If Hunter S. Thompson's real life contained anywhere near as much booze and other substances as portrayed in Fear and Loathing in Las Vegas and The Rum Diary, it's a miracle he was a productive writer for as long as he was—or that he even prowled the Earth as long as he did.
And if all you ever knew of Thompson was what was contained in these two films, it would be hard to understand why he was a significant figure in journalism and American culture.
In both, Johnny Depp portrays fictionalized versions of his late friend, and this time around, it's something of a tribute. There is much in Depp's approach to his work that reflects the nature, if not the ethos, of Thompson—even in Depp's work as Captain Jack Sparrow—so the connection between the two is easy to spot. There's an obvious Fear and Loathing reference in Depp's Rango, for crying out loud.
The Rum Diary, as presented here, is not much of a story. Paul Kemp (Depp) travels from New York to Puerto Rico in 1960 to write for a failing newspaper. It's a pivotal time in San Juan, with American money and homegrown rum flowing in vast quantities—but neither excess seems to favor the locals as much as the tourists.
Kemp, an undisciplined writer in comparison to his dedicated drinking, bounces from misadventure to misadventure with fellow writer Bob Sala (Michael Rispoli). Along the way, he encounters a Nazi enthusiast with an even bigger penchant for booze (Giovanni Ribisi, in the film's strangest but best performance), infuriates his editor (Richard Jenkins) and crosses paths with Sanderson (Aaron Eckhart), a scheming American financier who displays all the trustworthiness of a street hustler.
Then there's the girl. It's tough to ignore a character played with so much sizzle by an actress who is as qualified for sizzle as Amber Heard. You never see a loaded gun in a movie that goes unused, and it's usually the same thing for a loaded low-cut dress. And yet Heard's sexuality is not as big of a factor as it should be, because The Rum Diary is busy throwing everything else at the wall to see what sticks.
Although some of the scenes are peculiar—with Ribisi blaring Hitler records, how could they not be?—none of them really mean all that much. There is an effort to give the film a soul of some sort when Kemp realizes Sanderson's plans for the untouched shoreline on an island off Puerto Rico's coast, but it's too little, too late. The undercurrent also doesn't fit the erratic tone of the rest of the film; The Rum Diary would be better off just recounting debauchery instead of trying to get deep, even for a moment.
Evaluating this film's finish line for Depp is not easy. As a fan, is he trying to be faithful to the novel? As a producer, is he trying to make a great motion picture? As a friend, is he trying to raise his glass to a man who made a big impression on him? It's definitely not a great film, so maybe Depp, who has money to burn, just wants a few more people to get turned onto the gonzo world of Hunter S. Thompson. Surely there has to be an easier and more-successful way to do that.