By Bethonie Butler, The Washington Post
Throughout Bill O’Reilly’s long tenure at Fox News, the pugnacious TV host was a recurring presence on late-night television, where he sparred with David Letterman and enjoyed a particularly contentious rivalry with former “Daily Show” host Jon Stewart. Stephen Colbert famously parodied O’Reilly and other conservative talk show hosts on “The Colbert Report.”
On Wednesday, Colbert paid biting tribute to O’Reilly on “The Late Show” after 21st Century Fox announced that Fox News had parted ways with its marquee commentator amid a series of sexual harassment complaints against him.
Even when he wasn’t a guest, O’Reilly’s outspoken political views (and in recent weeks, the allegations against him) served as fodder for other late-night hosts, including Jimmy Kimmel and Bill Maher. Here are a few standout interviews and moments that illustrate O’Reilly’s late-night legacy.
Stephen Colbert
“I owe a lot to Bill O’Reilly,” Colbert said on “The Late Show” Wednesday. “I spent over nine years playing a character based largely on him — and then 12 months in therapy to de-bloviate myself.”
Colbert and O’Reilly go way back, even trading guest spots on their respective shows in 2007. After leaving his Comedy Central alter-ego to helm “The Late Show,” Colbert took a more straightforward approach when it came to challenging O’Reilly. The conversations were civil, but left no confusion about their vastly different political stances.
Last year, they debated federal spending after O’Reilly (promoting his book “Killing Reagan”) suggested Ronald Reagan’s military spending helped end the Cold War.
“That’s huge deficits that can be justified by military expenditure, but you’re saying huge deficits cannot be justified by the humanities, by educating people, by the social services, the safety net,” Colbert said. “They’re both vital aspects of our culture. What is the difference between those two – why is one justified and not the other?”
“This is a classic liberal position,” O’Reilly said. After Colbert pressed him to answer, O’Reilly told him “you’re having a stroke again.” Eventually, O’Reilly answered the question, telling Colbert that “you have to defend yourself from an enemy who is bent on either conquering you or killing you.”
“On the arts and education, we have to get away from this fantasy that the government can solve all the problems by kicking money in,” he added.
David Letterman
“In my mind, I think of you as a goon,” Letterman told O’Reilly while hosting him on “The Late Show” in 2009. The jab was part of a long-running rivalry between the two hosts, who over the years debated topics including the war in Iraq and the Occupy Wall Street protests. Though they rarely agreed, their exchanges were generally respectful. In an interview with Vulture last month, Letterman said he actually liked hosting O’Reilly on the show “before he became standard talk-show fare.”
“All I knew about him was that his ideology seemed counter to mine,” Letterman said. “My premise with him was that ‘You’re too smart to believe the things you’re saying. Aren’t you just playing the part of the right-wing buffoon?’ For a long time, I used to think that was true. I always liked having folks on that were not the mainstream.”
Jon Stewart
When it comes to O’Reilly’s late-night rivals, no one holds a candle to Stewart. In 2012, the hosts participated in the “Rumble in the Air-Conditioned Auditorium” at George Washington University, where Stewart’s opening statement helped explain their complicated relationship: “My friend Bill O’Reilly is completely full of (expletive),” Stewart said.
Stewart and O’Reilly famously battled in 2012 over Common’s performance at a White House poetry event. O’Reilly has often come under fire for his attacks against rap music and artists.
O’Reilly criticized the Obama administration for hosting Chicago native Common because his ample discography includes a song honoring Assata Shakur, who was convicted in the 1973 execution-style killing of a New Jersey State trooper and remains on the FBI’s list of most wanted terrorists. (Shakur, the aunt of late rapper Tupac, has been living in Cuba since 1984 after seeking political asylum from Fidel Castro. Her supporters have long maintained her innocence.)
Stewart didn’t relent when it came to O’Reilly’s criticism of Common, even busting out a few bars on “The Daily Show,” lambasting him and other Fox News pundits. Stewart asserted it was hypocritical of O’Reilly to focus on Common’s controversial lyrics while ignoring politically-charged songs written by Bono, Bob Dylan and Johnny Cash, each of whom were invited to the White House by various presidents.
Jimmy Fallon (but really, The Roots)
Fallon typically avoids playing hardball with guests on either side of the political spectrum. But O’Reilly wasn’t spared completely during his visits to “The Tonight Show.” When O’Reilly visited in 2015 to promote “Killing Reagan,” The Roots played Killer Mike’s 2012 song “Reagan.”
It wasn’t intended as a tribute. Fallon’s house band, led by Questlove, has been known to convey subtle messages through the walk-on music they play for guests. “Reagan” is a scathing track that ends with Killer Mike saying “I’m glad Reagan dead.” The rapper told NPR the song was more about Reagan’s ideology than the 40th president himself. On “The Tonight Show,” the band omitted all lyrics except for two words: Reagan dead.
