Depp plays Paul Kemp, a sort of proto-Thompson avatar who washes up in Puerto Rico having been hired from afar to work at an English-language daily that is blatantly collapsing. Depp's really good in it; he mostly abandons his Jack Sparrow mugging in favor of a deadpan nervousness with occasional twitching. (Remember when he played Ichabod Crane as a frightened little girl in Sleepy Hollow? It's weird how restrained that performance seems in hindsight.)
Even better is Michael Rispoli, who plays the staff photographer, Sala. He's the heart and the brains of the story, and everything gets sort of chilly when he's out of the frame. The villain is white-linen-suited developer (and ex journo) Hal Sanderson, played by Aaron Eckhart. He's too Evil to be a convincing character, but it's fun to see Eckhart being rotten again. Sanderson's girlfriend (Amber Heard) is supposedly a bewitching mermaid minx/damsel in distress, but I found her pretty dull. And Giovanni Ribisi shuffles around as sort of the Ghost of HST Future, a cautionary tale and/or inspiration, depending on which parts of the Hunter legend you're devoted to.
Anyway. Kemp's an idealistic young reporter who is easily seduced by alcohol and mermaids and also maybe by the cash and sweet car Sanderson throws at him in an attempt to get the writer to plant some PR stories currying public favor for a hideous and probably illegal development project. The project is a grody bait-and-switch that would ravage a pristine island and make Sanderson heaps of money. It's the kind of widespread-corruption story that would make a young reporter's career, if that young reporter's editor weren't somehow involved and thus reluctant to print anything more hard-hitting than astrology columns and bowling-league results. Kemp does protest, but not too much, and he's pretty happy to borrow Sanderson's car. That whole "nail the bastards to the wall" part only comes once the string of selfish greed causes the newspaper's payroll to vanish.
The movie is really well made, and there are scenes of pure alchemical beauty in it - notably a dark, still moment in which Kemp and Sala drop a mysterious liquid into their eyeballs and wait for it to kick in. (And there's a line in this scene that echoes Withnail & I: "You're giving me fear!") The whole thing is a lot of manic fun. And yet....
The thing people forget about Hunter Thompson - and the thing this movie seems intent on distracting its audience from - is how genuinely sad he could be. It's the same way they forget how funny Hemingway was. We inherit these established ideas of what these writers were like, and then we never feel the need to look deeper. There's both accidental and deliberate confusion between the man and the myth. In Hunter's case the real guy vanished early into the character of Raoul Duke. And then that character himself became cartoonified (literally and metaphorically). People associate him with a trunk full of drugs, bats on the highway, lizards in the carpet. Nobody thinks of Fear and Loathing in Las Vegas as a sad book. But that scene where he talks about seeing the high-water mark of the culture -- that's tragedy. He's staring out at the desiccated corpse of the American Dream, which back then you could still discuss without irony, and he's mourning. In The Rum Diary, there's a scene in which Kemp and Sala are watching Nixon on TV and Kemp says "When will this blizzard of shame finally end?" and you're supposed to laugh. And then he adds that in a few decades someone will come along who's so much worse that he makes Nixon look like a liberal. And again it's played for comedy.
Which is fine, I guess, because if you don't laugh at this stuff you end up spending your whole life drunk and then blowing your pickled brains out. But to me, the trouble with this movie is that it works so hard to distract you from its own substance. Even just the basic plot outline: aside from hallucinogens and cockfights and some really dodgy club scenes at Carnaval, what exactly happens? Kemp tries to play the role of journalist as scrappy superhero and save an island. He fails. Then he leaves. Sure, in the end maybe he gets the girl, but idealism and journalism and Puerto Rico all get shafted. And the way the movie's set up, we don't care -- we're psyched that Kemp and his pals didn't get shot or jailed. We're supposed to think they won, because they showed the bastards, they stuck it to the Man. But what about that island development project? what about the pillaged newspaper offices? Never mind - let's steal a boat and go chase that mermaid.
The lesson being that you can be a complete wreck of a person, fueled by rum and failure and a wholly untested idealism, and get just as much accomplished as if you're all freshly showered and sober in front of the typewriter, because whatever you write while sane is not what the Man will print anyway, so you might as well drop hallucinogens into your eyeballs - certainly beats working.
It is much, much cooler to imagine journalism this way, but it also kind of misses the point.
I should probably add that I've never read the novel; it came out after my love affair with HST had peaked. (It never ended, but it has ebbed slightly over the years.) I saw somewhere that Jann Wenner said Hunter would never have published the book 20 years earlier, and that was enough to make me avoid it, although at some point I'm sure I'll pick it up. (But never that last Hemingway novel, ever ever ever.) But if you really want to watch Hunter Thompson become Hunter Thompson, read Hell's Angels.
Anyway. Huge rant, probably incoherent. But there you have it.
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