0 hour(s) and 23 minutes - Movie - 2016 On the topic of History's Greatest Gangster, the six gangsters up for consideration between Craig and the panelists - astronomer Derrick Pitts, comedian Thomas Dale and actor/comedian Joel McHale - are: Joseph Stalin; Joaquín Guzmán Loera aka El Chapo; Pablo Escobar; Lucky Luciano; Bugsy Siegel; and Al Capone. Beyond the merits of each of the six as the greatest, the panelists talks about the public fascination with gangsters as opposed to other criminals, and their own history with gangsters. They discuss whether the good each may have done should be taken into consideration. They debate if Stalin, as a political leader, should be on the list, Craig who fought in pre-production for his inclusion. They conclude the discussion with naming gangsters that did not make the list but perhaps should have.