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Why Questlove's 201-Song Playlist For Keith Olbermann Is Bigger Than Hip-Hop

Or, how I became the third wheel in a weekend Twitter beef over rap, culture and politics following Eminem's Trump tirade.
"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

When it comes to music history, Questlove is an Afro-pick rocking compendium of knowledge. So when the co-founder of The Roots got wind that Keith Olbermann's come-lately compliment of Eminem's Trump smackdown was couched within a tweet that seemed to dismiss the entire genre of rap, he vowed to take the progressive pundit to school.

Olbermann, whose new book Trump Is F****** Crazy (this is not a joke) came out this week, was likely just tipping his hat to a fellow anti-Trumpite when he tweeted: "After 27 years of doubts about rap I am now an Eminem fan. Best political writing of the year, period." But the host of GQ's The Resistance unwittingly revealed his willful ignorance of the genre in the process.

"You have to have your that questioned how the political commentator — with whom the five-time Grammy Award-winner often agrees — could be so culturally un-hip. "Saying you ignored rap for 27 years is basically saying you're indifferent to the very black lives you champion on your platform."

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