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.