Any interest in a film based on the writings of late Hunter S. Thompson comes weighted by the unfilmable sense of the narrative Thompson concocted. How would a director capture a narrative that battled against the expectations of objective journalism by a writer fueled by drink, drugs and a borderline psychotic attitude toward— what he considered— the greedy hypocrites who have co-opted the American Dream for their own permit to mow down anyone and anything that stood in the way of their of insatiable fulfillment? Thompson showed no restraint, even peppering his writings with the hallucinations he suffered as a side-effect to his lifestyle. One of the most insane directors of the 20th century (Terry Gilliam) tried hard— maybe too hard— to realize Thompson’s writing with Fear and Loathing in Las Vegas… and failed. Now here comes the Rum Diary, starring Johnny Depp, who played Thompson in Gilliam’s now cultish failure (it flopped hard at the box office), hand-picking director Bruce Robinson as the man with the vision (both screenwriter and helmer). Though, in theory, Robinson should have been the right fit as director and writer, the Rum Diary never even comes close to that director’s long-ago apex in cinema: the over-the-top characters of Withnail & I (1987) and the black, surreal humor of How to Get Ahead in Advertising (1989).* Much less, does the 
Rum Diary, based on Thompson’s early novel, which would not see publication until long after the writer’s early years of achieving fame as a “Gonzo journalist,” ever capture the spirit of Hunter’s swagger, except maybe in the writerly manner the characters in the newsroom at the “San Juan Star” talk. I knew going into this movie any attempt to make a film out of Thompson’s prose would be an exercise in futility (and, no, I have not forgotten the 1980 biopic Where the Buffalo Roam starring Bill Murray), but, as a fan of Thompson’s writing, I wanted to see it through.
The film opens with the hung over Paul Kemp (Depp), an aspiring writer waking up hung over from a night of binge drinking just before he heads for his first day on the job at the “San Juan Star” in 1960. 
Already the film establishes this man as the alter ego of Thompson, well known for having started his illustrious career at “Rolling Stone” with a two-part dispatch from Las Vegas that became Fear and Loathing in Las Vegas in 1972, abusing drugs and alcohol (even ether) while running up a huge expense account for the magazine. What is less known about the author is that he tried to make it as a novelist by establishing himself at the actual “San Juan Star,” more than 10 years before his “RS” gig… which rejected him. While on the island, Thompson would write articles as a stringer on Caribbean affairs. In the meantime, he worked on two novels. The first has never been published and the second was the Rum Diary, a fictional account of a hero reporter out to undermine the development of the natural paradise that is Puerto Rico by US capitalist types who want to privatize beaches and push out the locals.
After an introduction to his hard-ass editor at the paper, Lotterman (Richard Jenkins), the film maintains a leisurely pace, delighting in the language of these newspapermen who all seem to have the quirk of alcoholism hanging over them, yet still banter with the strength of well-heeled news writers. 
I would have been happy if the film stuck to the newsroom and bar as the only set pieces. Still some other drama must drive these men as dictated by the Hollywood formula, and for awhile it seems like they are going to do some good with their intentions. Despite Kemp signing a confidentiality agreement with Sanderson (Aaron Eckhart), a developer seeking to exploit the writer for good press for his proposed beachfront hotel, Kemp turns against the businessman. Then there is the complication of Kemp’s affections for Sanderson’s fiance, Chenault (Amber Heard). Though Depp does a great job hunching over and drinking until he is nearly incomprehensible and obviously impaired in his decision-making, Chenault throws herself at him. Right. In the end, when mostly drunk heroes get together, nothing much cathartic happens, so an attempt for some grand revolution just becomes one over-long, drawn-joke that dulls any interest for these guys long before the final scene.
Though the resulting story on film is anti-climactic, Depp does his famed Thompson imitation well, down to the staccato mumblings of his words. The supporting news characters all prove themselves as the most interesting characters to watch, especially Giovanni Ribisi as the crime and religious affairs reporter Moberg
, a man who seems a further gone drunk than Kemp and looks like the future Thompson. In fact, the film slows down during all the vignettes of traveling across the island, accompanied by bland, typical of-the-era-and-location music choices that last too long. Though I do love the island, having been born there, the film drags during many of its set pieces. That said, the period detail in the sets are amazing, down to the poster art decorating the run-down apartment of Sala (Michael Rispoli), the paper’s photographer. Being filmed in Puerto Rico certainly helped, but while filming there, the filmmakers should have known that that the coquí only come out at night to make their distinctive sound.
I think it is great that Depp had such affection for Thompson to produce such a film, and God bless all those who think they can do justice to a man with such a unique voice. 
But the man was about the written word. It was as much about the medium as it was the message, which happens to have been unabashedly clouded up by drug and alcohol abuse (if there is anything sadder than movies that pay tribute to Thompson it just might be the writers who abuse illicit substances to try and imitate his style). The man was inimitable. The recent documentary Gonzo: The Life and Work of Dr. Hunter S. Thompson, narrated by Depp, is probably the best Thompson celluloid tribute, as Thompson is right at the center of the action, in the flesh, down to his funeral where his ashes were shot into the sky for a fireworks display. A Gonzo funeral for a Gonzo guy.
The Rum Diary is Rated R and runs 110 min. It opens Friday, Oct. 28, at most theaters. I attended a preview screening hosted by the film’s PR company for the purposes of this review.
*In between there was the ho-hum serial killer thriller Jennifer 8 (1992) and nothing else until the Rum Diary.
