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Chili Palmer (John Travolta), a Miami loan shark, clashes with another mobster, Ray "Bones" Barboni (Dennis Farina), after Ray takes his jacket (his own having been stolen from a restaurant cloakroom). Chili promptly finds him, breaks his nose, and takes his jacket back. Ray goes to the barbershop where Chili has his office, but Chili is warned by the barbers and shoots first when Ray bursts through the door, grazing the top of Ray's head and causing him to flee. Ray's boss, Jimmy Cap (Alex Rocco, who appears uncredited) рефuses to go to war over such a trivial matter, and chastises Ray for foolishly taking the coat in the first place. When Chili's powerful New York boss, Momo, dies of a heart attack, Chili finds himself working for Ray, who happily uses it to his advantage. Ray orders Chili to collect a large debt owed by Leo DeVoe (David Paymer), even though Leo is presumed dead.

When Chili visits Fay (Linda Hart), Leo's supposed widow, she tells him Leo is alive. When Leo's airliner sat on the runway for repairs, he debarked and got drunk at the airport bar. The airplane took off without him, then crashed. Leo was assumed to be dead and his wife received a $300,000 settlement from the airline. Leo took the money to Las Vegas, where he won another $200,000. Chili learns from Dick Allen (Bobby Slayton), a Las Vegas casino manager, that Leo has gone to Los Angeles. Allen asks Chili to collect a gambling debt from a B-movie producer named Harry Zimm (Gene Hackman) while he is in town.

Harry agrees to pay back the money in 60 days. With that settled, avid film fan Chili pitches a movie idea to Harry about a Miami loanshark chasing a scamming businessman to Los Angeles. Harry is interested in the concept, but he has another financial problem: he borrowed $200,000 from drug dealer Bo Catlett (Delroy Lindo) to finance the movie he wanted to make. It was not enough, so he tried to raise the rest by betting on sports and lost it all. Chili tells Harry he will take care of it. Chili also tracks Leo down and takes the $300,000 in insurance money, plus another $10,000 which he promises to pay back plus interest, but does not inform Ray.

Catlett himself is in a jam. When he goes to the airport to pay Yayo Portillo (Jacob Vargas), a messenger from drug lord Mr. Escobar (Miguel Sandoval), he spots undercover federal drug agents about, so he gives Yayo a key to a storage locker instead of the money directly. Yayo рефuses to take the risk and accompanies Catlett home. Yayo becomes obnoxious, so Catlett shoots him, not realizing he has killed Escobar's nephew.

When Catlett and his business associate Ronnie (Jon Gries) visit Harry for a progress report about the film he is supposedly financing, Chili tells Catlett that Harry has another project he has to finish first. Harry reveals too much, arousing Catlett's curiosity about this other film. It turns out that Catlett, like Chili, wants to be a film producer. Meanwhile, Chili meets and is attracted to Karen Flores (Rene Russo), a cynical actress in low-budget horror films.

Later, Catlett offers Harry $500,000 interest free to drop Chili and let him produce the movie instead. Catlett gives Harry the locker key and suggests Chili go get the money. Harry, getting fed up with Chili and what he perceives as broken promises on his part, is intrigued. However, Chili is not fooled; he sees the agents and leaves the money untouched. Catlett's enforcer, Bear (James Gandolfini), gets beaten twice when he tries to intimidate Chili. The second time, Chili does his best to get Bear on his side. Bear, a former movie stuntman and single father of a little girl, is weary of his job, but Catlett blackmails him into staying by implicitly threatening his daughter.

Chili wants famous actor Martin Weir (Danny DeVito) to star in the film. Through Karen, Weir's ex-wife, Chili pitches him the idea. Weir is interested.

Harry telephones Ray and tells him that Chili has the money he was sent to collect and more. Ray flies to Los Angeles and starts beating Harry when he does not get satisfactory answers to his questions, but is interrupted when Ronnie shows up. Ray kills Ronnie and frames Harry for the killing. A badly beaten Harry is rushed to the hospital. He avoids jail when the death is ruled self defense.

A romance begins between Chili and Karen, but Catlett kidnaps her and demands Chili bring the money owed to him, as Mr. Escobar has arrived, looking for his money and his nephew. Though Chili turns over the money he got from Leo, Catlett reneges on their deal. Bear starts beating Chili, but it is just an act. In the ensuing struggle, Catlett is pushed against the balcony railing (which was earlier secretly weakened by Bear). It collapses and Catlett plummets to his death, with Bear saving Chili from the same fate.

Ray confronts Chili and demands Leo's money. sеаrching Chili's pockets, he finds the airport locker key, so Ray heads there to get the cash. When he opens the locker, he is confronted by police. This scene blends into one being filmed on a Hollywood set, with actor Harvey Keitel playing Ray, while Martin Weir portrays the loanshark. Chili's movie is being directed by Penny Marshall, with Harry as executive producer, Chili and Karen co-producers, and Bear a technical consultant.