History's Biggest Douchebag

On the topic of History's Biggest Douchebag, the six people up for consideration between Craig and the panelists - film historian Leonard Maltin, comedian Echo Kellum and actor Kal Penn - are: Thomas A. Edison; Anthony Weiner; Marge Schott; Bernie Madoff; Donald Trump; and Martin Shkreli. Craig defines the pop cultural term "douchebag" for this context, the term which is meant to imply a bad person, not "Hitler" bad, but someone one would probably not want to be associated with while standing outside the Pearly Gates waiting for judgment. The panelists largely talk about the merits of each of the six as the biggest douchebag by talking about the many and varied exploits of the six which made them all douchebags. They discuss whether the good any of them have done unselfishly for others, like provide meaningful and often well-paid employment, should count in their favor. Because of his current run to become President, Trump is placed in a different standard than the rest. At one point, Craig unilaterally decides to give up control of the decision making, deferring specifically to Echo and Kal for a specific reason. They conclude by talking about the douchebags that did not make the list but perhaps should have.