Jon Stewart is glib. That's his act, but at the core it's just current received wisdom. It's the easiest position a person could possibly take.

I'd like to see him play the same scene on an issue that almost nobody feels comfortable about. Say the decision to use atomic weapons to end the Pacific war.

First he could call a Japanese orphaned child and ask if it seemed right and proper at the time to bomb Hiroshima and Nagasaki in order to avoid more Allied casualties in the alternate invasion scenarios.

Then, playing the counterfactual, he could call an American mother who lost her son in the invasion of Japan, for which hundreds of thousands of casualties were projected on each side, and ask if it seemed right and proper to waste her son's life when an alternative existed that would have precluded the invasion.

Stewart's approach is a garden variety example of studying the past only in order to look down on the past's inhabitants.