Veteran US satirist P. J. O’Rourke on Hillary Clinton, his fondness for Trump supporters and the gonzo ethos. By Susan Chenery.

Celebrated political satirist P. J. O’Rourke heads Down Under

Writer P.J. O'Rourke.
Writer P.J. O'Rourke.


P. J. O’Rourke is dispirited. The usually ebullient man finds himself deploying some of his pithiest one-liners in a world increasingly beyond satire. “One does have that feeling of shouting down a rain barrel,” the world’s most quoted living humorist says. “It doesn’t matter how true or how clever or how funny it is, it doesn’t seem to have any effect on the political process. It is very frustrating.” 

In O’Rourke’s America, the rise of Donald Trump is not funny at all. “The best comedians in the US have done the best job they could possibly do on Donald Trump,” he says, “and it hasn’t worked.”

And then there is the recently farcical Britain, which has turned into Monty Python meets Yes Minister with, after some frenzied backstabbing, the emergence of Boris Johnson as foreign secretary.

O’Rourke believes that Trump’s popularity and the sentiment that produced Brexit are driven by something similar. He has interviewed Trump supporters, and enjoyed it. “I liked them personally. What they were doing was giving the whole political system the middle finger. And of course one can’t blame them too much for that. I think Brexit was very much the same thing. But I listened to post-mortem interviews, especially in the areas that voted heavily in favour, and the interviews kept coming back to one thing, which was immigration. Not immigration per se, but specifically the refugee crisis that is engulfing Europe. People are very frightened of that … Australia is not without its experience there.”

O’Rourke, heading to Australia for several speaking engagements, is a Republican from a long line of Midwest Irish conservatives, and has been firmly this way since a brief flirtation with socialism as a fledging teenage writer. He is the fun Republican – the libertarian whose good-natured humanity shines through. Certainly the GOP took such a dim view of his book of essays, Republican Party Reptile, that it refused to let him promote it at the 1988 party convention.

In it, he set out the party agenda. “We are opposed to: government spending, Kennedy kids, seat-belt laws, busing our children anywhere other than Yale, trailer courts near our vacation homes, all tiny Third World countries that don’t have banking secrecy laws, aerobics, the UN, taxation without tax loopholes, and jewelry on men. We are in favour of: guns, drugs, fast cars, free love (if our wives don’t find out), a sound dollar ... a strong military with spiffy uniforms.”

But even he, the scion of generations of Republicans, a public comedic conservative, had to draw the line at Trump. In May he caused shock waves by endorsing Hillary Clinton – “the crone in crony capitalism”. He said she was “the second-worst thing that could happen to America”. That is how bad America’s “mass psychosis” has got. “Better a mangy cat than a rabid dog.”

In a spectacularly vituperative rant in The Daily Beast, he enumerated his reasons, none of them flattering. “Better a Marie Antoinette of the left saying, ‘Let them eat fruit and fiber,’ than a Know Nothing who would be Robespierre if he could spell it.”

But what, I ask O’Rourke, is wrong with Hillary anyway? Why don’t people trust her?

“It is an interesting question that I answer in a kind of chauvinistic way,” he tells me. “Every man looks at her and sees his first wife. I swear to God. It all comes back. It is not because she is a woman; it is because she is a particular woman. She is the particular woman in whose class you were in fifth grade wishing you were dead.”

He hasn’t met her but he knows a lot of people from the Clinton administration. “They have always said she is quite funny, quite warm, that she is a good friend and she is considerate of other people and so on, but she certainly doesn’t project that publicly.”

At 68, O’Rourke has not lost the boyishness he has carried through the years. He is, he says, “fine with every aspect” of growing older “except the arthritis”.

“That I could do without. I was out chainsawing the other day and I have not been able to stand up straight ever since.”

As a young man his exuberance was on the page with seminal pieces such as “How to Drive Fast on Drugs While Getting Your Wing-Wang Squeezed and Not Spill Your Drink”. Hard to image a young writer launching a career with such lack of inhibition now, especially when the entire premise of his article was illegal. Today, you would more likely be sacked than celebrated.

O’Rourke was part of the gleeful ’60s generation that stormed the citadel of moribund American journalism. He and his friend Hunter S. Thompson were the great gonzo journalists, breaking away from a tradition where bipartisan pursuit of truth meant barely having a byline. They threw themselves into the action – sometimes they created the action – and wrote journalism that read like fiction. O’Rourke spent 20 years as Rolling Stone’s international affairs editor, hurling himself into trouble spots and war zones, with a large cocktail in one hand, an infallible eye for the absurd, and a determination to have a good time. His 1988 book, Holidays in Hell, is a classic of the genre, where his dazzling riffs on humanity at its worst reached new heights.

“I have been shot in the direction of but never shot at,” he says now. “In those days everybody wanted to tell their story. And it was a kind of standing joke in the foreign press car that your biggest danger was having your ear talked off. The biggest problem was getting people to shut up.”

He gave it up when his daughter was born and he was 50. He misses the camaraderie but wouldn’t want to be doing it now.

“I feel sorry for the foreign correspondents in an ever more dangerous world. They don’t have the backing of big organisations with big budgets. They don’t have the good translators, the good drivers, the fixers. Back in the day, if harm came to a journalist it was usually the result of an accident.”

He and Hunter S. Thompson were close. But while drugs and alcohol were part of the gonzo ethos, he had neither the constitution nor the capacity for self-destruction that Thompson did. “If I got drunk and stoned one night, I couldn’t get up and do it again the next day.”

Beneath all the ballast and bawdiness, however, they were both deeply serious about their craft. When we previously spoke, in 2014, O’Rourke told me that while he admired the “jazz rhythm” of Thompson’s prose, when they got together they could be found discussing Jane Austen. “Our friendship was nothing to do with sex, drugs and rock’n’roll, and everything to do with the fact that Hunter was one of the best-read persons I have ever met. And that is what we talked about all the time. Not writing and not each other’s writing, but we talked about literature. How did Jane Austen do that? What kind of movie script would Henry James write? Hunter opined that it would be a long one.”

Last year, putting together yet another collection of his work, Thrown Under the Omnibus, O’Rourke was able to take the long view of his evolution over 40 years of writing, acknowledging in his foreword: “It is, I guess, interesting to watch the leftist grub weaving itself into the pupa of satire and then emerging a resplendent conservative blowfly.”

He hadn’t meant to be a journalist. He had wanted to be a race-car driver but didn’t have a car. “I meant to be a genius,” he says. “I was going to produce an oeuvre so brilliant, important and deep that no one would ever understand it.” But he didn’t have the “knack” for literature. “Fortunately, I discovered journalism. Talent hasn’t been a question since.”

There is a booming, big-band quality to O’Rourke’s work, a sense of chortling and shouting above the braying at a Republican Party conference. But while he seems taken aback when I mention that his work is loud, he says: “I like colourful writing, there is no doubt about that. I am not an AP reporter, I am a feature writer and I sometimes stretch a point to make a point.”

One of his most effective comedy devices is bringing ancient and modern history to current events. In a recent essay, “The Art of Ageing Gracefully”, he mused on what might have become of those who remain mythic and beautiful because they died young. “Do we really wish there were more Byron poems?” And “Imagine portly, blustering, red-faced Romeo, burgher of a provincial Italian town, and frumpy, shrewish Juliet.”

“I like history,” he admits. “After all, politics is an historical phenomenon.”

O’Rourke lives in considerable style between an apartment in Washington, D. C., and an 18th-century house in New England, with his wife Tina, their three children, dogs and chooks. In the country residence, he has taken up carpentry. “Very rough carpentry. I fall not into the fine cabinet department but more into the shelf in the garage. Possibly you would allow me to do a shelf in your closet if it was a closet you didn’t use a lot.”

It is a large property that is a tree farm, “technically”. 

“A couple of years ago we did a harvest on one area of the property that had grown to maturity,” he says. “You sort of rotate around the property cutting things down. It is like any other kind of farming: no matter what the weather or the circumstances, the crop has got to come in – every 30 years.” 

Presumably 20 books, most of them bestsellers, paid for all this before he, too, was caught by the digital age. “Total pain in the arse,” he says of the internet’s impact on journalism. “It wasn’t like writing for magazines and newspapers was ever a way to get rich, but now not only is it worse but it is uncertain. It has been an ugly period for people with jobs like yours and mine. I expect it will sort itself out. But when?”

Thanks to this and late parenthood he is going to have to keep working until he keels over. His generation, he told me in 2014, was “taking all sorts of drugs and paying no attention to the future”.

In the book he released that year, The Baby Boom: How It Got That Way... And It Wasn’t My Fault... And I’ll Never Do It Again, O’Rourke talked about the generation that “never grew up”. He wrote: “We’ll never retire. We can’t. The mortgage is underwater. We’re in debt up to the Rogaine for the kids’ college education. And it serves us right – we’re the generation who insisted that a passion for living should replace working for one.”

But he doesn’t regret it, not really. “I wish I had had the passion to be an investment banker,” he told me. “I lived with lots of passion and no cash. Cashless passion. But I can’t complain too hard. After all, it provided a very interesting life for me, if not an unbelievably lucrative one.”

In the “Ageing Gracefully” essay, O’Rourke pointed out the benefits of dying young. “Well, you could always take one’s own advice, but what kind of world would that be?”

This article was first published in the print edition of The Saturday Paper on July 23, 2016 as "Pithy party".

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Susan Chenery is a journalist who has lived and worked in Sydney, London, New York and Italy.

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