I have a friend who IS Hunter S. Thompson. He's always wearing those iconic amber-colored sunglasses, has the cigarette hanging out of his mouth, writes profusely, is extremely neurotic, and can produce a wide variety of illegal substances from his immediate person at any time. That is definitely a compliment, because Hunter S. Thompson is awesome.
Hunter S. Thompson is most famous for the counterculture classic Fear and Loathing in Las Vegas. He created what he called Gonzo Journalism, which means that the reporter involves himself in whatever he's writing about, and therefore becomes the main character in his own first-hand account. He was open about his lifetime drug use, including substances like alcohol, cannabis, LSD, mescaline, and cocaine. He loved guns and hated any authority, but especially Richard Nixon. He disagreed with the lack of real convictions he saw in the Hippie culture.
Perhaps unsurprisingly, he was always in trouble as a kid, including being kicked out of a prestigious high school club because of his criminal record. His first experience with the criminal system came when he was implicated in a robbery, because he was in a car with the robber after the crime was committed. When he joined the military, he received an honorable discharge because of his inability to follow orders, and he was fired from Time Magazine for his insubordination as well. One of his first successful writing projects was a book about the Hell's Angels, who he lived with for almost a year before they decided that he was using them to make money and so he got a "stomping." He lived in New York, San Francisco, and finally settled in a secluded spot in Colorado, where he remained for the rest of his life. In New York, he made friends with famous Beat writers like Allen Ginsberg and William S. Burroughs. In Colorado, he ran for sheriff of his county, on the Freak Power ticket, whose platform included legalizing drugs and abolishing paved roads and tall buildings, and he almost won. His best friends included Bill Murray and Johnny Depp, who both played him in different movies. He died by suicide, probably as a result of his chronic medical conditions, and at his funeral had his ashes fired from a cannon.