I've Got To Be A Colored Funny Man, Not A Funny Colored Man...,

WaPo |  Mr. Gregory ran for mayor against Daley in 1967 and for U.S. president in 1968 as a write-in candidate with the left-wing Freedom and Peace Party, campaigning against what he saw as rampant political corruption in the two major parties. 

Mr. Gregory said he was appalled that the Democratic Party would host its national convention that year in Chicago, a city where black demonstrators were regularly brutalized by the police. The convention drew a large contingent of white anti-Vietnam protesters, and the outbreak of violence that ensued prompted Mr. Gregory to take mordant glee in the melee. 

“I was at home watching it on TV, and I fell on the floor and laughed,” he told GQ magazine in 2008. “My wife said, ‘What’s funny?’ And I said, ‘The whole world is gonna change. White folks are gonna see white folks beating white folks.’ ”

Increasingly inclined to believe conspiracy theories, he was once arrested for attempting to wrap yellow “crime scene” tape across the front gates of the CIA, for what he alleged was the spy agency’s involvement in distributing crack cocaine in inner cities.

Like Muhammad Ali, “who always thought of himself as more than a boxer, Greg always considered himself more than a comic,” New York Times sports columnist and Gregory biographer Robert Lipsyte told the London Independent in 2004. “Both men suffered enormously for their political convictions. But unlike Ali, Greg was conscious of his role from the beginning. He knew that his presence at Southern demonstrations would save lives, even if it killed his career.”

He caught a break in 1961 when Hugh Hefner requested that the comedian perform one night at Chicago’s Playboy Club to substitute for Irwin Corey, who had canceled at the last minute. 

As Mr. Gregory told it, when he arrived at the club that night, he was stopped by the manager. The man feared an especially hostile audience — a convention of white Southern frozen-foods executives.

Mr. Gregory strode onto the stage anyway and grabbed the microphone. A heckler quickly stood up and threw out a racial epithet.

The comic was ready. He calmly explained that he had an arrangement with the club that he received a $50 bonus each time someone used that word and invited the audience to keep on saying it.

Another in the crowd asked Mr. Gregory if he’d consider performing in Mobile, Ala. He replied: “Mobile? I won’t even work the south of this room.”

He won over the audience, and an ensuing profile in Time magazine led to invitations to appear on Paar’s TV show and other career-building stops. As he rose in the national consciousness, he also relished playing the provocateur. He often said he titled his 1964 memoir “Nigger: An Autobiography” — a book co-written with Lipsyte — so that every time the slur was spoken, it would serve as advertising for the book. It quickly became a bestseller.