Based on the debut novel by Hunter S. Thompson The Rum Diary tells the increasingly unhinged story of itinerant journalist Paul Kemp (Johnny Depp). Tiring of the noise and madness of New York and the crushing conventions of late Eisenhower-era America, Kemp travels to the pristine island of Puerto Rico to write for a local newspaper, The San Juan Star, run by downtrodden editor Lotterman (Richard Jenkins). Adopting the rum-soaked life of the late 50s version of Hemmingway’s lost generation, Paul soon becomes increasingly obsessed with Chenault (Amber Heard), the wildly attractive Connecticut-born fiancée of Sanderson (Aaron Eckhart), a businessman involved in shady property development deals.