He was, a man, made legendary by his reputation for his consumption of illegal substances and borderline insane antics. He was a bit of everything. An extraordinary friend, a lunatic, a prolific writer, and so much more (frankly I feel pretty awful trying to pigeon hole the guy). The video I linked below is an interview with John Cusack after his death in 2005 and talks about the first time he met Hunter. (Cusack and Depp were close friends to Hunter and watching the documentaries and interviews with stories of all the ridiculous things they did together, is for the lack of a better word a hoot. )
Hunter S. Thompson was also one of the greatest social commentators of our time, and of course pioneered "Gonzo Journalism." His breakout piece tore the Kentucky Derby a new asshole by showing the decadent and depraved side of the event, and painting it in an absolutely filthy light. (With brilliant illustrations by Ralph Steadman that really drove the point home.)
There really is no way to articulate how much he inspired and continues to inspire me. He was someone who fought many battles to the bitter end, went out on his own terms, blew shit up constantly, kept his friends close, and even ran for Sheriff of Aspen (and nearly won). If it was up to me I'd be teaching him in High School. Then again, if I was a High School teacher I'd be fired promptly for swearing at the students and ignoring educational standards.
I also fiercely admire that you'd be hard pressed to find any story where his actions ever compromised his character. I've read numerous books and (also currently halfway through his biography) and although he may of used his words to cripple an individual to the point of slander, but I've never found his writing disingenuous. If he was biased towards the individual he told you and then continued on, allowing the reader to draw their own conclusion.
He was an incredible man, a powerful writer, and there are not enough blog posts to tell you all the crap he did. If you want to learn more about him, I would start off at the documentaries about his life, and then start reading some of his works. I felt learning about his life and connecting the dots with his work was extraordinarily interesting, but there's really no bad place to start.

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