Rubens worked on the show from 2003 to 2006, and the bio for his upcoming book says he wrote and directed field pieces for many of the correspondents on the show at the time, including Stephen Colbert. He explained that the reason people agreed to be in the field reports despite knowing they would most likely be mocked is for exposure, though they found more people declining interview requests as the show got more popular.
Kurtz asked Ruben how he felt about wringing laughs from all the people interviewed for these segments. Ruben admitted he did not always feel good about it, pointing to a few examples of interviewees who he expected to be crazy people, but instead turned out to be really nice people. Ruben said some of his liberal friends didn’t like his column because it humanized people that didn’t deserve it.