In The Great Gatsby, F. Scott Fitzgerald’s protagonist, Nick Carraway, describes Jay Gatsby as possessing a smile of the following sort:

He smiled understandingly-much more than understandingly. It was one of those rare smiles with a quality of eternal reassurance in it, that you may come across four or five times in life. It faced–or seemed to face–the whole eternal world for an instant, and then concentrated on you with an irresistible prejudice in your favor. It understood you just as far as you wanted to be understood, believed in you as you would like to believe in yourself, and assured you that it had precisely the impression of you that, at your best, you hoped to convey.

Gatsby was arguably Hunter S. Thompson favourite novel. If it was not his favourite, it was certainly the one he mentioned the most, and to which he compared his own work on a regular basis. He was always trying to compete with Fitzgerald in producing a novel with not a wasted word, and which captured an era perfectly.

I have written before about Thompson’s adoption of the cadence of the final pages of Gatsby in his famous “wave passage” in Fear and Loathing in Las Vegas – a book Thompson claimed to have surpassed even Gatsby in its brilliance. In that article, I asked what exactly made Thompson’s work so unique. Why is it that one could pick up almost any of his articles and know immediately that it was a work by Hunter S. Thompson? I speculated that there was a rhythm to his work, partly cribbed from Fitzgerald, that was totally his own, and I stand by that assessment. There are also other aspects, most of which are rather obvious, including his use of certain words and phrases (“atavistic,” “a monument to ___”) and of course the profanity, drug use, madness, and flights of fancy that otherwise mark much of his work.

In one of his breakthrough articles, “The Temptation of Jean-Claude Killy,” we can see Thompson very much at the height of his literary powers, and speaking in a somewhat restrained version of the voice millions would come to know and love a few years later in Fear and Loathing in Las Vegas. In the Killy piece, which ran in the first issue of the short-lived Scanlan’s magazine, Thompson used several more of his trademarks, including the use of a sidekick (in this case Bill Cardoso, the man who earlier coined the term Gonzo) and the idea of the story being the story – in other words, the difficulty of making an article about a boring man became the whole point of the article.


Yet it is in this article that we also see most clearly another element of Thompson’s work that makes it so brilliant, and that is his use of ridiculously specific phrases. Thompson’s work is often hilarious, partly because it is so over-the-top, but there is something else there. His later stories were madcap adventures, too, but by then he’d lost what made him funny: his wild, vivid imagination.

In “Jean-Claude Killy,” Thompson is warned by one of Killy’s press agents not to embarrass the skier, and instead be “discreet” by not digging into his past. Thompson raises an eyebrow, claims ignorance, and then states that Killy does not look like the sort of person whose kink involves “a cattle prod and two female iguanas.”

The result is hilarious because of its specificity and subtlety. A later Thompson would likely have accused the skier of being a pig-fucker or “Pervert” (capital P) but the young writer was keenly aware that this hyper-specific description – very definitely not an accusation – was much funnier. It puts a distinct idea into the reader’s mind – an idea that the reader had almost certainly never thought of before.

Elsewhere in his article, he compares a room hosting a bored Killy as being “like a bingo parlor in Tulsa.” The effect is far greater than describing what the room actually looked like, which would be comparatively mundane. When talking about travelling with United Airlines, rather than saying it was an uncomfortable or unpleasant experience, he simply says that it “is like crossing the Andes in a prison bus.” Again, he has imparted in the mind of his reader a distinct and unforgettable visual image. It is funny, informative, and memorable.

But perhaps the most brilliant description in the book is of the evasive Jean-Claude Killy himself, who Thompson describes as possessing a smile like James Dean but mixed with “a teen-age bank clerk with a foolproof embezzlement scheme.”

Every writer knows that it is hard to describe a man’s appearance in a way that will resonate with readers, but in this short sentence Thompson has succeeded mightily. He has placed an image in the head of his reader that will stick there permanently. He cannot help but bring Fitzgerald into the mix a few paragraphs later, quoting Fitzgeralds own words from the beginning of this article. Yet I do wonder if in this article Thompson has perhaps surpassed Fitzgerald. In just a few hilarious words, he has said more about Killy’s smile than Fitzgerald managed in his famous description of Gatsby’s.