Keith Olbermann Keith Olbermann

"How is [Keith] Olbermann on my side of the fence (politics) but not on my side (hip hop)?" The Roots' Questlove pondered before creating his Keith O Challenge crash course. Bryan Bedder/Getty Images for MTV/Getty Images for Paley Center for Media hide caption

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Bryan Bedder/Getty Images for MTV/Getty Images for Paley Center for Media