Stream It Or Skip It: ‘The One And Only Dick Gregory’ On Showtime, A Documentary About A Pioneering Voice On And Offstage

Underneath the title card for Showtime’s newest documentary, The One and Only Dick Gregory, reads the parenthetical “(Public Citizen #1 — Comedian — Activist — Health Pioneer).” Viewers may only have known Gregory as one of those things, but the sum of his parts added up to a lot more than we gave him credit for while he was still alive.

THE ONE AND ONLY DICK GREGORY: STREAM IT OR SKIP IT?

The Gist: Dick Gregory was a trailblazing comedian, but he blazed trails in other areas of life, too. A friend who stood beside both Medgar Evers and the Rev. Martin Luther King, Jr., giving up his newly lucrative comedy career to stump for them throughout the South for the civil rights movement of the 1960s. An activist who fasted for nearly two years to protest the war in Vietnam, who ran across America to promote healthier living and eating, who developed a supplement formula that begat the powdered Slim-Safe Bahamian Diet, which he began selling and marketing in the 1980s. He eventually came back around to show business in the 21st century, living such a full life that it’s a real feat to document it all in under two hours. But filmmaker Andre Gaines was up for the task, with executive production backing from the likes of Kevin Hart and Lena Waithe.
The One and Only Dick Gregory premiered last month at the Tribeca Film Festival before making its widespread debut on the Fourth of July via Showtime.
What Movies Will It Remind You Of?: Harry Belafonte is one of the many celebrities to speak on Gregory, which should remind you to watch the 2011 documentary about him, Sing Your Song. They were on similar paths. You also could check out I Am Not Your Negro or Quincy to see how other black American contemporaries such as James Baldwin or Quincy Jones navigated the civil rights movement and their own celebrity within it.
Performance Worth Watching: Gregory, even posthumously, commands your attention no matter whether you’re watching/listening to him in the 1960s, or from interviews he gave the filmmakers in 2015. Of the talking heads, there are plenty of amazing comedians to testify to Gregory’s greatness and legacy. But perhaps the most powerful commentary comes from Gregory’s widow, Lillian, and the widow of Medgar Evers, Myrlie Louise Evers-Williams, who were closer than anyone else to recount the sheer audacity and courage it took for Gregory to do what he did at the height of his stardom.
Memorable Dialogue: The first quote Gregory gives to an interviewer in the 1960s following the title card serves as a mission statement about comedy as social justice, as he said back then: “I happen to be a firm believer. I believe that you can’t laugh social problems out of existence. And the day we find a cure for cancer, it won’t be through jokes. It’ll be through hearts and a sea of work.”

Later, looking straight into a camera, we’re confronted by Gregory essentially selling us on why we need to get involved. Er, rather, why he got involved in the civil rights movement, after Evers invited Gregory to join him for voter rallies in Mississippi. Said Gregory: “I realized if I can subject myself to go to a foreign country, lay on some cold dirt, take a chance on losing my life to guarantee some foreigner a better way of life than my own family has in America, then it’s a must that I get involved.”
Later, still, on a talk show from 1965 in which Gregory was asked about rioting in Watts, he replied:  “Nobody ever talked about Watts. And there’s going to be a whole lots of Watts all over this country up North if we don’t go in and start solving, not only the problem of the Negro, but the problem of the poor white man. You have white people that live in the ghetto.” He adds: “This is not a Los Angeles problem. Not a Mississippi problem. It’s an American problem.” If you’re unsure how relevant his philosophy remains almost 60 years later, we’re treated to split-screen footage of protests from 2014 in Ferugson, Mo., and last year in Minnesota, alongside the riots of the 1960s.
Waithe observed: “What’s overlooked is how unafraid he was to not only call white people out — but he wasn’t afraid to call black folks out.” Wanda Sykes offered: “For him, making people laugh wasn’t enough. To be out there on the front lines of the civil rights movement, he made a huge sacrifice.”
Stylistically, there’s an engaging section in which the filmmaker has Chris Rock and Dave Chappelle separately talking about how cool Gregory was onstage. Rock noted that “Chappelle and Gregory have a lot in common. Dave and Dick have this really like GOD DAMN, these motherf—ers are relaxed.” Clips of Gregory on TV in the mid-1960s, sitting on a stool, lighting and puffing on a cigarette. Yeah, that’s a look Chappelle pulls now, albeit in much more casual, custom attire. As Chappelle said: “Dick Gregory’s a real handsome guy. Could rock a suit onstage. Could smoke a cigarette onstage. There’s a few comics who could do it, look real suave when they do it. They time themselves with their cigarettes. Say a funny joke. Punchline hits. He was one of the guys that just did it.”
Sex and Skin: None.
Our Take: In fact, seeing and hearing the 30-year-old version of Gregory, either onstage solo or alongside MLK, evokes an image of Gregory as MLK mixed with Idris Elba. That smooth.
Powerfully, Gaines accessed Robert Lipsyte, who recalled being a 25-year-old sportswriter for The New York Times when Gregory didn’t fire him, as he did other writers, to help craft Gregory’s 1964 memoir, “N—er: An Autobiography by Dick Gregory.” Lipsyte had held onto the original recordings from their interview sessions, which put Gregory’s famous star-making moment in a new light. Because he was only a couple of years removed from the experience, Gregory provided such vivid details of the night in 1961 when Hugh Hefner had called him over from a “black” club to sub in for a gig Hef’s original Playboy Club in Chicago, only to learn he’d be performing for “mostly Southerners” who’d rented the room as part of their frozen food convention festivities. The manager told Gregory that Hef said it was OK if he didn’t take the stage. To which Gregory replied: “I pushed him out of the way, and said, ‘You don’t know what I went through to get here.’”
Just getting there opened the door for all future black comedians. His secret? “I noticed that once you get a man laughing with you, it’s hard for him to laugh at you. And the whole thing changed then.”
Hearing the sounds of white men laughing heartily as Gregory regaled them with jokes about how the Ku Klux Klan treated Gregory differently during bad weather, or seeing white crowds for Jack Paar or Merv Griffin fete Gregory as he joked point-blank to them and at them about what America was really like in the 1960s for a black man, it’s still quite jarring.
Even more jarring? Learning that his appearance on Paar’s program bumped his salary from $250/week to $5,000/night; then learning that Gregory essentially gave all of that up, having to cancel gigs either because he was rallying civil rights audiences in the South, or because he was serving time in jail after one of his many police arrests for joining protests. He might’ve been killed alongside Evers, if he hadn’t gotten called back to Chicago for the death of his infant son. He himself got shot in the leg during the Watts riots. The FBI tried to secretly “neutralize” him as part of the federal government’s COINTELPRO effots. He lost almost 200 pounds on a juice fast that lasted nearly two years. While running across America to raise awareness for healthy living, he called on Muhammad Ali for support, and Ali gave Gregory a personal shout-out live in the ring immediately after his bout. He quit performing club gigs in the 1970s because the drugs and alcohol in nightclubs conflicted with his public persona and message. He concocted a nutritional formula that reportedly helped John Lennon and Yoko Ono quit drugs. His formula later begat the Slim-Safe Bahamian Diet — successful, yes, but ultimately broke down due to inter-company lawsuits that almost broke Gregory. It took that infamous 2001 Roast of Hugh Hefner (the one where Gilbert Gottfried told “The Aristocrats” joke) to bring Gregory back into show business; and a small part in the Rob Schneider movie, The Hot Chick, to get Dick and Lillian Gregory health insurance again?!
None of this. Not even his anger or the mental lapses that came with aging could dampen his legacy. I’m proud to have sat with him and witnessed his legacy firsthand for a podcast in 2016, a year before he died.
Belafonte said: “If young people were to ask me what distinguished him, I would say that he shook the body politic. That he enjoyed flirting with the establishment on his terms.”
And this, from Chappelle, recognizing the weight of Gregory’s influence: “The sacrifices he made aren’t necessarily required of every artist. But there are very special people, every few generations we’re blessed with, that are willing to do that. And when you see these people, you should give them your love and respect. Protect them to whatever extent you can. And try to recognize that they’re doing something very difficult for the benefit of all of us. He set a very high bar for the people that came after him.”
Our Call: STREAM IT. Dick Gregory was both ahead of his time and of his time. It’s about time a documentary gave him his due.

Sean L. McCarthy works the comedy beat for his own digital newspaper, The Comic’s Comic; before that, for actual newspapers. Based in NYC but will travel anywhere for the scoop: Ice cream or news. He also tweets @thecomicscomic and podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.

Watch The One and Only Dick Gregory on Showtime