Bill Carter: How Jon Stewart Changed Media (and Made Megyn Kelly Cry)

This story first appeared in the Aug. 7 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.

On Nov. 4, 2008, the night Barack Obama was elected president, I was sitting with the audience of The Daily Show With Jon Stewart in its studio on the west side of Manhattan. No one would have been gobsmacked by the rooting interests that night of both the guests or the host. Stewart has never hidden his point of view; and on this night he looked, to put it simply, pumped.

The show was a live election-night special. Stephen Colbert of The Colbert Report was co-anchoring, and, as the returns came in, the celebratory mood grew in intensity. When the news networks called enough states to make it official, Stewart looked straight into the camera and told his audience: “At 11 o’clock at night, Eastern Standard Time, the president of the United States is … Barack Obama.”

As the crowd unleashed a roar of approval (and Colbert did his best faux harrumphing, saying it was still only a “maybe”), Stewart exerted a visible effort to swallow down the grin that threatened to explode across his face. It was only after he left the air a short while later that the explosion came, as first he and Colbert shared what looked like a victory hug, and then Jon met his wife, Tracey, who was in the audience, and they also embraced.

That night was momentous both for Obama and Stewart, who cemented his position as the comic voice (and conscience) of the political left-of-center in 21st century America. Since then, Stewart has used that position to become the left’s most trusted critic of political hypocrisy and mendacity.

Stewart usually was seen as an ardent defender and friendly host during frequent (seven) Obama appearances — though he took on the president over several issues where he was disappointed, including veterans affairs and the massively botched launch of Obamacare. So it certainly rang a bit discordantly July 23 when the former correspondent (and the show’s only black writer at the time), Wyatt Cenac, described a charged confrontation with the host over what Cenac perceived as a racially insensitive impression of 2012 Republican presidential candidate Herman Cain. Cenac recounted a shouting match that ended with Stewart telling him he was “done with him.”

Stewart’s bona fides as a progressive on race are legit and long. Most recently he won huge praise for his heartfelt commentary on the slaughter of black churchgoers by a white supremacist in Charleston, S.C.; he also was singularly responsible for promoting black comic and writer Larry Wilmore — first on The Daily Show and then as Stewart’s handpicked successor to Colbert on the 11:30 p.m. Comedy Central program The Nightly Show, which Stewart produces. Wilmore has been effusive to me in his praise for Stewart’s generosity and leadership.

The Cenac episode stirred a round of surprised reactions, though veterans of the show know well that Stewart can be a demanding boss. But the incident is likely to have little impact on Stewart’s legacy as he heads for his exit from the show on Aug. 6. Mainly that departure is expected to leave a void for loyal followers of liberal causes, though it also may inspire sighs of relief from the horde of public officials Jon has eviscerated over the years.

The only place those sighs will echo louder is within the newsrooms of the major media enterprises, which have, if anything, endured an even worse bludgeoning thanks to Stewart’s relentless scrutiny. It is no exaggeration to say it: When Jon Stewart goes, the country will be losing the most focused, fiercest and surely funniest media critic of the past two decades.

As one longtime executive at CNN put it to me: “The irony always was that most people in the place truly enjoyed his show, never missed it. So it was always incredibly painful that he would attack us the way he did.” And oh he did. When Larry King asked him directly why he picked on CNN so much, Stewart memorably fired back: “You’re terrible!” Terrible, in Stewart’s view, for blowing stories (like “poop cruises” or missing planes) out of proportion; for substituting holograms of reporters in place of substantive news; for foisting on viewers what he perceived as poseurs (favorite Stewart pinatas included Tucker Carlson, Rick Sanchez and Eliot Spitzer — none of whom survived long after the eviscerations); but mainly for not living up to Stewart’s — and by extension his viewers’ — expectations.

Inside CNN, many felt Stewart’s barbed contempt tilted unfairly in their direction — and it may have, because it sprang from chagrined disappointment more than pure disdain. Colleagues reported that Wolf Blitzer took Stewart’s hectoring especially hard. (Among other instances, Stewart memorably spit-roasted Blitzer the night CNN jumped the gun to report the Supreme Court had overturned Obamacare, only to backtrack with Blitzer citing “widely different” reports.)

But CNN hardly was lonely inside the Stewart bull’s-eye. The litany of Stewart takedowns of media figures and institutions extended across the television and print landscape. In June, Stewart kicked The New York Times around for nitpicking at Marco Rubio for his traffic tickets and buying a boat while in debt. “Paying off law school loans. How dare you?” Stewart jabbed at the Times. “At long last, senator, have you no sense of insolvency?”

The Fox News Channel took Stewart’s wrath particularly hard. Officially, Fox News has been largely dismissive of Stewart as just another lefty ideologue who mocked the conservative-leaning channel to gin up ratings. But star anchor Megyn Kelly once acknowledged that an especially comprehensive takedown of her by Stewart had reduced her to tears.

Stewart never has disputed his ideological differences with the network, conceding, as he did in an interview with Rachel Maddow on MSNBC, that there was “a special place in our hearts for Fox.” Nor has he run from his identifiably progressive point of view. “My comedy is informed by an ideological background,” he told Chris Wallace on Fox. He argued, though, that he was neither a rigid ideologue nor an activist. His friendly interaction with Fox’s Bill O’Reilly seemed genuine (which consistently surprised his harder-left fans), and he took O’Reilly’s jibes (“You have an audience of stoned slackers who love Obama”) with apparently unflappable good humor. Both hosts clearly benefited from the cross-cultural exchanges.

MSNBC got ladled into that soup as well. Stewart told Maddow her network was just as guilty of the sin of setting out to “amplify division” in the country. When the network’s Chris Matthews visited to pump his memoir, Life’s a Campaign, Stewart’s jaundiced reaction led Matthews to accuse the host of “trashing my book.” No, Stewart said, he wasn’t trashing the book, he was “trashing your philosophy of life.”

And then there was CNBC, whose host Jim Cramer came in for perhaps the most classic Daily Show disemboweling. With Cramer having denied he proposed a buy on Bear Stearns after the investment firm’s epic collapse, Stewart pulled the clips. “Very big upside, very limited downside,” Cramer was caught saying on tape. When Cramer appeared as a guest to defend himself, arguing that there was a market on television for stock-touting, Stewart responded: “There’s a market for cocaine and hookers!” (Stewart later acknowledged he probably went too far chewing on Cramer.)

Stewart clearly has had an impact on other media careers and decisions, most notably on the termination of the political debate show Crossfire on CNN. The then-CEO of the network, Jon Klein, said when he canceled the show in 2005 that he was “firmly in the Jon Stewart camp” on the issue of cable news offering too much partisan arguing. One veteran CNN executive told me that Stewart’s determined efforts to hold that network’s feet to the fire had had an impact all the way to the top of CNN’s management. “The purists at the network” began to make the argument that Stewart was “not a comic curmudgeon but a truth-teller.”

Truth is often subjective in contemporary media, of course. Fox News’ Kelly accused Stewart of having “no foothold in the facts.” Few other charges would be more likely to raise Stewart’s hackles. Some of his most effective media critiques have been built around scrupulous fact-based research, the kind other media outlets might have done had they been as thorough.

In May, in response to what he saw as deliberately skewed Fox News coverage of Obama’s policies on poverty, Stewart tossed the Fox host Stuart Varney on his grill. After a shot of Varney saying Fox never criticized the “recipients” of welfare, Stewart showed clip after clip of Varney disdaining the poor, saying they aren’t really poor because they own things like refrigerators and microwaves, and what they really lack is “a richness of spirit.”

“If you see a boy on crutches, push him down,” Stewart said, in his best Dickens voice, as though shouting out the window as Scrooge on Christmas morning. “He’s not crippled. He’s crippled at heart. He lacks a richness of legness.” How could Fox News be so unaware of these “glaring contradictions,” he said, in how their protestations of innocence were undermined by a raft of previous coverage? “Is it a product of lack of self-awareness, or cynicism or stupidity or evil?” Stewart asked, clearly boggled.

Stewart then expanded the critique to include commentary on MSNBC by Mike Barnicle, who said he had never heard the poor described on Fox in terms like “lazy, sponges and leeches.” “Well, I guess it’s time for our favorite game show: Did You Even Try to Research This?” Stewart said, incredulous, introducing clips where Fox commentators used those exact words. Time and again, The Daily Show under Stewart embarrassed other quarters of the media as its assiduous video researchers ferreted out precise examples of hypocrisy or outright lying.

Presumably the holdover staff can keep up that standard after Stewart is gone. (Comedy Central’s talent drain — with Stewart, Colbert, John Oliver and Key & Peele all gone in the span of about a year — has left much of the rest of the television business boggled.) But replacing the filter of his high expectations and righteous anger will be much more difficult.

Stewart always twisted himself into a knot denying that he held a significant place in the world of journalism or media — or criticism. He professed to be a comic, first and always. “There is no honor in what I do, but I do it as honorably as I can,” said Stewart (getting it half right). “I don’t take any satisfaction in just being a critic.” Many of his viewers certainly did.

Bill Carter has covered television for 40 years, mostly at ‘The New York Times,’ and is a CNN contributor.