Top 10 Confrontational Jon Stewart Moments

Most of the entries on this list deal with rather serious subject matter. New York pizza, for Stewart, is in no way trivial. In 2011, future President Donald Trump was showing former Alaska Governor Sarah Plain around New York City when the pair decided to try the dish. Stewart first critiqued Trump’s choice to take Palin to a chain, Famous Famiglia, and named quite a few alternate authentic NYC options they could have gone to instead. Stewart started losing it when Trump stacked up two pizzas but went full rant mode when the TV businessman and aspiring politician started using a knife and fork. Stewart questioned Trump’s status as a real New Yorker, suggesting he might as well stick that fork in New York’s eye.

Jon Stewart versus FOX News host Bill O’Reilly was one of the great TV rivalries of the George W. Bush years. It started with both hosts mocking each other’s takes on the news on their respective shows. Then they appeared on each others’ shows, taking combative yet comedic jabs at each other. They would later sell out a public streamed debate, “The Rumble in the Air-Conditioned Auditorium,” and would continue to spar as long as they both had shows. Stewart shines when out of his element, so the times he made the trip across town and appeared on “The O’Reilly Factor” are the standouts of this pundit feud.

In 2015, a white supremacist opened fire in the Emanuel African Methodist Episcopal Church, killing nine people. Stewart dispensed with all comedy, as he had done before. But this time he also called out the media narrative that said tragedy had visited the oldest black church in the southern US. Stewart remarked that “this wasn’t a tornado, this was a racist.” He went on to mention that the roads the churchgoers drive on are all named after Confederate generals, and that the Confederate Flag flies over South Carolina. It did fly over the State House at the time, but officials removed it shortly thereafter as a direct result of the shooting. Whether Stewart’s words helped that cause is unclear, but they certainly didn’t hurt it.

One of Jon Stewart’s greatest qualities as a debater is his ability to bluntly, calmly, and politely call someone a liar to their face. Always backed up by the facts, his unsuspecting opponents don’t stand a chance. After describing recent right-wing trans panic to his audience, Stewart sat down with Arkansas Attorney General Leslie Rutledge to discuss denying gender-affirming care to trans youth. Rutledge responded to Stewart’s first question by claiming there are as many doctors and scientists against providing medication as there are for it. Stewart simply replied “but you know that’s not true” and didn't let up from there. He spends the rest of the interview attacking the validity of the AG’s data underlying her arguments with classic Steward deadpan sarcasm.

In 2009, Stewart set his critical sights on CNBC, accusing the network of irresponsible financial journalism that contributed to the 2008 Financial Crisis. Stewart singled out “Mad Money” host Jim Cramer, who, in turn, publicly objected to the critique. The two had a showdown on “The Daily Show” with Stewart not pulling any punches, using archival footage to make the point that Cramer’s on-air presentation lacks honesty. A subdued Cramer argued some points, but admitted he could have done better in his financial coverage and would strive to do so. This widely shared segment would prove detrimental to CNBC’s credibility, and viewership. Cramer would go on to say that he wasn’t prepared for Stewart’s intense interview style, which he characterized as an unfair attack.

“Stop hurting America.” That’s what Jon Stewart pleaded to “Crossfire” hosts Tucker Carlson and Paul Begala when he was a guest on their CNN show. They thought Stewart would be funny. Instead he was deadly serious, critical of the partisan divisions “Crossfire” promotes. When the hosts tried to turn the tables and attack Stewart for giving Democratic Presidential Candidate John Kerry a few softball questions, Stewart responded by reminding Carlson and Begala that they were on CNN, while his lead-in was puppets making crank phone calls. The audience in attendance sided with Stewart, so did the internet, and it looks like CNN may have as well. A few months after this interview, the network canceled the show after 23 years on the air.

Stewart and Apple TV parted ways in 2023, after two short years of working on “The Problem with Jon Stewart.” The host would reveal in broad terms that they disagreed on some proposed segments for the show’s third season, but when he took back the helm of “The Daily Show,” we finally got the real dirt. Stewart had Federal Trade Commission Chair Lina Kahn as a guest, and during the interview, he revealed that he had tried to book her on a podcast, but Apple TV executives nixed it. Stewart says he feels that Apple has every right to censor what they want. But he contrasts their actions with those of Comedy Central parent Viacom, who just want him to be provocative.

In what can be described as a master class in using logic to win a debate, Jon Stewart sat down with Oklahoma State Senator Nathan Dahm to discuss gun control. Dahm is a self-professed Second Amendment absolutist, against all forms of gun regulation and control. Stewart showed how this position makes Dahm an agent of chaos, not order. Stewart then used the senator’s declared stances on border security, fentanyl, and drag queens reading to children to show how his views on guns are inconsistent with everything else he believes. Dahm attempted to label Stewart’s arguments as opinion, which Stewart demonstrated wasn’t the case. After showing Dahm the hypocrisy in his gun views, Stewart concluded by directly calling him out for it.

Jon Stewart has a history of fighting for 9/11 first responders. He advocated for them multiple times on “The Daily Show,” back when Congress was debating their health benefits Sometimes Stewart would drop the comedy entirely and let the real responders tell their stories. Congress would pass the James L. Zadroga 9/11 Health and Compensation Act, but in 2019, they were debating cuts to the 9/11 Victims Fund. Stewart went to the Hill to oppose the cuts in person, but was shocked to be met with a nearly empty room. He shamed the elected officials for their seeming lack of interest. Stewart’s speech went viral, and, as a result, Congress reauthorized the 9/11 Victim Compensation Fund until 2092.

Do you agree with our list? Are there any times Jon Stewart fought the good fight that you’d like to see included? Let us know in the comments.