It's not often that an actor gets to portray any real life personality twice on film, much less at two wildly different stages in their career. Johnny Depp, a close friend and follower of the late Gonzo journalist Hunter S. Thompson, has now had the chance to play the man at his alcohol and drug fueled later years, and here in The Rum Diary as he's just beginning to find his journalistic voice. Written by Thompson when he was only 22 years old, Depp makes for an odd bit of casting considering he's in his 40s, but he's clearly playing on his memorable earlier performance in Fear and Loathing in Las Vegas. When not embarking on one of his more outlandish, cartoony characters like Jack Sparrow or the Mad Hatter, Depp has sometimes taken a "relaxed" approached to tackling regular people. Disinterested might be a better word. But with Thompson, Depp attacks the role with gusto and a sparkle we don't get to see nearly enough.
There's just one problem: the film, much like the novel, is a mish-mash of episodic comic events that don't always make sense taken as a whole. Set in 1960, Depp plays Paul Kemp(a version of Thompson), a somewhat brash writer/journalist who escapes the big city of New York for what he thinks will be a beneficial gig writing for the San Juan Star, a crappy, failing English language newspaper run by an odd assortment of folks ripped from the Peanut Gallery. Or the Betty Ford clinic.
It's immediately a terrible combination. Kemp wakes up hungover and badly bloodshot on his first day at work, which irritates his weary editor(Richard Jenkins) tired of employing drunks looking for an escape. Even worse, the fluff pieces Kemp is asked to write run counter to his cynical outlook. He wants something hard hitting, something of worth. But living in a Paradisaical vacation hot spot, nobody cares about the real troubles plaguing the world. Kemp's indifference finds him embroiled in a series of comic misadventures mostly spurred by too much rum and the occasional hallucinogenic, alongside his buddies Sala(Michael Rispoli) and Moburg(Giovanni Ribisi).
Most of the film consists of aimless encounters that are amusing, but don't add up to much. Chicken fights, random run-ins with local thugs, and partaking of the active Puerto Rican nightlife. These are made tolerable by Depp's staunch commitment to the character, experienced mostly through revealing voice over, as Kemp actually doesn't say very much to the people around him. He's more of an observer, chronicling the little injustices he finds on a daily basis.

Bruce Robinson, pulled out of a long retirement by Depp to pen and direct this Thompson tribute, and while the script is lacking there's no denying how beautiful Puerto Rico is represented here. Loyal followers of Thompson's may be enchanted by the opportunity to see their hero in his developmental stage, but others will consider The Rum Diary little more than a well shot, liquor soaked diversion.