Amid plumes of cigarette smoke, iconic comedian Dick Gregory developed a distinct and sophisticated approach to addressing racism via humor. Unexpectedly finding himself entertaining an all-white audience, his unwavering commitment to his beliefs revealed a unique ability to reach across the aisle and awakened in him a passion for affecting change. As the civil rights movement intensified throughout the 1960s, Gregory would channel his celebrity to support it more directly and would remain an activist for social and political causes throughout the course of his over sixty-year-long career. In this affectionate tribute, entertainers such as Chris Rock, Dave Chappelle, Kevin Hart and Harry Belafonte describe the complex, sincere and ever-evolving personality of Dick Gregory who, after decades clouded in a legitimate anger, would find humor again before his 2017 passing.