The Rum Diary, Bruce Robinson's amorphous hodgepodge of a film, wants to be many things: period recreation, social commentary, morality play, romance, an insider look at the newspaper game. But above all, this is a portrait of the artist as a young man, or rather a portrait of the artist of a young man as played by an actor in his late 40s. Based on the Hunter S. Thompson novel of the same name which the gonzo journalist wrote when he was 22 (though it wasn't published until several decades later), Robinson's film trades on an odd bit of casting, calling on Johnny Depp to once again embody a Thompson stand-in, as he had back in 1998 in Terry Gilliam's Fear and Loathing in Las Vegas.
Depp, playing a booze-inclined journalist and unpublished novelist named Kemp who travels to San Juan, Puerto Rico in 1960 to take a gig at a failing English-language newspaper, is all brash quips and superior smiles, but they come across less as youthful arrogance than middle-aged intransigence. Of course, there's nothing in Robinson's film to explicitly define Kemp as a young man, but everything about the journo's situation, his searching for his calling as a writer, his intact idealism, suggest a tyro's journey of self-discovery.
But even apart from the oddity of hearing Depp delivering lines like "I don't know how to write like me," the film suffers from trying to include too much material, surely a pratfall whenever a novel is whittled down to screenplay size. Handsomely shot (whenever Robinson doesn't overplay his hand), pleasant enough in the moment (except for a few misguided sequences), the film too often feels like a series of perfunctory episodes that don't cohere into a satisfying whole. So we get, for example, the romantic angle, unfortunately introduced by having a beautiful naked woman arise mermaid-style from the water to greet Kemp, and the obligatory mescaline trip, but neither feels anything like integral to the film.
More organic to the movie's central artistic self-discovery storyline is a complementary narrative about land development in Puerto Rico, perpetrated by greedy Americans like the oily Sanderson (Aaron Eckhart), who befriends Kemp and tries to hire him to write favorable press for his condo project. By suggesting an ongoing American economic imperialism and insisting on the tax loopholes that accompany such projects, Robinson manages to contemporize his source material, but he also uses it as a means of crafting gross caricatures, as in one sequence where Kemp interviews a fat American couple at a tourist bowling alley.
In the end, Kemp's moral reckoning resolves itself into a sudden stance of self-righteousness, and in a few moments of screen time we see the uncertain would-be writer begin thundering out his newfound sense of purpose as a journalist, ready to take on all comers, and speaking in the glib prose of Hunter S. Thompson. This transformation feels as forced as anything else in Robinson's movie, an attempt to mold a lot of disparate material into one final triumphant declaration. Or semi-triumphant, since the film ends on an odd note of failure, requiring the insertion of film-ending titles to assure us that this setback was later converted by the young writer into a stunning lifetime of success. It's an oddly unsatisfying way to end a movie, but then, despite its occasional moments of flair, The Rum Diary had never proved a very satisfying piece of work in the first place.