Having Johnny Depp as Paul Kemp is really a no-brainer. Depp had become friends with Hunter S. Thompson, the author of The Rum Diary and of whom Kemp is based on in an autobiographical sense. Depp had previously played Raoul Duke (another autobiographical character) in Terry Gilliam's adaptation of Thompson's Fear and Loathing in Las Vegas and even narrated Alex Gibney's documentary Gonzo: The Life and Work of Dr. Hunter S. Thompson. If what I've heard about Thompson's speech patterns and behavior is to be believed, Depp has arguably inbued a little bit of Thompson in many of his roles. Don't get me wrong, Depp has an unbelievable range that can be seen in his ever-expanding list of accomplishments starting for me with What's Eating Gilbert Grape? and perhaps most recently witnessed in Sweeney Todd: The Demon Barber of Fleet Street.
In The Rum Diary, Kemp is a bad boy agitator who can still appear suave as to mix with the high-society types, but he is still just as natural at hanging out with his blue-collar co-workers and knocking back shot after shot of a variety of liquors. Kemp is a journalist who has begun working for the San Juan Star in Puerto Rico and he uncovers a land-buying conspiracy involving a private island that is being overseen by a shady businessman (Aaron Eckhart). We witness Kemp/Thompson go from being inexperienced to an experienced man in terms of the passion for his craft. Still, that one notable arc doesn't prevent the film from being dull, boring, and feeling like it went on for thirty to sixty minutes too long.
Depp plays the character very one-sided and it feels weird that a character so confident has to sit around and act second-fiddle to everyone from businessmen to even his own editor (Richard Jenkins). Maybe this is because I can't help but think of Depp as this superstar actor/celebrity, but remembering my affinity for his work in films like Finding Neverland, I think I would be able to deal with having to watch Depp go from visiting private beaches to slumming with alchololism. Without a focused character, you have a wandering story. The other actors (the ones I've mentioned as well as Michael Rispoli and Giovanni Ribisi) play some interesting characters, but the characters that matter such as Kemp and Chenault, played by Amber Heard, are just to plain and simple. At least Heard was sensual in her portrayal, that helped keep my attention.
Writer-director Bruce Robinson had previously directed the phenomenal Withnail and I where he showcased the "high-end of social" drinking (as Kemp puts it) and managed to create a multi-dimensionality that really made the piece feel coherent. That is completely lacking in The Rum Diary and for all of Depp's passion for his late friend, Hunter S. Thompson, the film just feels like an exercise in digging oneself into a ditch.