Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967

by Hunter S. Thompson

  But you should see this house. It’s the finest thing I’ve ever laid eyes on. I’m on the side of a mountain in a pine grove overlooking the Neversink River. The cabin has a big living room, a bedroom, a kitchen, a bath, and an excellent screen porch. I’m about two hours out of New York City in the lower fringes of the Catskill Mountains. All in all, it’s too good to be true and I suppose some terrible heaven-sent justice will descend on my shoulders in the near future. Until then, however, I shall continue to live as I am today. Like this:

  I got up about ten, fed the dog, took a bath, and had a huge breakfast while I read The New York Times for news of the end of the world. I then took the dog, my pipe, and a bottle of wine and walked about a hundred yards down the hill to the river, where I spent two hours sitting on a huge rock above the rapids, smoking, sipping the wine, and planning a short story. It’s 2:30 in the afternoon now and I should finish this letter by 3:00. I shall then step into the Jaguar and drive about six miles across the mountain to meet a friend of mine from New York who is coming up with his fiancée to spend the rest of the week with me. We have a monstrous chicken dinner planned at another friend of mine’s house in Otisville, and after that we’ll probably come back here about ten and hike over to the waterfall to sit on the rocks and drink wine.

  The whole day would be 100% better if you could be here and I’m getting damned impatient over the question of your trek to the north. Since I haven’t heard from you in several weeks I won’t be surprised at anything I get in the next letter. Perhaps you and “the boy” have decided to set up housekeeping by this time, for all I know, or perhaps you’ve merely decided to stop writing. Whatever you’ve decided, I’d appreciate hearing from you. I suppose you’re in Palatka4 by now, so I’ll have this forwarded. I’m getting a little tired of being the lone wolf at these mountain gatherings and if you’ve decided not to come up I’d like to know about it so I can advertise in the local papers for a mistress. This is too fine a place not to share with someone and if I can’t do it with you, then I might as well import some sort of a pleasant decoration who’ll at least cook breakfast for me.

  I just reread your last letter and it makes me feel a little ashamed of the paragraph I just wrote. It’s one of the best letters I’ve ever received, incidentally, and I appreciate your going to the trouble to explain your concept of individuality. I agree wholeheartedly with what you say, but I hope you’re not like so many of my friends who find it very easy to talk about being an individual and very hard to be one. I don’t think you are, though, and I probably shouldn’t have said that.

  I’m also sorry, very sorry, that I couldn’t get down there for a few days. The truth of the matter is, though, that I simply have no money at all and it would have been impossible for me to come. The past three or four weeks have been absolute chaos as far as I’m concerned, and yesterday and today have been the first peaceful moments I’ve had. I wrote you a letter about two weeks ago, but I’ve saved it until the time comes for it to be mailed. The time is not now, but perhaps it may be here by the time I hear from you. Try to write soon and let me know how things are coming in Palatka, as well as in that beautifully-encased mind of yours. So until then, I remain, unnaturally yours.

  Love,

  Hunter

  TO JUDY BOOTH:

  Booth, another of Thompson’s Louisville girlfriends, was a junior at Smith College in Massachusetts. She accepted Thompson’s invitation to spend a weekend in Middletown, meeting up with him at the local post office.

  March 27, 1959

  Cuddebackville

  New York

  Dear Judy,

  Yes, Peyton,5 April fourth will be as convenient as any other time. We’ll have to work out something in the way of transportation to Cuddebackville, which is somewhat removed from the mainstream as far as population mass is concerned, but we’ll do that in a few moments when I feel more like thinking and less like rambling.

  I have just pulled through one of the most terrifying nights of my life, surviving with nothing more than a cold, I hope, to show for it. I ran out of oil about seven last night and by midnight the temperature in the house had fallen to 38 degrees. It had begun to snow again, the wind outside was one notch above intolerable, and a blanket of sleet fell on me about dawn. I had to stay in bed until three in the afternoon because it was simply too damned cold to get up. When I finally forced myself out of bed there was nothing but a half a quart of milk and two slices of swiss cheese for breakfast. I managed to limp over here to Otisville for breakfast and a bit of much-needed warmth and wine. An artist friend of mine from New York has been up here most of the week with some girl from Baltimore and I left them in Otisville last night because the girl was about to freeze to death in the cabin. The dog and I returned to the wretched place for the night where we spent the next twelve hours with the thermometer hovering around the forty-degree mark.

  The motto of this story is “never be fool enough to brave the elements unless you have no other choice.” At any rate, if I get a cold now, I should be through with it by the time you get here.

  My situation is, of course, unchanged as far as employment is concerned. At the moment I have three dollars to my name, a can of tuna fish and a can of soup in the cabin, no oil for the furnace, one bag of dried food for the dog, and about enough gas in the Jaguar to make it back to that freezing hellhole for the night. Perhaps, on second thought, I’ll stay here tonight.

  I have resolved, finally and without reservation, that I shall never again spend a winter further north than Atlanta, Georgia. Barring the event of war in the near future, I’ll probably jump off for Europe, probably Spain or Italy, sometime around September. If the car doesn’t blow up by then I’ll have a liquid asset which should provide me with enough money for food and wine across the sea—for a while, at least.

  No sense in going on about this as long as you’re going to be up here in a week or so, so I’ll save it for later. You’ll have to let me know how you plan to get here so I can pick you up somewhere.

  I’m trying to bring about some sort of uneasy peace right now between my dog and these people’s black cat, so I’ll wrap this up and expect you on April fourth, sometime in the morning, until I hear otherwise. Keep in mind that I have absolutely no money, of course, and that we’ll both starve to death unless you can buy some groceries and some scotch. Until then, take care.

  Heroically,

  Hunty

  TO WILLIAM FAULKNER:

  Thompson genuinely admired Faulkner’s novels, particularly The Sound and the Fury. This letter—sent to Faulkner’s home in Oxford, Mississippi—failed to elicit a response.

  March 30, 1959

  Cuddebackville

  New York

  Dear Mr. Faulkner,

  I thought you’d be interested in this item I clipped from today’s Times. It recalled a statement of yours I once read in something called Writers at Work. I don’t have the book at the moment, but the statement seemed to involve Henry Ford, Robert Frost, and the concept of “the writer as a fine dog.”

  As I look back on the past year, however, I feel inclined to disagree with both you and Mr. Sulzberger.6 As for as I can see, the role, the duty, the obligation, and indeed the only choice of the writer in today’s “outer” world is to starve to death as honorably and as defiantly as possible. This I intend to do, but the chicken crop in this area is going to be considerably depleted before I go.

  And, incidentally, if you feel, as a result of this letter, a ripping desire to send me a weekly cheque, please feel free to do so. My corruption tolerance has been tested and found firm. I am the only chicken-thieving, novel-writing Southerner in the Catskills who drives an ancient Jaguar, lives in an un-heated cabin, and spends the large part of his weekly unemployment cheque to buy high-test gasoline.

  The solicitation is in jest, of course. I am so used to writing letters to creditors that I can’t seem to get a grip on myself when I try to write a coherent letter. I’d intended to write
no more than a few lines here, so I’d best close before things get too wild. If you ever get up this way, I’d be happy to have you drop in on me. I have several extra beds and the troutfilled Neversink River runs right past my front door. An excellent place, all in all. A little cold in the winter and no food, of course, but a fine place to rest.

  And so, until we all dissolve in a blaze of radioactive newsprint, I remain, very sincerely:

  Hunter S. Thompson

  TO ROGER RICHARDS:

  Richards, an aspiring writer from uptown Manhattan, was Thompson’s constant drinking companion throughout much of 1958.

  June 3, 1959

  Cuddebackville

  New York

  Dear Roger,

  Sorry to be so late with this reply, but even though I have nothing at all to do I seem to be busy all the time. Your letter was excellent, though, and I’ll try to do it justice by writing something more, here, than just a short note or a long, drawn-out banality.

  I was in New York last weekend, but spent most of my time out on Long Island and didn’t get an opportunity to give you a ring. It was good to get away from the damned place again, and I don’t think I’ll get down there for quite a while, now that the weather is getting warm up here. Every time I come down there I seem to spend all my money, stay drunk most of the time, and waste the entire visit in a dull frenzy of looking for something that I don’t really believe is there. All of New York’s glitter is on the surface, like a huge, moonlit bay. It’s beautiful and clean and awe-inspiring on the top, but not many of us can walk on water. Not for long, anyway.

  You did a damned good job, I think, in evaluating the effect of your companionship last year. You were indeed depressing, and I had enough things to worry about without adding you to my list. There was no mention of Jo7 or the baby in your letter, so I have no way of knowing whether you severed that connection, as you threatened now and then, or whether you stuck it out for whatever it might be or might have been worth. I thought then and still think that it was none of my business. Advice is almost always useless, especially when it comes from someone as confused as I was this time last year. You say I seemed to be “sinking or retreating into some inviolable isolation,” and perhaps I was. It was a time of near-desperate evaluation—not only of self, but of all that had gone into the creation of self over the course of some twenty years. This past year, I think, will turn out to be the most critical of my life. It gave me a direction which only accident can change from here on in. I am in no position, anymore, to “go back and choose again.” As things stand now, I am going to be a writer. I’m not even sure that I’m going to be a good one or even a self-supporting one, but until the dark thumb of fate presses me to the dust and says “you are nothing,” I will be a writer.

  I write this letter naked, sitting on a stool in the sun outside my back door with a borrowed typewriter on the chair before me. Fifteen feet away is a black Jaguar sedan which I own and intend to sell in the near future for enough money to get to Europe and live a while. Two feet away my dog lies in the sun, pregnant and useless as only a love-starved female thing can be. Behind me is my cabin, a three-room structure with a front porch overlooking the Neversink River. I have no phone, no neighbors, and the closest friend is ten miles away, which suits me fine. I am situated in a pine grove above a river some seventy miles northwest of New York. Once a week I drive the Jaguar into Middletown and sign for my unemployment check. It is good of the State to support me while I learn my trade.

  At the moment I have two stories in the mail: one good, and one fairly useless.8 I am working on two more, both of which should be good. I am also working on a novel9 that could go a long way, as you say, toward helping me “make it in a big way.” It will be the story of Hunter and Hunter, the way he went and the way he could have gone. And, incidentally, why. I’m using the narrator-participant technique—à la Gatsby—and shooting for a short (300 pages or so) account of three people living a year in New York City that will decide the courses of their lives. That’s a pretty poor sentence, but I hope it’s clear. As I see it now, I should come up with something of a cross between Gatsby and On the Road. If you can imagine such a thing. God only knows when it will be finished.

  Before I forget, read a book called Lie Down in Darkness, by William Styron. This man is a Writer.

  Your flashback to the college football game was not only vivid and welldone, but it helped me get going on a short thing I sent to Esquire. If they don’t use it, I think I’ll try the Atlantic “Firsts” thing. And if not there, somewhere else. Keep hustling, hustling, hustling, hustling, hust.…

  I think I’ll run over to the lake, now, and soak up a bit of sun and cool water. I’m beginning to see what they mean by “the good life,” and all I need now is to sell a few stories to be right smack on top of the world. I hate to say things like that, because they always precipitate a fall of some kind. So I take it back; all I need now is to sell a few stories to get out of the hole.

  At any rate, thanks for writing and here’s hoping things are better for you now than they were last year. Drop me a line, while you’re at it, and fill me in on the rest of the Richards clan. If you’re still with Jo, tell her hello for me, and by all means kill the baby. That’s far and away the best thing you can do for the poor bastard. Between leukemia, bomb blasts, Russians, Africans, and Red Chinese, I don’t envy this next generation one damned bit. It would be merciful to kill them all.

  Leaving you with that bit of psychotic sarcasm, I remain,

  haphazardly,

  Hunter S. Thompson

  TO LARRY CALLEN:

  Callen was still in Iceland but now preparing to leave the Air Force for a civilian life as a public-relations copywriter.

  June 7, 1959

  Cuddebackville

  New York

  Dear Larry,

  Your letter found me in the same spot—literally. Since I have not held a job since March 1, I have been all but rooted to the goddamned chair in front of this typewriter. To no avail, of course; I might as well be sitting in front of an un-tuned kettle drum.

  Oh, I get a lot of letters written. Make no mistake on that. I write like hell—generally searching for outright loans or for visitors who will come loaded to the beltline with rent money. The goddamned thing is due again in about six days and I don’t have a cent to my name. I put an ad in The Times today, trying to sell my Jaguar. If and when that goes, I suppose I’ll have to get a bicycle so I can get in (13 miles) to sign for my unemployment check each Thursday. That’s another and a very long story. No time for it here. At any rate, I have two stories in the mail: one at Esquire and one at some rotten Science Fiction magazine. If either one of them sells I think I’ll spend the entire check on scotch. I don’t seem to be able to get drunk anymore. All I do is get diarrhea.

  Our last letters must have crossed somewhere in the vicinity of Cincinnati—or maybe Memphis. I hope it made you laugh, anyway. Your point about not being blue was a good one and made me think a bit. I immediately sat down and tried like hell to be blue. After about two weeks it finally “took.” I had a real good fit of the blues for about two hours. It didn’t compare, though, with those real fine late-night, many-cigarette, soft-lonely blues I used to get. I miss that martyred feeling, that heart-squeezing, lump-in-the-throat, June Christy10 kind of blues that I don’t think I have the capacity for anymore. The only time I get that is when I can identify with one of my characters; especially when it’s one who has all of his illusions intact.

  Maybe that wasn’t what you meant at all, but that’s how it came through to me and I thank you for making me think about it.

  The rest of your letter didn’t sit so well on my weary shoulders. This civil service thing sounds real nasty, and public relations sounds like the bog-bottom of journalistic swampland. You know how I am about this kind of thing, though, so don’t take it too seriously. Once I stop whistling in the dark, I’ll be lost.

  I’ve just been reading over two l
etters I sent you in Iceland. Perhaps I’ll try to publish my collected letters before, instead of after, I make history. At any rate, I notice a change in both our attitudes. Can’t go into this now, but maybe later. So until then, good luck in the swampland and write when you can. With absolutely no choice but to carry the banner, alone or otherwise, I remain:

  compulsively, HST

  TO ANN FRICK:

  Thompson and Frick were drawing apart over basic life philosophies. She wanted to settle in Tallahassee and raise a family; he longed to see the world and “make it” as a writer.

  June 8, 1959

  Cuddebackville

  New York

  Dear Ann,

  I don’t know why I bother to answer your letters so promptly, in view of your recent failures. Perhaps it’s just to set a good example. At any rate, here it is.

  I find it interesting that you say in the same breath that you don’t want to come up here, but that you “would like very much to be near me.” It typifies, I’d say, your present outlook on life. Something about having your cake and.… You finish it. What I think you really mean to say—perhaps without realizing it—is that you wish I could fit in with the pattern of life you’ve tentatively laid out for yourself. You say you “don’t really know what you want to make [your life],” but I’m inclined to think you’re wrong. Not knowing what you want out of life is a pattern in itself, perhaps the most rigid pattern of all. As a matter of fact it’s probably the most predominant pattern in the country today, and just another name, in the long run, for what we call the “American way of life.” You are in a large and very crowded boat, floating around aimlessly and complacently in a very treacherous sea.

  At times I seriously regret that I’ve divorced myself so completely from that pattern. Life is much simpler that way, and very often much more pleasant. I’m sorry, in a way, that I wasn’t brought up to believe in it. I regret, also, that I no longer have a taste for cotton-candy.