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Dick Gregory's unapologetic comedy helped shape American conversations on race and activism

Gregory, who died this weekend, was a prime example of the power and necessity of political comedy.

Humorist and activist Dick Gregory
Humorist and activist Dick Gregory at the Roger Ebert Memorial Tribute on April 11, 2013 in Chicago, Illinois.
Timothy Hiatt / Getty Images

Humorist-activist Dick Gregory was a man of many words whose fighting spirit helped transform conversations and action around race and justice in an often divided and discriminatory America.

Gregory — who died of heart failure on Saturday, August 18, at the age of 84 after a decades-long career in comedy — was known for his off-the-cuff, no-holds-barred humor. He could captivate any crowd with his cool but passionate demeanor and keen, often unsettling observations, which focused on everything from the Ku Klux Klan to Michael Jackson, a poor black man who grew up “to be a rich white man.”

For one joke, Gregory recalled walking into a restaurant and being told that they “don’t serve colored people.” “Well,” Gregory replied, “I don’t eat colored people.”

His career took shape during the civil rights era, a topic that remained at the center of his comedic identity throughout his life. Breaking out in the 1960s after catching the eye of Hugh Heffner, Gregory became one of the first black comedians to cross over into the white circuit, enduring racist jeers and insults with dignity and disregard — a response he practiced at home with his wife, who rather reluctantly hurled those same words at him to help him prepare.

During that time, Gregory made an unprecedented visit to Tonight Starring Jack Paar in 1961. After initially refusing to appear on the show, he accepted Paar’s offer to perform under a seemingly simple yet groundbreaking condition: Gregory would only perform if he could sit on Paar’s couch after his routine. Gregory’s appearance on The Tonight Show marked the first time a black performer had ever graced those late-night cushions.

He openly refused to shy away from stinging subjects, but often reminded people that humor was not enough. “Humor can no more find the solution to race problems than it can cure cancer,” Gregory said. “We didn’t laugh Hitler out of existence.”

In a time when dissenting opinion on race and discrimination could put a literal target on your back, Gregory wasn’t just peddling funny. He said it like he saw it, and then he did it, marching for voting rights and performing at benefits for civil rights groups. He was even shot in the leg while serving as a peacemaker during the 1965 Watts riots in Los Angeles.

It was moments like those — earnest calls to put humor and pleasantries aside when the occasion called for more — that helped make his work onstage that much more resonant.

As Gregory got older, he took some of that biting wit to the stage in a different way, doing panels at festivals and talks to college audiences about his career, his interests, and the evolving face of racism. (He also increasingly dabbled in nutrition theory and conspiracy theories about the long-reaching arm of “the system.”) His life and his work unapologetically ran the gamut, and his panel talk during the 2010 Chicago Humanities Festival is a near-perfect example of the unique and definitive nature of his work.

At one point during the talk, Gregory addressed an audience question about a Southern judge who refused to marry interracial couples, and his response epitomized the comedian and activist’s unyielding but purposeful honesty.

“He didn’t resign,” Gregory told the audience. “He embarrassed the whole state and the whole nation.”

He continued:

There’s a whole lot of things that embarrass us. ... This is not just some thug on the corner. This is a judge — with that attitude. But whole lots of Americans got that attitude, and we tolerate it because you can hide your feelings. You don’t have to come out. ... Once you flush it out, he’s not the only one. Suppose he would have gone on and married them. He still would have felt that way. ... That’s why we got to work to flush this whole thing out.

Gregory’s approach both subtly and unsubtly forced America to look at itself in the mirror and reckon with its ugly side. His life and career were a fine example of the power of speech, and the most ordinary man’s ability turn words into action.