To that end, Gregory put his life, not just his career, on the line, enduring multiple arrests and a savage beating with bats while marching in Birmingham, and being targeted by J. Edgar Hoover’s FBI as an enemy of the United States. Like many prominent individuals who got involved with the movement, he lost friends to murder, including Medgar Evers, who was shot to death in his driveway while Gregory was at home in Chicago grieving the demise of his own infant son, and Martin Luther King, pictured in photographs roaring with laughter at Gregory’s routines and listening attentively to his comments during private conversations.
Nothing that follows that section of the movie has nearly the same emotional power, so it’s questionable whether the documentary needed to spend quite as much time as it does on Gregory’s legal and financial troubles or his work as a nutritionist (which was important, too, of course, but less inherently cinematic). A good portion of the final third of “The One and Only Dick Gregory” takes so much of its structure and information from an Ed Bradley-hosted “60 Minutes” profile that it starts to feel as if you’re watching “60 Minutes.”
Despite these miscalculations, “The One and Only Dick Gregory” is a thoughtful film about a politically committed artist that doesn’t short the politics or the art, but instead examines how one fueled the other, and shows us that Gregory was always political even before he started marching for Civil Rights and becoming friends with soon-to-be-martyred heroes of the movement. Modern-day artists and surviving historical personages from the ’60s contribute deeply-felt observations on Gregory’s craft and substance, including Lipsyte, Chris Rock, Wanda Sykes, Questlove, Harry Belafonte, and Evers’s widow Myrlie Evers-Williams. Questlove, Sykes, and Rock are particularly astute, breaking down Gregory’s matter-of-fact tone and relaxed pace (a contrast to other Black comics from the period) and going deep on specific choices, such as the way he used a cigarette to time his setups and punchlines.
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