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.