Dick Gregory’s big break almost didn’t happen. The national press was buzzing over his killer 1961 performance at Chicago’s Playboy Club, where as a last-minute substitute he played before an audience filled with white Southern food executives. Gregory handled the heckling with ease, told political jokes and even won the crowd over. Afterward, as Gregory recalled decades later, he expected a call from “Tonight Starring Jack Paar,” a show he had watched without fail for five years.