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Why is America infatuated with its anti-heroes?

What do Andrew Dice Clay, Al Davis, O.J. Simpson and Bill Clinton have in common? Why does anybody who wants to be bad on purpose want to be like the Raiders?

What do Andrew Dice Clay, Al Davis, O.J. Simpson and Bill Clinton have in common? Why does anybody who wants to be bad on purpose want to be like the Raiders? And why do Americans who are born knowing the lyrics to Eagles songs insist on loving to hate the band?

The Daily Rundown's Chuck Todd sat down with music journalist, New York Times ethicist and self-proclaimed low culture expert Chuck Klosterman to talk about his eighth book “I Wear the Black Hat: Grappling with Villains (Real and Imagined).”

Arguing that the ultimate anti-hero is “the person who knows the most and cares the least,” Klosterman explains why he thinks Bill Clinton emerged from the Monica Lewinsky scandal a Teflon politician when Richard Nixon never could have. He considers why O.J. Simpson’s “If I Did It” is so bizarre there are no cultural comparisons, and he shares his thoughts about what modern-day bad guys can teach us about ourselves.

Watch the full interview between the two Chucks below.