David S. Wills, in Quillette, celebrates the great and degenerate Hunter Thompson who successfully turned bad behavior into art.

[W]hen Thompson called Hinckle at three o’clock one morning in April 1970 and said he wanted to write a feature about the Kentucky Derby, Hinckle readily agreed. Thompson had been having dinner with his friend, Jim Salter, in Aspen, Colorado, when the subject came up. Salter had asked him if he was planning to attend the derby and Thompson said he wasn’t. After the spell in jail that had cost him his high school diploma, Thompson had joined the Air Force and considered his escape from Louisville to be more or less permanent. He did not particularly feel like going back to rub shoulders with the people who had looked down on him and, finally, turned their backs as he wept in a lonely courtroom.

Thompson was a night owl and, after dinner, he stayed up pondering Salter’s question. Maybe it was time to go back and see the derby. It might be the sort of thing he could write about: the outsider returns after more than a decade on the road. This needn’t be a dull article for a conservative newspaper or magazine, which was the sort of work on which he’d cut his teeth in the early Sixties. So, he called Hinckle up in the middle of the night and asked if he would pay for a flight to Kentucky plus expenses. “The story, as I see it,” he explained, “is mainly in the vicious-drunk Southern bourbon horse-shit mentality that surrounds the derby than in the derby itself.”

Thompson’s writing was already beginning to resemble what readers would later come to call Gonzo journalism. He tended to insert himself into the prose as observer and participant, embark on weird and irrelevant digressions, recount conversations and events that probably never happened, discard any pretense of objectivity, lurch erratically in and out of hyperbole and paranoia, and dust his prose with a litany of stylistic quirks and a peculiar lexis that included words like “atavistic,” “swine,” “savage,” and “doomed.” It was a subjective, chaotic, and messy approach to journalism unsuited, Thompson felt, to the blank objectivity of a photojournalist’s camera. So, he asked Hinckle to assign him an illustrator instead.

Ralph Steadman was one of the best young cartoonists in Britain and, just like Thompson, had a wonderful talent for bringing out the inner ugliness of his subject. Neither of them liked to dress a subject up and make it look pretty; they preferred to identify a flaw and blow it out of all proportion. The art director at Scanlan’s had heard that Steadman was looking for work and called him up. On the way to the airport, he realized he’d forgotten his artist’s toolbox. He stopped briefly at the home of one of the magazine’s editors to scavenge what he could and left with eyebrow pencils and lipstick.

Among the Kentucky Colonels, Thompson and Steadman stood out like sore thumbs. Fresh from his failed Freak Power campaign for sheriff in Aspen the same year, Thompson was sporting a shaved head. He was also tall, handsome, and usually dressed in bright clothes. Steadman, on the other hand, had long hair and a wild beard. The two men should have found it easy to locate one another, but somehow it took them two days before they finally met in the press room. They immediately set about drinking and did not stop until several days after the race.

When eventually it came time to leave Louisville and produce the article and illustrations, Scanlan’s brought both writer and artist to New York and had them hole up at the Royalton Hotel. It took Steadman two days to complete his illustrations, but Thompson found himself confronted with a brutal case of writer’s block. He lay in the bathtub, slugging whisky from the bottle, and awaiting inspiration. Eventually, his frantic editors called and demanded something. The magazine was due to go to press and there was still a huge hole in the middle of the issue where Thompson’s story was supposed to go. Thrown into a panic, Thompson ripped pages out of his notebook and handed them to the copyboy. Hinckle called and declared it brilliant. Within an hour, the copyboy was back for more, and Thompson’s story appeared as scheduled in the next issue beneath the eye-catching headline “The Kentucky Derby is Decadent and Depraved.”

Thompson later admitted that he felt guilty and ashamed about his failure to write the article. The magazine’s editors and readers, however, felt differently. It was, they thought, a triumph. The first half recounts Thompson’s arrival in Kentucky, a prank played on a gullible racist at the airport, and then his meeting with Steadman. The second half is a disjointed but somehow intensely personal account of a day spent staggering around the derby in an inebriated state, terrifying attendees and spraying a restaurant full of patrons with mace. Thompson and Steadman didn’t bother to actually watch the race they had been sent to cover. Instead, they went in search of a “special kind of face” that they hoped would allow Steadman to produce a representatively scathing portrait of Kentucky’s upper class. As they are about to despair of finding someone suitable, Thompson glances in a mirror and realizes:

There he was, by God—a puffy, drink-ravaged, disease-ridden caricature… like an awful cartoon version of an old snapshot in some once-proud mother’s fancy photo album. It was the face we’d been looking for—and it was, of course, my own.

It was a highly unusual piece of writing that trashed the conventions of traditional reporting in favor of a freewheeling rock’n’roll antagonism. It was funny but aggressive, satirical and cruel, and only loosely factual. It was neither exactly journalism nor exactly fiction… it was something in between and something quite new.

RTWT