Jon Stewart v. Apple: ‘Our Aims Do Not Align’

Jon Stewart’s return to The Daily Show seems to be an unqualified success, but his two-season run on Apple TV? Mmmm, not so much. What went wrong? Stewart talked to Matt Belloni on The Town podcast to dissect the uncomfortable marriage between satirical comedy and colossal corporate interests.

The Problem with Jon Stewart was shaky at the start, he said, partly because he was rusty after a few years off. But a bigger issue was a disagreement over his approach to the show. If The Daily Show dealt with the weather (a metaphor for the troubling issues of the day), The Problem would address the climate — the larger environmental factors that cause society’s problems. “I felt invigorated again,” he explained. “There was something about changing that perspective and looking at it from this slightly askew place that felt revelatory to me.

“And then Apple said we would prefer you not do that.”

That was a change from Stewart’s Comedy Central days, when “provocative” and “explicit” were considered positives for an emerging brand featuring Dave Chappelle and South Park. But Apple isn’t just a content company, Stewart learned. “They have a whole other side business making… adapters? Dongles, I think they make dongles.”

Content, in other words, wasn’t core to Apple’s brand. If Ted Lasso hit big, great. “But if there's some asshole who's out there perhaps damaging relationships that (Apple) thinks are more important? I learned I could not help them in the way that maybe I had been able to help Comedy Central,” Stewart said. “But I think in their determination, I could hurt them.”

Belloni couldn’t fathom why Apple went shopping at the Jon Stewart Store and came home baffled to discover it had purchased a Jon Stewart. “Wait, he wants to talk about China? He wants to talk about A.I.?”

Stewart doesn’t hold a grudge. Even at Comedy Central, “the deal is I get to do what I want until they think it’s going to hurt their beer sales or whatever it is that they want to sell. And that’s the deal we all make. Nobody is owed a platform.”

There wasn’t a single dealbreaker with The Problem with Jon Stewart, but an example of pain on both sides was a show that featured an interview with Larry Summers, the former Secretary of the Treasury. Post-pandemic, worker wages shot up, and the Fed sought to cool inflation by cutting interest rates. That approach works, but usually at the cost of millions of jobs. The bigger problem, in Stewart’s mind, was excessive corporate profits. 

Summers attempted to corner Stewart by asking if his interview would be appearing on Apple TV. The answer was yes. Summers pointed out that Apple had done very well during the recession. Was Stewart suggesting that Apple was price gouging? “Yeah,” he said, “I’m suggesting all of them do.”

There was more to the segment, but that’s the gist. When the interview was played for Stewart’s live studio audience, “they explode like we just hit a three-pointer at the buzzer.” After the show, Stewart and his staff walked off the set like it was the end of the movie Rudy, basking in their triumph. But Apple executives were waiting in the dressing room with ashen looks. 

“Are you going to use that Summers interview?”

The interview that the crowd just cheered? 

“It was then that I realized, ‘Oh, our aims do not align,’” Stewart said. “We're trying to make the best, most insightful execution of our intention that we can make. But they’re protecting a different agenda. And that’s when I knew we were in trouble.”