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P.J. O'Rourke poses for a photo after a reading in The Brigantine Room at the Harbourfront Centre on Wednesday, March. 21, 2007.

Philip Cheung/The Globe and Mail

P.J. O'Rourke is a frighteningly funny man; although for left-leaning types (O'Rourke describes such earnestness as "stupidity that was sent to college") the emphasis may lie on frightening. The popular American satirist and former hard-living gonzo journalist is rabidly Republican. Constant ranting, and a tough coating of cynicism, colour all his work.

But O'Rourke is also a chimera, whose contradictory career was built upon the shoulders of Rolling Stone, Esquire and even Vanity Fair. While his widely published essays reek of cocksure swagger, he routinely admits to being unsure about nearly everything (a healthy habit). He is clearly smart as heck, yet hides behind an endless smokescreen of self-deprecation. His trenchant commentary, as perceptive as it is outrageous, comes peppered with moments of humanity. He projects himself as both an elite and an everyday man, an intellectual redneck who can inspire and horrify in a single sentence. Yet beneath the pithy zingers and relentless insouciance lie glimpses of disarming honesty.

O'Rourke polarizes readers, not always along political lines. Those who like him, like him a lot. And those who don't, well, it's a safe bet O'Rourke doesn't give a rat's hoot.

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Reading O'Rourke can be challenging. First-timers often need to acclimatize to his snappy, almost barbaric prose, to find their way through the steady sarcasm and obfuscation to his razor-sharp observations and sophisticated commentary.

O'Rourke's first travel book, Holidays in Hell (1989) was a masterstroke. The collection of stories, which drags readers through "the world's worst places" (essentially war zones) is eye-wateringly hilarious; shocking for its insolence and piercing with its insights. When O'Rourke is on his game, his ability to capture the entire essence of foreign lands and people with a single comic caricature is unrivalled.

Fourteen books and more than two decades later, O'Rourke has ventured into travel writing again (bringing, of course, his politics along) with Holidays in Heck. He now explores more pedestrian lands, often with his wife and three young children in tow.

The book is a collection of previously published and slightly tweaked essays (for the most part, assignments from Forbes Life), which lumbers between destinations without any apparent connective tissue, often without any apparent point.

The 17 chapters offer a peek inside the Toulouse Airbus 380 factory, a treatise on modern art (no surprise, O'Rourke hates it), a family ski vacation to Ohio, a river boat down the Yangtze, a visit to the USS Theodore Roosevelt aircraft carrier, and a horse journey across Kyrgyzstan. He takes the kids – rather unenthusiastically – to Disneyland's House of the Future, to the Foreign Correspondents Club in Hong Kong, and to Chicago's Field Museum. There is a particularly poignant (but no, not earnest) chapter about his cancer diagnosis.

Many of the best moments come via his children, whose innocent observations offer a beautiful counterbalance to O'Rourke's snide outlook, and he captures their essence deftly. His wife, sadly, remains clichéd, an apparition that slips in and out, apparently interested only in shopping.

There is plenty of vintage O'Rourke. On Asian traffic: The English drive on the left. The Americans drive on the right. The Chinese respect both customs. On Hong Kong's Ocean Park amusement park: "I was on a continent where You Must be Taller than the Clown to Ride is a profound insult to half the population." On the environmental consciousness of Republicans: The son of a Republican friend, when asked by his preschool teacher if he could name the four seasons, proudly said, "Dove, ducks, deer, and quail!"

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In titling his book Holidays in Heck, O'Rourke begs comparison to his earlier, breakthrough effort. Unfortunately, the fury of Hell has lost focus in Heck. O'Rourke's overbearing politics, once a source of constant humour, no longer feels funny. The tone is sour, and the author appears to have slipped from hip contrarian to grumpy old man.

Ultimately, Holidays in Heck will satiate long time O'Rourke fans, but is unlikely to win new ones.

Bruce Kirkby is a weekly columnist for Globe Travel.

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