- American journalist Paul Kemp takes on a freelance job in Puerto Rico for a local newspaper during the 1960s and struggles to find a balance between island culture and the expatriates who live there.
- Hard-drinking journalist Paul Kemp takes a job at a besieged newspaper in San Juan, Puerto Rico. His volatile editor, Lotterman, assigns him to tourist pieces and horoscopes, but promises more. Paul rooms with Sala, an aging and equally alcoholic reporter, in a rundown flat. Sanderson, a wealthy entrepreneur, hires Paul to flack for a group of investors who plan to buy an island near the capital and build a resort. Sanderson's girl-friend, the beguiling Chenault, bats her eyes at Paul. His loyalties face challenges when he and Sala get in trouble with locals, when a Carnival dance enrages Sanderson, and when the paper hits the skids. Is the solution always alcohol?—<jhailey@hotmail.com>
- Paul Kemp is a freelance journalist who finds himself at a critical turning point in his life while writing for a run-down newspaper in the Caribbean. Paul is challenged on many levels as he tries to carve out a more secure niche for himself amidst a group of lost souls all bent on self-destruction.—Joshua Lake
- It's 1960 in Puerto Rico. Paul Kemp (Johnny Depp) is an author who hasn't been able to sell a book. 1960s in Puerto Rico was a period marked by increasing activism and a renewed focus on the island's political status, particularly concerning its relationship with the United States. The island was in the grip of a communist takeover, and the Americans were generally not trusted and treated with disdain.
He gets a job at a newspaper in San Juan, Puerto Rico, where his editor & boss Lotterman (Richard Jenkins) is looking to infuse fresh blood into the newspaper to arrest its ailing circulation. The paper is mostly run by American staff and hence is being boycotted by the locals. Paul lives in a fancy hotel paid for by the newspaper. Lotterman warns Paul not to get too drunk as he showed up for his interview with Lotterman with a hangover and wearing sunglasses. Lotterman gets Paul to start writing the daily horoscope section of the paper.
There, Kemp meets Bob Sala (Michael Rispoli) staff photographer, who gets him acclimated and tells him he thinks the newspaper will fold soon. He says that he is sticking around for the $3000 redundancy payment after which he will move to Mexico. Sala says that the whole paper is being held together by 3-4 professionals who still value their creative integrity. Kemp checks into a hotel and while idling about on a boat in the sea, meets Chenault (Amber Heard), who's skinny-dipping while avoiding a Union Carbide party. Kemp is immediately smitten with her.
Kemp and Sala immediately go on a drinking binge, which earns Kemp the enmity of his editor, Lotterman. Kemp also meets Moburg (Giovanni Ribisi), a deadbeat reporter who covers Crimes and Religious Affairs. Lotterman cannot fire Moburg as he is never seen at the office at all. While waiting for an interview at the airport, Kemp meets Sanderson (Aaron Eckhart), a freelance Realtor and a PR consultant flaunting a luxurious lifestyle, who offers him a side job writing public relations material for his latest venture. Sanderson is engaged to Chenault, who pretends not to know Kemp. Sanderson used to work for the paper, but then went into business on his own, selling Puerto Rico assets to the Americans as an investment opportunity. The Americans love to come to Puerto Rico for its bowling alleys and the casinos.
Later, Kemp moves in with Sala, who also rooms with Moburg. Kemp begins to see the poverty of San Juan & starts to write articles about it, but Lotterman doesn't want him to write about it, as it's bad for tourism. Moburg returns with leftover filters from a rum plant which contains high-proof alcohol. Moburg has been fired, and rants about killing Lotterman.
Kemp visits Sanderson and spies him making love to Chenault. He meets Zimburger (Bill Smitrovich) and Segarra (Amaury Nolasco), who want him to help with a real estate scam. The scam is that Sanderson & his partners want to build a hotel at a ecologically sensitive island. So they want Kemp to write articles in his newspaper & publicize the fact that they want to build many hotels, that way the public officials will be happy to compromise & allow them to build at least 1.
Later, Sala and Kemp go to a local restaurant and berate the owner for refusing them service for being "gringos". Kemp senses that the owner wants to kill them, and he and Sala beat a hasty retreat, pursued by angry locals. The police arrive and break up the fight, then throw Sala and Kemp in jail. Sanderson bails them out. The whole episode simply highlights the struggle between Puerto Rican locals & the immigrant US population that is intent on buying up the whole place & force the locals out.
The next day, Kemp meets with Sanderson's partners, who introduce him to the venture. The plan is to build a resort on a "pristine" island off the coast of Puerto Rico. Kemp meets with Sanderson's crew, who tell him that the US military is relinquishing the lease on some prime real estate and is asked to pick up Chenault from her house. Kemp and Chenault share a moment but resist temptation.
Zimburger takes Kemp and Sala to see the island, part of which is still used as an artillery range by the US military, then they head to St. Thomas for Carnival. Kemp finds Chenault, and they wind up on Sanderson's boat. Sanderson berates Kemp for involving Sala in the deal. At night, they go to a club, and a drunk Chenault dances with local men to provoke Sanderson, with whom she has been fighting. When Sanderson tries to intervene, he is forcefully removed from the dance floor by locals and led out of the club by Kemp and Sala for his own safety. Chenault stays behind at the club.
The next day, Chenault is gone, and Sanderson tells Kemp that their business arrangement is over. When Sala and Kemp return home, Moburg tells them that Lotterman has left and that the paper will go out of business. He also sells them hallucinogens, which they take. Kemp has an epiphany while under the influence and resolves to write an expose on Sanderson's shady deals.
Lotterman returns but won't publish Kemp's story. Chenault shows up at Kemp's place, and Sanderson disowns her. Out of spite, he withdraws his bail, meaning that Kemp and Sala are now wanted by the police. Moburg also tells them that Lotterman has closed the paper. Kemp decides to print a last issue, telling the truth about Lotterman and Sanderson, as well as the stories Lotterman declined.
To make money to print the last edition, Kemp, Sala and Moburg place a big cockfighting bet. They visit Papa Nebo (Karimah Westbrook), Moburg's hermaphrodite witch doctor, to lay a blessing on Sala's prize cockerel. They win but return to the office to find that the printing presses have been confiscated.
Kemp continues his quest, stealing Sanderson's boat. Kemp makes it back to New York, marries Chenault, and becomes a successful journalist, having finally found his voice as a writer.
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