The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967, Hunter S. Thompson

Ballantine Books, 1997 (1998 paperback re-issue), 683 pages, C$24.95 pb, ISBN 978-0-345-37796-8

My lofty intentions to read Hunter S. Thompson’s entire output in strictly chronological order of publication don’t make much sense considering The Proud Highway, a 1997 collection of letters written between 1955 and 1967. In a bid to solidify Thompson’s position as an American writer of some renown (and to please legions of fans accumulated since 1972’s Fear and Loathing in Las Vegas), Thompson authorized noted academic Douglas Brinkley to dig in his archives and assemble volumes of correspondence.

Thompson famously kept copies of nearly everything he wrote, even from a young age, and it’s those copies that fuel this collection of letters published before his first book (Hell’s Angels) hits the market. Those are the letters of a young man, a cocksure writer just waiting for greatness. Some juvenalia aside, the first letters collected here date from Thompson’s years in the Air Force, where he channels his renegade energies into sports writing, and then in engineering his own departure from the US military forces.

The rest of the book follows Thompson as he travels across America, and then from one continent to another. Thompson fans will track his travels from New York to San Juan to Big Sur to South America to San Francisco, only to end up, pages before the end of the book, in his home base of Woody Creek, Colorado.

This is as close as we’ll ever get to a Thompson autobiography, as we track his progress through quasi-weekly letters written from always-desperate circumstance. A vivid letter describes as Thompson manages to write in the cargo hold of a military flight heading back to his usual post; another hilariously portrays Thompson as battling insects while writing to his friend. One thing’s for sure: Thompson’s character was forged well before he hit his stride with Hell’s Angels: even his early letters show an aggressive and self-assured spirit: in fact, some of his letters to female acquaintances are uncomfortably pointed –especially for those who don’t know the context.

Still, life wasn’t easy for the young Thompson. Nearly every single letter mentions monetary difficulties of some sort, to the point where it becomes tiresome. Small wonder if Thompson-the-older-man would remain fixated on monetary issues, often to the detriment of his relationships.

Readers with specific interests may learn a few good details of trivia through those nearly seven hundred pages of letters. As a science-fiction fan, for instance, I was amused to find out that Thompson had sent a few stories to SF magazines at the beginning of the sixties –what an alternate universe that would have been if he had found success in that field! Similarly, the first editor to buy something from Thompson was Frank M. Robinson, an editor who would move west to San Francisco, become Harvey Milk’s speechwriter and eventually develop in a fine SF writer in his own right. Small world…

It almost goes without saying the The Proud Highway is aimed squarely at Thompson fans and scholars: Brinkley’s contextual input is slight, and the book’s best moments often illuminate other aspects of Thompson’s work. (The whole bizarre “American ambassador to Samoa” allusions in Fear and Loathing: On the Campaign Trail ’72 finds an explanation in a series of letters actually sent to Democratic Party honcho Larry O’Brien, for instance.) A lot of the material is either repetitive or desperately trivial, and casual readers may not want to wade through it all.

But for the Thompson fans, The Proud Highway is a look at the early years of a noteworthy writer. The 1967 date at which the book ends is significant, since it finds Thompson safely housed in Woody Creek Colorado, waiting for Hell’s Angels to hit bestseller lists and the subsequent events that would catapult him to national fame. But that story is covered in a second book of letters, aptly named Fear and Loathing in America

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