In a remarkable article from October 1960, Ebony magazine asked why there were no Black stars in comedy, blaming racist double standards held by audiences and television bookers as well as a new sensitivity (the term “politically correct” had not been coined) that wouldn’t tolerate performers trafficking in stereotypes from the minstrel era. Three months later, Dick Gregory, mentioned briefly as a “newcomer,” made the question irrelevant in one night.
When the manager at the Playboy Club in Chicago discovered the crowd was made up of white Southern businessmen in town for a convention, he suggested that Gregory postpone. The comedian refused, went onstage and killed. He did so well, his contract there was extended, and led to national press and an appearance on “The Tonight Show.” Gregory became a crossover star, a pioneering comedic social critic who inspired a generation of stand-ups.
“The One and Only Dick Gregory,” an aptly titled new documentary, does justice to this fabled performance, setting the scene and the stakes. But what stands out most about this revolutionary moment in comedy is what a small role it plays in the overall portrait here. Gregory, who died in 2017, lived so many lives that he presents a challenge for anyone trying to document them. The director Andre Gaines tries to capture as many as possible, to a fault. By covering so much ground, it doesn’t have room to dig too deep. But along with some very funny footage of a master of his craft, it offers a convincing argument that while Gregory became famous for his comedy, what made him such a riveting cultural figure is what he did after he left it behind.
Gaines recruits a talent-rich cast of comics (Wanda Sykes, Dave Chappelle) to describe the performer. Chris Rock is particularly insightful and blunt, comparing Gregory’s relaxed, patient, cigarette-wielding delivery with that of Chappelle. Gregory was ahead of his time in his material on police brutality and racism, but just as he became a star, his activism heated up. A demonstration for voting rights in Mississippi was a turning point, and the movie covers his work and relationships with the Rev. Dr. Martin Luther King Jr. and the N.A.A.C.P. leader Medgar Evers. By the 1980s, Gregory had stopped playing clubs and became an early health and wellness guru while still waging a broad array of political fights, going on fasts and long runs to earn attention for causes like fighting hunger and obesity.
There’s clearly a price to pay for living as active a life as Dick Gregory did. He was rarely home to see his family (his kids are astute talking heads), and toward the end of his life, legal troubles led to financial collapse and the loss of his home. The last half-hour is jarringly downbeat if slightly underexamined, with Gregory returning to clubs and appearing in a Rob Schneider movie, “The Hot Chick,” that allows him to get much-needed health care coverage.
The legend of Dick Gregory gives way to a peek of him as a more complex man, albeit one much funnier than most everyone else. On the reboot of his talk show, Arsenio Hall asked him what drove him. Gregory retorted: “My bills.”
The One and Only Dick Gregory
Not rated. Running time: 1 hour 53 minutes. Watch on Showtime platforms.