Date: November 12, 2003

The Moment: Dipset is not exactly the kind of rap act prominently known for its consciousness or political activism. Yet, there was Cam'ron, somehow on The O'Reilly Factor debating the social and artistic merits of hip-hop with one of the most infamous blowhards in American history, alongside Dame Dash, no less. Along for the ride was an inner-city Philadelphia elementary school principal, who objected to the chosen profession of the two men, with O'Reilly acting as mediator/instigator.

The Impact: Whoever booked this for Bill O'Reilly's deserves a special award. Let's just say the conversation got really interesting, really fast. The first words out of Cam'ron's mouth were mocking Bill O'Reilly's description of his music. Killa Cam deadpanned to the camera: "Pimping. And bitches." It only got better from there. If you desire the full effect, feel free to read along with the transcript or watch the video. Suffice to say, what happened was nothing short of amazing. Bill O'Reilly was shouted down, for one of the only times on his show, by Cam'ron in a way that, if not effective, was at the very least, hilarious. "Why don't you want to let him talk? You mad. You mad."

The Upshot: It may not have been rap's finest moment in the world of politics, but the video would quickly went viral among rap fans, Dipset fanatics, and the political media, who rarely got a look into what defeating Bill O'Reilly on his home court looked like. It wasn't the most dignified victory, but it was still an incredible one. It set the precedent for what happens when you put Cam'ron on "serious" television, until 2007, when he was interviewed by Anderson Cooper on the matter of snitching (and how, even if he lived next door to a serial killer, never would he ever).