Born in St. Louis, Missouri, United States, Gregory was one of six children who grew up poor and fatherless. His family was supported by a combination of his mother's wages as a maid and welfare benefits. Enduring taunts from other children because of his family's financial condition, he began using comedy as a way of disarming their attacks.
As described in his autobiography Nigger, the family was nearly destitute, going without necessities such as electricity and running water for extended periods of time. Despite these hardships, his mother told him, "We aren't poor, just broke. There's a difference."
As a poor student who excelled at running, Gregory was aided by high school teachers such as Warren St. James and earned a track scholarship to Southern Illinois University Carbondale.
His college career was interrupted by two years in the U.S. Army where he got his start in comedy, entering and winning several Army talent shows at the urging of his commanding officer, who had taken notice of his penchant for joking.
After completing military service, he performed as a comedian in small, primarily black nightclubs while working for the United States Postal Service during the daytime. In 1961, he was hired by Hugh Hefner to work at the Chicago Playboy Club after Hefner heard him wow an entirely white audience with the following routine:
Good evening ladies and gentlemen. I understand there are a good many southerners in the room tonight. I know the South very well. I spent twenty years there one night.
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."
Then these three white boys came up to me and said, "Boy, we're givin' you fair warnin'. Anything you do to that chicken, we're gonna do to you." So I put down my knife and fork, I picked up that chicken and I kissed it. Then I said, "Line up, boys!"
He soon began appearing nationally and on television, with his 1964 autobiography, Nigger, selling seven million copies. At the same time, he became more involved in struggles for civil rights, activism against the American War in Vietnam, economic reform, anti-drug issues, conspiracy theories, and others. As a part of his activism, he went on several hunger strikes.
Gregory began his political career by running against Richard Daley for the mayoralty of Chicago in 1967. Though he did not emerge victorious, this would not prove to be the end of Dick Gregory's dalliances with electoral politics.
Gregory unsuccessfully ran for president of the United States in 1968 as a write-in candidate of the Freedom and Peace Party, which had broken off from the Peace and Freedom Party. He won 47,097 votes (including one from Hunter S. Thompson) with fellow activist Mark Lane as his running mate, garnering more than the party he had left. The Freedom and Peace Party also ran other candidates, including Beulah Sanders for New York State Senate and Flora Brown for New York State Assembly. His efforts landed him on the master list of Nixon political opponents.
He then wrote Write Me In about his presidential campaign. One controversial anecdote he mentioned in the book was about one hundred Dick Gregory dollar bills that were circulated at Operation Breadbasket in Chicago advertising their campaign. Some were passed in cash transactions and caused problems, but gained reams of publicity.
On July 21, 1979, Gregory appeared at the Amandla Festival where Bob Marley, Patti LaBelle and Eddie Palmieri, amongst others, had performed. Gregory held a speech before Marley's performance, blaming President Carter and the political failures.
Gregory was an outspoken activist during the US Embassy Hostage Crisis in Iran. In 1980 he traveled to Tehran to attempt to negotiate the hostages' release and engaged in a public hunger strike there, weighing less than 100 lbs (45 kg) when he returned to the United States.
Gregory's education in nutrition seems dubious; in one of his cookbooks, he suggests that his readers should eat twigs because the elephant is the true king of the jungle, not the lion, and they eat twigs. Similar statements, apparently serious in nature, are also present.
However, in recent years, he has been a figure in the health food industry, becoming better known as a nutrition guru during the 1980s, advocating for a raw fruit and vegetable diet. Gregory first became a vegetarian in the 1960s, and has lost a considerable amount of weight by going on extreme fasts, some lasting upwards of 50 days. He developed a diet drink called "Bahamian Diet Nutritional Drink" and went on TV shows advocating for his diet and to help the morbidly obese. He is probably best remembered for his attempts, chronicled in the media on daytime talkshows in early 1988, at helping 1,200 pound (540 kg) Long Island man Walter Hudson drop nearly 600 pounds (270 kg) in only a few months on a liquid diet. Mr. Hudson shortly gained the weight back and later died from complications from his extreme obesity. Nonetheless, Gregory claims his diet has kept him in good health and continues to advocate for a natural diet lifestyle.
In early June 2005, during the late stages of the 2005 trial of Michael Jackson, he was invited by Jackson's father, Joseph Jackson, to advise Jackson on his health. On June 4, Gregory brought a blood-circulating machine to Jackson's house, but Jackson refused to use it. On February 26, 2006 in Atlanta, Georgia, while making a speech at Soul Vegetarian, he fainted; paramedics arrived soon afterwards.
Gregory married his wife Lillian in the 1960s, and they now have twelve children. As of 2005, he resides in Plymouth, Massachusetts.
At a Civil Rights rally marking the 40th anniversary of the Voting Rights Act, Gregory criticized the United States, calling it "the most dishonest, ungodly, unspiritual nation that ever existed in the history of the planet. As we talk now, America is 5 percent of the world's population and consumes 96 percent of the world's hard drugs," Gregory said.
He is number 81 on Comedy Central's list of the 100 greatest standups of all time and has his own star on the St. Louis Walk of Fame.
Gregory is a member of Alpha Phi Alpha, the first intercollegiate Greek-letter fraternity established for African Americans.
Gregory appears as "Mr. Sun" in the television show Wonder Showzen (the third episode, titled "Ocean", aired in 2005). As Chauncey, a puppet character, imbibes a hallucinogenic substance, Mr. Sun warns "Don't get hooked on imagination, Chauncey. It can lead to terrible, horrible things." Gregory also provides guest commentary on the Wonder Showzen Season One DVD. Large segments of his commentary were intentionally bleeped out, including the names of several dairy companies, as he makes possibly slanderous remarks concerning the alleged ill effects that consumption of cow milk has on humans.
Gregory attended and spoke at the funeral of James Brown on December 30, 2006 in Augusta, GA.
* In Living Black and White (1961)
* East & West (1961)
* Dick Gregory Talks Turkey (1962)
* The Two Sides of Dick Gregory (1963)
* Dick Gregory Running for President (1964)
* Dick Gregory On: (1969)
* The Light Side: The Dark Side (1969)
* Dick Gregory's Frankenstein (1970)
* Live at the Village Gate (1970)
* At Kent State (1971)
* Caught in the Act (1974)
* The Best of Dick Gregory (1997)
* Nigger: an autobiography, by Dick Gregory with Robert Lipsyte, Pocket Books, (Simon and Schuster), 1964. (one account says 1963) ISBN 0-671-62611-6
* Write me in!, Bantam, 1968.
* From the Back of the Bus
* What's Happening?
* The Shadow that Scares Me
* Dick Gregory's Bible Tales, with Commentary, a book of Bible-based humor. ISBN 0-8128-6194-9
* Dick Gregory's Natural Diet for Folks Who Eat: Cookin' With Mother Nature!
* (with Shelia P. Moses), Callus on My Soul : A Memoir ISBN 0-7582-0202-4
* Up from Nigger
* No More Lies; The Myth and the Reality of American History
* Dick Gregory's political primer
* (with Mark Lane), Murder in Memphis: The FBI and the Assassination of Martin Luther King
* (with Mel Watkins), African American Humor: The Best Black Comedy from Slavery to Today (Library of Black America)
* Robert Lee Green, Dick Gregory, daring Black leader
* African American Humor: The Best Black Comedy from Slavery to Today (editor) ISBN 1-55652-430-7
* "One Bright Shining Moment" (2006)
* The Hot Chick (2002)
* Children of the Struggle (1999)
* Panther (1995)
* Sweet Love, Bitter (1967)