The Rum Diary tells the story of Paul Kemp, played by Johnny Depp. Exhausted by his failed career as a novelist in New York and the madness of Eisenhower-era America, he moves to San Juan, Puerto Rico to take up a job working for the local English newspaper, The San Juan Star. Although the paper is barely able to stay afloat, Kemp lands the position — one that no one else even applied for — and is assigned to doing horoscopes and rewrites.
Between his booze-ridden exploits, Kemp manages to fall into the company of Sanderson (Aaron Eckhart), a shady American entrepreneur looking to cash in on Puerto Rico’s prime real estate by building an island resort. Sanderson signs Kemp up to write up some cleverly placed articles about their scheme. While Kemp realizes he may be making a mistake, his morals are swayed by a fancy new car, a $500 cash advance, and Sanderson’s young free-spirited fiancée Chenault (Amber Heard), whom Kemp becomes increasingly infatuated by. With the newspaper sinking fast, Kemp is faced with the biggest decision of his career — sell out to Sanderson’s corrupt but lucrative business ventures, or use his insider status to reveal all the dirty secrets of San Juan’s many expats.