1. He once knew how to write. His mechanics were extraordinarily good; he used language really well. My favorite Thompson book is his first, Hells Angels, when he's pursuing a legitimate journalistic quest (one that most journalists shied away from) and only occasionally do his inner excitements puncture through the narrative. Like Picasso, he learned how to do it right before he decided to tear the whole thing down.
2. He didn't just tear down traditional notions of the journalist as a detached figure. He also tore down traditional notions of the journalist as a chronicler of literal truth. I remember my reaction to Fear and Loathing in Las Vegas: This is stylistically fun, but I don't really believe he did all those drugs -- and if he didn't, who cares? The book was marketed as nonfiction, because its power came from the idea that American politics and society were so screwed up that journalists and lawyers had to take lots of drugs to cope. But in a later memoir Thompson admitted that in fact he hadn't done all those drugs.
I'm sure he saw it as societal truth he was writing, if not factual truth. But as a nonfiction writer who believes in the sanctity of facts, I really wish he hadn't crossed that line, and I really wish people hadn't been so accepting of it.
3. He came to represent something unusual and incredible about the Rocky Mountain West. Who would think that a drug-addled, highly creative, anti-authoritarian scion of the South would find a home among conservative cowboys? Yet he did. In fact he made a very credible showing in several Aspen political races (running not as a joke candidate, and coming close to winning). To me this shows that our notion of cowboys needs to be a little more complex than the John Wayne image, and our notion of the counterculture a little broader than Haight-Ashbury.
Gary Ferguson gives a great tasting of the Rockies hippie movement in his "Season of the Freaks" chapter in the book The Great Divide, but I think a fuller history of that era could still be written.
And sadly, one of its key sources is no longer available to interview.
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