Bill O’Reilly’s Most Outrageous Black Moments

Twitter screenshot
Twitter screenshot

After more than 20 years, Fox News forced Bill O’Reilly out after a series of sexual harassment allegations came to light.

What’s worse, after an internal investigation of O’Reilly’s behavior, the company apparently found more. It all came to a head after an April 1 New York Times article revealed that Fox News and Twenty-First Century Fox had reached settlements with five women who reported incidents of sexual harassment totaling close to $13 million.

As O’Reilly’s reign of terror comes to an end, I think it’s informative to reflect upon those moments when he was almost impressive in his embodiment of white ignorance.


1. Sylvia’s

Remember that time Billy Boy discovered that black folks can own a “classy” business?

“I couldn’t get over the fact that there was no difference between Sylvia’s restaurant and any other restaurant in New York City. I mean, it was exactly the same, even though it’s run by blacks,” he once said on his nationally syndicated radio show about a dinner with the Rev. Al Sharpton. “There wasn’t one person in Sylvia’s who was screaming, ‘MF-er, I want more iced tea!’”

Yeah. He said that—and kept his job.

2. Ludacris

I first heard of O’Reilly in 2002 when he got Pepsi to drop an ad that included Chris “Ludacris” Bridges because of his “vile and woman-hating” lyrics.


This prompted Mr. Bridges to begin the song “Number One Spot” with the verse, “Respected highly, hi Mr. O’Reilly/Hope all is well, kiss the plaintiff and the wifey … ”

I find it ironic that the week Billy Bob is fired, Ludacris is in the biggest movie in America and Pepsi is still trying to figure out how its “Pepsi can fix racism” ad went wrong.


Luda didn’t know it at the time, but that verse was prophetic.

3. Maxine Waters

By now we all know that Ol’ Boy showed his misogynoir by comparing California Rep. Maxine “Tha Gawd” Waters’ hair to a James Brown wig.


She clapped back in epic fashion.

“Let me just say this: I’m a strong black woman and I cannot be intimidated,” Waters said while being interviewed on MSNBC. “And I’d like to say to women out there everywhere: Don’t allow these right-wing talking heads, these dishonorable people, to intimidate you or scare you. Be who you are. Do what you do.”


She ultimately got the last laugh: “Bill O’Reilly is not going to be recorded favorably in history,” Tha Gawd said to CNN’s Anderson Cooper just hours after the news of O’Reilly’s ouster broke.

No, it will not.

Also, because I’m petty:


4. Slavery

America has a history of undermining the viciousness of slavery. From a Texas high school textbook calling Africans brought to the U.S. between the 1500s and 1800s “workers” to Uncle Ben Carson calling the sojourn of black folks in America an “immigrant” story, many on the right have worked diligently to rewrite history in a positive light. O’Reilly has been no different.


Responding to first lady Michelle Obama’s statement that she was living in a house “made by slaves,” O’Reilly took to the air and engaged in a white supremacist rewriting of history.

“Slaves that worked there were well-fed and had decent lodgings provided by the government, which stopped hiring slave labor in 1802,” he said on The O’Reilly Factor. “Don’t let anyone ever tell you that this country isn’t great, that somehow we need to make it great again, because this right now is the greatest country on earth.”


Yes, it is … if you’re a mediocre white man like O’Reilly—because then you can engage in sexual harassment and walk away with as much as $25 million.

5. Cam and Dame

Without question, the best moment in the history of Fox News happened when Cam’ron and Dame Dash were guests on O’Reilly’s show to discuss hip-hop music.

O’Reilly thought he could ambush them by teaming up with a black principal to verbally accost the two, but Cam remained steadfast in his unapologetic assholeness, while Dame systematically and brilliantly poked holes in each and every accusation leveled at him. That segment is a master class in rhetoric. Cam and Dame did us all a service that day, and their contributions to black history have not gone unnoticed.


Peace out, Billy Boy. I am not sad to see you go.

Lawrence is a philosopher of race at his day job and a curator of dopeness when time allows. Words in The New York Times, Slate Magazine, and others. Email him at

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JujyMonkey: unstable genius

So what do you think this smug little prick’s first gaffe will be?

It’s like they gave Stilwell from “A League of Their Own” a news & opinion show, but hired the kid version.