Jon Stewart is about to learn a hard truth about the state of media and culture

Jon Stewart left “The Daily Show” in August 2015, which was not all that long ago — but was a vastly different media and cultural environment. “Celebrity Apprentice” host and celebrity billionaire Donald Trump had taken his golden escalator ride down for his presidential announcement less than two months earlier, and the tidal wave of societal change was a mere ripple.

Stewart found other avenues for media output, writing and directing a solid movie (“Irresistible,” a political farce) and hosting a couple seasons of a little-watched Apple TV show. Now he’s back as the Mondays-only host of “The Daily Show.”

He has no idea what he’s in for.

He got some glowing pre-show coverage, and even after his first episode late Monday there was some positive press as well. But Stewart is a political comedy star from an era that has completely disappeared, ever since large portions of the American media became hopelessly addicted to the drug that is Donald Trump, obsessed with their perceived existential fight with the former (and potentially future) president.

Stewart’s “Daily Show” reign went from 1999 to 2015, spanning the full scope of the Bush and Obama years. Divisiveness in our politics and culture was rampant then, but Americans also were being served by a media that valued objectivity, basic fairness and intellectual consistency.

In the years since Trump rose to power, “objectivity” has become seen as a sign of ignorance, or worse. There are hysterical screams of “false equivalency” and “bothsidesism” and “whataboutism” — because if you’re not focused solely on Trump alone, you’re simply part of the problem. (Former New York Times journalist Amy Chozick told me in my book “Uncovered” — out in paperback next week — that there’s a new generation of young journalists who believe “objectivity is akin to white supremacy.”)

There were valid criticisms of Stewart from his glory years. He played the “comedian” card whenever he got pushback for portraying events or comments out of context in an attempt to avoid accountability. He was sometimes needlessly sophomoric and petty.

But Stewart’s “Daily Show” also made a regular practice of criticizing his “own” side. He’d go after the hypocrisy of the left, seeming to relish making his audience uncomfortable at times. Stewart was occasionally masterful at exposing the ridiculous contortions we perform to defend powerful figures we support, and he did so not by attacking the people but by attacking the powerful.

In 2024 — and since 2017 — the “Daily Show” oeuvre, and the corporate media apparatus, has been the opposite. It wasn’t enough to simply attack Trump or his administration — no, the target was the “deplorables” who put him there in the first place.

But more antiquated than Stewart’s former refusal to be deferential to one party was his tendency, even if occasional, to go after the left. His Apple show was all over the map, but even it showed that perhaps he had learned some lessons about how to properly navigate the current consensus incentive structure. In one particularly egregious example, he allowed writer Andrew Sullivan to be browbeaten as a racist for refusing to properly atone for his inherent whiteness.

Which brings us to Monday night, and Stewart returning with a manifesto of sorts, tackling the “Biden-Trump rematch that nobody wants.” He set the table on 2024 by describing in detail the threat of Trump, but also spent significant time calling out the obvious cognitive decline and mental fitness of President Biden — including those Democratic defenders who are spinning a false storyline after the damning special counsel report. He referred to Biden as “Chocolate Chip Cookie Guy” and mocked Biden’s awkward TikTok debut.

This was capital-U Unacceptable for some in the press. “Centrist Democrats … were appalled at what they saw as a betrayal by one of their own,” wrote Rolling Stone. “Stewart’s main segment was classic bothsidesism,” wrote Slate.

The ratings for the premiere were great — the show’s top-rated episode in nearly six years. But that’s secondary, because anyone who follows Stewart on social media knows how thin-skinned he can be about criticism from his peers.

Jon Stewart is about to learn a hard truth about the current media and cultural environment — his brand isn’t welcome anymore. I’d almost feel bad for him, if it weren’t partially his fault we’re in this mess to begin with. From the time he went on “Crossfire” and called out smart people from different sides of the debate arguing on television back in 2004, there’s been a slow push toward viewing the other side as not just wrong but “dangerous” and “hurting” our democracy.

And now here we are — Stewart has “appalled” the left because of his “betrayal” for daring to state the obvious about Joe Biden. Welcome to the all-or-nothing future you helped build, Jon. Good luck — you’ll need it.

Steve Krakauer, a NewsNation contributor, is the author of “Uncovered: How the Media Got Cozy with Power, Abandoned Its Principles, and Lost the People” and editor and host of the Fourth Watch newsletter and podcast.