Díck Gregory is an activist, writer and comedian who is known for his witty brand of comedy that attacks racial prejudices. He was born in 1932 and grew up poor. His college education at Southern Illinois University Carbondale was interrupted when he was drafted into the U.S. Army in 1954. It was in the army that Gregory got his start in comedy where he won multiple talent shows for it. After dropping out of college, Gregory moved to Chicago and joined the ranks of Nipsey Russell, Bill Cosby, and Godfrey Cambridge in breaking the minstrel tradition of black comedy.
During the early 1960s, Gregory worked as a postal worker during the day and performed at small nightclubs at night. He became one of the first black comedians to win widespread acclaim by performing for white audiences. It was during this time that Gregory was spotted by Hugh Hefner who gave him a job at the Chicago Playboy Club. From there, Gregory’s career took off and he appeared at venues across the country as well as on television.
It was also during the early 1960s that Gregory’s activism took off when he began participating in the Civil Rights Movement. He also spoke out against the Vietnam War, economic reform, and anti-drug issues. He ran for mayor of Chicago in 1967 and ran for President in 1968.
After his failed runs for office, Gregory became an outspoken critic of the Warren Commission which had ruled that Lee Harvey Oswald fired a single shot that killed President John F. Kennedy. He has continued to speak out about different conspiracy theories that also include the assassination of Martin Luther King Jr. Through it all, he uses he unique and brash humor to open people’s eyes to truths they may have not previously known.
The following video is a recording of a radio interview Gregory completed with Underground Railroad radio in which he discusses the the assassination of John F. Kennedy, Maya Angelou, the Donald Sterling controversy, and other events and their impact on the black community in the way that only he can.