I’m sitting in a dark and smoky bar, going drink for drink with one of America’s top political commentators, pouring down Scotch and sodas as if I had a large investment in Cutty Sark futures. P.J. and I (by now I’m calling him P.J.) are swapping stories and laughing it up, and he’s giving me plenty of quotable material by intoning his views on current events. He’s also giving me pointers on how to make the jump from struggling and unknown writer to wealthy and esteemed author. As we order another round, Hunter Thompson shows up and joins us. He pulls a zip-lock bag full of mushrooms out of his pocket and then we...

Okay, that’s not what really happened. Fact is, I did have dinner with P.J. Sure, so did about a hundred other people and I didn’t sit at the same table as him, but still and all. There’s always that moment in a freelancer’s life when you realize just how low on the food chain of journalism you really are. Trying to get an interview with P.J. O’Rourke, the no-holds-barred political humorist, turns out to be an exercise in futility. O’Rourke is much too busy.

So it was that I found myself in the unenviable position of trying to get to O’Rourke at one of his speaking engagements by attending it like a normal person. Luckily, he was making a few appearances in Southern California so I went to see O’Rourke speak at Claremont College. A dinner for O’Rourke preceded the speech. So I shelled out the 15 bucks to get in and thought that maybe I could ambush the author while he unsuspectingly chatted with the other guests. As it turned out, getting to him was much easier than I expected.

There was P.J. in the middle of the Claremont College Athenaeum (a beautiful building that bespeaks academia with every fiber of its being), looking for all the world like the host of an elegant dinner party. I watched as O’Rourke politely greeted the guests, shaking hands firmly and introducing himself as "P.J. O’Rourke," as if the assembled didn’t know whom they were coming to see.

In a blue blazer and red and white striped tie, O’Rourke could’ve passed for one of the college’s professors at parents’ night. O’Rourke’s reputation, however, is anything but professorial. A former ‘60s radical, he forged a reputation in the Reagan ‘80s as a conservative political commentator with an edge or, to quote the title of one of his first books, a "Republican Party Reptile." O’Rourke argued for limited government, a strong defense and a free market, while indulging in less than conservative behavior such as binge drinking and snorting cocaine. He essentially became to the Right what Hunter Thompson had become to the Left, an articulate and caustic hit man but with the emphasis on alcohol rather than drugs. (Indeed, O’Rourke cites Thompson as a major influence and interviewed him for Rolling Stone for the 25th anniversary of its running of Fear and Loathing in Las Vegas.)

After a stint as editor of National Lampoon, O’Rourke contributed to a variety of magazines and landed a regular gig as foreign affairs correspondent for Rolling Stone. His books, such as Parliament of Whores, Holidays in Hell, Give War a Chance and All the Trouble in the World, became national best-sellers and established O’Rourke as one of the preeminent conservative writers in America. In them, he skewered politicians, baited liberals and put forth his political philosophies, as well as reporting from various foreign hotspots. But O’Rourke is no shill for the GOP. He will criticize Republican leaders (though his specialty is lambasting liberal Democrats), and he has a decidedly libertarian streak. Though portraying himself as a hard-drinking Cro Magnon with a word processor, O’Rourke’s writing, as well as being funnier than shit, is incisive, intelligent, witty and finely crafted, whether you agree with his viewpoints or not.

O’Rourke’s latest work, The CEO of the Sofa, finds a mellowed O’Rourke musing on marriage, having kids and other domestic concerns, while adding his usual political commentary and travel writing in the form of a chapter on a trip he took to India. While the book is a bit of a departure from his other works, O’Rourke still manages to skewer politicians (especially Hillary and her Mister), bait liberals and put forth his political philosophies. I was hoping to get five minutes alone with him to gather material for the article that would, if all went well, expedite my entrance into the big time.

Thankfully, O’Rourke magnanimously allowed me to interview him before and after the speech. Though my time was limited, I managed to chat with him about various subjects. Concerning the current war against terrorists in Afghanistan, he admitted to not having any great insight. He is, however, "worried about us forming alliances. Some of the people we’re trying to form alliances with aren’t much better than what is in Afghanistan now." When asked how his book is faring, he said, "I haven’t the slightest idea."

O’Rourke makes reference in The CEO of the Sofa several times to his aversion to modern technology, specifically the Internet. Why does it scare him? "It doesn’t scare me. I just don’t like it because it’s noisy and complicated," he said. "My assistant downloaded AOL for me, and it was all this crap. I prefer books. Books are quiet, books are pretty and they smell good."

However disenchanted with the worldwide web he may be, one could quickly ascertain that the use of the net for making loads of money and promoting unfettered capitalism is something of which O’Rourke is a big proponent. The upshot of his speech to the assembled collegians, alumni, fans and faculty at Claremont College was that the surest way to avoid the type of mentality that allowed the events of September 11th to happen is by insuring that people are prosperous enough that fanaticism, religious or otherwise, doesn’t become a serious alternative. And economic freedom is a pre-condition for the establishment of the democratic institutions necessary to back them up. Nations where terrorism is rampant have neither. Additionally, according to O’Rourke, using government power to level economic inequalities will always fail. "All the years of government programs haven’t gotten rid of poverty," said O’Rourke in his comments. "Giving people money to make them not poor doesn’t work very well."

The audience was made up mostly of students, who were young (man, I feel old!), clean-cut and full of energy. They don’t look like your typical college students (or do they? I’ve been out of college for a while so I’m not quite sure). At least they don’t look like I did in college; they look like they actually have some money, and they’re much nicer dressed. I talked with a few of them to get a feel for the political mood in the room.

Jamie, a guy who looks like he could play on the Claremont football team (do they have one?), said he’s a big fan of O’Rourke and has read all of his books. Politically, he considers himself a libertarian and said there are many like-minded people on campus. Meredith and Laura consider themselves conservative Republicans. Meredith said she was there because she "thoroughly enjoyed Eat the Rich" (O’Rourke’s penultimate book). When I asked if either is a member of the campus Young Republicans, Laura replied, "We’re not fanatics!" Hmm. Jeremy considers himself "a socialist, more of a populist." Did he vote for Ralph Nader? No, he explained, he missed the election. I’m perplexed. Was he out of the country or something, I asked? Well, no, it’s just that he wasn’t 18 when the election occurred (man, I feel really old!). "I’m opposed to Bush’s tax cut and the government’s economic policies, and I missed my opportunity to do something about the rich/poor gap," Jeremy said. "I came to get a better understanding of what the other side thinks." So it’s a pretty wide range of political ideas gathered to see O’Rourke tonight.

O’Rourke’s comments were well received and his humorous comments appreciated. His speech, like his writing, was replete with quotable bons mots: "Is Al Gore growing that beard just in case the Taliban wins?" "My friends who are Democrats tell me ‘I’m glad you guys won.’ It’s a case of it’s hip to be square, and the squares are in power. We know how to work all the bombs and missiles. Democrats would be fumbling with the trigger locks." "We’re not the scared country, we’re the scary country. Bin Laden is all dressed up in his holy war costume and came trick or treating at the wrong house. " "Bill Clinton got $12 million for his book deal, which is more than the Pope got. And the Pope is franker about his sex life."

When the explosion rocked the Pentagon the day of the terrorist attacks, O’Rourke explained that he didn’t hear it because, although his house is near the Pentagon, his two pre-school-age children live there; in addition to the din that entails, the Teletubbies were on, which, he pointed out, was ironic. "The terrorists tried to turn us into Teletubbies. Terrorists thought they could turn us into helpless blobs running into each other and saying ‘uh-oh!’"

As well received as his speech was, during the question and answer session that followed, some students challenged O’Rourke’s view that in order to make a better world we should, as he said, all "make a shitload of money." Some would argue (and a hell of a lot of them are on college campuses) that a totally free market economy is inherently unfair and that it leaves too many people behind because those who get rich do so at the expense of everyone else. This, according to O’Rourke, is complete horseshit. "Economics is not a zero sum game," he replied when an earnest coed raised just such a concern. "There is no fixed amount of wealth. It’s not a case of where if I have too many slices of pizza you have to eat the Domino’s box." Another questioner raised concerns about corporate monopolies. But monopolies, O’Rourke pointed out, are anathema to a true free market, not an aim of it, and they usually happen due to government meddling and always with the best intentions. "It’s under the guise of helping us that monopolies happen," he said. "Government is always behind corporate monopolies."

O’Rourke, for his part, seemed satisfied with the response he got. After the speech and the Q and A, he adjourned to the far corner of the room to sign books and do the old grip and grin. As soon as the last person had his book signed and the last pictures-with-the-famous-author were out of the way, I sidled up to O’Rourke to get in a few more questions, which he obligingly answered. (My hopes to waylay him into the nearest bar, however, were dashed by the fact that O’Rourke had to be up early for another appearance the next day.) Has parenthood mellowed him? "I’m not mellowed, I’m fatigued," he said. "I don’t think parenthood mellows a person; it tires and impoverishes a person." When asked how he would like people to regard him years from now, O’Rourke was unsure. "I don’t know, a funny journalist, I guess." But though his work is often categorized as humor, it is full of insights and serious political thought and isn’t simply a collection of one-liners and smart-ass remarks. O’Rourke admitted that there is a difference between his work and the work of those who are aiming only for a laugh. "It’s different if it’s reported humor, it’s like a reported essay; you hope it has a little more to it," he said. "If it’s just jokes and it’s good, it’s because there’s more to it, like Dave Barry’s stuff."

As Hunter Thompson (whom O’Rourke calls "my good friend") influenced a generation of writers and journalists, I wonder if O’Rourke sees himself having a similar impact. "I haven’t had any impact. My style isn’t a radical departure from his," he said. "As with other geniuses, Hunter created a new style." Big proponent of and believer in the free market and in smaller government that he is, O’Rourke is always perplexed by the fact that people are willing to cede power over to the feds and trust in big government. "People want government to supply structure and security they’re not getting in modern society," he said. "But they might as well ask Fed Ex."

After shaking O'Rourke's hand and thanking him for his quotes, I went out into the balmy southern California night feeling satisfied. The mission had been accomplished, though not under ideal circumstances. The job done and my scenario of tossing back cocktails with P.J. unrealized, I repaired to the nearest bar and drank enough for both of us.