On a theoretical list of Thompson’s top fans, I’m just below his agent, editor and mom, jockeying for position with his wife and oldest friend. I read Smile When You’re Lying: Confessions of a Rogue Travel Writer three times. Partly because of his excellent storytelling, humor and how strongly I identified with his views on the travel writing industry and partly because it was one of only two books I had with me for five weeks of slo-mo travel in Thailand and Burma last year.

My only real gripe was that he didn’t write it in 2003, so I would’ve had more realistic expectations as I was quitting my career, selling my home, car and all possessions and setting out on what turned out to be 4 and 1/2 years of nomadic, global meandering and paying my travel writing dues, but that’s hardly his fault. Hardly.

To Hellholes and Back: Bribes, Lies, and the Art of Extreme Tourism (Holt) starts as many travel memoirs do: the back-story of the journey peppered with doubt, fear, curiosity, resolve and, finally, execution. Thompson decides, for apparent want of self-inflicted misery, to visit four destinations that he has spent his career actively avoiding: Africa, India, Mexico City and Disney World.

This part of travel memoirs is always tricky, surpassed only by the epilogue for highest Boredom Potential Quotient. The somewhat dry details of his trip planning for his first objective, the Congo, unfortunately fall victim to this phenomenon, with a few overachieving jokes falling flat. But Thompson is soon on the ground in Kinshasa where he hits his stride, slam dunking glorious turns of phrase as I had so eagerly anticipated. Kinshasa turns out to be a real dud of a destination, but Thompson nevertheless manages to seed nearly every page with vivid and hilarious metaphors that would take Tucker Maxs 20 pages to match.

The India and Mexico City narratives are equally fun. Parts of the text are so brilliant that I feel a bit like a poseur by claiming the same job title as Thompson. I was especially sucked into the arc of the book, as I have a similar no-go list, though mine also includes Russia, Egypt, the Caribbean, and the entire southern half of the US.

Moreover, I never get tired of the priceless freedom and bluntness with which he fires off lectures and insults on deserving people/places/things. This is the kind of editorial autonomy that most travel writers can only dream about. Sure, I get to sneak in the occasion dig in guidebooks and blog posts, but to go on for three unapologetically brutal pages on the maddening tactics of Indian merchants is the sort of long-form, literary spanking that me and my travel writing brethren/sisteren rarely get to dish out.

Unfortunately the entertainment dips as Chuck enters the mysterious and unsettling world of Floridian theme parks. The section that I had assumed would incite the most scathing, thousand word, series of hilarious diatribes is only ho-hum as Thompson, probably to everyone’s surprise, doesn’t completely hate the place. The epilogue also feels phoned-in at times, though this seems to be the section where even people like Bill Bryson can get bogged down in babbling resolution and perhaps I just need to change my expectations.

I think what makes Thompson so fun to read is his strong, unwavering opinions on virtually every subject, occasionally bordering on, albeit charming, crackpotdom. He ain’t afraid to offend people, as is plainly demonstrated when he merrily alienates approximately two billion soccer fans during a ruthless two-page condemnation of the sport and later frankly lectures an employee at the biblical theme park the Holy Land Experience about his utter lack of understanding of basic Christian values.

Thompson makes these polarizing convictions work largely because he’s able to deftly balance these extremes with an overriding self-effacing humbleness and wit that you don’t see in most crackpots, mostly because they’re patently insane or intolerably stupid, and Chuck is neither of these things. Mark my words, 25 years from now one of Chuck’s offspring is going to launch the 2035 equivalent of “Shit My Dad Says”, zapping Chuck’s hilarious, self-esteem crushing quotes to a global audience in all their vitriolic glory (and winning the world’s fastest and easiest, non-vacuous celebrity book deal a week later – not that I’m bitter, kudos Justin).

Unfortunately, though it pains me to admit, it seems the curse of the Second Travel Memoir has struck again. While Hellholes is undeniably replete with the kind of wit and spit-take metaphors written by a different Thompson that first inspired me to be a writer, I don’t think I’ll be reading it three times and keeping it in an easy-to-reach place like I did with Smile When you’re Lying. Truly, you’ll be courting a nostril-flushing disaster if you attempt to enjoy a beverage while reading parts of this book, but when travel writing students in the Class of 2030 are reflecting on the canon of Thompson travel memoir classics, I don’t believe Hellholes will be among them.