Dick Gregory understood the political power of comedy

Dick Gregory died last weekend at age 84 after leading a bunch of lives.

He was at various times a standup comedian, social critic, political activist, political candidate, nutrition regimen entrepreneur, diet consultant and, increasingly in his later years, obsessive purveyor of bizarre conspiracy theories.

But my favorite memories of Gregory come from 1961 when I was a Midwestern kid watching his fame rise on TV like a Jackie Robinson of black standup comedians.

Robinson broke Major League Baseball's color bar. Gregory broke the nightclub color bar, and did it with controversial political subjects long before Larry Wilmore, Trevor Noah, Wanda Sykes or W. Kamau Bell.

Until Hugh Hefner hired Gregory to fill in at the Chicago Playboy Club, blacks tended to be hired in white-owned clubs as singers or dancers, not to stand flat-footed and talk. Otherwise, Gregory explained to me in an interview in the 1980s, "the System would know how brilliant you are."

Understanding "the System" helped him to beat it.

He learned, above all, to be entertaining before trying to make a serious point. He explains how he studied audiences in his best-selling 1964 autobiography, which he titled "nigger" with a lower-case "N." (In a note to his mother on its dedication page, he explained: "If ever you hear the word 'nigger' again, remember they are advertising my book.")

In the "big white night clubs," he decided, "I've got to go up there as an individual first, a Negro second," he continued. "I've got to be a colored funny man, not a funny colored man."

He also prepared himself for hecklers. He enlisted his wife to call him by the N-word over dinner, so he could prepare funny comebacks ("You hear what that guy called me? Roy Rogers' horse. He called me 'Trigger' ") without losing his cool.

Fortunately, he prepared himself well because, as luck would have it, his big break came on a January night in 1961 at the Playboy Club before an audience of "frozen food executives from the South." He might have backed out, he recalled, had he not been broke.

Instead, he followed his plan. He led by making fun of himself: "Just my luck. I bought a suit with two pair of pants today — and burnt a hole in the jacket!"

Then he broadened out to the elephant in the room: "Wouldn't it be a hell of a thing if all this (gesturing at his face) was burnt cork and you people were being tolerant for nothing?"

Heckling quickly gave way to laughter, applause, encores and a regular gig at the Playboy Clubs, which led to a Time magazine profile, "The Tonight Show" and a heroic sort of national stardom. He was the black comedian who could have white audiences laugh at the absurdities of racism.

But show biz was not enough. In 1964 he joined the civil rights movement. He traded nightclubs for college campuses. He became a healthy food apostle and a political activist.

In 1967, at the height of his popularity, he ran a write-in campaign for mayor of Chicago against incumbent Richard J. Daley and in 1968 for president of the United States. He lost, of course, but he provided a model for the later African-Americans who would win.

In recent decades, Gregory's obsessions with conspiracy theories made him something of a joke, even among his friends. Yet here, too, he had a following among fellow conspiracists. Conspiracy fanatic Alex Jones' InfoWar website eulogized Gregory as a "Jedi-level infowarrior."

Yet I could not fault Gregory for believing in conspiracies. According to papers obtained by a Chicago Tribune reporter in 1978 under the Freedom of Information Act, former FBI director J. Edgar Hoover had ordered the bureau's Chicago office to secretly "neutralize" the comedian-activist in 1968, perhaps by informing Mafia bosses about some impolite remarks Gregory had made about them.

"Look, if the FBI was going to contact La Cosa Nostra, they had to know who was in La Cosa Nostra," a stunned Gregory told the Tribune after he was told about the memo. "And if the FBI knew who they were, why weren't they arrested?"

Why, indeed? As an old saying goes, even paranoids have enemies — who might be even more paranoid.

Clarence Page is a columnist for the Chicago Tribune. Email, cpage@chicagotribune.com.

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