When Bill O’Reilly appeared on The Colbert Report in January 2007, “Stephen Colbert” introduced the interview as a “friendly conversation between peers who respect each other and agree on everything.” Some in the audience booed the Fox News host, but Colbert celebrated the moment with a “Mission Accomplished” banner and a portrait of O’Reilly over the set’s mantle.
At that point, Colbert had been playing his right-wing blowhard character for barely a year, but it was already established that he had based “Stephen Colbert” almost entirely on his “papa bear” O’Reilly.
It was this backdrop that made O’Reilly’s first appearance on the “real” Stephen Colbert’s Late Show Monday night so momentous. This time, Colbert teased his guest by telling the audience how much they have in common: “We’re both Irish-American, we both wear suits, and I think that’s it.”
A regular on David Letterman’s couch, O’Reilly entered and immediately started to brag about Fox News’s high ratings and suggested that everyone on CNN and MSNBC is “on crack.”
“I have not watched it much in the last year,” Colbert admitted. Since leaving his O’Reilly-inspired character behind, he no longer needed to keep up with Fox’s every move.
Asked why Donald Trump is doing so well in New Hampshire, O’Reilly described the GOP frontrunner and Bernie Sanders as the “same guy, because they’re both tapping into the anger of the voter who feels they’re getting hosed.” While Trump supporters are angry about the border and ISIS, O’Reilly explained that Sanders voters don’t want an economy run by “the billionaires,” doing his best Bernie impression.
Colbert was not impressed. “I’m sorry, did you just have a stroke right now?” he asked.
O’Reilly said people want an “avenger” this time around, not a politician—something that has worked well for both Trump and Sanders. But he said, their followers “don’t care” that they are promising the impossible.
Things got a little more down and dirty after the break when O’Reilly defended Ronald Reagan’s deficit increases by saying it was all for the greater good of the Cold War. “You bring down your major enemy and you have to do it by spending money,” he said.
“That’s huge deficits that can be justified by military expenditure but you’re saying that huge deficits can’t be justified by humanities, by educating people, by social services? What’s the difference to those things?” Colbert asked to cheers from his audience. “They’re both vital aspects of our culture. What is the difference between those two and why is one justified and not the other?”
“This is a classic liberal position,” O’Reilly replied, uttering something Colbert’s conservative character would never have heard on The Colbert Report.
“We don’t have to pick sides,” Colbert insisted. “Why do we have to be liberal and conservative? Why can’t we just love each other?” When O’Reilly suggested that the late-night host didn’t know where he stands on the issues, a shocked Colbert replied, “Everything you’ve said could be a lie? I trusted you, Bill O’Reilly.”
In the end, the two men may not have seen eye-to-eye. But it was the first real conversation they have ever had on television.