The Rum Diary by Hunter S. Thompson was written in 1960, but not published until 1998 when the manuscript was found among Thompson’s papers by Johnny Depp. In 2011, the novel was made into a movie starring Depp, Aaron Eckhart, Amber Heard, and Giovanni Ribisi.
The main character of the novel, Paul Kemp, is a journalist in New York City who longs for adventure and excitement. Looking for something new, he moves to San Juan, Puerto Rico and gets a job at a paper there. Paul gets drunk before getting on the plane to Puerto Rico; as he boards, he notices a beautiful woman with whom he wants to talk. He attempts to entice the woman to sit next to him on the plane, but an old man takes the seat Paul had been saving for her. Paul gets into an altercation with the man, and the girl leaves in disgust.
After arriving in San Juan, Paul looks for someplace to eat dinner, but none of the restaurants appeals to him. Eventually, he goes to the offices of his new paper,
The San Juan Daily News, instead. There, he meets the newspaper’s photographer, Richard Sala. Richard takes Paul to a local restaurant where they drink and have dinner. Several other reporters from the paper are there, including Yeamon, a dangerous and sinister man, who is dating Chenault, the beautiful woman Paul saw on the plane.
In spite of the awkward situation, Paul becomes friends with Yeamon and several other colleagues at the paper, who warn him about the paper’s editor, a paranoid and ineffectual boss whom the employees do not respect. The paper is run with little oversight and always seems to be under financial pressure. Paul is told not to get too comfortable in his new job as the paper might fold at any time.
Yeamon invites Paul to visit him and Chenault at their home in the country. Paul arrives early and sees the couple swimming in the nude. He is jealous of Yeamon, envious of how easily he and Chenault get along. He leaves for a while, returning at the scheduled time. Enchanted by Chenault, Paul is annoyed by the way Yeamon seems to treat her in a controlling way.
The next week at the paper, Yeamon gets in trouble with the boss for refusing to edit a piece he has written that is much too long for publication. The boss gives Paul the piece to edit; Paul suggests running it serialized and uncut. Furious, the boss fires Yeamon. A few days later, Paul and Richard go to visit Yeamon to see how he is doing. They walk in on him beating Chenault. Yeamon insists they go to a local bar. The three get very drunk; when the time comes to pay their bill, Yeamon refuses and will not let Paul or Richard pay either. The three run out and are chased down by local police and beaten. Some of their friends from the paper arrive, dropping some important names to convince the police to set bail.
One of the friends who helps bail Paul out is a PR man named Sanderson. In exchange for his help getting out of jail, Paul agrees to write some pieces for some of Sanderson’s clients. One of these requires him to visit a small island where a resort is being built that will cater to wealthy visitors from the mainland.
After he finishes this piece, Paul goes to visit Yeamon and Chenault on St. Paul. Carnival season is in full swing, and the city is one large, crowded, noisy party. The three head to the outskirts of town where several quieter parties are in effect, mostly being put on by the locals. At one house party, Chenault dances with some local men who move to surround her, forcing her to leave with them. Yeamon and Paul try to intervene, but the other people at the party stop them.
Paul worries about Chenault, who disappears after the party, but the police refuse to help him find her. A few days later, a disturbed Chenault shows up on Paul’s doorstep. Yeamon knows that she was assaulted at the party and refuses to take her back, so Chenault moves in with Paul. A few days later, the paper goes out of business. The furious reporters plan to attack the editor at a party, where Yeamon joins them. The editor has a heart attack and dies during the course of the attack. Yeamon is blamed for his death.
Paul helps Yeamon escape the island, and then he makes plans to return to New York with Chenault.