A Kentucky native, Thompson began his career in 1956 as a sports journalist, writing for the base paper at Eglin Air Force Base in Niceville, Florida, where he was enlisted. After the Air Force, Thompson worked briefly as a copyboy for Time Magazine while living a beat-inspired lifestyle in New York City.
Thompson began vacationing extensively in the Caribbean Islands and South America, using his unique locale to freelance articles to a number of daily newspapers stateside. He befriended the journalist William Kennedy while in Puerto Rico, who would later win the Pulitzer Prize for his novel Ironweed. Thompson eventually became a somewhat celebrated South American correspondent for a Dow Jones owned weekly magazine called The Observer.
In the meantime, Thompson wrote two serious novels (Prince Jellyfish and The Rum Diary) and copious amounts of short stories, none of which were published despite relentless submissions to publishers. Kennedy later remarked that he and Thompson were cohorts in the fact that they were, at the time, failed novelists who had turned to journalism in order to make a living.
Thompson got his big break when he pitched a story to Harper's Magazine about his relationship with the Hell's Angels motorcycle gang, known erroneously at the time for exploits in murder and gang-rape. After the article was published, numerous book offers on the subject were awarded his way.
He later worked for Rolling Stone magazine, where his next two books Fear and Loathing in Las Vegas and Fear and Loathing on the Campaign Trail 1972 were first serialized.
Published in 1971, Fear and Loathing in Las Vegas is a first-person account by a journalist of a trip to Las Vegas with his "300-pound Samoan" attorney to cover a narcotics officers' convention and the "fabulous Mint 400" motorcycle race. During the trip, the journalist and his lawyer become sidetracked by a search for the American dream, with the aid of heroic amounts of LSD, ether, adrenochrome, ibogaine and numerous other drugs. The journalist and the attorney are never named, but they are obviously thinly-disguised versions of Thompson himself, and his friend and lawyer Oscar Zeta Acosta.
Thompson frequently referred to himself as "Raoul Duke" or "Dr. Gonzo." He received his 'doctorate' from a mail-order church in the sixties.
Some of Thompson's other books include Fear and Loathing on the Campaign Trail '72, a collection of Rolling Stone articles he wrote while covering the election campaigns of President Richard M. Nixon and his unsuccessful opponent, Senator George McGovern. The book focuses almost exclusively on the Democratic Party's primaries and the breakdown of the party as it splits between the different candidates.
In 1970, Thompson made an unsuccessful bid for Sheriff of Pitkin County, Colorado. He ran on a platform promoting decriminalization of drugs and the sale thereof, and renaming Aspen, Colorado as "Fat City." The Republican sheriff against whom he ran had a crew cut, prompting Thompson to shave his head bald and refer to his opposition as "my long-haired opponent."
Thompson identified the death of the American Dream as his “reporter’s beat”, and covered the subject in one fashion or another throughout his writing. During an interview with salon.com, however, Thompson was asked whether he was not, in fact, the living embodiment of the classic American Dream. He answered the question by first screaming a string of frustrated obscenities and then admitting that, in actuality, he probably was.
A slogan of Thompson's, "When the going gets weird, the weird turn pro," appears as a chapter heading in Fear and Loathing in Las Vegas. He was also quoted as saying, "I hate to advocate drugs, alcohol, violence or insanity to anyone, but they've always worked for me."
Thompson's last book, Kingdom of Fear, is an angry commentary on the passing of the American Century. Thompson also wrote a Web column, "Hey Rube," for ESPN. He had at times also toured on the lecture circuit, once with John Belushi, but also with G. Gordon Liddy. Another appearance was through cartoonist Garry Trudeau, who based his Doonesbury character Uncle Duke on Thompson, to loud protests from Thompson himself. Similarly, Spider Jerusalem, the gonzo journalist protagonist of Warren Ellis's Transmetropolitan, is (more lovingly) based on Thompson.
Thompson was an admitted fan of firearms and was known to keep a keg of gunpowder in his basement.
Thompson died at his home in Woody Creek, Colorado, on Sunday, February 20, 2005 of an apparently self-inflicted gunshot wound to the head. He was 67 years old.
Thompson is generally regarded as the grandfather of the blogging movement.