Top 3 Times ‘The Problem With Jon Stewart’ Host Squared Off With His Interview Subjects (Video)

If you’re going to sit down for an interview with Jon Stewart, you best be ready to get properly pressed on the subjects you’re talking about. The talk show host doesn’t shy away from challenging subjects on guests’ views, as plenty of politicians have learned.

Over the last year, Stewart sat down with several officials across multiple states for his Apple TV+ series “The Problem With Jon Stewart,” digging in on issues like gun violence and election misinformation. Sometimes, it gets heated.

Stewart has never been shy about his own opinions, so we rounded up several top moments from the show in which he pushed back (in no particular order).

1. Arizona Attorney General

In October 2022, Stewart sat down with Arizona Attorney General Mark Brnovich and, despite Stewart’s best efforts, Brnovich would not admit that Donald Trump’s lies about the 2020 election being stolen were just that: lies.

During the interview, Brnovich noted that there were roughly 20 criminal cases under investigation related to the 2020 election. Stewart curtly replied, “Out of 4 million votes.”

Stewart continuously pressed Brnovich to admit that Trump lost the election, but Brnovich would only concede that he definitively lost the state of Arizona. In reference to the 2020 election as a whole, Brnovich kept referring to the ongoing investigations, arguing that people could form their own interpretations of the results of those cases.

“People cannot draw their own conclusions,” Stewart shot back. “That’s the point of the law. The law is, you have facts and you have fiction. The fact is the election in Arizona was well-run, not fraudulent, and not stolen from Donald Trump.”

Stewart was eventually left only able to marvel at Brnovich’s denials, saying, “this is blowing my mind.”

2. Oklahoma State Senator

In March, Stewart welcomed Oklahoma state senator Nathan Dahm to the show, sitting down for a conversation on gun control. By the end of it, Stewart was calling out Dahm for “hypocrisy at its highest order.”

In his time as a state senator, Dahm has written multiple bills loosening gun restrictions. That includes the nation’s first anti-red flag law against restricting gun access for those deemed dangerous. Dahm is also among those who argue that the cause of gun violence is primarily mental health issues — something Stewart honed in on immediately.

“If you don’t have background checks, and you don’t have registration and permitting, how do you know who has a problem, in terms of the people who you’re giving a gun to?” Stewart asked. “You don’t want anything that could help law enforcement or society determine whether or not a person is a good guy with a gun or a bad guy with a gun.”

As the conversation progressed, Stewart brought up Dahm’s support for banning drag show readings to children. After Dahm said that gun rights should never be infringed upon, Stewart argued that those drag reading bans infringe upon the right to free speech.

When Dahm came back by saying that that particular brand of free speech can and should be silenced “because the government does have a responsibility to protect” kids, Stewart openly derided him.

“What’s the leading cause of death amongst children in this country? And I’m going to give you a hint: It’s not drag show readings to children,” Stewart sniped. “It’s firearms — more than cancer, more than car accidents.

“And what you’re telling me is, you don’t mind infringing free speech to protect children from this amorphous thing that you think of, but when it comes to children that have died, you don’t give a flying f— to stop that, because that ‘shall not be infringed.’ That is hypocrisy at its highest order.”

3. Arkansas Attorney General

“The Problem With Jon Stewart” also got a bit tense when Leslie Rutledge, the attorney general of Arkansas, appeared on the show. That was after Arkansas became the first state to pass a ban on gender-affirming care for minors.

All while remaining perfectly calm, Stewart picked apart Rutledge’s reasonings for the ban, specifically calling out the fact that it ignored the recommendations of the American Medical Association, the American Association of Pediatrics and the Endocrine Society.

To drive his point home, Stewart asked Rutledge who she would listen to if she were to learn her child had pediatric cancer. Rutledge conceded that she’d likely turn to those organizations — unless she disagreed — but argued that Stewart’s example was “very extreme” because children can die from pediatric cancer.

“I’ve got some bad news for you. Parents with children who have gender dysphoria have lost children, to suicide,and depression,” Stewart bluntly fired back. “And so these mainstream medical organizations have developed guidelines through peer-reviewed data, and studies.”

He continued, “And through those guidelines, they’ve improved mental health outcomes. So I’m confused why you follow AMA guidelines and AAP guidelines for all other health issues in Arkansas — because we checked — but not for this.”

Rutledge steadfastly maintained that banning gender-affirming care was to protect kids from an “irreversible decision.” Stewart gave a plainspoken response.

“You’re making it sound like a 9-year-old walks into a doctor’s office and says, ‘give me some testosterone,'” he said. “And the doctor goes, ‘Oh, thank God, because we’re wanting to create an army of transgenders, because we’re crazy.’ And they go right in.”

Rutledge remained unconvinced.

“The Problem With Jon Stewart” is now streaming on Apple TV+.

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