Showtime's "The One and Only Dick Gregory" pays tribute to the legend who left comedy for activism

At one point, the entertainer "was making more money than Frank Sinatra. But Gregory was giving the money away"

Published July 4, 2021 2:30PM (EDT)

Dick Gregory in "The One and Only Dick Gregory" (John Bellamy/Courtesy of SHOWTIME)
Dick Gregory in "The One and Only Dick Gregory" (John Bellamy/Courtesy of SHOWTIME)

Dick Gregory was a groundbreaking comedian who spoke truth to power. He used humor as a way of calling attention to politics and social issues. Andre Gaines' terrific documentary, "The One and Only Dick Gregory," debuting on Showtime on July 4, shows Gregory's activism was more important to him than his comedy and wealth. In 1962, he went to Mississippi to help Medgar Evers with voting rights. "He could have sent a check," someone in the documentary acknowledges, but Gregory put in the time and money to assist others — even at the expense of raising his family. 

"The One and Only Dick Gregory," traces the comedian's brilliant career from his groundbreaking set in 1961 at the Playboy club in Chicago — performing for a white, Southern audience, no less — and his appearance on "The Jack Parr Program," which generated a big salary bump. He gained considerable fame and success but stopped performing to work for social justice in the civil rights movement. He was frequently jailed and spoke out against police brutality, the Vietnam war, and was under surveillance by the FBI

Later in life, Gregory reinvented himself yet again. He went on a fast (and lost nearly 200 pounds) to advocate about obesity, hunger and inequality. He eventually became an entrepreneur, developing the Bahamian diet, and working on weight-loss products while also advocating for vegetarian and vegan diets.

Gaines recounts all this and more (but not Gregory's run for president) in "The One and Only Dick Gregory." The film uses interviews, archival footage, film clips, and commentary by Chris Rock, Lena Waithe, Wanda Sykes, Harry Belafonte, and others. Gaines spoke with Salon about the legendary comedian and activist, and what he learned from Dick Gregory during the recent AFI DOCS festival. 

Where did you first see Dick Gregory? What do you recall about him? 

I was child of the '80s, and Dick Gregory had this Bahamian diet, which was the answer to Slim Fast, and was a slim-slow system. Pretty much every Black family had this shake — it was a powder that you mix with juice or water — and he was doing a multi-level marketing thing. It was super-popular, and mentioned in "House Party," and "Martin" and "Seinfeld." That was my first introduction to him — as a drink. I didn't know hm as the contemporary comedian of my youth. That was Bill Cosby and "The Cosby Show." I knew about Richard Pryor, and Eddie Murphy. It was comedy we were not allowed to listen to as kids. 

Later in life, as an adult grad student at NYU film school, I discovered Dick Gregory as this comedian and a precursor to Bill Cosby and Richard Pryor. Their styles were sort of ripping off this guy. I fell in love with [Gregory's] work. In 2008, when Barack Obama first ran for president, there was something called "State of the Black Union," which was an annual symposium of America's best Black thinkers, politicians, academics, etc. that would get together and discuss the state and condition that Black America was in. Dick Gregory was on this panel, and he brought the whole house down. He was incredible. Really, really funny, poignant, heartfelt and, at the same time, hilarious. He had an incredible gift and technique and skill. He was able to outshine everyone on that panel, and I thought I've got to make a movie about him. 

So, you didn't you know his whole story when you started the project? What did you learn from immersing yourself in his life? You didn't even get to his running for president. 

Yeah, we had to take that [running for president] out. The funny thing is that so many people who knew Dick Gregory, and felt that they knew his story, were amazed by what they didn't know after watching our film. That was really astounding to discover. Even his own children didn't know all of the facets of their father's life. A lot of people, including his colleagues, managers, agents, and publicists did not know every facet of Dick Gregory's life.

Obviously, it was such an enormous burden to try to adequately tell this story in a single film. Had I known the vastness of Dick Gregory's life I might not have volunteered to do this project. I was fascinated with the man. I loved him. He was an incredible mentor and a brilliant, brilliant mind. And he was fun to be around. He would curse you out, then tell a joke and embrace you, and ask you how your family was doing all in the same breath. It was a joy to be around him and get to know him. But the heavy lift, and the complicated nature of his many lives — which we couldn't adequate cover in two hours — was really complex. 

How did Gregory inspire you, or influence your behavior?

When you look at a life like Dick Gregory's — but there really was no other life like Dick Gregory's; he was the one and only Dick Gregory, which is why we named the film that — you think, Man, I need to do more. Most of us are preoccupied with a slew of mundane tasks on a daily basis, responding to email and social media. Our lives are occupied with us staring down at a phone and considering that as getting something done. But the reality is that there is so much more than you can do to make a difference. Take one of Dick Gregory's lives, or the subset of one of those lives, and use that as tool or a blueprint for yourself. He inspired me not just as a storyteller, but as a man, particularly as a Black man in America, to spend my time doing a lot more. He inspired me to do and was impressed upon when first meeting him, was being concerned with the lives of others. 

There is a line Gregory has in the film about the true test of a man is to strip away everything he has to see his real worth. It was as if he was foreshadowing what would happen to him. What observations do you have about his highs and lows? 

When you look at most of these stories, when it relates to entertainers making a lot of money and losing it, it has to do with an accountant or an agent or manager ripping them off and having them sign contracts that are not in their favor. Or when you hear stories of musicians or comedians, you hear about them taking their millions and squandering their money on drugs, or alcohol, or addictions to gambling or women, or whatever vices that they had. Dick Gregory is none of that. The uniqueness of his story is that he could have gone on and continued to make millions of dollars. At the time, he was making more money than Frank Sinatra. But Gregory was giving the money away. His mismanagement of it as a businessman had more to do with the fact that he didn't put value in the money he was making. The value was for the sacrifice for the movement. He wasn't squandering it in scandalous vices, like drugs, alcohol, gambling or women. He was literally giving it away. 

Because he was going down to these marches and protests in the South, that meant that the gigs he had booked anywhere in the world were being lost. They filled those [gigs] with Bill Cosby and Richard Pryor, so literally by Gregory abandoning his career to fight for the movement, he's launching the careers of these titans — comedians who went on to open the doors for Eddie Murphy, Dave Chappelle and Chris Rock. His sacrifices were noble, but they did have consequences in his personal life, and his family life, and his pocketbook.

I was impressed how magnanimous Gregory was. Do you think he always operated in everyone's best interest? He helped the cause — but at what cost? The FBI was after him. 

We formulated, as a filmmaking team, a narrative question that we would theoretically answer in the film: What did it cost him? When you talk to a lot of these comedians and entertainers — Chris Rock, Nick Cannon, etc. — they appreciated and accepted the noble sacrifices that Dick Gregory made. But pretty much anyone you talk to, is not willing to make that degree of sacrifice themselves. Dave Chappelle says it best at the end of the film. It's a level of sacrifice that is not always required of every artist, but when you see people who do that, you have to praise them and give them as much respect, and honor, and attention as you possibly can to say thank you for what they did so we can enjoy the luxuries that we enjoy now. Dick Gregory stands alone as the one entertainer who abandoned it all and stepped away from it entirely to fight for the movement. We pay homage to that. And reiterating what I was saying about the consequences, something is going to be neglected. You can't give 100-150% of yourself to any one thing without something falling apart to some degree. Without his wife Lilian there as the cornerstone of the family, Dick Gregory would not have been able to be the man we know and see in this film. 

Likewise, there are certainly parallels drawn in the film between then and now. You contrast the Los Angeles riots and other scenes of unrest with Ferguson and Minneapolis. Things have not changed enough in Dick's lifetime. How do you think we are continuing the fight that Gregory started? 

He would often say to me that the universe is cyclical. What's past is prologue and what is present is what we are going to see in future. He would always laud the progress that we made and felt that not acknowledging the progress we made is a disservice and disrespectful to the freedom fighters who got us here in the first place, himself included. What I wanted to do as the director was really show the parallel of what he was saying as far back as 1963 to what we are dealing with now in 2020 and 2021. "The fight just continues," he would always say. It is a fight that is going to continue, and what we have to do is follow the path of our ancestors, but also look toward the future and try to understand how to rectify some of the mistakes of our past.

He would say America is a country with no mother. Your mom would clean out your ears, and nose and wash you up and put you in a new suit and send you out into this world. But America is this place that has no Mother. It has never cleaned up the filth of its past. It just put on a new suit and went out to the world still covered in the same stink that it had from the past. It is our job to shed light on that and clean it up and create a better future for our kids That was inspiration, that so many folks in the industry, entertainers, and activists now see this as call for action. 

Your film creates a legacy for Gregory. Some folks remember him for his humor, others for his activism, and others for being an entrepreneur and his advocacy. He was always in someone's eye, but he had different impacts. What was your agenda?

That was not the impetus to start the film, but it was definitely the motivator to finish it. He had not gotten his due. There were several filmmakers who attempted to tell his story over the decades, and they were not able to find the financing. My company, Cinemation, self-financed it until Showtime purchased it. For a lot of these filmmakers, they were not able to pin down this story because it was still a work in progress. So, it was hard to find an ending. It was the right place, right time for me, but once I started to lift up the hood and talk to these other filmmakers and talk to entertainers and comedians, from Judd Apatow and Bill Maher, and Rob Schneider, and Lawrence O'Donnell to Chris Rock, W. Kamau Bell, and Dave Chappelle, that love this man — and considered him a guru and mentor and provided a road map for their careers — I realized how much impact that he had on everyone. It was my duty to get this to the finish line.  

I was inspired by his need to perform at the Playboy club — that he worked too hard to get here to turn this gig down. If he had walked away, he wouldn't have the career he did. 

It was a metaphor for his life. He was kind of this "celebrity celebrity." When you talk to celebrities, the "celebrity celebrity" they all talk about is like, Michael Jackson, who was larger than life. But Michael Jackson called on Dick Gregory and deferred to him. Muhammad Ali deferred to Dick Gregory and his guidance and the influence that he had. They reached out to him when they needed spiritual or nutritional support, or to get off drugs, or get their health back. He was this "celebrity celebrity." There is a story we couldn't put in the film about the first time Nelson Mandela met Dick Gregory, and Dick Gregory was bowing to Nelson Mandela, and he instead, turned around and bowed down to Dick Gregory and kissed his feet. This story about how somebody like Nelson Mandela would have a degree of deference for what Dick Gregory provided to this world is a testament to the power of what it is that Dick Gregory imbued upon the sacrifices he made for the rest of us.

"The One and Only Dick Gregory" airs Sunday, July 4 at 9 p.m. on Showtime.

By Gary M. Kramer

Gary M. Kramer is a writer and film critic based in Philadelphia. Follow him on Twitter.

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Andre Gaines Dick Gregory Interview Movies Showtime Stand-up Comedy The One And Only Dick Gregory