Paul Kemp (Johnny Depp) arrives on the island of Puerto Rico after being enlisted to become the newest reporter for the San Juan Star. Kemp is introduced to his newest co-workers, old veteran Bob Sala (Michael Rispoli) and oddball Moburg (Giovanni Ribisi) as well as his cigar-chomping editor boss Edward J. Lotterman (Richard Jenkins) and is told he will be doing color stories for the paper.
The movie revolves around the many adventures Kemp gets himself into, eventually including a plot by a corrupt realtor Hal Sanderson (Aaron Eckhart) to purchase a nearby unspoiled island and turn it into yet another tourist destination. And things get even more complicated when Kemp ends up falling for Sandersons' girlfriend, Chenault (Amber Heard).
- Adaptational Skimpiness: The scene with Chenault dancing at the bar is greatly toned down. In the book, she strips naked in the middle of the dance floor and gets dragged off by island locals, and is heavily implied to be raped. In the film, she wears a red dress and the scene fades away as she's dancing with the locals, making it more ambiguous whether she was raped or not.
- The Alcoholic: Most of the main cast, but especially the side character Moberg whose booze consumption puts the rest of the cast drunken characters to shame.
- Bar Brawl: Sanderson ends up getting beaten by the angry locals at the St. Thomas bar when Chenault decides to go dancing there just to spite him.
- Beastly Bloodsports: To make money to print the last edition, Kemp, Sala and Moburg place a big cockfighting bet. They visit Papa Nebo, Moburg's hermaphrodite witch doctor, to lay a blessing on the strongest fighting cockerel on the island, which Sala manages to borrow. They win, but return to the office to find that the printing presses have been confiscated.
- Big Fancy House: Sanderson has a big palatial beach home, which greatly contrasts with the poverty of San Juan.
- Bittersweet Ending: The newspaper gets shut down, the printing presses are confiscated before Paul can print the expose' he had planned, he and Sala are out of a job and wanted by the law. Fortunately, they just made a big wad of cash from cockfighting, there's a convenient boat owned by Sanderson for Paul to steal, Chenault is waiting for him and they marry according to the epilogue, but most importantly, the seed of Gonzo Journalism has been planted.
- Black Comedy Rape: What happened to Kemp's predecessor as "Madame Le Zonga"? Raping to death is mentioned, but his editor admits he was fucking with him.Kemp: The raped him to death?
- Booze Flamethrower: Kemp manages to fend off an angry mob (and accidentally set fire to a police officer) by drinking "470 proof alcohol" and breathing on a lighter.
- Corrupt Corporate Executive: Sanderson is a corrupt American realtor, who uses various shady dealings to defraud Puerto Ricans.
- Da Editor: Lotterman is a corrupt, cigar-chomping and pompous editor of The San Juan Star and Kemp's Bad Boss who only cares about making money, not real journalism.
- The Film of the Book: The film is an adaptation of the novel of the same name by Hunter S. Thompson.
- Foreshadowing:Lotterman: This is the American dream, Paul.
Paul: You did me the best favour I ever had. There is no dream, Chenault. There's a piss-puddle of greed spreading throughout the world.
Paul: I want to make a promise to you, the reader. And I don't know if I can fulfill it tomorrow, or even the day after that. But I put the bastards of this world on notice; that I do not have their best interests at heart. I will try and speak for my reader. That is my promise. And it will be a voice made of ink, and rage.
- Hero's Evil Predecessor: Moburg is a kind of proto-Hunter S. Thompson. He's resourceful, fearless, and has grit to spare. He's also a Neo-Nazi.
- Historical In-Joke: Watching the 1960 Presidential debates.
- Horrorscope: The trope is name-dropped. Paul is assigned to the horoscope section of the San Juan Star paper by his boss because Paul's aims as being a brutally honest journalist conflicts with the feelgood, profit-over-journalistic-integrity that the paper is going for. Paul goes at it with very little enthusiasm, at one point referring to it as a "horrorscope".
- Interrupted Intimacy: Just as Kemp and Chenault are about to have sex, Moburg's old vynil acts up, with Hitler giving a speech. Needlessly to say, that kills the mood.
- Intrepid Reporter: Kemp grows into one, putting himself and his job in danger in order to expose the real problems of San Juan.
- Male Gaze: The camera zooms from Chenault's breasts onto her legs in one scene.
- Ms. Fanservice: Chenault is a blond-haired bombshell who's often wearing revealing outfits and shows plenty of skin.
- Naked First Impression: Downplayed. Kemp first meets Chenault while she's Skinny Dipping in a lake at night, but her body is submerged the entire time, so both he and the audience only see her Shoulders-Up Nudity.
- The Peeping Tom: Kemp spies on Chenault having sex with Sanderson in the water via telescope.
- Rich Suitor, Poor Suitor: Chenault is in the middle of a Love Triangle between her rich corrupt boyfriend Sanderson and the poor Starving Artist Kemp. She eventually grows tired of Sanderson's ego and shady dealings and decides to go for Kemp, as she becomes attracted to his romantic and artistic aspirations.
- Screw the Rules, I Have Money!: Rich corrupt realtor Sanderson's Modus Operandi is to just throw money at his problems to make them go away, which actually works in Kemp's favor when he pays for his bail... but also ends up screwing him over when he antagonizes Sanderson who them retracts his bail and makes Kemp a wanted man.
- Sexy Surfacing Shot: One scene has a focused shot of Chenault and Sanderson coming out of the ocean, her in a skimpy red swimsuit and him shirtless.
- Shameless Fanservice Girl: Chenault doesn't care much for modesty, she goes Skinny Dipping at night, Sanderson claims she often sunbathes nude (and apparently draws a crowd to the propertys fences when she does it) and overall wears very revealing outfits.
- Shout-Out: Multiple to Fear and Loathing in Las Vegas:
- The bottle containing Moberg's drug looks to be a replica of the adrenochrome bottle.
- The scene with Kemp monologuing while typing facing out a shuttered window is a direct lift from scene where Duke sits in the same pose and makes the famous Wave Speech from Fear and Loathing.
- Shower of Love: Downplayed. Chenault invades Kemp's bathroom as he's showering and starts kissing him, but they soon move on to the bedroom to have sex.
- Spiritual Successor:
- Starving Artist: Kemp is an aspiring writer, but he been unable to sell his unpublished novels, thus he gets a job at a newspaper writing horoscopes and puff pieces to support himself.
- Toplessness from the Back: When Kemp and Chenault are undressing to have sex, we only see her bare back once her shirt and bra are removed, and she's only wearing jeans by the time they get interrupted by Hitler.
- "What Now?" Ending: Kemp leaves the island on a stolen boat, and doesn't seem to know even where he's going.
- Wretched Hive: Many parts of San Juan are incredibly impoverished and crime-ridden.