FOX And Frenemy: Celebrating Jon Stewart And Bill O’Reilly’s Rivalry

For the last 14 of the 16 years Jon Stewart has hosted The Daily Show, he’s regularly interviewed, debated, and shouted at conservative Fox News host Bill O’Reilly. Like two lawyers who argue fervently in the courtroom before going out for drinks afterward, there exists a very strong sense of mutual respect, and often a sense of thoughtfulness when it comes to their disagreements. With Jon Stewart’s last episode of The Daily Show slated for Thursday, we took look back at a cable news bromance for the ages.

The Daily Show – Jan. 22, 2001

While The Daily Show was still a middling, humorous fake news show that had not yet reached its stride under Stewart, O’Reilly came on as someone at the top of his game, hosting the highest rated program in cable news, and the author of a best-selling book. There’s an instant rapport between the two, and O’Reilly comes off as a sort of mentor, and he ends up coaching Stewart on how to ‘shake up’ someone in an interview.

The O’Reilly Factor – Sept. 17, 2004

After The Daily Show had inched its way into a kind of relevancy, Stewart appears on O’Reilly’s show with a best-selling book of his own. O’Reilly’s tone toward Stewart is noticeably shifted, starting the interview off asking him “You know what’s scary, you actually have an influence on this year’s presidential election,” condescendingly ridiculing the “stoned slackers” that watch his show, whose ability to vote frightens him. Stewart plays it light, while he excuses his program as being a simple “comedy show” with a peripheral influence, which O’Reilly clearly doesn’t buy.

The Daily Show – Oct. 18, 2005

“Why so angry?” Stewart asks O’Reilly after his noticeable aggravation over the premiere of The Colbert Report (an obvious send-up of The O’Reilly Factor) the day before. O’Reilly then reflects about the performance aspect of his show, and the outrage he has to bring night after night for nine years. “We’re not playing it for yucks,” he reminds Stewart. While his tone implies him talking down to Stewart and his audience demographic, it moreover speaks to a commonality the two share, and they start to seem like two sides of the same coin.

The Daily Show – Nov. 13, 2008

If their interview in 2005 was the two on even ground, Stewart gleefully assumes the upper hand throughout this interview, given Obama’s victory just days earlier. Although the rapport between the two is still unquestionable, O’Reilly almost willingly lets Stewart have his heyday, and graciously accepts Stewart’s offer of consolation in the form of hot cocoa and a stuffed animal.

The O’Reilly Factor – May 16, 2011

Back on O’Reilly’s turf, the camaraderie the two had developed seems to have eroded during their discussion of Common’s visit to The White House. Stewart sticks to his point, reiterating his “I can’t speak for him, but I think…” standpoint. The rest devolves into a spiteful disagreement over what Common’s visit entails. While Stewart’s occasional moments of humor go largely unanswered, he ends up constructing a solid argument against O’Reilly’s logic, but by the end of the segment seems to deliver it through gritted teeth.

Rumble In The Air-Conditioned Auditorium – Oct. 6, 2012

After another appearance on The O’Reilly Factor a couple weeks earlier — a spirited shouting match that started with the Republican National Convention and morphed into a dialogue about birth control — the two decide to take their public relationship (now a story in itself) to the next level, so to speak. In this case, a 90-minute debate that was available online, splitting its time between a Presidential Debate format and a Town Hall style question and answer. It was wildly successful, and a showcase of their mutual respect, as their frequent disagreements never cross over into personal attacks.

The Daily Show – May 23, 2013

Back on The Daily Show, the two quickly return to common ground after their debate. “What’s up, man?” Stewart greets him enthusiastically. O’Reilly then opens the conversation about Fox News correspondents being arrested, which leads to their shared opinions on the government’s intrusion on their now shared craft. It’s worth noting that, by now, O’Reilly is as at home among Jon Stewart’s audience as he is.

The Daily Show – Sept. 20, 2013

With O’Reilly there promoting another book, the two have become experts at entertaining one another as much as the audience by now. Their debates continue without rancor, and with less spirited ferocity, and even some unexpected moments of shared beliefs. Their big disagreements, namely Obamacare, even come through as thoughtful, while O’Reilly seems particularly open-minded, and again flaunting his ability to play to Stewart’s audience. Stewart’s good-natured ribbing, particularly about O’Reilly’s latest book, Killing Jesus, comes off as genuinely endearing moments.

The Daily Show – Oct. 15, 2014

“I want you to admit there is such a thing as white privilege,” Stewart implores O’Reilly. Their following debate, while not breaking any new ground, shows two friends who’ve grown so comfortable with one another that one can shout at the other and get only a smirk in return. Their respect for one another is also palpable, as O’Reilly jokes with Stewart “you have a vampire movie coming out,” a nod to Stewart’s film Rosewater.

The Daily Show – Feb. 24, 2015

While O’Reilly wasn’t a guest, he was the focus of the show’s opening segment, when Brian Williams’ own journalistic embellishments were still a hot topic, O’Reilly found himself facing similar accusations about claims he’d made when covering the invasion of the Faulkland Islands in 1982. While Stewart didn’t necessarily defend or deride O’Reilly, but in the typical style of The Daily Show, a rapid-fire series of clips of O’Reilly that make Stewart’s point for him.