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.