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The book's story centers on Chili Palmer, a small-time shylock (or loanshark) based in Miami. After a run-in with mobster Ray "Bones" Barboni over a stolen coat, Chili is sent after Leo Devoe, who has scammed an airline out of $300,000 in life insurance by faking his own death. Leo had been aboard a plane whose flight was delayed, prompting him to disembark and go drinking in the airport bar. Leo misses the plane's takeoff, and when it crashes, his "widow" receives a check for $300,000, money which Leo takes to Las Vegas.
After relieving Leo of the money in Vegas, the loan shark finds a more interesting assignment: the casino is looking to collect from Harry Zimm, a horror film producer based in Los Angeles. Palmer, himself very interested in the movie industry, heads for L.A. to make Zimm pay.
Palmer lets his love of movies overshadow his collection job. He sneaks into the house of actress Karen Flores in the middle of the night, startling both Zimm and Flores, who are together in bed. After he warns Zimm to pay his Las Vegas markers, he explains that he has an idea for a movie. Zimm is immediately taken in by Palmer's charm and his movie premise, whereas Flores is still skeptical.
Palmer recounts Leo Devoe's story to Zimm in the third person, as if it were a work of fiction. Flores is on to him, pointing out that the story clearly isn't fictional because she saw the plane crash in the news, realizing Palmer is obviously the shylock in Chili's movie idea.
The next morning, Zimm asks for Chili's help in dealing with a script he wants to buy. Zimm tells him this script, Mr. Lovejoy, could be Academy Award worthy material. "It'll be my Driving Miss Daisy," Zimm assures Chili. There are, however, two problems: Zimm does not own the script, his writer's widow Doris Saffron does, and she wants $500,000 for it; and he guaranteed a $200,000 investment from Bo Catlett, a local limo driver and drug dealer, to make another movie called Freaks. (Zimm gambled Catlett's $200,000 away in Vegas in hopes of making the $500,000 he needed for Mr. Lovejoy). In a meeting with Catlett and his sidekick Ronnie Wingate, Zimm and Palmer tell them that, while their investment in Freaks is sound, they are making another movie first. Catlett tells them to move the money into this new picture; Zimm says he cannot, as the new movie deal is "structured."
Meanwhile, Catlett is involved in a Mexican drug deal which doesn't go through. He has left the payment in a locker at the L.A. airport, but the Colombian sent to receive the money, Yayo Portillo (Catlett keeps calling him Yahoo), doesn't feel safe unlocking the locker with so many DEA agents staked out nearby. Catlett later meets Yayo back at his home, and after Yayo threatens to tell the DEA who Bo is, Bo shoots him.
Catlett soon offers the locker money to Zimm as an investment, telling him to send Palmer to get the money. Palmer senses something wrong, signs out a nearby locker as a test, and sure enough is taken for questioning by drug officials when he tries to open it.
Palmer and Flores are meanwhile seeking the interests of Michael Weir, a top-tier Hollywood actor to whom Flores was once married, to play the lead in Zimm's film.
The loose ends are tied up when Ray Barboni comes to Los Angeles looking for the money Palmer collected from Leo Devoe, only to find the key to the locker from the failed drug deal in one of Palmer's pockets. Thinking Palmer has stashed his cash in a locker, he goes to the airport and is busted by drug officials. In a final showdown with Catlett, Catlett is double-crossed by his partner, Bear.
The novel ends with Zimm, Palmer and Flores having visited a few production studios and wondering why writing the ending of a story was always the hardest part.