008 Stewart managed to get the next best thing – ex-UK Prime Minister and Bush’s main European teammate, Tony Blair. Now that his lucrative career as the bitch of American Imperialism was drying up, Blair was promoting his new course at Yale. Stewart proceeded to tear him a new one over supporting the invasion of Iraq, ending with this splendid tirade: “Our resources are not limitless; we cannot continue to go into other people’s countries, topple any regime we find distasteful and occupy that country. We need to be much smarter about the way we’re handling this.”

5. Bill Kristol, July 27 2009

Bill Kristol started the interview smooth, but his smile soon turned white and died when he came up against Stewart’s eagle eye for contradictions. The Fox neoconservative pundit began by arguing that the military deserved a better standard of health care than the average US citizen, and was then forced to admit that military health care was effectively public health care. “So you’re saying the government can run a first-class healthcare system and it’s better than the private system?” said Stewart, with the satisfaction of a bird of prey impaling a mouse with its talons. Kristol attempted to backtrack but was forced to nervously laugh it off. The statement was hailed as a major journalistic coup for Stewart and a major “Oh God, get me out of here” moment for Kristol.

4. Mike Huckabee, December 9 2008

Governor Mike Huckabee had the smackdown laid on him on the Daily Show in 2008 over the issue of gay marriage. Huckabee’s attempts at an argument ad populum (“68% of the voters across America have affirmed traditional marriage”) were shot down when Stewart pointed out that “traditional” monogamous marriage has only existed for a small part of human history. He then pointed out to the libertarian Huckabee that, “Religion is far less of a choice than homosexuality,” and that it was inconsistent to support freedom of lifestyle in some respects but not others. He followed up on the unamused Governor with one of the ballsiest Jon Stewart lines ever: “At what age did you choose not to be gay?” then argued that discriminating against people for something which is part of their biology could be seen as being a slippery slope into segregation.

3. George Lucas, January 5 2010

Stewart is a self-proclaimed Star Wars geek, but when George Lucas appeared on his show in January 2010 it was less a fanboy’s dream come true and more a bruising boxing match for Lucas. Stewart fired some pretty tough questions at the director, effectively accusing him of being less creative than he had once been and of letting down an entire generation of fans. Possibly the most devastating part of the interview, however, was Lucas’ “whatever” response to the question of whether fans liked the prequel series or not and his insistence that people loved CGI punch bag Jar Jar Binks (sample Urban Dictionary definitions include: “One of the more irritating pieces of crap to come out of George Lucas’ brain” and: “The most hated Star Wars character ever”). This interview finally confirmed fans’ suspicions since the prequel series; Lucas has gone over to the Dark Side for good.

2. Betsy McCaughey, August 20 2009

Notorious former Lieutenant Governor of New York Betsy McCaughey is best known for single-handedly derailing Bill Clinton’s Heathcare Bill in the 1990s, and she’d taken similar pot-shots at Obama’s sequel, Healthcare Bill II since it debuted in Congress. When she appeared on The Daily Show in August 2009 to discuss it the result was like a baby rabbit taking on the Terminator; the “debate” was an utterly one-sided drubbing in which Stewart repeatedly called her out on all her misstatements and half-truths about the bill. Particularly notable was the moment when Stewart challenged her on her statement that the bill would end living wills for relatives who were sick in hospital and actually forced her to go through her paper copy of the document which she’d brought into the studio. He then pointed out that the bill did not, in fact, support her reading at all. “That would be really wrong if that was in any way what this [document] said.”

1. Bill O’Reilly, May 16 2011


‘Friendly’ rivals Bill O’Reilly and Stewart have had many entertaining interviews on each other’s shows, but probably the most impressive was on The O’Reilly Factor in 2011. O’Reilly and Fox News had run a number of stories opposing the rapper Common being invited to the White House by president Obama, calling him a “thug” and claiming that his music glorified Black Panthers cop-killer Assata Shakur. Stewart gleefully pointed out that Bono from U2, who had been invited to the White House several times and who O’Reilly had said was doing “God’s work” when he appeared on his show, had also written a song about a cop killer. He followed this claim by accusing Fox News of having: “A selective outrage machine… which pettifogs only when it suits the narrative that suits them,” and quipping “Booyah! That’s a rap word.” Probably while putting on a pair of sunglasses with The Who going “Yeeeaaah!” behind him.

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