Dick Gregory’s big break almost didn’t happen.
The national press was buzzing over his killer 1961 performance at Chicago’s Playboy Club, where as a last-minute substitute he played before an audience filled with white southern food executives. Gregory handled the heckling with ease, told political jokes and even won the crowd over.
Afterward, as Gregory recalled decades later, he expected a call from “Tonight Starring Jack Paar,” a show he had watched without fail for five years. But when a friend pointed out that Paar had never invited a black comic to join him on his couch after a set — the pinnacle achievement for a stand-up comic — Gregory was devastated.
“Next thing I know, I’m walking home … crying,” Gregory said in 2016. “I get home and [my wife] says, ‘Are you okay?’ And I say, ‘Yeah, I’m okay.’ I was embarrassed to tell her. I just knew I would never work that show.”
So when Paar’s producers asked Gregory to come on, the comic said no and hung up on them. Then Paar himself called and asked why Gregory didn’t want to perform on his show. Gregory told Paar: “Because the Negro has never been able to finish his act and walk to the couch.” Paar then insisted that Gregory would sit down on the couch.
It was the turning point not just for Gregory’s career, but for stand-up.
“He broke the color barrier in comedy,” said Kliph Nesteroff, author of “The Comedians,” a history of American comedy.
Gregory, who died Saturday at 84, was both the first black comic on Paar’s couch and the first to play in white comedy clubs.
“Prior to Dick Gregory, stand-up comedy was segregated,” Nesteroff added. “There was a separate circuit for black comedians and a separate circuit for white comedians.”
Gregory’s big break led to other “mainstream,” or white, clubs booking him — and it became “almost a trend to book a black comic in a white nightclub,” Nesteroff continued. Older comics who had been around long before Gregory were, for the first time in their careers, starting to play white nightclubs. And Gregory inspired a new crop of comics, such as Bill Cosby, Godfrey Cambridge and Richard Pryor, who were then able to get work on mainstream television.
The response to Gregory’s first time on Paar’s show was overwhelming. NBC was flooded with calls from viewers who loved his appearance, and the comic returned 22 more times, Gregory said in a 2014 interview.
“Thousands of letters came in saying, ‘We didn’t know Negro children and white children were the same,’ ” Gregory would later recall. “My momma wasn’t going to discuss her children around white folks, so where else would a white person hear someone like you talking about [it] other than on TV?”
Gregory followed in the tradition of a wave of comics — Lenny Bruce, Mort Sahl — who talked about hot-button social issues and politics on stage. But white audiences hadn’t heard such takes from a black man’s perspective.
“Never before had white America let a black person stand flat-footed and talk to white folks,” Gregory said in 2006. “You could dance, and you could stop in between the dance — Pearl Bailey could talk about her tired feet or Sammy [Davis Jr.] could tell a joke — but you could not walk out and talk with white America.”
His approach wasn’t without blowback. Count Basie fired him from a gig because he didn’t like Gregory’s act. Other black entertainers balked, too.
“They felt politics didn’t belong on the stage, that you could reach some semblance of acceptance or racial equality simply by doing quality work on stage, and white people would appreciate you that way,” Nesteroff said.
Gregory would go on to be something other than just a pure comedian. As an activist, he marched in Selma, was shot in the leg in Watts, jailed in Birmingham. He ran for mayor of Chicago, then president. Some criticized that he was taking himself too seriously and endangering his comedy career.
“Well, these critics who feel I’m destroying myself as an entertainer, all they know is show business,” Gregory told Playboy in 1964. “They’re concerned nightclub-wise, not news-wise. A political reporter would never say I’m taking myself too seriously. You see, there comes a time when you got to decide what you are and what you want. Way I see it now, I’m an individual first, an American second and a Negro third. But I’m a Negro before I’m an entertainer.”
Gregory’s activism meant he’d have to cancel gigs at the last minute because he was in jail. He was also spending hundreds of thousands of dollars on causes connected to the civil rights movement. Playboy asked him, “Can you afford to keep up this kind of outlay on the income from your irregular nightclub appearances?”
“Can’t afford not to,” Gregory responded in 1964. “If I’m willing to pay the price of dying for the cause, what I care about a few bucks more or less?”