Gregory is an influential American comic who has used his performance skills to convey to both white and black audiences his political message on civil rights. His social satire helped change the way European-Americans perceived African-American comedians since he first performed in public.
As a poor student who excelled at running, Gregory was aided by teachers at Sumner High School, among them Warren St. James. Gregory earned a track scholarship to Southern Illinois University Carbondale. There he set school records as a half-miler and miler. His college career was interrupted for two years in 1954 when he was drafted into the U.S. Army. The army was 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 Gregory's penchant for joking. In 1956, Gregory briefly returned to SIU after his discharge, but dropped out because he felt that the university "didn't want me to study, they wanted me to run".
In the hopes of performing comedy professionally, Gregory moved to Chicago, Illinois, where he became part of a new generation of black comedians that included Nipsey Russell, Bill Cosby, and Godfrey Cambridge, all of whom broke with the minstrel tradition, which presented stereotypical black characters. Gregory drew on current events, especially racial issues, for much of his material: "Segregation is not all bad. Have you ever heard of a collision where the people in the back of the bus got hurt?".
This routine caused a direct request from publisher Hugh Hefner and he was booked as a replacement for the white comedian Professor Irwin Corey. Until then Gregory had worked mostly at small clubs with predominantly black audiences.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 giving you fair warning. 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!"
Gregory's first TV appearance was on the late night The Tonight Show Starring Jack Paar. He soon began appearing nationally and on television.
Gregory is number 82 on Comedy Central's list of the 100 Greatest Stand-ups of all time and has his own star on the St. Louis Walk of Fame. There is a grassroots effort afoot to get him a star on the Hollywood Walk of Fame, spearheaded by Radio One host Joe Madison.
Gregory is a member of Alpha Phi Alpha fraternity.
He was a former co-host with radio personality Cathy Hughes, and is still a frequent morning guest, on WOL 1450 AM talk radio's "The Power", the flagship station of Hughes' Radio One. He also appears regularly on the nationally syndicated Imus in the Morning program.
Gregory appears as "Mr. Sun" on the television show Wonder Showzen (the third episode, entitled "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 made potentially slanderous remarks concerning ill effects that the consumption of cow milk has on human beings.
Gregory attended and spoke at the funeral of James Brown on December 30, 2006, in Augusta, Georgia.
Gregory is an occasional guest on the Mark Thompson's "Make It Plain" Sirius Channel 146 Radio Show from 3pm to 6pm PST.
Gregory appeared on The Alex Jones Show on September 14, 2010, and again on March 19, 2012.