Chilli Palmer, played by John Travolta, is a loan shark residing in Miami. After the sudden death of his boss from a heart attack, Palmer finds himself entangled with his old adversary, Ray 'Bones' Barboni (Dennis Farina). Bones is furious at Palmer for failing to collect a debt from dry cleaner Leo Devoe (David Paymer), who was supposedly killed in a plane crash. Bones orders Palmer to retrieve the money from Devoe's widow (Linda Hart).
However, upon visiting the widow, Palmer discovers a shocking twist: Devoe has actually faked his death to evade the loan and is cashing in on a $300,000 airline settlement, leaving his wife in the dark about his whereabouts. Fueled by anger, she informs Palmer that Devoe is now in Las Vegas.
Determined, Palmer heads to Las Vegas, where he learns from a casino manager that Devoe has turned his initial winnings into $500,000 and has now moved to Los Angeles. The casino head asks Palmer to check in with low-budget movie producer Harry Zimm, who owes the casino $150,000.
Upon tracking down Zimm to the home of his sometimes-girlfriend and actress Karen Flores, things take a turn. Later that night, Zimm descends to find Palmer engrossed in a Letterman episode. Palmer takes the opportunity to remind Zimm of his debt, and their conversation soon shifts to cinema. Enthusiastic about filmmaking, Palmer pitches a narrative based on his current predicament with Devoe. However, Flores, unhappy with the duo, eventually throws them out.
Meanwhile, action shifts to gangster Bo Catlett (Delroy Lindo), who is in the midst of a drug deal with a Columbian cartel member, Yayo Portillo (Jacob Vargas). The deal goes awry, leading to a murder that sets off a chain reaction of events involving drug money and deception.
Zimm shares with Palmer a movie concept he wants to develop titled "Mr. Lovejoy," believing it has Oscar potential, but he struggles to fund it due to his financial troubles with Catlett. Palmer takes it upon himself to negotiate with Catlett, believing he can defer the production of Zimm’s current project.
As tensions rise, Zimm mismanages the meeting with Catlett, who learns about the lucrative script, escalating his demands for a cut. In a twist of fate, Palmer begins to garner help from Flores, who rekindles her connection with the ex-husband, actor Martin Weir, who ultimately joins the project after they charm him into accepting the role.
In the ensuing drama, Palmer successfully corners Devoe, taking a large chunk of his cash, but leaving him with enough to secure his safety. Bones soon catches wind of these developments, and soon, conflict ensues leading to confrontations that embroil everyone involved.
With stakes at an all-time high involving drug lords, debt collectors, and a chaotic film production, Palmer’s life begins to echo the very script he has been developing. In a climactic showdown, with Flores held captive and all essentials hanging by a thread, Palmer, with ally Bear (James Gandolfini), turns the tables on Catlett, mirroring his earlier machinations.
As the dust settles, Palmer must face Bones who, now eager to claim the remaining debts, unknowingly walks straight into the web of the law. The finale is a remarkable transition where the audience realizes a cinematic production is unfolding around them, culminating in a meta-narrative that showcases the intertwining lives of all characters involved, from Zimm producing to Palmer and Flores taking on executive roles. The story illustrates the chaos that arises when life imitates art, and as the credits roll, the audience is left to ponder the boundaries of fiction and reality in a world driven by greed, ambition, and unexpected alliances.
