“Why Are You Making a Film About Dick Gregory?”

Andre Gaines grapples with what drove him to direct his documentary about the iconic comedian and activist, which is now airing on Showtime.

For six years, my producer Valerie Edwards and I worked on The One and Only Dick Gregory, a documentary about the legendary comedian, activist and health pioneer. For six years, people would ask me, repeatedly and constantly, “Why are you making a movie about Dick Gregory?” I would always respond with some explanation, but honestly, I did not have an answer. I kind of still don’t.

For a good three years, our film didn’t even really have a name. We considered calling it The Black Survival Guide, and then it became How to Survive in America, both of which were direct reactions to the era we were living in six years ago. People have short memories, but 2015 was a lot like 2021, minus the pandemic. We were surrounded with a lot of Black death.

Andre Gaines with his producing partner Valerie Edwards.

Less than a year before I started filming Dick Gregory in 2015, Mike Brown was killed by a police officer in the middle of the street. By the time we actually flew Dick Gregory out to Los Angeles to sit him down in front of a camera and let him talk, Eric Garner had been choked to death by New York City police while crying out the words, “I can’t breathe.” Fast forward to June 2020, and George Floyd would say the same thing before he too was killed by the police.

The last six years was a strange time, and as a producer back in 2015 (I had not yet stepped into the director’s chair), I felt obligated to use my platform to amplify the history and struggle of Black survival in America, and there was no better central character to elucidate this point than Dick Gregory. He was one of the few historical figures who not only survived the turbulent 1960s, but thrived – and did it all while cracking jokes.

To make the film, though, I had to finance it myself, because for five years I struggled to find anyone else who cared enough to invest. When we first announced the project to the industry, two major filmmakers reached out to me saying that they too had tried to make a film about Dick Gregory in decades past, but could not get it off the ground because of lack of funding. Dick Gregory was just not “popular” enough, it seemed. In fairness, if someone else had pitched this film to me – with such a long return on investment – I would have likely passed on it too.

Andre Gaines meeting Dick Gregory at the airport.

However, I always came back to that question, “Why are you making a movie about Dick Gregory?” Even though I still didn’t have an answer, there was something special about this project. Something unique that I could not quite put my finger on. Dick Gregory, the man, was transcendent. Historically speaking, he was a giant. In real life, he was much shorter in stature than I’d imagined, weighing maybe all of 150 pounds soaking wet, with a stark white beard that seemed like it nearly reached his belly button. His attitude and personality were a mix of aggressive and deferential; he regularly asked me, “How’s the family?” as if he personally knew my mother and father, which made me feel comforted, loved and warm.

There were tons of other projects I could have chosen to make as my directorial debut. Given how long this project took to make, I could have likely directed two or three narrative films instead. In fact, I produced four fiction features in that time span! Furthermore, the subject himself was extremely difficult. Not only was Dick Gregory 80 years old, he was cantankerous and angry, and suffering from an insidiously slow form of dementia that fueled both of those negative personality traits, keeping me and my team on edge most of the time. Yet he had lived a life filled with the ups and downs usually found only in adventure novels, where authors would have to make things up to merely rival this man’s true-life story – like shaking hands with presidents, then serendipitously dodging multiple assassination attempts, running across the country (twice), starving himself for social experimentation more than 65 times, getting celebrities like Marvin Gaye, John Lennon, Yoko Ono, Charlie Mingus and Michael Jackson off drugs, then selling the same formula to the public for millions. His story reads like fiction, and that’s not even the half of it.

Andre Gaines interviewing Dick Gregory.

He had also met, talked to, had dinner with and even gone on vacation with some of the world’s most iconic figures, such as Nelson Mandela, Bill Clinton, Oprah Winfrey, Muhammad Ali, Michael Jackson – and he was seemingly somewhat annoyed at having to answer questions about his life from some young unknown producer in a random Hollywood hotel. He even went so far as to say that if we were as smart as we pretended to be, he wouldn’t have to sit there and talk to “all you cute people,” which was the first time in my life I could remember being so thoroughly insulted with a compliment.

After my first day of filming Dick, which was disastrous, I remember thinking, “Why the hell am I doing this?” The same film that sat for three years without a name could have easily been titled that night as, Dick Gregory: Fuck You!

“He was one of the few historical figures who not only survived the turbulent 1960s, but thrived – and did it all while cracking jokes.” (Image via Showtime.)

I prayed that night. I was already fasting in preparation to film this titan, and out of all of the bad things that happened that day, fasting was the one topic over which Dick and I bonded. “You don’t need all that food,” he said to me, after I mentioned how much energy I had. On day two, we regrouped and I realized that part of Dick’s annoyance was the size of the audience. It was too small! We had a crew of only 15 people, and we were all very serious, as filmmakers tend to be. Everyone has to be silent on set. That room was not conducive for a comic who was used to noise. So when I asked Dick to directly address the camera instead of talking to me, his audience multiplied into millions. “Talk to the world,” I said to him. “Not to me.” Suddenly, he was his old self.

Although filming was back on track, I still did not have an answer to the burning question of why I was making this film, neither when people asked me, nor when I asked myself. Maybe part of it is my nature. When I start something, I have to finish it, no matter how painful, or risky, or ill-advised it might be. Some people call that persistence. Others call it being a glutton for punishment. I guess it is a little bit of both.

I did know, however, where the spark of the film had come from. In 2008, when Barack Obama first ran for president, I saw Dick appear on a program called the State of the Black Union. It was an annual forum where Black leaders, entertainers, politicians and ministers would gather in front of a large audience to talk about the condition of our people. Dick was on the panel that year, and he was astounding. Mesmerizing.

Dick Gregory talking to Andre Gaines during the making of The One and Only Dick Gregory.

Just like on our film set that first day, everyone on that panel was very serious. The other speakers were philosophical and, at times, self-righteous. But Dick was just there enjoying himself, dressed in a sweater vest and an oversized gray striped blazer. After our best and brightest leaders had droned on and on about what we needed to do to save our community, the moderator finally called on Dick, who said: “First, let me forget the intellectual stuff right now – which I love – and I’ve got to get down to some personal business, which you’ll probably find out about after we leave here …” He then proceeded to break into a routine he had clearly written down while waiting for his turn.

His performance was miraculous – poignant and hilarious at the same time. When I talked to comedians about it, like W. Kamau Bell, or even Chris Rock or Kevin Hart, they considered Dick’s performance on that stage as one of the greatest comedy sets of all time. I was hooked, but it would not be until 2015 that I would finally have the time, the resources and the confidence to make a movie about the miracle I had witnessed on that stage.

Not less than 48 hours after our bumpy start to filming, Dick and I became friends, and remained so until he passed away in 2017. I received a lot of condolences when he passed away from people who knew I was working on a film about him, and who were reaching out to me almost to say, “Sorry it’s over.” I considered it, but only for a moment, all while the bigger question remained, “Why am I making a film about Dick Gregory?”

Dick Gregory (October 12, 1932 – August 19, 2017).

Maybe it was because he meant so much to the world, even when there was a 50-50 chance that people knew who he was, when asked. Maybe it was because we’d get a lot of pats on the back and recognition for completing something no one else could. Maybe I am a glutton for punishment, like some people say. Or maybe, just maybe, it was the same reason Dick Gregory left comedy to become a full-time activist: It just felt right.

Now that the film’s completed and out in the world, I’m left with both satisfaction and sadness. Satisfaction, because Dick Gregory finally got his due, and I have people calling to tell me that they’ve watched the movie two, three and four times. Sadness, because when you’re with something for so long, as I’ve been with this film, there’s always something to look forward to. My producer Valerie said it was like giving birth to a grown man who wouldn’t leave the basement. Maybe I’m just an empty nester.

All images courtesy of Andre Gaines, unless otherwise stated.

Andre Gaines is a director, producer and financier based in Los Angeles. Through his company Cinemation Studios, Andre has produced or financed the HBO series The Lady and the Dale with Mark and Jay Duplass, Spike Lee’s Da Sweet Blood of Jesus, the SXSW winning documentary Bill Nye: Science Guy for PBS’s POV and Netflix, the remake of Stephen King’s Children of the Corn, and the award-winning animated feature The Immortal Warrior starring Rodrigo Santoro for Amazon. He made his feature film debut at the Tribeca Film Festival 2021 with the highly anticipated film The One and Only Dick Gregory, about the legendary comedian and activist,, which premiered on Showtime July 4, 2021. Andre and his wife Lauren are the parents of two young boys, Julian and Wesley. He can be found on Instagram @andrelgaines.