From taking on political figures to championing important causes, we're looking at the most powerful moments when this legendary host stood his ground. Whether through biting satire or serious discourse, these confrontations changed conversations and sometimes even policy.
Category
🗞
NewsTranscript
00:00Thousands more poured in to continue to fight for their brothers and sisters.
00:09Welcome to WatchMojo, and today we're counting down our picks for the top 10 confrontational Jon Stewart moments.
00:16We're looking at the times Jon Stewart confronted a person, a group of people, or a system,
00:22either satirically or deadly serious, on a show or behind the scenes.
00:26You're right, and Cinco de Mayo, we had the Trump Tower Taco Bowl, and that's one of the healing-est meals on the Trump Tower menu.
00:35Number 10. Critique of the Department of Government Efficiency, Doge.
00:41Let me see if I can noodle. You know what, let me join Doge. I'm going to see if I can noodle some ideas here.
00:46I want to get down some certain ideas.
00:50If anyone thought Jon Stewart would be less passionate, or at least turn things down a notch after the 2024 U.S. election,
00:58they should watch his takedown of Doge.
01:01Stewart picks apart Elon Musk's Department of Government Efficiency in true Daily Show comedic style,
01:07and then pulls out a light, a calculator, and a ceramic mug.
01:10The props are for a bit where Stewart tries to figure out better ways for the government to save money.
01:15He quickly abandons the character, and declares that subsidizing oil, gas, and pharmaceutical companies is the problem.
01:23Stewart's delivery is so passionate that he accidentally injures his hand by breaking the mug.
01:28Because we've already paid for it with our subsidies!
01:31Oh, f***ing thanks! Come on!
01:34He finishes the segment with his hand under the desk, and references the injury the following week.
01:40If I could just pick up something from the last time that I was out here.
01:45I'd made a bit of a critique of Elon Musk and the Doge program.
01:48Let me reset the scene.
01:55I am not allowed to have big boy mugs anymore.
02:02Number 9. Pizza Rant.
02:04With all due respect, you stack slices of pizza, the steam from the bottom of the slice is gonna make the top crust, you piece of s**t.
02:13Most of the entries on this list deal with rather serious subject matter.
02:17New York pizza, for Stewart, is in no way trivial.
02:21In 2011, future President Donald Trump was showing former Alaska Governor Sarah Palin around New York City when the pair decided to try the dish.
02:30Stewart first critiqued Trump's choice to take Palin to a chain.
02:34Famous Familia, and named quite a few alternates, authentic NYC options they could have gone to instead.
02:42No disrespect. I apologize. Let's, let's continue with the meeting and say, are you eating it with a fork?
02:48Stewart started to lose it when Trump stacked up two pizzas, but went full rant mode when the TV businessman, an aspiring politician, started using a knife and fork.
02:59Stewart questioned Trump's status as a real New Yorker, suggesting he might as well stick that fork in New York's eye.
03:07Donald Trump, why don't you just take that fork and stick it right in New York's eye?
03:13Number 8. Versus Bill O'Reilly.
03:16You actually have an influence on this presidential election.
03:19That is, that is scary.
03:20That is, if that were so, that would be quite frightening.
03:22But it is, it's true.
03:23Jon Stewart versus Fox News host Bill O'Reilly was one of the great TV rivalries of the George W. Bush years.
03:30It started with both hosts mocking each other's takes on the news on their respective shows.
03:36Then they appeared on each other's shows, taking combative yet comedic jabs at each other.
03:41You know, when you say younger, you're talking 9, 10, what are we talking here?
03:44No, I'm talking about 18 to 25, you know.
03:46Done.
03:47The people who are on your intellectual level.
03:49They seek that.
03:50They would later sell out a public streamed debate, the rumble in the air-conditioned auditorium,
03:57and would continue to spar as long as they both had shows.
04:01Stewart shines when out of his element.
04:04So the times he made the trip across town and appeared on The O'Reilly Factor are the standouts of this pundit feud.
04:09Don't you think that these guys want to be hip when McCain goes on with you?
04:14Bush hasn't been on with you, right?
04:17You would be a member of that, would you?
04:18George Bush?
04:19Yeah.
04:19I don't recall the president stopping by the program.
04:23Number seven, the Charleston shooting.
04:26Tragedy has visited this church.
04:28This wasn't a tornado.
04:30This was a racist.
04:31This was a guy with a Rhodesia badge on his sweater.
04:35In 2015, a white supremacist opened fire in the Emanuel African Methodist Episcopal Church, killing nine people.
04:43Stewart dispensed with all comedy, as he had done before.
04:45But this time, he also called out the media narrative that said tragedy had visited the oldest black church in the southern U.S.
04:52Stewart remarked that, quote,
04:54In South Carolina, the roads that black people drive on are named for Confederate generals who fought to keep black people from being able to drive freely on that road.
05:17That's, that's insanity.
05:22It did fly over the statehouse at the time, but officials removed it shortly thereafter as a direct result of the shooting.
05:28Whether Stewart's words helped the cause is unclear, but they certainly didn't hurt.
05:32We're bringing it on ourselves.
05:34And that's the thing.
05:35Al-Qaeda, all those guys, ISIS, they're not s*** compared to the damage that we can apparently do to ourselves on a regular basis.
05:44Number six, defending trans rights.
05:47Ninety-eight percent without that medical treatment.
05:50That's an incredibly made-up figure.
05:54That doesn't comport with any of the studies or documentation that exists from these medical organizations.
06:01One of Jon Stewart's greatest qualities as a debater is his ability to bluntly, calmly, and politely call someone a liar to their face.
06:09Always backed up by the facts, his unsuspecting opponents don't stand a chance.
06:14After 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.
06:25Rutledge responded to Stewart's first question by claiming there are as many doctors and scientists against providing medication as there are for it.
06:34Stewart simply replied,
06:35He spends the rest of the interview attacking the validity of the AG's data, underlying her arguments with classic Stewart's deadpan sarcasm.
07:02You're making it sound like a nine-year-old walks into a doctor's office and says,
07:08Give me some testosterone.
07:10And the doctor goes,
07:11Oh, thank God, because we're wanting to create an army of transgenders because we're crazy.
07:18Number five, taking down Jim Cramer.
07:21And I didn't do this, but I'm trying to explain to people, this is the shenanigans.
07:25It sounded like you were talking about that you had done it.
07:27Then I was inarticulate.
07:28In 2009, Stewart set his critical sights on CNBC, accusing the network of irresponsible financial journalism that contributed to the 2008 financial crisis.
07:39Stewart singled out Mad Money host Jim Cramer, who in turn publicly objected to the critique.
07:46The two had a showdown on The Daily Show, with Stewart not pulling any punches,
07:50using archival footage to make the point that Cramer's on-air presentation lacks honesty.
07:56Well, see, that's interesting. Roll 210.
07:59I would encourage anyone who's in the hedge fund game to do it, because it's legal.
08:03Right.
08:03And it is a very quick way to make money, and very satisfying.
08:08Okay.
08:09By the way, no one else in the world would ever admit that, but I do care.
08:12That's right, and you can say that here.
08:13I'm not going to say it on TV.
08:17A subdued Cramer argued some points, but admitted he could have done better with his financial coverage,
08:23and would strive to do so.
08:24This widely shared segment would prove detrimental to CNBC's credibility and viewership.
08:30Cramer would go on to say that he wasn't prepared for Stewart's intense interview style,
08:35which he characterized as an unfair attack.
08:38It was very clear that he was attacking me personally.
08:41I was trying to keep it at a high level, but he was vicious, and he was ad hominem in the way he attacked me.
08:48And then when I tried to defend myself, he said he was attacking the network.
08:51So his method of arguing was brilliant in the way it was meant strictly to try to get me fired.
08:56Number four, taking on Crossfire.
08:59It's not so much that it's bad, as it's hurting America.
09:04Stop hurting America.
09:07That's what Jon Stewart pleaded to Crossfire hosts Tucker Carlson and Paul DeGala when he was a guest on their CNN show.
09:14They thought Stewart would be funny.
09:16Instead, he was deadly serious, critical of the partisan divisions Crossfire promotes.
09:22Part of their strategies, your partisan, what do you call it, hacks.
09:28Wait, Sean, wait.
09:29When the hosts tried to turn the tables and attack Stewart for giving Democratic presidential candidate John Kerry a few softball questions,
09:38Stewart responded by reminding Carlson and Begala that they were on CNN while his lead-in was puppets making crank phone calls.
09:46Are you kidding me?
09:47You're on CNN.
09:48What did we say?
09:49The show that leads into me is puppets making crank phone calls.
09:53What is wrong with you?
09:55The audience in attendance sided with Stewart.
09:58So did the Internet.
09:59And it looks like CNN may have as well.
10:01A few months after his interview, the network canceled the show after 23 years on the air.
10:08Number three, Lena Kahn and Apple TV.
10:11But when we're going up against some of these monopolistic companies, they can outmatch us, outgun us, sometimes one to ten, just if you're looking at lawyers.
10:20Stewart and Apple TV parted ways in 2023 after two short years of working on The Problem with Jon Stewart.
10:27The host would reveal in broad terms that they disagreed on some proposed segments for the show's third season.
10:33But when he took back the helm of The Daily Show, we finally got the real dirt.
10:37Stewart had Federal Trade Commission chair Lena Kahn as a guest.
10:41And during the interview, he revealed that he had tried to book her on a podcast, but Apple TV executives nixed it.
10:48I got to tell you, I wanted to have you on a podcast.
10:51And Apple asked us not to do it, to have you.
10:56They literally said, please don't talk to her.
10:59Stewart says he feels that Apple has every right to censor what they want.
11:02But he contrasts their actions with those of Comedy Central parent Viacom, who just want him to be provocative.
11:09That hurts Americans and American communities in all sorts of ways, and even leads to, for example, planes falling apart in the sky.
11:17Wait, what?
11:21I always thought that was just, I always thought that was all just DEI.
11:26Number two, debating gun laws.
11:30A potential...
11:31But more guns makes us safer.
11:33So why don't, when the police go to a house filled with guns, why don't they breathe a sigh of relief,
11:40knowing that this Second Amendment that shall not be infringed is being exercised so fruitfully?
11:48In what can be described as a masterclass in using logic to win a debate,
11:53Jon Stewart sat down with Oklahoma State Senator Nathan Dahm to discuss gun control.
11:58Dahm is a self-professed Second Amendment absolutist against all forms of gun regulation and control.
12:05Stewart showed how this position makes Dahm an agent of chaos, not order.
12:09What you're doing is you're bringing chaos to order.
12:13That's your subjective opinion, that it's bringing chaos to order.
12:16It's not my subjective opinion.
12:17We have 50,000 gun-related deaths.
12:19That's not a subjective opinion.
12:21That's dead people.
12:22Stewart then used the Senator's declared stances on border security, fentanyl,
12:27and drag queens reading to children to show how his views on guns are inconsistent with everything else he believes.
12:34Dahm attempted to label Stewart's arguments as opinion, which Stewart demonstrated wasn't the case.
12:40After showing Dahm the hypocrisy in his gun views, Stewart concluded by directly calling him out on it.
12:46So your solution to that is, give them more guns.
12:52So I'm saying that because people are the problem, we need to look at the problems that those people are facing and how do we address it.
12:59But you've removed the ability for the state to do that.
13:03Before we continue, be sure to subscribe to our channel and ring the bell to get notified about our latest videos.
13:09You have the option to be notified for occasional videos or all of them.
13:13If you're on your phone, make sure you go into settings and switch on your notifications.
13:17Number one, shaming Congress for 9-11 first responders.
13:23A filled room of 9-11 first responders and in front of me, a nearly empty Congress.
13:33John Stewart has a history of fighting for 9-11 first responders.
13:37He advocated for them multiple times on The Daily Show, back when Congress was debating their health benefits.
13:44Sometimes, Stewart would drop the comedy entirely and let the real responders tell their stories.
13:49Congress would pass the James L. Zadogra 9-11 Health and Compensation Act,
13:54but in 2019, they were debating cuts to the 9-11 Victims Fund.
13:58Stewart went to the Hill to oppose the cuts in person, but was shocked to be met with a nearly empty room.
14:04He shamed the elected officials for their seeming lack of interest.
14:08This hearing should be flipped.
14:10These men and women should be up on that stage, and Congress should be down here answering their questions
14:16as to why this is so damn hard and takes so damn long.
14:26And why no matter what they get, something's always pulled back and they've got to come back.
14:31Stewart's speech went viral, and as a result, Congress reauthorized the 9-11 Victims Compensation Fund until 2092.
14:40They responded in five seconds.
14:44They did their jobs with courage, grace, tenacity, humility.
14:5618 years later, do yours.
14:59Do you agree with our list?
15:02Are there any times Jon Stewart fought the good fight that you'd like to see included?
15:07Let us know in the comments.
15:09I thought Donald Trump was going to speak.
15:11Ivanka said that he was going to come out.
15:13She said he was really compassionate and generous.
15:15But then this angry groundhog came out.
15:18And he just vomited on everybody for an hour.
15:21He was right.