A mobster travels to Hollywood to collect a debt, and discovers that the movie business is much the same as his current job.
Chilli Palmer is a loan shark in Miami. When his New York based boss dies of a heart attack, Palmer finds himself working for Ray 'Bones' Barboni an old rival who hates, Palmer. Bones is upset with Palmer for not collecting a loan from dry cleaner Leo Devoe who was killed in an airliner crash. Bones directs Palmer to get the money from Devoe's widow.
Visiting the widow Palmer realizes that Devoe is not actually dead, but got off the plane at the last minute and has used the accident to get out of the loan and, through his wife, collect a $300,000 settlement from the airline. Devoe has taken the money out of the state, but never sent for his wife. Angry, she lets Palmer know that he is in Las Vegas.
Palmer travels to Vegas and meets with a c
asino chief who tells him that Devoe has managed to gamble his winnings up to $500,000 and has moved on to Los Angeles. The casino chief asks Palmer while he is in L.A. if he can visit low budget movie producer Harry Zimm and remind Zimm that he owes the casino $150,000.
Palmer traces Zimm to the house of his sometimes girlfriend, sometimes star, Karen Flores. Late at night when Flores hears the TV playing downstairs she sends Zimm down to turn it off and he finds Palmer watching Letterman. Palmer delivers his reminder to Zimm about the casino debt and Zimm promises to pay. Palmer is a big film fan and engages Zimm in a conversation about his work eventually pitching him a story which is a fictionalized version of his hunt for Devoe. Flores comes downstairs to find them talking over drinks and, less than happy with both, and throws them out.
Action switches to the airport where gangster Bo Catlett is meeting a representative of a Columbian cartel, Yayo Portillo to buy a shipment of drugs. Catlett takes the drugs and gives Portillo the key to an airport locker where the $500,000 in cash is stowed. Portillo, suspecting a set up and that the locker is being watched by the Federal agents, does not go to the locker, but shows up at Catlett's mountainside house. Catlett shoots him and his body falls over the balcony down the mountainside. Catlett sends his bodyguard, Bear a sometimes stunt man, to retrieve the key and hide the body.
Zimm tells Palmer about a movie he wants to produce, "Mr Lovejoy," which has what he thinks is an Oscar winning script. He can't produce it, however, because Catlett has already lent Zimm $150,000 to do a film called "Circus Freaks." Zimm can't return the money because he lost it at Vegas in attempt to gamble it up to $500,000, the amount he needs to buy the Lovejoy script from the late writer's wife Doris Saphron. Palmer tells Zimm to let him handle the next meeting with Catlett and he will get Circus Freaks put off for a few months. Palmer will get the money from Devoe to finance Mr. Lovejoy.
Zimm gets nervous in the meeting with Catlett and Catlett's tough subordinate Ronnie Wingate. Zimm screws it up so that Catlett finds out about the valuable script and wants a piece of the production. He even offers to give Zimm $500,000 for the picture and suggests he send Palmer to get it from a locker at the airport.
Palmer goes to the airport and senses a setup. He tests what is going on by seeming to open the locker with the money when actually he opens the locker next to it. He is grabbed by federal agents, but then released when they realize that they have made a mistake. Afterward Bear confronts Palmer in the parking lot to get the key back, but is outmatched by Palmer who levels him with a few blows. As Bear recovers Palmer asks him about his stunt work and flatters him by knowing about the movies hes been in. Palmer mentions that he thinks Bear can do a lot better than working for Catlett.
The key to making Mr. Lovejoy a success is to get star Martin Weir to sign on. Flores is Weir's ex-wife and still has a good relationship with him. Flores starts to become romantically involved with Palmer and helps him get access to Weir. As it turns out Weir's current girlfriend is Rock star Nicki an old friend of Palmer's from Miami. Soon Palmer, who is familiar with Weir's work and flatters him, manages to talk him into signing on for the picture. Palmer also interests Weir in playing the fictional version of himself in the story he is developing.
Palmer tracks down Devoe and takes $310,000 of the $500,000 leaving him with just his Vegas winnings. Devoe complains, but Palmer tells him if Bones had found him instead Bones would have taken all the money and killed him.
Meanwhile Bones has learned of the money Devoe has scammed from the airline. He comes to LA when Zimm foolishly contacts him and tries to get him to invest in his film. A meeting between the two doesn't go well and leaves Zimm in a cast and head brace. At the same meeting Wingate appears and is shot by Bones, who then makes it look like Zimm killed Wingate in self defense.
The fact that Yayo has disappeared along with $500,000 has brought Colombia drug lord Mr. Escobar to L.A. with two goons. Though Catlett denies knowing what happened to Yayo or the money, it is clear that Escobar holds Catlett responsible giving him just a couple of days to find both of them or there will be fatal consequences. Desperate, Catlett confronts Palmer to get Devoe's money, kidnapping Flores and taking her to his house until the cash is delivered.
Palmer arrives at the house to rescue Flores. Catlett plans to take the money and kill them both, but with Bear's help (Bear has secretly switched sides), Palmer turns the tables on Catlett and sends him flying over the balcony to his death. Something Catlett had planned for Palmer.
Bones finally catches up with Palmer and demands Devoe's money. Finding the airport locker key in Palmer's coat, Bones assumes that Palmer has hid the money at the airport. When Bones goes to the airport and opens the locker we see the federal agents close around him
The scene suddenly switches to an airport set at a movie studio. A voice addresses Bones and when he turns around we see that the character is now portrayed by. Threatening him is Weir playing the fictional version of Palmer. Weir screws up the shot and as the movie company breaks for lunch we see that is the director and Bear a technical consultant with Zimm producing and Palmer and Flores as executive producers. There is a long helicopter pull out shot from the studio and the credits roll.