O’Rourke’s career took off with his tenure at National Lampoon, where he ultimately served as editor in chief, helping to launch some of the biggest names in comedy as well as writing his own widely praised work, such as coauthoring National Lampoon’s 1964 High School Yearbook. One of his most well-known pieces was the memorably titled, “How to Drive Fast on Drugs While Getting Your Wing-Wang Squeezed and Not Spill Your Drink.”

A leftist in his youth, O’Rourke became a staunch libertarian, an about-face that informed much of his commentary on life, society, and politics. He was known for his deadpan and sardonic style, mocking pretensions on both sides of the aisle, and reveling in revealing the dysfunction of institutions and ideologies.

After his time at National Lampoon, he became the foreign affairs desk chief for Rolling Stone. In that capacity, he filed searing and irreverent dispatches from places as diverse as war-torn Beirut and a televangelist retirement village. He later became a columnist for the Atlantic Monthly, bringing his wit and insight to such sober topics as Social Security reform, campaign finance, and a wide range of other policy issues.

During this time, he also authored more than twenty books, among which Parliament of Whores and Give War a Chance reached number one on the New York Times bestseller list. His quips were so well known that he had more citations in the Penguin Dictionary of Humorous Quotations than any other living writer.

But as Cato’s executive vice president David Boaz notes on the Cato at Liberty blog, there was serious education behind all the jokes. “Parliament of Whores is a very funny book,” he writes, “but it’s also a very perceptive analysis of politics in a modern mixed‐​economy democracy. And if you read Eat the Rich, you’ll learn more about how countries get rich—and why they don’t—than in a whole year of econ at most colleges. In fact, I’ve decided that the best answer to the question, ‘What’s the best book to start learning economics?’ is Eat the Rich.”

O’Rourke also had a long-running collaboration with Cato, where he was an H. L. Mencken Research Fellow. He frequently presented his new books at Cato forums, and Cato helped arrange book tours that took him to dozens of cities. Cato was able to produce an abridged version of Eat the Rich for distribution in high schools as well as an original series of short essays, Eight Little Civics Lessons, covering the first few months of the George W. Bush administration. O’Rourke was a frequent presence at Cato events, including both the opening of Cato’s current building in 1993 and Cato’s 40th anniversary in 2017, and made his last of many Cato appearances in a 2020 online forum for the launch of his book, A Cry from the Far Middle: Dispatches from a Divided Land.

“We’re going to miss P. J. terribly,” writes Boaz. “But as long as we have his books and his other writings, we will remember how much he made us laugh and how much we learned along the way. We extend our deepest condolences to his wife, Tina, and their three children.”