Dick Gregory - Career

Career

After completing military service, Gregory performed as a comedian in small, primarily black-patronized nightclubs while working for the United States Postal Service during the daytime. In 1961, while working at the Black-owned Roberts Show Bar in Chicago, he was hired by Hugh Hefner to work at the Chicago Playboy Club after Hefner heard him perform the following material before a largely white audience:

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!".

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.

Gregory's first TV appearance was on the late night The Tonight Show Starring Jack Paar. He soon began appearing nationally and on television.