Dick Gregory, Trailblazer of Stand-Up Comedy, Dies at 84

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He broke ground at the Playboy Club in Chicago and on Jack Paar's 'Tonight Show,' then became a potent activist for civil rights.

Dick Gregory, a pioneering force of comedy in the 1960s who parlayed his career as a stand-up comic into a life of social and political activism, died Saturday of heart failure, his rep confirmed to The Hollywood Reporter. He was 84.

"It is with enormous sadness that the Gregory family confirms that their father, comedic legend and civil rights activist Mr. Dick Gregory, departed this earth tonight in Washington, D.C.," his son Christian Gregory said via a statement from his father's rep. "The family appreciates the outpouring of support and love and respectfully asks for their privacy as they grieve during this very difficult time."

"He was one of the sweetest, smartest, most loving people one could ever know," his publicist of 50 years, Steve Jaffe, tells THR. "I just hope that God is ready for some outrageously funny times." A full statement and details of Gregory's funeral will be released Sunday, said Jaffe.

According to an Aug. 17 statement written by his son, Gregory was recently hospitalized.

Regarded as the first African-American comic to perform regularly in front of white audiences, Gregory appeared on all of the top TV talk shows of the 1960s and 1970s.

The St. Louis native cynically satirized racism and other social ills during his routines ("Segregation is not all bad. Have you ever heard of a collision where the people in the back of the bus got hurt?"). As a way to mine his always timely material, Gregory followed a lifelong habit of stripping articles out of newspapers and magazines. He rarely employed profanity in his act.

Gregory's big break came in 1961 when he was booked into the Playboy Club in downtown Chicago as a one-night replacement for Prof. Irwin Corey, a white comic who didn't want to work seven nights a week.

"When I started, a black comic couldn't work a white nightclub. You could sing, you could dance, but you couldn't stand flat-footed and talk — then the system would know how brilliant black folks was," Gregory recalled in a 2016 interview.

Playboy founder Hugh Hefner had spotted Gregory performing for a black audience, and he was paid $50 for the Playboy Club show — a huge payday for him at the time. One of Gregory's jokes: "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. Being me a whole fried chicken.'"

The crowd during that first show, mostly white executives from a frozen-food company, loved him. He stayed on at the Playboy Club for three weeks (the gig turned into three years), and the attention got him a profile in Time magazine — "Dick Gregory, 28, has become the first Negro comedian to make his way into the nightclub big time."

He was invited to perform on The Tonight Show in 1962, but Gregory said he wouldn't go unless he was able to sit down next to host Jack Paar after his routine and be interviewed. A black performer had never done that before.

"I went in, and as I sat on the couch, talking about my children, so many people called the switchboard at NBC in New York that the circuits blew out," he said. "And thousands of letters came in and folks were saying, 'I didn't know black children and white children were the same.'"

After the Tonight Show appearance, Gregory noted that his salary jumped from $250 for seven nights of work (three shows a night) at the Playboy Club to $5,000 a night. "And the next year and a half, I made $3.9 million," he said. "That is the power."

Gregory used his newfound fame to become a civil-rights activist and opponent of the Vietnam War. He made friends with Martin Luther King Jr. and Malcolm X; honored a request from Medgar Evers to speak at a voter-registration rally in Jackson, Mississippi; delivered food to NAACP offices in the South; marched in Selma, Alabama; got shot while trying to keep the peace during the 1965 Watts riots; was arrested in Washington for protesting Vietnam; performed benefit shows for the Congress of Racial Equality; and traveled to Tehran, Iran, in 1980 to attempt to negotiate the hostages' release.

Gregory ran for mayor of Chicago in 1967 but lost to Richard Daley, then entered the race for U.S. president a year later. A write-in candidate on the Peace and Freedom Party ticket, he received some 47,000 votes.

"Had I won, first thing I would do is dig up that Rose Garden and plant me a watermelon patch," Gregory said in 2016. "And it would be no more state dinners, but watermelon lunches. We'd eat watermelon and spit the seeds on Pennsylvania Avenue."

Richard Claxton Gregory was born Oct. 12, 1932, in St. Louis. Raised by his single mother, Lucille, he did odd jobs to help support his family and used humor as a defense against the neighborhood bullies.

He attended Sumner High School, then won a track scholarship to Southern Illinois University, where he ran the half-mile and received the school's outstanding athlete award. While a student, Gregory was drafted into the U.S. Army in 1954 and did comedy routines in military shows. Two years later, he returned to school after his discharge but departed without a degree.

Gregory began his professional career as a comedian in Chicago in 1958, serving as a nightclub emcee at the black-owned Herman Roberts Show Bar while he maintained a day job at the U.S. Postal Service.

After his life-altering shows at the Playboy Club, Gregory wrote a profound 1964 autobiography titled Nigger, which described his impoverished childhood and the racism he experienced. He wrote a note in the foreword: "Dear Momma, wherever you are, if ever you hear the word 'nigger' again, remember they are advertising my book."

He then played an alto saxophonist named Richie "Eagle" Stokes in Sweet Love, Bitter (1967), a story loosely based on the life of Charlie "Bird" Parker.

In 1973, Gregory stopped performing in clubs because smoking and drinking were allowed (his activism surely cost him work), and it would be more than two decades before he returned to the stage. Until recently, he was doing more than 200 shows and lectures a year.

The comedian also published a 1973 book, Dick Gregory's Natural Diet for Folks Who Eat: Cookin' With Mother Nature; founded Health Enterprises, which marketed weight-loss products; and introduced the Slim-Safe Bahamian Diet Drink Mix. He was diagnosed with cancer in 2001 but beat it.

In 2016, Emmy-winning actor Joe Morton (Scandal) portrayed Gregory in the off-Broadway play Turn Me Loose, produced by John Legend.

Survivors include his wife, Lillian, a secretary whom he had met at a club in Chicago. They were married in 1959 and had 11 children (one died at birth).