Prince Williams/WireImage; Richard Drew/AP Photo; Taylor Hill/FilmMagic)
Christian Holub
April 20, 2017 AT 05:09 PM EDT

Bill O’Reilly’s recent termination from Fox News marks the end of an era in more ways than one. In addition to changing the face of the conservative news network, O’Reilly’s departure concludes one of the longest-running feuds of in modern pop culture: Bill O’Reilly vs. hip-hop.

During his 21-year tenure at Fox News, O’Reilly often singled out hip-hop and rappers as the target of his outrage — in 2002, he even successfully pressured Pepsi to drop an ad featuring Ludacris because O’Reilly claimed the rapper “degrades women” (never mind that O’Reilly’s recent downfall was catalyzed by revelations of his history of alleged sexual harassment). Rappers responded to O’Reilly’s ire in kind, and the conflict often created unexpected results. The most famous example is probably O’Reilly’s 2003 interview with rapper Cam’Ron and his manager, Dame Dash, during which Cam’Ron said, “you mad” — a phrase that soon became a popular meme. But even in more recent years, O’Reilly has made a great foil for rap; during Kendrick Lamar’s headlining set at Panorama last year, the rapper used footage of a mid-’90s O’Reilly meltdown as an effective backdrop. After all, while O’Reilly became a superstar on the strength of his public fits of outrage, rappers are often condemned and vilified for voicing similar levels of anger.

Take a look below at some of the best rap lines about O’Reilly over the years. Ludacris has a few, of course — but only Chamillionaire had two different O’Reilly disses on the same album.

Ludacris, “Hoes In My Room” (2003)
Lyric: “I know who let ’em in, it was Bill O’Reilly (F—-t) (Ya’ white bread, chicken-sh– n—a!)”

Ludacris, “Number One Spot” (2004)
Lyric: “Already offers on my 6th album from labels tryin’ to sign me / Respected highly, ‘Hi, Mr. O’Reilly! Hope all is well, kiss the plaintiff and the wifey'”

Killer Mike, “That’s Life” (2006)
Lyric: “Now whatcha white audience gon’ think about we / The same white audience that watch Bill O’Reilly / I saw the smirk on they face when you came at Luda”

Chamillionaire, “The Morning News” (2007)
Lyric: “Bill O’Reilly’s an idiot, he ain’t the only one with an opinion fool”

Chamillionaire, “Evening News” (2007)
Lyric: “Flavor Flav get a lot of ratings, Bill O’Reilly somewhere is hating”

The Game, “Cali N—-z” (2007)
Lyric: “Don’t call them rappers, address them as Bill O’Reilly n—-s”

50 Cent, “Smile (I’m Leavin’)” (2007)
Lyric: “Bill O’Reilly can’t stand me but his woman think I’m cute / I bet she wanna see me in my birthday suit”

Talib Kweli, “Over the Counter” (2007)
Lyric: “Questioning my teachers like ‘Oh, really?’ so they feel me / Based on fraudulent facts as they practice like O’Reilly”

Nas, “Sly Fox” (2008)
Lyric: “The Fear Factor got you all riled up / O’Reilly? Oh really? No rally needed, I’ll tie you up”

Jay Z, “Off That” (2009)
Lyric: “Please tell Bill O’Reilly to fall back / Tell Rush Limbaugh to get off my balls / It’s 2010, not 1864”

Chamillionaire, “I Know Ya Mad” (2009)
Lyric: “I-I-I know ya mad, every one of my whips is bad / Like Cam and Dash told Bill O’Reilly — ya mad”

Lupe Fiasco, “All Black Everything” (2011)
Lyric: “Malcolm Little dies as an old man / Martin Luther King read the eulogy for him / Followed by Bill O’Reilly who read from the Qu’ran”

Tyler the Creator, “Radicals” (2011)
Lyric: “Random disclaimer: Hey, don’t do anything that I say in this song, okay? It’s f—in’ fiction / If anything happens, don’t f—in’ blame me, white America / F— Bill O’Reilly”

Kirko Bangz, “So Playa” (2011)
Lyric: “Bill O’Reilly plain sinner / A Factor with a pencil so clear Stevie Wonder get the picture”

R.A. the Rugged Man, “Shoot Me in the Head” (2013)
Lyric: “Bill O’Reilly he would hate my guts, so what?”

Vic Mensa, “Go Tell ‘Em” (2016)
Lyric: “‘Cause even Bill O’Reilly daughter out here drinkin’ Ciroc / Now that’s what I call the 21st Century Fox”

Nicki Minaj, “Down in the DM (Remix)” (2016)
Lyric: “He said, ‘Kylie, wuss good?’ I said, ‘Miley, wuss good?’ / I said, ‘Could you pay my bills, like O’Reilly? Wuss good?'”

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