I just finished this oral biography by Jann S. Wenner and Corey Seymour. I'd heard about Thompson here and there over the past few years, watched his biopic. But I'd never gotten a sense of the man, have only a sense of him after reading the biography and still haven't read any of his books.
Sandy Thompson, his wife of many years, summed him up at the end of the book and said that "underneath his bravado and violence and anger and fear, though, was an under-standing that he was not living the right life--that he was hurting people" by his power to seduce and manipulate them. Such anger and manipulation do not arise in a void, I would say, but deep inside one's life; that his antics and the constellations of both great interpersonal difficulties and charms were fundamentally due to that roiling void; and that his gigantic drug and alcohol addictions were also spawned by that dearth. Many might disagree with the attribution of inner discontent to behavior, but whatever literary prowess and burgeoning humor that I have I would attribute to the sharp scraping of a similar inner discontent against the wit and artistic sensibility that fashions art and humor out of life's dross; which is close to the psychoanalytic postulation of the origin of these modalities as an interaction between instinct and conscience through the higher-order functions of the ego.
Another product of such interaction is fun, and what fun he concocted along his way! Later in life he was fond of blow-up porn dolls and posted one on his lawn to mark his house for visitors. During his first years writing for "Rolling Stone" he established arriving at their offices with a large bag containing his tricks, one of which was a siren, which he would blast up and down the office corridors.
I've not read of another man so talented, flawed and fun.