While on a trip home to support the annual festivities of the Gateway Classic Sports Foundation in 2009, comedy legend Dick Gregory stopped by a set at The Ambassador to check out a couple of rising comics who were passing through the city. The audience of 150 or so was swallowed up in the huge space, but the comics performed as if they were playing a sold-out show at Madison Square Garden.
Gregory laughed so hard his big white beard appeared to shake along with the rest of his body. During intermission, he took it upon himself to walk backstage to greet the comics – and offer a “job well done” to the duo who didn’t let the scores of empty seats affect their funny in the least. They were Kevin Hart and Tony Rock.
“Yo! Do y’all know who this is?” Rock asked at the top of his lungs, barely able to grasp the moment. “Do y’all even know? This is the cat that started it all.”
Rock then asked if Gregory would be so kind as to pose with him for a photo.
After the photo and greetings, Gregory went back to his seat to catch Hart’s set. Rock was still raving after casually running into one of his comedy idols. “I just got a picture with Dick [expletive] Gregory. Dick [expletive] Gregory came to my [expletive] show!”
It would have been easy to write off him and Hart as too young to understand Gregory’s impact and groundbreaking legacy on the genre. The reaction that night proved otherwise. His passing on Saturday at the age of 84 served as a somber reminder that the world feels the exact same way.
“We lost a king,” Tony’s older brother Chris Rock said via Instagram. “There will never be another.”
Though Richard Pryor is often credited for creating the blueprint for urban comedy as it is today, Pryor himself was quick to point out that the distinction wasn’t his to claim.
“Dick Gregory was the greatest,” Pryor told the Independent Newspaper in 2004, a year before he passed away. “And he was the first.”
He wasn’t the first black comedian. But he catapulted black humor from the “chitterling circuit” to mainstream America. The Washington Post called him “the Jackie Robinson of comedy.”
“Greg opened the door,” fellow St. Louis native and late comedy legend Redd Foxx told The New York Times in 1961. “Somebody had to be first. There’s room for all of us.”
Foxx was right. Through that door came Bill Cosby, Richard Pryor, Eddie Murphy, Martin Lawrence, Chris Rock, Dave Chappelle and Hart – who since their 2009 encounter, exploded to become the reigning comedy “it guy” and fellow St. Louis natives, Foxx and Cedric The Entertainer.
A funny bone rooted in St. Louis
Gregory sharpened his humor on the playgrounds, schoolyards and street corners of his historic neighborhood, commonly known as The Ville.
“St. Louis is where I learned everything that I’m doing,” Gregory told The American in 2011. “Everything that gets the world’s respect started here.”
He used jokes as a defense mechanism against the bullies who targeted him because of his impoverished upbringing. Born in St. Louis in 1932, he came into this world at height of the Great Depression. Everybody was poor, but the Gregory family was poorer still.
In author and Washington University Professor Gerald Early’s 1998 book Ain’t But a Place: An Anthology of African American Writings about St. Louis, Gregory spoke of the transformative moment that birthed his signature style. His childhood best friend Charles “Boo” Simmons unwittingly helped him take the first steps towards becoming a comedy pioneer.
“At first, Boo wasn’t around to help me. I’d just get mad and run home and cry when the kids started,” Gregory said in the book. “And then, I don’t know just when, I started to figure it out. They were going to laugh anyway, but if I made the jokes they’d laugh with me instead of at me.
“Hey Gregory, get your [expletive] over here,” Boo said, according to Gregory. “Want you to tell me and Herman how many kids sleep in your bed.”
“Googobs of kids in my bed, man,” Gregory responded. “When I get up to pee in the middle of the night, gotta leave a bookmark so I don’t lose my place.”
Kids from the neighborhood went from terrorizing him to becoming his first captive audience. They would crowd around him on the corner waiting for what he had come up with since the last time he held court.
“This is one of those guys so into performing that when he opens the icebox and the lights come on he ends up doing 15 minutes,” Ron Gregory joked of his big brother back in 2012.
Breaking down barriers
He moved to Chicago in the 1950s to establish his comedy career – and applied the same method of laughing at the pain of his poverty when it came to framing his material around the black American experience during segregation and the Jim Crow South.
A 1961 performance at Hugh Hefner’s Playboy Club changed his life and the course of black comedy.
“While you could sing and you could dance, you couldn’t stand flatfoot before a white audience and talk to them,” Gregory told The American in 2011. “I didn’t know that you couldn’t, so that’s exactly what I did.”
His observations elicited laughter. The punch lines lingered – and became conversation starters about the taboo topic of racism.
“What was laughable, Dick turned it into extra, extra laughable because he turned it back on the perpetrator,” Bill Cosby said in the 2012 television special “Why We Laugh: Black Comedians on Black Comedy.” “He’s very, very, very brilliant.”
One of his most recited jokes went, “The last time I was down South I walked into this restaurant and this White waitress came up to me and said, ‘We don’t serve colored people here.’ I said, ‘That’s all right. I don’t eat colored people. Bring me a whole fried chicken.’”
He became a resident performer at the Playboy Club, which landed him a spot on “The Tonight Show Starring Jack Paar Show.” Gregory became the first black comic to have a seat on “The Tonight Show” couch following a performance.
Within the year he was on top of the world of comedy – and on the cover of Time Magazine.
The following year, Dr. Martin Luther King Jr. reached out to him asking him to join the Civil Rights Movement.
“That was interesting because that’s where my spirit changed.” Gregory said. “Comedy pushed me into the movement, and through the movement I found what I was looking for.”
The biggest entertainer in comedy – and standup’s first black breakout star – immersed himself in the fight for equal rights.
“Comedy didn’t free grandma or open up jobs for men or women,” Gregory said. “All of that happened from the movement – not from a Negro getting on stage telling jokes.”
He became so committed to the cause of Civil Rights that while on the top of his game, he simply walked out of the door he kicked open – but not before delivering the brilliance of black comedy to the rest of the world.
“[He was a] True legend, trailblazing comedian and outspoken leader of the causes,” Cedric The Entertainer said. “He was tough on me (my character in ‘Barbershop’) and anybody he felt offended the culture. I appreciated him for that. He helped me see things another way.”
His love for his people and work through the Civil Rights Movement expanded to Gregory’s life’s work as a human rights activist and frontline solider against the oppression through numerous causes that continued until his final days.
“Read his books. Look him up. You won’t be disappointed,” Chris Rock said. “Unfortunately, the America that produced Dick Gregory still exists.”
