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But O'Rourke is your typical white-bread, middle-class suburban kid from Toledo. His father, a car salesman, died when O'Rourke was nine and left his mother, who later went to work as a school secretary, with very little. She remarried, and O'Rourke detested her new husband. "I was a fairly unhappy kid with a very active fantasy life," he remembers. He left home in high school, then returned for a short time before studying English at Miami University in Ohio. He recently married 26-year-old Amy Lumet, daughter of film director Sidney Lumet and also Lena Horne's granddaughter, and the couple split their time between a 60-acre spread in Shannon, N.H., where Amy is completing college, and a spacious apartment in Washington.
When he writes, O'Rourke retreats to a third-floor hideaway in his New Hampshire home. It's a manly place, replete with fireplace, dark wood paneling and mementos of his world travels scattered about. He shows no interest in computers, choosing instead to hammer away on an IBM electric typewriter. Up close, O'Rourke, like many funny writers, comes across as a fairly normal guy. He holds doors open for women, he likes kids, and he's proud of a tangy hors d'oeuvre he fashions from sliced cucumbers, black pepper and the cheapest vinegar you can buy. At the grocery store, he waits patiently in line to buy swordfish, but he refuses to purchase any lettuce you cannot toss from home plate to first base. His satiric quips often surface without warning, and nearly two decades of pun drill have honed this trademark skill, allowing him to punctuate any point with a snappy one-liner: "This country is so urbanized we think low-fat milk comes from cows on aerobic exercise programs." But beneath this talent is an immense desire to succeed. Perhaps O'Rourke's troubled childhood or his mother's death in 1973 helps explain this unfettered ambition, which, along with his right-wing politics, is about the worst trait anyone pins on him. He made some enemies when he took over National Lampoon. "He went from combat boots to two-tones over a weekend," says former Lampooner Sean Kelly, who calls him a chameleon. But even Kelly concedes a grudging respect for O'Rourke's success. Although Koreans are still smarting from his essay that described them as "hardheaded, hard-drinking, tough little bastards, 'the Irish of Asia,' " O'Rourke bristles at charges of racism and sexism, claiming he spares no group, including his Irish ancestors, from abuse. "I don't think there's anything in my writing that says being a male or white is better," he says, "but it's definitely the thing I'm most familiar with."
His worst flaw may be a rah-rah jingoism that informs some of his pieces, like the one in which he cheers the fall of the Berlin Wall. "The privileges of liberty and the sanctity of the individual went out and kicked some butt," he says. Or it may be that he feels no compunction to propose any answers to the problems he raises. Or perhaps it's that he often invokes the "I'm-just-kidding" defense as an all-purpose shield. But, hey, who can hold a grudge for long against a guy who explains that the Ottoman Empire got its name "because it had the same amount of intelligence and energy as a footstool"? O'Rourke simply calls them as he sees them.