Bill O'Reilly's All-Time Wackest Hip-Hop Rants

The Media Assassin revisits the FOX anchor's rap battles.

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Why was Barack Obama re-elected as President last Tuesday? Was it because he put forward a powerful vision for the nation? Was it because he ran a technically sophisticated campaign, driven by testable metrics? Or was it because he was the superior candidate?

Most pundits would say it was for all these reasons, and more. But not famed FOX talking head Bill O'Reilly. "Obama wins," he said, "because it's not a traditional America anymore. The white establishment is the minority. People"—meaning, in O'Reilly's curdled tongue, people who aren't white—"want things."

"This is a shocking thing to hear during primetime television," said The Atlantic, reporting the comments on their website, "but it is not entirely out of character for O'Reilly. Bill O'Reilly says racist things all the time."

You don't know the half of it. Here, at Complex, we've been keeping a running tally of O'Reilly's rants, especially against hip-hop artists—so many we had to start keeping score.

For this list, we've left off the bombastic Irishman declaring himself a "brother," on Martin Luther King Jr. Day, because he could tell the certain rappers apart.

We're not even including his notorious smear of Sylvia's, the world-famous Harlem eatery: "I couldn't get over the fact that...it was exactly the same [as any other NYC restaurant], even though it's run black, [with a] primarily black patronship." In a culture "dominated by Twista, Ludacris, and Snoop Dogg," noted O'Reilly, "white America" would be surprised to know that "there wasn't one person in Sylvia's who was screaming, 'M-Fer, I want more iced tea.'"

No, we're only presenting Bill O'Reilly's most outrageous, spittle-flecked rap battles: What happened, what he said, what the rappers said back, and who—in our opinion—won and why. So, ding ding ding. Let the games begin...

Written by Harry Allen (@HarryAllen)

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O'Reilly vs. Ludacris

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O'Reilly vs. Ludacris

Date: August 2002

In 2002, offended by Ludacris's Pepsi endorsement deal—given the artist's often ribald raps—O'Reilly calls out the beverage maker. Pepsi ends the relationship the next day.

Luda plots revenge, and, after years of dissing Bill on wax, and him returning fire, runs up on O'Reilly at a White House event. "The look on his face when he saw me approaching... priceless," laughed Ludacris. "I think he talks about certain [rappers], but he never thinks he's going to meet these people in person, let alone [at] the type of events and the circles that he's in."

O'Reilly's Best Line: Whatever he said to Pepsi.

Luda's Best Line: Whatever he said to O'Reilly: After their 1600 Pennsylvania Ave tete-a-tete, O'l Blue Eyes made a donation to Luda's organization large enough to leave him, in his own words, "definitely" impressed.

WInner: Ludacris. Money talks, baby.

O'Reilly vs. Cam'ron & Dame Dash

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O'Reilly vs. Cam'ron and Dame Dash

Date: November 2003

When a Philly elementary school principal voices outrage over rap lyrics, and the harm he says they're doing to children, he finds an ally in Bill O'Reilly, who hosts him in a roundtable with Cam and Dash.

Camron's Best Line: [Defending Dash.] "Why you won't let 'im talk? You maaad! You maaad! You maaad!"

O'Reilly's Best Line: "I can give my opinion: It's my program."

WInner: Cam and Dash. By engaging in delighted, obnoxious cross-talk, they treated O'Reilly like the joke he is.

O'Reilly vs. Jadakiss

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O'Reilly vs. Snoop Dogg

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O'Reilly vs. Snoop Dogg

Date: March 2007

Over a period of several years, O'Reilly baits Snoop from the FOX News studios with barbs about the rapper's arrests for guns and drugs.

O'Reilly's Best Line: Responding to Snoop's invitation, on Dutch TV, that they tape The O'Reilly Factor in his neighborhood, "so I can kick his motherfuckin' ass when the show is over with," O'Reilly said: "Is a pool boy going to beat me up there, Snoopy?"

Snoop's Best Line: "Suck…My…Dick."

WInner: O'Reilly—for sheer tenacity, and the power of the home advantage.

O'Reilly vs. Nas

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O'Reilly vs. Nas

Date: September 2007

O'Reilly turns his sights on Nas, after the rapper agrees to perform at beleaguered Virginia Tech, the fall after a gunman killed 32 students and faculty there. Noting gun references in "gangster rapper" Nas's music and an arrest in 1995 for illegal possession of a firearm, O'Reilly deems his participation offensive to the memory of the deceased.

Nas returns fire, calling O'Reilly "a racist," challenges him to a debate, speaks at an anti-Fox News rally in front of their studios, and records "Sly Fox" for his Untitled album.

O'Reilly's Best Line: "Enough's enough, governor. Having a rapper who trades in violence performing at Virginia Tech insults the victims, the university, and the entire Commonwealth."

Nas's Best Line: Have you heard "Sly Fox"?

WInner: Have you heard "Sly Fox"? Nas. Hands down.

O'Reilly vs. Mos Def and Jadakiss

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Date: September 2007

Remembering 9/11 in 2007, O'Reilly hails those who lost loved ones during the tragedy… then turns on those "who continue to put us all in danger by misusing their freedom," particularly Jadakiss and Mos Def.

Mos Def and Jadakiss' Best Line: "Bin Laden didn't blow up the projects / It was you, [BLEEP]. Tell the truth, [BLEEP] / Bush knocked down the towers," from Immortal Technique's"Bin Laden."

O'Reilly's Best Line: These rappers are "the deniers, the loons who spit in the face of the 9/11 victims by saying America attacked itself on 9/11. I mean, how low is this? It's true these people are usually mentally unbalanced."

WInner: O'Reilly is at his bitter best, but Mos Def and Jadakiss don't really get a chance to respond. Called due to rain.

O'Reilly vs. Young Jeezy & Jay-Z

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O'Reilly vs. Young Jeezy and Jay-Z

Date: November 2008

The day after Barack Obama becomes president for the first time, O'Reilly and Dennis Miller try to shame Jeezy and Jay for their now-legendary inauguration eve performance of "My President Is Black." The Factor duo are offended by their racial partisanship, in the wake of Obama's post-racial glow.

"Now Jay-Z should know better," O'Reilly says. "I don't know much about Young Jeezy."

"I don't give a flying bleep what these two guys think," Miller argues. "I thought it was a beautiful day yesterday. If they couldn't ratchet down the hate for a day, then that's their problem, not mine."

Jay ignores the blather, but Jeezy is incensed, particularly by Miller referring to him as "Emphysema." ("Did you say 'Little Weezy' or something?" he'd smiled at O'Reilly.)

O'Reilly's Best Line: Dennis Miller's, in fact: "Role models in the Black community like that are about to be done in by a shooting star named Barack Obama."

Jeezy's Best Line: From "My President Is Black (Remix)": “Bill O’Reilly eat a dick, nice try / You’re really being a racist asshole in a nice tie / And tell Dennis Miller his show suck anyway / and I’d rather watch Jimmy Kimmel any day.”

WInner: Jeezy.

O'Reilly vs. Kanye West

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O'Reilly vs. Kanye West

Date: December 2008

O'Reilly deems Kanye West a "pinhead" during one of his "Pinheads & Patriots" segments. The reasons? West's "George Bush doesn't care about Black people" statement, and his "Beyoncé made the best video of all time!" diss of country singer Taylor Swift.

O'Reilly's Best Line: "He is one troubled guy."

Kanye's Best Line: Oddly, Kanye does not appear to have ever responded to O'Reilly; unique for rappers. As well, Bill subsequently names West a "patriot" when the rapper co-hosts a pro-veterans MTV special.

WInner: President Barack Obama, who, in an off-the-record comment, labels Kanye West "a jackass" for hating on Swift, and suffers no counter-hate backlash!

O'Reilly vs. Eminem

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O'Reilly vs. Eminem

Date: April 2009

O'Reilly takes issue with crude remarks by Eminem about Sarah Palin and Mariah Carey, and ridicules his "no profanity in the house" rule. (The rapper has three young daughters.)

O'Reilly's Best Line: Eminem "represents the lowest form of entertainment in this country."

Eminem's Best Line: Bill O'Reilly's "fucking hilarious."

WInner: Em: Brevity is the soul of wit.

O'Reilly vs. Common

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O'Reilly vs. Common

Date: May 2011

An invitation from the President and First Lady for Common to perform at the White House sends FOX News into high alert mode. O'Reilly leads the pack.

O'Reilly's Best Line: "This guy has sympathized with convicted cop killers. He also does the usual rap stuff, touting guns and other anti-social behavior."

Common's Best Line: "Politics is politics and everyone is entitled to their own opinion. I respect that."

WInner: Entertainment Weekly, who, while commenting on a battle of words with, otherwise, no true high points, voiced outrage at Common being attacked, describing him "as edgy as LeVar Burton." Ooooh….

O'Reilly vs. Lupe Fiasco

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O'Reilly vs. Lupe Fiasco

Date: June 2011

In a CBS News interview, Lupe Fiasco calls President Obama, and the United States of America, "the biggest terrorist." Oh, no: Bill circled that radius like a shark hungry for hemo, and had the touring rapper on his show two weeks later.

O'Reilly's Best Line: Lupe offered a free license if O'Reilly would change the name of the show to The Fiasco Factor. O'Reilly, pointed out the artist's dark shades. "Do I have to wear the glasses if I do that?"

Lupe Fiasco's Best Line: "Actually, they're prescription."

WInner: Draw.

O'Reilly vs. 50 Cent

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O'Reilly vs. 50 Cent

Date: July 2011

Annoyed by 50 Cent's support for singer Chris Brown ("He paid for his mistake assholes"), Factor guest Laura Ingraham picks at the rapper ("I just call him 'quarter'") while Bill O'Reilly invites him on the show. 50 declines O'Reilly ("O’Reilly’s views are [a] representation of someone’s grandfather's") and hits on Ingraham ("Between me and you, I’ve been rumored to be pretty well-endowed.") Hilarity has officially ensued.

O'Reilly's Best Line: Comes from Ingraham: "'He mad.' Yeah, there’s a little issue with syntax and grammar but, ya know, whatever, it’s all disposable language right now."

50's Best Line: "My tweets are national news. I get world wide coverage from my cell phone SUCKER."

WInner: 50 Cent, just off declining O'Reilly, and that "I'm pretty well-endowed" line.

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