To get to the heart of the mess that is The Rum Diary, Johnny Depp's deeply personal cinematographic tribute to his late friend Hunter S. Thompson, one needs to backtrack to the mess that was The Rum Diary, the novel Thompson began working on as a novice writer in 1960, which would not be published until 1998.

The story goes something like this: In 1960, Thompson — an arrogant, violent 22-year-old from Louisville, Ky., who was convinced he was the next Hemingway — became impatient at not being instantly recognized as a literary genius in New York. He hatched a plan: He would move to Puerto Rico, get a day job as a journalist and immediately start working on a career-making novel about his experiences there, his tropical version of The Sun Also Rises.

His stay was brief, a few chaotic months, characterized not only by Thompson's volatility but also by his complete disconnection to actual Puerto Rican life, its language or anything beyond his solipsistic fantasies. Those fantasies were a blend of Hemingway's idealistic machismo, Fitzgerald's Gatsby at his most mawkish and self-pitying, the romantic allure of the Beats, and healthy cribbing from Men's Adventure–type pulp magazines — particularly with regard to women.

Thompson left Puerto Rico for further South American adventures inspired by even sketchier dreams. By 1963, Thompson had returned to the States, where he continued to behave like the very model of the “Ugly Americans” he had spent his years abroad railing in print against.

All this foreign travel, motivated as it was, essentially, by egotism, was not very conducive to understanding anything outside of Thompson's own psyche, so it's no surprise that his literary output during those years was not very good. “He'd been referring to The Rum Diary as 'the Great Puerto Rican Novel,' ” writes Thompson biographer William McKeen in 2008's excellent, balanced Outlaw Journalist. Thompson apparently was convinced that he was treading “into semivirgin terrain, since the only Western writer mining Latin America was Catholic-obsessed Graham Greene.”

Thompson was both completely ignorant of, and uninterested in, the massive boom in Latin American literature exploding all around him while he drunkenly chased Hemingway's shadow.

By 1962, Thompson had completed a 1,000-page manuscript called The Rum Diary, which he unsuccessfully peddled to editors, and he continued to revise it to make it more controversial and sellable. In 1964, as incendiary civil rights debates became a daily feature of politics and the news, Thompson callously bragged about adding an extreme “interracial sex scene” that would shock readers. The scene in question features the nubile femme fatale Chenault, a cock-teasing tanned vision in a white bikini, gangbanged by several black men while the white antiheroes are carried away helplessly.

But no amount of added shock value could disguise the fact that Thompson's novel was a clunker, and he knew it. “Like most young writers, I am a natural ingrate,” he wrote to a friend in 1962, “and will always think that my work and my views are above and beyond advice — at least until I finish one thing and can get far enough away from it to see it clear and mean like a girl who drives you mad when you're drunk and then looks like hell in the morning.”

As we know, when Hunter S. Thompson finally stopped running away from the United States and his troubling Southern roots, he found his voice as a nonfiction innovator and vernacular prose stylist, first with a very good (and commercially successful) book about the Hells Angels, and then with a string of on-the-money magazine articles culminating with his signature tour de force, which he later annoyingly dismissed as “the Vegas book.” He found his niche chronicling “the Death of the American Dream,” that is, the angst of the white middle class in the anticlimactic '70s — preferably from a hotel room, out of his mind on someone else's expense account.

Thus The Rum Diary lay dormant until 1998, when Johnny Depp found the manuscript while doing research for Terry Gilliam's carnivalesque Fear and Loathing in Las Vegas adaptation, in which he starred. Depp thought of the unpublished novel as eminently cinematic and an excellent potential source of income for the constantly cash-strapped countercultural icon.

The Rum Diary came out when it did because [Thompson] needed money, absolutely,” confirms his longtime agent Lynn Nesbit in Gonzo, the official oral history prepared by Rolling Stone's Jann Wenner as a mythmaking tribute. “He never would've published that 20 years before.”

Six hundred pages were discarded from the manuscript and the resulting short book earned lukewarm praise from critics as a welcome appetizer for Thompson's later work. The current paperback has a blurb by Jimmy Buffett.

And now, six years after Thompson's suicide and after a protracted production schedule that had to be squeezed around humongous blockbuster obligations, Johnny Depp's pet Gonzo project has finally been unveiled. Thanks to the inane Pirates of the Caribbean franchise, Depp can do pretty much whatever he wants in Hollywood, and what he wanted in this case was to hire the director of Withnail and I out of directorial semiretirement and make him reinterpret the “spirit” (though not the precise plot) of The Rum Diary as “Hunter would have wanted it.”

The result is, inevitably, a strange mélange: a glossy Puerto Rico tourism infomercial mashed up with some Mad Men fashions, a couple of anachronistic “psychedelic” scenes tipping the (Panama) hat to Gilliam's Vegas phantasmagoria, and confused ranting against “bastards” and The Man — a little ridiculous coming out of the mouth of a man who profit-participates with Disney and owns a freaking island. True to the novel and to Thompson's real-life attitude during his late-1950s sojourn, Puerto Ricans are either inscrutable or comedic foils; when the Depp/Thompson character sets one local's face on fire, it's played for laughs. And yes, they did include the “interracial gangbang” (though offscreen — the film, and Depp, are strangely chaste). Inserted for intentional offensiveness 50 years ago, in 2011 it feels shockingly bad, not in a racist, exploitative way but rather in a Lambada: The Forbidden Dance–reminiscent way. “Hunter was a genius,” Depp wrote in 2007 for the introduction to the Gonzo oral bio, “who revolutionized writing in the same way that Marlon Brando did with acting, as significant, essential and valuable as Dylan, Kerouac and the Stones.”

Depp is sincere in his adolescent worship for Thompson's myth, going all the way to justifying the writer's suicide as a heroic act. The image of an old guy shooting himself in a bleak Colorado ranch shortly after the bitter disappointment of George W. Bush's second, incontestable re-election, unable to cope with the horror of aging or to complete a second great work, is rewritten at the end of Depp's Rum Diary into an allegorical Viking funeral.

But Depp's passion-project homage, which has him reciting invectives against squares in stoned, poetry-slam tones over footage of sunny locales, is less a tribute to Thompson than to the actor's own bohemian billionaire sense of cool. In contrast, Bill Murray's Gonzo avatar in 1980's Where the Buffalo Roam got to the core of the writer's sad neuroses, with a kind of sympathy that is antithetical to the Hollywood rebel continuum — Brando, Hopper, Nicholson, Penn and, of course, Depp — a coterie of cool that Thompson himself always sought for his alt version of the Rat Pack.

The cold truth is that, while Thompson might have been touched by Depp's reverence, he also knew deep down that the closest he'd ever come to genius was “the Vegas book.” Everything else, and particularly this piece of literary juvenilia that so impressed his latest Hollywood buddy, was just a lot of work, and often a lot of disappointment.

“I had always been an observer,” Thompson wrote in The Rum Diary. “One who arrived on the scene and got a small amount of money for writing what he saw and whatever he could find out by asking a few hurried questions. Now I felt for the first time in my life that I might get a chance to affect the course of things instead of merely observing them. I might even get rich; God knows, it seemed easy enough.”

It wasn't. Still isn't.

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