Jon Stewart
Jon Stewart, former host of Comedy Central's "The Daily Show" speaks at a news conference following the Senate vote on the "Never Forget the Heroes Act" on Capitol Hill in Washington, DC, July 23, 2019.
Eric Thayer/Reuters
  • Jon Stewart says he dismissed how Trump's "shamelessness" made him "dangerous."
  • "What it did is made him the perfect vessel. You have to be shameless to do shameful things," Stewart told THR.
  • Stewart's new show "The Problem with Jon Stewart" will premiere on Apple TV+ on September 30.
  • See more stories on Insider's business page.

Comedian Jon Stewart says he missed how former President Donald Trump's "ridiculousness" and "shamelessness" made him "dangerous" ahead of the premiere of his new biweekly streaming show on Apple TV+.

Stewart is just now stepping back into the spotlight for the first time since leaving his role anchoring Comedy Central's The Daily Show in 2015 after a blockbuster 16-year run that made him a household name.

Stewart has kept a low profile since leaving The Daily Show, undertaking a few creative projects and occasionally reappearing on The Late Show with his friend Stephen Colbert and lobbying for benefits and healthcare for 9/11 first responders and firefighters on Capitol Hill often alongside New York Sens. Chuck Schumer and Kirsten Gillibrand.

In an interview with the Hollywood Reporter published Wednesday, Stewart explained what he got wrong when he dismissed Trump's political chances and said at the time Trump was a "gift from heaven" for comedians like himself.

"What I missed there is that his certainty, his ridiculousness, his shamelessness is what made him dangerous. I thought it made him a buffoon, and I thought that's what would disqualify him. What it did is made him the perfect vessel. You have to be shameless to do shameful things," Stewart told the outlet, offering his version of how the mogul and former reality TV star could command so much fealty among Republicans and his MAGA-base even a year after his election defeat.

Stewart added that "the most dangerous figures are the ones that seem comic and absurd," making clear that while he wasn't comparing Trump to those brutal dictators, "Saddam Hussein seems absurd. Muammar Gaddafi would stand in a kaftan and rant like a madman."

Instead of returning to a nightly show on live television, Stewart is taking on the streaming sphere with a new biweekly political show, The Problem With Jon Stewart, set to premiere September 30 on Apple TV+. It will also have an accompanying podcast, CNN Business reported.

While the show will have a humor component, episodes will spend less time mocking politicians and instead dive deep into a political or social issue in every episode featuring the stories of people directly affected.

The premiere episode of The Problem, Stewart said, will cover how many US military veterans suffer negative effects and health problems from being exposed to toxic burn pits while deployed abroad - an issue he has repeatedly championed as an activist.

"I felt like the experiences that I'd had on The Daily Show combined with the experiences I'd had in D.C. enlightened me in a way that maybe I hadn't been aware of previously," Stewart told The Hollywood Reporter. "And it's still just a TV show, but I was so struck by how the most seemingly obvious, simple things got derailed by the systems that are put in place to actually get them done."

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