He is the author of 14 books, most recently On The Wealth of Nations, a commentary on Adam Smith's An Inquiry into the Nature and Causes of the Wealth of Nations (and the first in The Atlantic Monthly's "Books That Changed The World" series). According to a 60 Minutes profile, he is also the most quoted living man in The Penguin Dictionary of Modern Humorous Quotations.
O'Rourke did his undergraduate work at Miami University, in Ohio, and earned an MA in English at Johns Hopkins University. He recounts that during his student days he was a left-leaning hippie, but that in the 1970s his political views underwent a volte-face. He emerged as a political observer and humorist with libertarian, sometimes conservative, and anti-leftist viewpoints.
O'Rourke wrote articles for several publications before joining National Lampoon in 1973, where he served as managing editor among other roles and authored articles such as "Foreigners Around the World." He received a writing credit for National Lampoon's Lemmings which helped launch the careers of John Belushi, Chevy Chase and Christopher Guest. Going freelance in 1981, O'Rourke began publishing in magazines such as Playboy, Vanity Fair, Car and Driver, and Rolling Stone. He became foreign-affairs desk chief at Rolling Stone, where he remained until 2001. In 1996, he served as the conservative commentator in the point-counterpoint segment of 60 Minutes.
O'Rourke was married to Amy Lumet, a daughter of movie director Sidney Lumet and a granddaughter of Lena Horne, from 1990 to 1993. Since 1995 he has been married to his second wife, Tina, and they have two daughters and one son. O'Rourke splits his time between New Hampshire and Washington, DC.
O'Rourke has published 14 books, including three New York Times bestsellers. Parliament of Whores and Give War a Chance reached #1 on the New York Times Best Seller List. O'Rourke is a "Real Time Real Reports" commentator for Real Time with Bill Maher covering the 2008 Presidential Election.
O'Rourke revealed on September 28, 2008 that he has been diagnosed with treatable anal cancer, from which he can expect "a 95% chance of survival." His announcement is typical of his writing in that it handled a very serious subject within his humorous style.
O'Rourke was an early proponent of Gonzo journalism; his nascent masterwork was "How to Drive Fast on Drugs While Getting Your Wing-Wang Squeezed and Not Spill Your Drink", a National Lampoon article in March 1979. The article was republished in his third book, Republican Party Reptile (1987), which became a bestseller. O'Rourke is well known for his combination of conservative economic views and liberal views on vices such as sex and drugs.
O'Rourke has described himself as a libertarian. He has sarcastically proposed two other American political parties: one for those with his mixture of views, another for those who hold the opposite mixture.
O'Rourke types his manuscripts on an IBM Selectric typewriter, though denies he is a luddite, asserting that his short attention span would make focusing on writing on a computer difficult. In a January 2007 interview, O'Rourke gave an example of his view of computers and writing by referencing novelist Stephen King, whom he paraphrased - saying had he a computer he could have written three times as much in his early days . To which O'Rourke remarked-- "Does the world need three times as many Cujos? Three times as many Jane Austens, maybe."