Emmy and Tony award-winning comic and social commentator Jackie Mason died this weekend at 93. Though Wisconsin-born, Mason became a quintessential New York character, and his career witnessed extreme ups and downs across 60 years of making people laugh. His laugh-out-loud political commentary was a staple of his act, but it often caused him trouble, as many of his worst moments stemmed from politically related incidents.

Born in 1928, Mason came from a long line of rabbis on his father’s side. He went to City College in New York and, following family expectations, received rabbinical ordination from the great Rabbi Moshe Feinstein. He led congregations in North Carolina and Pennsylvania, though his heart was not in it. He described his transition from rabbi to comedian via a fictionalized but typically humorous bit, noting that he started telling jokes to keep the congregation interested. Word got around, and gentiles started coming just to hear his jokes. Eventually, he joked, his congregation was all gentile, and he started charging an entrance fee.

The true story is that he only felt liberated to go into comedy after his father died in 1959. He rose up quickly, performing at the legendary Copacabana and becoming a staple on The Ed Sullivan Show. While on the show, he had a great—and typical—joke about John F. Kennedy in 1962, in which he expressed faux outrage that Kennedy hosted a $15,000, 300-person dinner at the Waldorf. “My bar mitzvah didn’t cost that much,” he fumed. The audience loved it.

Unfortunately for Mason, the potentially career-making Sullivan show nearly became career-ending in 1964, when the program was about to be preempted by a Lyndon Johnson speech. Sullivan held up fingers to indicate how much time Mason had, and an irritated Mason responded by displaying fingers to the audience, saying, “I’ve been getting lots of fingers tonight. Here’s a finger for you, and a finger for you, and a finger for you.” The prickly Sullivan felt Mason had given him the finger and banned him from the show for two years. Worse, Sullivan privately vowed, “I will destroy you in show business.” He largely did. In later years, Mason—who denied deploying the middle digit in the way Sullivan saw it—believed he had been blacklisted more broadly in the entertainment world. He hit a further setback in 1969, when CBS cut some of his jokes from The Smothers Brothers Comedy Hour. He sued CBS, arguing that the deletions fostered the perception of him as a “censored comedian.”

Sullivan later apologized to Mason, and Mason did eventually return to the show, but the reputational damage was done. For two decades, he labored largely as a has-been rather than the rising star he had been in 1964, even declaring bankruptcy in 1983. “It took 20 years to overcome what happened in one minute,” Mason complained.

He did overcome it, though, with a triumphant return in a 1987 one-man Broadway sensation, The World According to Me. His timing was perfect: Borscht-belt jokes, which had gone out of style in the 1960s with the rise of the hippies and the Me generation, had come back into favor. Mason’s act was not unlike that of the fictional Austin Powers—frozen in time and reappearing a few decades later exactly as it was. Jokes that Mason told on The Ed Sullivan Show in the early 1960s had them rolling in the aisles in late 1980s New York. He was on top of the world again and loving it, appearing on magazine covers and hanging out with celebrities, including a young Donald Trump, whom he visited numerous times in Trump Tower and for whom he emceed a book release for The Art of the Deal in 1989. He also got involved with politics, which both elevated his profile and gave him new headaches.

Mason’s act had always had a political element. His politically incorrect humor poked fun at everyone, including presidents dating back to Harry Truman. (About a retired and decidedly not well-off Truman he joked: “Truman gets up every morning and walks for speed. Why is he walking for speed? He’s looking for a job.”) In his Broadway show, he did an eight-minute riff on presidents, largely about Reagan but also taking jabs at Johnson, Nixon, and Carter along the way. Of Nixon, he said, “With Nixon every day was interesting, every day with a new mystery, you didn’t know what. I used to get up every morning to see if my furniture was still there.” About Carter, he joked that “nobody voted for Mondale because Mondale reminded everybody of Carter, who was nauseous and miserable.” And about Reagan, he observed, “He came back from Reykjavík from that meeting with Gorbachev. Everyone said ‘What happened?’ He said, ‘Nothing.’ Everybody said, ‘Thank G-d.’” This was not only funny, but also spot-on. At the time, the news media portrayed the lack of agreement at Reykjavik as a setback, but it was later widely recognized as one of Reagan’s wiser moves.

Mason also weighed in heavily in favor of Rudy Giuliani over David Dinkins for mayor in both 1989 and 1993. New York was a mess at the time, suffering from more than 2,000 annual murders, and Mason was on board with Giuliani’s pledge to make the city safer. He did go too far in his criticism of Dinkins, calling him “a fancy shvartze with a mustache”; shvartze (literal meaning: “black”) is a Yiddish word for African-Americans. Many years later, he got in even more trouble for using the word to describe Barack Obama.

Though Mason was criticized for the Dinkins comment, he was not cancelled. In fact, Bill Clinton even used a Mason line in one of his speeches. In 1994, while promoting his crime bill to the National Association of Police Officers, Clinton mocked a Republican congressional procedural maneuver with a Mason line, saying, “Well, I would have voted for it if only it would have been there for me to vote on.” Mason of course told Clinton jokes as well: “Is there anybody on this Earth dumb enough to believe he didn’t inhale? Would you put a pastrami sandwich in your mouth if you didn’t want to swallow it?”

Mason’s political humor was perceptive. At a time when comedians were at best making gentle fun of Obama, Mason made this trenchant observation:

[Sarah Palin] told a little joke when she said, ‘I can see Russia from my window,’ but because she said that, she became the biggest idiot in the world. Now, Barack Obama has said a million stupid things, and everybody says, ‘Look, how cute, how a genius could make a funny mistake like that.’ Remember when he was in Austria and he apologized because he didn’t speak Austrian? . . . Or when he thought there were 57 states. Or when he was talking in Iowa and thought he was next to Pennsylvania. Did you ever see a word of criticism for such stupid remarks? But Sarah Palin says something wrong, that proves she’s a moron.

In recent years, Mason faced criticism for supporting his old friend Trump. His joke, “Have you ever heard of a black person who gave a Jew a quarter?” also got him denounced in Jet, which retorted with some stirring examples of African-American philanthropists who gave to Jewish causes. But Mason’s kind of comedy was always bound to offend. He embodied a certain type of New Yorker, one who makes fun of everyone—his own group perhaps most of all. Today’s woke warriors would no doubt take offense at every word that came out of his mouth, but that did not stop him from making jokes, and it certainly did not stop him from being funny.

Photo by Mario Ruiz/Getty Images


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