It was during this period that Thompson most smoked pipes, though that
would later change to his signature long cigarette holders and mostly
Dunhill cigarettes, along with cigars. In The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967
(1997), a series of his letters during that time span, Thompson
mentions his pipes several times, such as, "Feeling a fit of nostalgia
coming on, I hurriedly lit up my charred but tasty pipe." In another
instance he wrote:
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.
In another letter he describes a typical morning:
Eat in Old San Juan at six-thirty, out to pick up mail in Rio Piedras at
nine. Read your letter on way over here, take off clothes and go naked
down to beach with pipe and glass of brandy. Smoke pipe, drink brandy,
swim, come back in for shower and to write this letter.
He mentions his pipe in yet another letter: "I keep applying for jobs
and people keep running me out of offices because of my hair and my
pipe-thing." The subject of pipe smoking arises again when Thompson
relates his attendance at an auto show featuring the famous
triple-Olympic skier Jean-Claude Killy:
Meanwhile, slumped in a folding chair near the Killy exhibit, smoking a
pipe and brooding ... I am suddenly confronted by three young boys
wearing Bass Weejuns and Pendleton shirts, junior-high types, and one of
them asks me: "Are you Jean-Claude Killy?"
... "Well," I said finally, "I'm just sitting here smoking marijuana." I held up my pipe. "This is what makes me ski so fast."
They stared at me — waiting for a laugh, I think — then backed away.
Five minutes later I looked up and found them still watching me, huddled
about 20 feet away behind the sky-blue Z-28 Chevy on its slow-moving
turn-table. I waved my pipe at them ... but they didn't wave back.
He wasn't actually smoking marijuana at that event, though it wouldn't
have been uncharacteristic later. He just liked messing with people. He
mentions his pipe again in a letter to someone named Mrs. Boyle: "Thanks
for sending the Styron Report; I read it and actually considered, for
the first time, that perhaps I might drop the habit. Which really
shouldn't be too hard, with a pipe and cigars in reserve. Odd, how
language can convince a man, where reason fails entirely."
E. Jean Carroll, in Hunter: The Strange and Savage Life of Hunter S. Thompson (1993), quotes Thompson about his earlier pipe smoking:
We all joined the Sunday school class because we could, ahhhh, we had
special activities. At night we had all taken up smoking pipes. We would
go to the Walgreen's drugstore across from the library. And we got
pipes of tobacco. And sneaked out of the Sunday school and smoked our
pipes on the stairs of the church.
Carroll goes on to describe a visit with Thompson:
I went down on spring vacation and visited Hunter in New York after he'd
been up to see me at Yale. He was in a very bleak apartment in
Greenwich Village, with absolutely no food except a jar of peanut
He smoked a pipe. Wore a long overcoat buttoned up to his neck. And he
was thin. I think he was enjoying New York, from an impoverished point
of view. He drove this old car and parked it with impunity wherever he
wished. And wherever he parked the car he'd get a ticket. And he'd just
slide that ticket into the glove compartment. At one point I think he
had a hundred and twenty-two tickets. I mean the glove compartment was
jammed with parking tickets.
In Outlaw Journalist (2008), by William McKeen, Thompson's pipe
is again described as part of his persona: "Gerald Tyrrell was lining
up a shot at the pool table of his fraternity house at Yale when he
looked up to see Hunter nonchalantly walk into the room, puffing on his
"If you're going to be crazy, you have to get paid for it or else you're going to be locked up." (Hunter S. Thompson)
McKeen also chronicles Thompson's use of his pipe to impress the
opposite sex: "When speaking to women, Hunter could make them feel as if
they were the center of his universe. His eyes bore into theirs, and
while they spoke, he drew thoughtfully on his pipe, often nodding in
agreement with what they said. It was an act, his friends said, and it
Thompson's pipe was indeed something that he enjoyed in his early years.
McKeen records a visit shortly after Thompson lost his newspaper job in
the Catskills for vandalizing a candy machine: "The combination bedroom
and kitchen made up the other room. The rest of the place was strewn
with newspapers, empty beer bottles, and half-downed drinks. He smoked a
pipe in those days, so the sweet smell of its tobacco permeated the
cabin and drifted out into the fresh air of the Catskill Mountains."
The only reference to a specific brand of pipe found for this article,
aside from a Dr. Grabow that Thompson "stuffed with hash," is from When the Going Gets Weird (1993) by Peter O. Witmer: "He wore his normal uniform for that time period — coat and tie, Kaywoodie Briar pipe."
However, as Thompson's life progressed, he seems to have drifted away
from his pipe smoking, though never giving it up entirely. He loved
tobacco, whether in cigarettes, cigars, or in pipes.