P.J. O’Rourke (RIP) Explains Why You Can Never Win Over Your Political Adversaries by Mocking Them




Donald Trump, as his supporters and detractors alike can agree, is immune to humor. All the parody, satire, ridicule, and insult with which he was ceaselessly bombarded during his four years as the President of the United States of America had, to a first approximation, no effect whatsoever. If anything, it just made him more powerful. “There has been tremendous scorn for and fun made of Trump, and indeed Trump supporters,” says the late humorist P.J. O’Rourke in the clip above from a 2106 Intelligence Squared event. But “when you are angry at the establishment, and you see the establishment not just disagreeing with your candidate but mocking your candidate, there is an element that says, ‘They’re mocking me.'”

As a result, “every time you went out to make fun of Trump, you increased his support, because people were feeling scorned.” The result of the 2016 election, which happened the next month, would seem to have borne this out. “When people feel they are outsiders,” O’Rourke says, “you cannot convince them by mocking them.” This may, at first, sound somewhat rich coming from a writer who spent half a century turning everything that so much as approached the world of politics into joke material. But O’Rourke didn’t engage in mockery, per se; rather, he straightforwardly observed that which came before him. “Humor isn’t about being funny,” he once said in another interview. “It’s about putting emotional distance between yourself and the patterns of human behavior.”


I’ve long kept that observation in mind, as I have so much else O’Rourke wrote and said. If any one thing made me a writer, it was all the fifteen-minute breaks from my high-school job at the Gap I spent reading his books at the Borders on the other side of the mall. I took a rebellious pleasure, at that age and at that time, in getting laughs from the work of a writer who was clearly not a man of the left. Or rather, a writer who was formerly a man of the left: a self-confessed 1960s hippie, he like many of the Baby Boom generation underwent a political conversion after noticing the deductions from his paycheck. “I’d been struggling for years to achieve socialism in America,” goes one of his oft-quoted lines, “only to discover that we had it already.”

Yet O’Rourke was never a doctrinaire right-winger. Forged at the National Lampoon (for which he wrote the well known piece “How to Drive Fast on Drugs While Getting Your Wing-Wang Squeezed and Not Spill Your Drink”) he emerged as a 1980s libertarian-libertine. In recent decades, during which he often appeared as a convivial political outsider on shows like National Public Radio’s Wait, Wait… Don’t Tell Me, he shifted to the territory referenced in the title of his last book, 2020’s A Cry from the Far Middle. In the video above he reads its introduction, a dispatch from a time of not just “moron populism and idiot partisanship” but also a “grievous health crisis, lockdown isolation, economic collapse, and material deprivation.” Once a wisecracking correspondent from the world’s trouble spots, he knew to bet that even in America, “human nature will triumph over adversity and challenge. And I don’t mean that in a good way.”

You can read O’Rourke’s obituary here.

Related content:

Noam Chomsky on Whether the Rise of Trump Resembles the Rise of Fascism in 1930s Germany

Comedians Speaking Truth to Power: Lenny Bruce, George Carlin & Richard Pryor (NSFW)

Kurt Vonnegut Ponders Why “Poor Americans Are Taught to Hate Themselves” in a Timely Passage from Slaughterhouse-Five

Monty Python’s John Cleese Worries That Political Correctness Will Lead Us into a Humorless World, Reminiscent of Orwell’s 1984

Bill Hicks’ 12 Principles of Comedy

Based in Seoul, Colin Marshall writes and broadcasts on cities, language, and culture. His projects include the Substack newsletter Books on Cities, the book The Stateless City: a Walk through 21st-Century Los Angeles and the video series The City in Cinema. Follow him on Twitter at @colinmarshall or on Facebook.


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  • Gregory Wade says:

    Is it a Hasty Conclusion to conclude you can win against liberals thru mockery? The plain old Fact is you cannot win against liberals because there are things so evil – so despicable – that you will refuse to do them to advance your politics. Liberals have no such limitation.

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