Comedian Kevin McCaffrey was one of the first established comedians that Will met at his job as a doorman at the Laughing Devil Comedy Club. He talks to Will about the joy of getting passed at your first comedy club in NYC, growing up in the suburbs of Chicago as the oldest son in a single parent house, Hosting a radio show in High School, Getting crowds in red states to laugh a political material that they disagree with, and what performing on the Late Show with David Letterman meant to him growing up as a fan, former NBC page, and what the experience taught him about writing and performing comedy.