Don Rickles caught his big break when Frank Sinatra showed up at one of the comedian’s nightclub gigs in the late 1950s; Rickles immediately started insulting the Chairman of the Board. Sinatra actually laughed, perhaps to the surprise of the audience, and Rickles’s reputation began to grow. A few years later, Dean Martin introduced Rickles to a national audience when he invited the comedian to perform on the Dean Martin Hour, television’s top-rated show in the early 1960s. Rather than have Rickles do straight stand-up, the producers recruited Hollywood celebrities—including Bob Hope, Pat Boone, and Ernest Borgnine—to sit in the audience. Rickles spent half the show abusing them. He dared to make fat jokes about Dom DeLuise and poke fun at Ricardo Montalban’s Mexican heritage. “Here’s some mud. Finish your hut,” he told Montalban. Far from derailing his career, Rickles’ appearance made him a superstar.

It’s almost impossible to imagine a comedian like Rickles, who died yesterday at age 90, succeeding today. Performers who just 30 years ago flocked to colleges to perform, prompting critics to dub comedy “the rock and roll of the 1980s,” now avoid campuses for fear of too easily offending someone or invading their safe space. Jerry Seinfeld drew heat when he attempted to promote an appearance on his podcast by the comedian Lewis Black with the tweet, “Black’s life matters.” Even Amy Schumer, who describes herself unironically as a “devout feminist and lover of all people,” caught hell for observing, “Nothing works 100 percent of the time, except Mexicans”—about as inoffensive and pandering an ethnic joke as one can imagine.

It’s not as if the prime years of Rickles’s career, the 1960s and 1970s, were an era noted for their complacency. He thrived during the era of the civil rights protests and the free speech movement that grew out of them on campuses. Unlike the university protests of today, however, those demonstrations actually helped liberate comedy, igniting the careers of comics like George Carlin, whose “seven words you can never say on television” sparked a Supreme Court case on free speech, and Richard Pryor, who dared title one of his albums That Nigger’s Crazy. Performing in his tuxedo in Las Vegas and on late night TV, Rickles was another kind of agent of the counterculture, hurling an equal-opportunity barrage of insults at mostly middle-class audiences—in the process saying that if we’re all equal, then we’re all fair game.

Though Rickles first made a national name for himself insulting celebrities, in the nightclubs and concert halls where he performed the audience mostly consisted of ordinary people. When they discovered that they were his target, they ate it up, mainly because no one was exempt. In his Las Vegas shows, Rickles would usually wade into the audience looking for people to pick on. To an Asian man he’d say, “Are you Japanese? I spent three years in the jungle chasing your uncle!” Spotting a black man in the front row, Rickles says, “God bless you, black brother,” and then in a loud stage whisper calls offstage to someone, “find out how he got in here!” If you admitted to being Italian-American, you could expect to hear, “Italians are terrific people. They can work you over in an alleyway while singing opera.” (This was, after all, the guy who said to Sinatra in front of a crowd, “Hey Frank, make yourself at home. Hit somebody.”) Even as American society splintered into more and more interest groups, Rickles invented barbs to offend as many constituencies as possible. He even said to someone who was dressed badly (this was in the 1970s, after all)—“Who picks your clothes, Stevie Wonder?”

Rickles’s routines demonstrated that you could be socially conscious without being ideological. A lifelong Democrat, he rarely picked topics that hinted at his political beliefs, though he did make politicians his targets. Roasting California governor Ronald Reagan, Rickles said: “Black, white, Jew, gentile, we’re all working for one cause—to figure out how you became governor.” Reagan later invited Rickles to perform at his inaugural.

For the most part, Rickles continued his insult routines to the very end, with little censorship. Perhaps that had to do with the audiences that showed up to see him, and their expectations. But even he wasn’t immune to the times. Appearing at a 2012 American Film Institute ceremony, Rickles said, “I shouldn’t make fun of the blacks,” but then added, “President Obama is a personal friend of mine. He was over to the house yesterday, but the mop broke.” That joke never made it into the televised version of Rickles’ appearance.

Still, Rickles went out on top, largely untamed by the PC madness that has stifled comedic expression. His like may not pass our way again.

Photo by Mark Mainz/Getty Images


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