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Adapted from the lost then found first novel by Hunter S. Thompson, this film version is more aptly described as a sloe gin fizz; it's content with its own moderate buzz and works well enough as a prologue to All Things Thompson. What it is not, however, is a groundbreaking film that sheds much more than a dim, languid light on who Thompson was prior to his groundbreaking journalistic work for Rolling Stone and other magazines.
Set in San Juan, Puerto Rico, in 1960, Depp plays a semifictional version of the writer for the second time (the first, of course, was Terry Gilliam's psychotically inspired Fear and Loathing in Las Vegas). Actually, Depp plays Thompson's alter ego, Paul Kemp, a budding journo-cum-novelist who's living in suspended, rum-infused doldrums while working for the English-language newspaper, The San Juan Star. The new kid on the beat, he's joined in the sugary haze by somewhat more seasoned (i.e., cynical) newshound vets the photographer Sala (Rispoli) and Giovanni Ribisi's stewed prune of a writer, Moburg, a man so far gone down Thompson's own fearful and loathed spiritual trail that he appears to be less human than haunting.
Kemp, socializing with the best and worst of them eventually catches the eye, and vice versa, of Chenault (Heard), the sigh-worthy if spoiled rotten wife of yanqui developer Sanderson, who envisions San Juan as one gigantic capitalist playground. Sanderson and his cronies are a vivid lot: precursors to the raving serpents and Nixon-era cultural monstrosities, the older, far wiser Thompson. Here, however, Depp plays Kemp as a youngster more or less uninitiated in the ways of the predatory American scumbag.
What The Rum Diary lacks in narrative astonishment it almost makes up for in boozy charm. Depp, Ribisi, and Rispoli are a sight to behold. They're like something out of Beckett, having a tumbler of Puerto Rico's finest while waiting for good dough, or at the very least, a good story that actually stirs them to outrage and a seat at their typewriters. It happens, for Kemp at least, but it takes its own sweet time in coming. Director Robinson was handpicked by Depp for the job, and this film bears some slight vibratory similarities to the his cult classic Withnail & I. In the end, The Rum Diary feels like a work of writerly juvenilia, half-baked but not unpleasant. Like the tropical breezes that fairly waft off of the screen, it reeks of promise yet to be fulfilled. And booze. Lots and lots of booze.