With more than 5,000 episodes of “The O’Reilly Factor” airing on
Now, 21 years later, O'Reilly is on his way out at the cable news network, after an April 1 New York Times report revealed that he and the network had paid out more than $13 million in settlements to women who accused him of sexual harassment.
During his decades of dominance — "The O'Reilly Factor" held the No. 1 spot on cable news ratings for 60 consecutive quarters through March 2015 — the Fox News stalwart was a volatile and controversial figure, who viewers loved and/or loved to hate.
Here are six moments that perfectly capture the tempestuous personality that helped build a cable news empire.
Bill O’Reilly vs. Maxine Waters (March 2017)
Just days before the New York Times revealed the harassment claims that spurred the advertiser pullout for "The O'Reilly Factor," O'Reilly was in hot water for mocking California Rep. Maxine Waters' hair as she delivered an impassioned speech criticizing President Trump.
"I didn't hear a word she said, I was looking at the James Brown wig," O'Reilly stated during an appearance on "Fox & Friends."
Though O'Reilly later apologized, he immediately pivoted from the inappropriateness of his comments to how Waters' thoughts about the president were unpatriotic.
Bill O’Reilly vs. Ludacris (August 2002)
In a move that some might view as deeply ironic, given O'Reilly's current circumstances, the embattled host was victorious when he encouraged Pepsi to cut ties with rapper Ludacris because the latter was "a man who degrades women."
O'Reilly credited Pepsi's decision to discontinue the ad campaign featuring Ludacris to his audience.
"Apparently thousands of you let Pepsi know Ludacris was unacceptable, and today they canceled him," O'Reilly stated.
Bill O’Reilly vs. David Letterman (ongoing)
Though successor Stephen Colbert is growing increasingly comfortable filling David Letterman's shoes when it comes to grilling political figures, Letterman was still the best at holding pundits' feet to the fire.
Letterman and O'Reilly had a long-running relationship that was both respectful and cantankerous, including this interview where Letterman informs O'Reilly that he thinks he's a goon.
In a recent interview with Vulture, Letterman told the outlet that before he became "standard talk show fare" O'Reilly was one of his favorite guests.
Bill O’Reilly vs. Michelle Obama (July 2016)
During the Democratic National Convention in July, O'Reilly took issue with then-First Lady Michelle Obama's remarks that marveled at being the first black family to occupy the White House, a structure partially built by slave labor.
While O'Reilly did acknowledge the use of slave labor in the construction of the White House, he went to great lengths to emphasize that the slaves were well-fed and had "decent lodgings."
Bill O’Reilly vs. Jon Stewart (ongoing)
Like Letterman, Jon Stewart also had a history of sparring with the face of Fox News. Stewart never failed to roast O'Reilly for his perceived failings during his years spent hosting "The Daily Show."
The O'Reilly/Stewart feud was so prominent that the two even participated in a mock presidential-style debate in 2012 to raise funds for charity.
But, also like Letterman, Stewart reserved a certain amount of latent respect for O'Reilly, even going so far as to defend him in 2015 from criticism surrounding his claims to war-zone reporting.
While some outlets accused O'Reilly of exaggerating his experience reporting from dangerous locales, Stewart accused those same outlets of being disingenuous, saying they were "putting in a tremendous amount of work to say the emperor has no clothes, when the emperor has spent, like, the last 20 years going… 'I'm naked!'"
Bill O’Reilly vs. Alan Colmes (March 2013)
Fox News liberal contributor Alan Colmes left O'Reilly in a tizzy during a 2013 segment during which O'Reilly accused Colmes of being a liar for defending President Obama's budget plans.
Colmes held his ground, chastising O'Reilly, saying that there's room for disagreement without accusations of lying.
When Colmes died in February of this year, O'Reilly gave his colleague a glowing tribute during "The O'Reilly Factor."