Dick Gregory, long time civil rights activist, writer, social critic, and comedian, talks to the crowd at the 16th annual Tampa Bay Black Heritage Festival, MLK Leadership Luncheon in Tampa, Fla. on Jan. 20, 2016.
Scott Keeler—Tampa Bay Times/AP
August 24, 2017 6:29 AM EDT
Smiley is host and managing editor of Tavis Smiley on PBS and author of 50 for Your Future: Lessons From Down the Road

Dick Gregory was one of the freest black men I have ever known.

For American blacks of Gregory’s generation, freedom took some figuring out. But Gregory, who died Aug. 19 at age 84, knew that real freedom can come only from real truth. Sometimes he masked the truth with a joke, but you were always going to get the truth.

Gregory once told me about the time Martin Luther King Jr., with a tear in his eye, told Gregory that he knew he was soon going to die. Gregory, trying to lighten King’s load, shot right back, “Better you than me, Martin!”

But Gregory didn’t just tell jokes, he fought for justice. He was loved and respected by the lions of the civil rights movement because he wasn’t afraid to tarnish his brand by getting arrested right alongside them. There were many days he went fresh from his jail cell straight to the stage. And killed.

In so doing, he won the affection of black America and the respect of white America and somehow managed to make us all laugh.

Smiley is a TV host and author

This appears in the September 04, 2017 issue of TIME.

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