The Proud Highway
Saga of a Desperate Southern Gentleman, 1955-1967
by Douglas Brinkley · first published 1998
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This first volume of the Fear and Loathing Letters begins with a high school essay written in 1955 - when Hunter S. Thompson was a wise (perhaps too wise) teenager in Louisville - and takes us through 1967, when the publication of Hell's Angels made the author an international celebrity (and nearly resulted in his death). In the intervening years, Thompson's prolific and often profound correspondence gives us an unforgettable vista of the America of the Eisenhower and Kennedy years as well as an authoritative introduction to the cultural revolution of the sixties. With a vicious eye for detai
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…collection of letters, published across a 3 book series, which he preserved over the years from being teenager in the 1950s to becoming a famous journalist in the late 60s. http://www.amazon.com/The-Proud-Highway-Desperate-Gentleman/... For example one of his letters that went viral recently, written while he was 20: http://www.brainpickings.org/index.php/2013/11/04/hunter-s-t...
on “The Kentucky Derby Is Decadent and Depraved (1970)” ↗…friends (some very famous friends like Tom Wolfe and other great writers). Both the letters and articles were released in 3 book series each. These are my favourite books from each series: (letters) The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967 (The Fear and Loathing Letters, Vol. 1 https://www.amazon.com/Proud-Highway-Desperate-Gentleman-195... (articles) The Great Shark Hunt: Strange Tales…
on “Hunter S. Thompson on Finding Your Purpose (1958)” ↗…called the Gonzo Letters: https://www.goodreads.com/series/64386-the-fear-and-loathing... Only the 2nd one has a Wikipedia page for some reason (the 3rd one came out in 2014) but the first one (The Proud Highway: The Saga of a Desperate Southern Gentleman 1955–1967) as a young writer who is often desperate and broke was most interesting IMO, even though his life or writing wasn’t yet as it would become famous…
on “Show HN: I made a site where you practice typing by retyping entire novels” ↗I strongly suggest reading his book "The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967" It's a collection of his letters, and responses, from people he wrote during that era. Incredible insight into this amazing man.
on “How Hunter S. Thompson Became a Legend” ↗Two things: 1. This does exist. See Hunter Thompson's letter collections (the first one is called The Proud Highway) from 10 years before he was ever famous. It's interesting, if very unfocused. 2. If enough people started doing this, people would still cry survivor bias about those who made it. What about all the…
on “The Geek Talk with Derek Sivers” ↗OP was likely referring to Thompson's The Proud Highway: Saga of a Desperate Southern Gentleman, 1955-1967 (The Fear and Loathing Letters, Vol. 1) https://www.amazon.com/dp/0345377966 http://www.goodreads.com/book/show/10880.The_Proud_Highway
on “Hunter S. Thompson on Finding Your Purpose (1958)” ↗I'm a big fan of "The Great Shark Hunt: Strange Tales from a Strange Time" which is a collection of articles from the first part of his career. I haven't read The Proud Highway but it sounds good.
on “How Hunter S. Thompson Became a Legend” ↗