By Larry Smith

By Cheryl Della Pietra

“A day without fun is a day that eats shit.” —Hunter S. Thompson, circa 1992

In 1998, as the movie version of Hunter S. Thompson’s Fear & Loathing in Las Vegas was about to be released, Cheryl Della Pietra wrote a story for P.O.V. Magazine about her experience serving as Thompson’s assistant at his storied Woody Creek, Colorado compound. Her editor on the piece was SMITH Magazine founder Larry Smith, who asked Della Pietra if he could reprint her terrific tale here, as something of a compliment to SMITH’s excerpt of Gonzo: An Oral History of Hunter S. Thompson. What follows is that story, with small edits for clarity, mostly reflecting the fact that at the time of Della Pietra’s writing Thompson was alive.

Wanted: Editorial Assistant

Job Description: Must enjoy late-night hot-tubbing, chain-smoking, binge dessert eating, drinking hard alcohol, mixing margaritas and driving large cars in a reckless manner. Should be able to withstand frequent yelling and loud noises, unintelligible rantings, and handle firearms and exploding targets with ease. Knowledge of soft porn a plus. Curiosity about the limits of sleep deprivation helpful. Knowledge of housecleaning and faxing imperative. Young and sexy recreational drug users encouraged to apply.

That’s what someone should have told me. But I could barely understand the mumble on the other end of the phone at 3AM as it was.

“Who the hell is this?” I barked.

“Hunter Thompson.”

“Oh, shit.”

The mumble told me to get my ass on a plane the next day. The author of Fear and Loathing in Las Vegas was looking for an assistant to help out on his forthcoming novel, Polo Is My Life, and had received my letter and resume. “Come out for the weekend, we’ll see how things work out.” There would be a ticket waiting for me at the airport.

I didn’t go back to sleep.

When the Going Gets Weird

“It was Easter Sunday. A friend and I were out driving and she fired a couple of those little screamers you use to scare away birds, and all of a sudden they were threatening to arrest me…”

—Hunter S. Thompson, Playboy magazine, October 1992

I guess there are more compromising ways a 22-year-old woman can end up in the pages of Playboy. I had barely been in the company of Hunter 24 hours before I got us in trouble with the law. For any other job, this was grounds for dismissal, for this one, it was like gunning for a promotion.

Hunter, with his trademark Tilley hat, cigarette holder and sunglasses, greeted me himself at the Aspen, Colorado, airport, following a bumpy plane ride made worse by my fear of flying. Other than a welcome lunch filled with an excess of Champagne and tequila, the man seemed downright normal. I was brought to his Woody Creek compound, a remote tract 8,000 feet above sea level, and I settled into a small cabin adjacent to the main house, which I would share with his longtime personal assistant, Deborah. I went to sleep wondering what the fuss was all about. Day Two started out innocently as well, with breakfast at the famed Woody Creek Tavern, where groupies hang out hoping to catch a glimpse of the local hero. There was no sense of impending mayhem when we decided to go for a Sunday drive up the mountain.

Then we packed the car. One bottle of Champagne, one .44 magnum, one pipe, one pack of Dunhill blues (for me), one pack of reds (for him), a bottle of green Chartreuse, a whole chocolate cake, a bag of, uh, fungus, a screecher gun used for scaring away birds, one glass of scotch with lots of ice and a blanket. A picnic for a madman—and his new hire. Driving in the red convertible up the mountain, sampling the assembled feast, I could feel the mischief rising like a fever.

When we reached the top of the mountain and were met by a bunch of snowmobilers blocking the road, it never entered my mind that anything was wrong with taking the screecher gun and firing two times into the air. All right, I guess it looked like a real gun, and since Hunter was behind the wheel, I was just as shocked as anyone that it wasn’t.

On the way back down the mountain, we set up exploding targets on the side of the road and I shot at one with the .44. For me it was like losing my virginity to John Holmes. I had never even touched a real gun before, and between the kickback and the noise, I was hooked. By the time I noticed the sirens behind us, I was too messed up to fully understand what was happening—and almost totally deaf. When the cops asked for my ID, I just smiled and laughed. When they asked my name, Hunter reprimanded, “You don’t have to talk to the cops!” Well, he would know. I just smiled and laughed. Luckily—shockingly—the fuzz didn’t search the car. And I realized later on this warm spring day, that’s what the blanket was for…But who did I think I was dealing with? An amateur?



Looking back, it’s clear that Day Two was decision time. I had passed Hunter’s test. I had managed to piss off the cops, keep my mouth shut and not rat on anyone—in other words, do all the things a faithful assistant to the father of gonzo journalism is supposed to do. And while I could easily have shoved off and gone back east, as most people would have, I was trying to figure out exactly who I was and what I wanted to do. And something told me that hanging around this man—this deranged man whose legendary tales I had devoured throughout my college years—would help me learn exactly that.

Notes on Gonzo

For the uninitiated: Hunter S. Thompson was the originator of “gonzo” journalism. Loosely translated, to be gonzo is to embed yourself in a subject matter so thoroughly that you actually live it. Thompson perfected this craft through a series of ground-breaking works: Hell’s Angels, Fear and Loathing in Las Vegas, On the Campaign Trail ‘72, The Great Shark Hunt, among others. And although one of the great mistakes many writers make is thinking that everything that happens to them is interesting; in the case of Hunter S. Thompson, it is.

In defining the generation of the sixties and seventies, he is in the company of John Lennon. As a writer, he rivalled Norman Mailer in both pure ego and utter eloquence. And as an addict and a madman, he put Keith Richards to shame. All this comes together in Fear and Loathing in Las Vegas, the book—and later film, with Johnny Depp as Hunter—that remains firmly at the center of what has become the Cult of Thompson.

Hunter S. Thompson FAQs

How exactly does one land a job with Hunter Thompson? Pure luck, actually. A friend was working at Rolling Stone, and Hunter (long after most of his reporting for the magazine was behind him, Thompson remained on the masthead, cloaked as his alter ego, Raoul Duke) had informed the magazine he was looking for an assistant, preferably female. I wrote a fairly unorthodox letter, and he rang me up two days later. It didn’t hurt that I was a bartender at the time.

Does he really do all of those drugs?

Yes. Constantly. This monumental intake is accompanied by a tall tumbler of scotch on the rocks, which is replenished with fresh ice and booze—constantly—from morning till night. He unapologetically didn’t 12-step his way into old age; indeed, at the point in his life when I met him, he’d probably have croaked if he stopped.

What did you do there?

This is a tough one to explain at a job interview. I went, ostensibly, to help him work on his long-promised novel, Polo Is My Life. The project has been in the works for seemingly forever, and the lack of progress makes sense. Thompson writing a work of fiction is like Madonna trying to act. What’s the point? When the political campaign of 1992 started to heat up, he just couldn’t help himself. The writing that ensued eventually turned into Better Than Sex: Confessions of a Political Junkie.

Did you have any, you know, shenanigans with him?

Actually, no. There was a fumbled kiss in the car on the day we almost were arrested, but the instant I rebuffed, he went out and got himself a girlfriend. I did not envy her.

We Are, After All, Professionals

All insanity aside, there was work to be done. There were no rules and no routine, and the recipe for success was different every night. The general organizing principle: to have Hunter’s hands on the typewriter by 2 (AM, that is). My job was akin to caging a wild animal and slowly cornering it into submission. The mentor/apprentice roles were blurry. Obviously he was the mentor, but it was almost impossible to get him focused; I was the apprentice, yet it was I who was sometimes forced to bark orders. I was considered successful if pages were stacked up the next day, no matter what words landed on them. In effect, it was my job to usher in the environment that would make the magic happen. While that job description might sound like a glorified babysitter, when you’re babysitting a lunatic genius, it’s a hell of a job.

The evenings went down like this:

What I wanted to do: Sit down, talk about the current text, see if we couldn’t get a direction going for the next chapter.

What he wanted to do: Jump into the hot tub with a whole key lime pie, a cell phone, a bottle of Champagne and Caligula on in the background.

Well, he was the boss.

The Night Shift

My stint slinging drinks had weaned me off the nine-to-five shift, but this was more like active vampirism. Deborah would help him with his personal affairs during the day; at around 9 PM, we’d have an unspoken shift change and I’d take over to help him with his writing.

When everything was working, the good nights were magic. The constant feed of CNN on the large-screen TV was our background noise, the typewriter would sing, he’d crank up Lyle Lovett. These wholly private moments—the night shift—would lend a dark creativity apparent in most of Thompson’s work. We’d be left with a respectable stack of pages, then at sunrise we’d go out on the shooting range and fire off a few.

As one would expect when dealing with a person of extremes, the bad nights with Hunter were like being chained to a bar where the bad drunk really wants to talk to you. “You stupid 22-year-old WOP! Didn’t you read anything?!” This was one of the major reprimands—not having memorized every goddamn word the man ever wrote, or even read. I was once banished to my cabin at three in the morning to reread The Great Gatsby. I was once kicked out after failing to recall a portion of the end of his book Songs of the Doomed. I witnessed broken lamps, broken dishes. (The latter was a Frisbee throw that just missed my head. “I did not try and hit you, so don’t go around saying that I’m abusing you.” Even though he was serious, it actually made me laugh.) Evenings like this were a race to see who could be reduced to a quivering mess first. To leave would be to admit defeat. But to stay was sure torture. Eventually I would leave and go back to my cabin next door. The morning would almost always bring a note of apology, or a phone call to the same effect. That’s just how things worked. He was a Southern gentleman at heart, and at least he could apologize like one.

Coming Down

Three months later, I was growing weary, not unlike Jennifer Jason Leigh toward the end of Rush. I was nervous, sleep deprived and so tired of everything being so BIG. Trips to the gardening center wound up as portable flower shows. Every jaunt to the liquor store was like buying for a wedding reception. Lunch was like a damn buffet. I began to understand that tedium can occur under any circumstances; even the most extreme can turn dull with repetition. Scotch for breakfast? Again? Really?

Additionally, I had too much ego for the position. Thompson always hires young women, and I think I figured out why. The job, ultimately, is to nurture. Become selfless. Stroke. The insecurity and paranoia that are inevitable accessories to genius gave way to this giant ego. With the lot of us around him almost constantly—his personal assistant, his girlfriend, myself—there were no large egos to fight his. At least that was the deal if you wanted to stay. But how long can you feed the dreams of others before you lose sight of you own? I found I could do it for one long summer. Then it was time to go.

The Way You Wear Your Hat

My last day was everything a last day at a job is supposed to be—only, of course, bigger. Most jobs involve lunch out with your coworkers, perhaps a nice parting gift. (A beige blouse? Gee, thanks!) But at this one, Hunter, his girlfriend and I caught a chartered plane to Denver. We were going to a party at his attorney’s place. As I looked out the window of the turboprop, I realized that my fear of flying had disappeared. Perhaps it was the fact that I had been living on the outer edges for the previous months, but the perspective it lent made my everyday worries seem, well, boring.

We landed and were met by a limo that carted us to the party. It was my first time away from Woody Creek in a while, and I experienced a low-level culture shock. The schmoozing legal and political types might as well have been a bunch of hedges on the lawn. Get me a drink, was all I could think.

I can only imagine the picture we cut: Hunter and his two ruby-red-lipsticked, chain-smoking vixens. We, in color, wove through the black-and-white crowd. (I vaguely remember meeting Gary Hart.)

I was here that I realized I had become an addict. I was addicted to the rush of life—to a degree I had never imagined, a degree most people never know. And as if to put an exclamation point on this, Hunter threw me into the pool, fully clothed, and when he went to offer me a hand out, I pulled him right in with me. So we swam, Hunter and I…until it was time to go. And indeed, it was.

He left me in Denver to catch my plane. During our last moments in the limo, he peeled off a couple of hundred-dollar bills, gave me a kiss and thanked me for my time there. Then he was gone. The limo driver escorted me to the airport, and as I was gathering my things, I realized I was sitting on something. Oh my God. The Hat. I put it on, grabbed my flight, and never thought once about sending it back. It looked good on me.

There are certain moments that make impressions that stay with you no matter how far away from them you travel. Strangely, most of the time I spent with Hunter, both high points and nightmares, stands out in bold relief six years later. But of all the strong memories I have from that time, this is the one I remember most: “A day without fun is a day that eats shit.” Hunter paused and looked at me like I was an idiot. “Write that down!” he barked. Dutifully, I added it to the random notes I had been keeping and noted “HST, 12:48 AM, 4/8/92.” Although the one notebook I smuggled out of Woody Creek has other bizarre unintelligible notations, all written down in the name of some split-second inspiration (”He gained 25 pounds of pure muscle and 100 pounds of rage. Write that down!” “Yesterday the circus meant nothing to me; today it means everything. Write that down!”), six years later, the only thought from Hunter I really remember writing down is the one about fun.

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READ an excerpt from Gonzo: An Oral History of Hunter S. Thompson.

READ Gonzo for Beginners in Rolling Stone.

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