Word of his death was a shock to me, but not particularly surprising since I'd called him a week or so before and heard from [his wife] that he was right on the edge. More than anything else, it came as a harsh confirmation of the ethic that [he] had always lived but never talked about...the dead-end loneliness of a man who makes his own rules...

Now, what? While the new wave flowered, Lenny Bruce was hounded to death by the cops. For "obscenity." Thirty thousand people...are serving time in the jails of this vast democracy on marijuana charges, and the world we have to live in is controlled by a stupid thug from Texas.
—Hunter S. Thompson, "The Ultimate Free Lancer"; a 1967 obituary of journalist Lionel Olay, as collected in The Great Shark Hunt

Just this past Friday night, I had 45 minutes to kill in a Manhattan Barnes & Noble, so I headed off to the sports section to see if Bill James had come out with anything new. Before I even made it to the baseball books, though, a newish title jumped out at me: Hey Rube: Blood Sport, the Bush Doctrine, and the Downward Spiral of Dumbness—Modern History from the Sports Desk. As always, I lunged happily for the latest Hunter Thompson collection and flipped to the Author's Note, because I knew at least one sentence or turn of phrase, and probably more, would make me laugh out loud.

There are people, and I have been one of them, who will tell you that Thompson hasn't written anything of transcendent value since 1975. (Leaving aside for the moment that hardly anyone—let alone his critics—have ever climbed that particular mountain.)

But it speaks volumes about the height of his peak and the mastery of his language that 31 years later he was still one of the handful of writers I can think of with at least a 50 percent chance of making you laugh every time out, even when spitting out political hyperbole in half-cocked ESPN.com "sports" columns.

"Things haven't changed much where George W. Bush comes from," he wrote before the election last year, in a passage typical of his later work. "Houston is a cruel, crazy town on a filthy river in East Texas with no zoning laws and a culture of sex, money and violence. It's a shabby, sprawling metropolis ruled by brazen women, crooked cops and super-rich pansexual cowboys who live by the code of the West—which can mean just about anything you need it to mean, in a pinch."

Thompson will rightly be remembered for his astonishing 1967-73 burst of first-person counter-cultural reportage: Hell's Angels, Fear and Loathing in Las Vegas, and Fear and Loathing on the Campaign Trail '72; plus the lesser-known 1962-76 magazine work collected in The Great Shark Hunt. Yet for a writer so popular and over-exposed, his singular achievements and dying-breed worldview have been blurred by the perfunctory tales of drug antics, Woody Creek pilgrimages, incoherent lecture gigs, and multiple assault charges.

Hell's Angels, for instance, is more than just a machete-sharp portrait of an outlaw California motorcycle gang careening through the mid-1960s—it's also a perfect bridge, in both style and substance, between the Beats and the Hippies, and one of the first and best pieces of book-length media criticism. Thompson spends the first 60 pages regurgitating large chunks of official verbiage—from the The New York Times, Time magazine, the California Attorney General—and then demonstrating, through participatory reporting, that most of the received wisdom was hysterical, self-important garbage.

The "participatory" part was crucial to Thompson's best work, the missing ingredient during his decline, and one of several qualities separating him from media critics then and now. It's one thing to "Fisk" a news article or opinion column with whose politics you disagree; quite another to disprove the factual basis of serious journalism through extended first-hand observations of 300-pound sociopaths named "Tiny."

Thompson's tactic of lifting the veil on the reporting process (especially his own) was expanded in Campaign Trail '72, that rare national-politics book that doesn't end up in the Goodwill bin within six months (it was Number 43 on Amazon early Tuesday afternoon). For years, I've been asking political reporters to tell me their favorite campaign books, and fully half have selected Thompson's frantic, partisan take on McGovern vs. Nixon.

But it wasn't just Thompson's writing that couldn't be duplicated, no matter how hard generations of college kids tried (just as he and his generation tried—too hard, maybe—to imitate Ernest Hemingway). Hunter's political persona also broke the mold.

He was that rare journalist who took the Second, Fourth, and Fifth Amendments as seriously as the First, regardless of who currently occupied the White House. Unlike the Boomers and journalists who indulged him as a guilty, don't-go-there pleasure, late-in-life financial success did nothing to dull his outrage at overzealous prosecutors, lying cops, opportunistic legislators, and the enablers of the obscene Drug War. He was a patriotic, don't-tread-on-me lefty who shot firearms, despised nanny-state restrictions on speech, and only occasionally voted Democratic for president. He spoke, wrote, lived, and died, with a freedom few of us can contemplate.

In the words of the writer Thor Garcia, with whom I met Thompson for three memorable hours when we were both 18-year-old wannabes, "It wasn't about Drugs and Drug-Concepts, and it wasn't about the Guns, though both are of course crucial to his Art & Philosophy. It was about Independence."

In the end, it's easy to imagine that Thompson could not quite declare independence from the cartoon image that kept him well-fed after years of subsisting on the teasing combination of fame and poverty. Or maybe, like the Rolling Stones, his 1966-74 peak was simply too exhausting to keep up.

"That power of conviction is a hard thing for any writer to sustain, and especially so once he becomes conscious of it," Thompson wrote, in an eerily premonitory 1964 essay entitled "What Lured Hemingway to Ketchum?"

"He was an old, sick, and very troubled man, and the illusion of peace and contentment was not enough for him—not even when his friends came up from Cuba and played bullfight with him in the Tram. So finally, and for what he must have thought the best of reasons, he ended it with a shotgun."