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 "BeyoncĂ© 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!