After a decade, Jon Stewart revived what he once called The Daily Show’s “worst legacy” by reuniting with Bill O’Reilly to talk about this “terrible fucking week.”
On Tuesday night, Stewart acknowledged that Monday’s episode of the show—which was supposed to have been filmed in Milwaukee during the Republican National Convention—had been canceled following Saturday’s attempted assassination of Donald Trump in Pennsylvania. Instead, Stewart taped Tuesday’s show from New York, where he said, “We dodged a catastrophe, but it was still a tragedy.”
Then came a visit from O’Reilly, the former Fox News host who appeared on The Daily Show multiple times between 2001 and 2014, back when Stewart was the show’s permanent host. This was the first time in a decade that Stewart and O’Reilly, who exited his own show in 2017 amid claims of sexual harassment (which O’Reilly denied), had been reunited on cable TV.
“I like coming on here, in front of all of your friends out here—and the audience should know, I have no friends here,” O’Reilly said. “Well, not just here,” Stewart cracked in response.
O’Reilly acknowledged that he and Stewart “have a history” of on-air battles. “If you Google Stewart and I, we are able to disagree without hating each other,” said the former Fox News host. “Now, I truly hate him—but I don’t show it.” Said Stewart, “You hold it very well.”
It didn’t take long for the former sparring partners to argue about ideology. O’Reilly criticized the liberal urge to emphasize that Trump’s alleged shooter was a registered Republican, to which Stewart shot back: “You and I are both somewhat fossilized practitioners of the rhetorical arts that are confrontational at times, provocative at times. And we made a really spectacular living pushing those envelopes.”
O’Reilly, who has penned several books about the actual and attempted assassinations of presidents (“It’s like you reproduce books like mold,” Stewart quipped in 2013), said that all the assassins had been mentally ill. In response, Stewart brought up President Abraham Lincoln’s killer, John Wilkes Booth. “Well, John Wilkes Booth was a fanatical conservative and racist who hated Lincoln,” O’Reilly began.
“Good thing that’s gone out of the country,” Stewart joked.
As a registered independent, O’Reilly distanced himself from Trump, but also condemned President Joe Biden by saying that prices and overdose rates have risen during Biden’s time in office. “I respectfully say, yes, inflation was too high, and that hurts American consumers,” Stewart replied. “So what did Biden do to create that, though?”
“I don’t know, and that’s what I would ask,” O’Reilly said in response, causing Stewart to jump from his chair as the audience laughed.
“Basically, you wrote down on a piece of paper, but you didn’t look up the answer?” Stewart said, telling O’Reilly at another point: “You really make it too easy.”
O’Reilly and Stewart have a long history of public tussling. During their last Daily Show conversation, they got into a grudge match over white privilege (you can guess who took which side). In 2012, they fronted a charity debate called “The Rumble in the Air-Conditioned Auditorium.” But for all their televised beefing, the two men have supported each other in the public sphere. O’Reilly penned a late-night farewell to Stewart in 2015, writing that his supposed nemesis was “good at spotting phonies.” Stewart, meanwhile, backhandedly defended O’Reilly against allegations that he had exaggerated stories from his time as a war correspondent. (O’Reilly denied the accusations.) Stewart posited that no one was watching Fox News “for the actual truth,” adding, “You’re basically putting in a tremendous amount of work to say the emperor has no clothes, when the emperor has spent, like, 20 years going, ‘Look at my dick! I’m naked!’”
But speaking to The New York Times in 2020, Stewart expressed regret over offering O’Reilly a platform. “The question was always, Why would you talk to him? Why do you have him on the show if you can’t destroy him? If you want to talk about the worst legacy of The Daily Show, it was probably that,” he said. “Those moments when you had a tendency, even subconsciously, to feel like, We have to live up to the evisceration expectation. We tried not to give something more spice than it deserved, but you were aware of, say, what went viral. Resisting that gravitational force is really hard.”
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