Chili Palmer, played by John Travolta, steps in to assist Edie Athens, the grieving widow of his late friend Tommy Athens (James Woods), to revive a struggling record company. The endeavor involves spotlighting a promising young artist, Linda Moon (Uma Thurman), who possesses both vocal talent and songwriting skills. However, the journey to musical revival is fraught with challenges.
For starters, Chili navigates a complex array of connections akin to a loan-shark situation from Get Shorty, where he finds himself becoming a "producer" who holds deals with various players. He also faces threats from the Russian Mafia, led by Roman Bulkin (Alex Kubik), who want him dead for witnessing Tommy's untimely demise. Meanwhile, Tommy's record company struggles with substantial debts, particularly a hefty $300,000 owed to gangster-producer Sin LaSalle (Cedric the Entertainer).
Chili is a talented filmmaker with a disinclination towards sequels. During a fateful lunch meeting with Tommy to discuss a potential film about his life in music, tragedy strikes as a Russian assassin takes Tommy's life right before Chili’s eyes. When Chili returns from the restroom, he identifies the assassin, a man with a toupee, deepening his entanglement in this deadly scenario.
Detective Marla (Debi Mazar) is assigned to the investigation, suspicious that Chili may have orchestrated Tommy's murder. In a twist of fate, Linda persuades Chili to help her escape from detrimental contracts held by Nick Carr (Harvey Keitel) and Raji (Vince Vaughn). She recounts how they misled her when she arrived in Los Angeles, trapping her in a deal that yields nothing but despair. With five years left on her contract, she desperately seeks chili’s intervention.
The plot thickens when Nick's bodyguard, Elliott (Dwayne Johnson), a struggling actor often the butt of Raji and Carr's jokes, is sent to eliminate Chili. Instead of conflict, though, Chili forms a bond with Elliott and offers to assist him in breaking into acting.
As the story unfolds, Chili decides to produce Linda’s music, aiming to resurrect the Athens record label through a spectacular live performance featuring Aerosmith and Steven Tyler. This presentation would not only serve as Linda's launch pad but also significantly reduce costs for her debut album. Amidst the chaos, Tiffany (Kimberly J. Brown), Tommy's assistant, informs Chili that the Russian assassin had been lurking around Tommy's office, further complicating matters.
Raji and Nick, not pleased with Chili's meddling, employ hit-man Joe "Loop" Lupino (Robert Pastorelli) to eliminate him. Meanwhile, LaSalle puts immense pressure on Chili and Edie for the overdue payment, only for them to convince him to extend their deadline. However, when a Russian assassin makes an attempt on Chili’s life, the bullets mistakenly hit their intended target, leading to dramatic confrontations in the criminal underworld.
As events spiral, Chili discovers that Roman was behind Tommy's assassination. He also learns that the Federal authorities are keeping a close watch on Roman, presenting an opportunity for Chili to confront him directly. Tensions continue to rise, culminating in a fateful basketball game with Edie sitting next to Steven Tyler.
In a series of strategic moves, Chili ensures that the right people get what they deserve, leading to hilarity and chaos alike. Raji’s intent to maintain control over Linda and his subsequent downfall reveals his nature, while Elliott's character growth adds a layer of depth, highlighting the unpredictability of the situation.
After an intense series of betrayals and confrontations, climaxing at the MTV Video Music Awards, Linda Moon emerges victorious, winning accolades whereas the malevolent characters face their just desserts. In the conclusion, Chili and Edie share a moment of joy amidst the swirling chaos, marking a fitting end to their wild ride in the music industry. As Chili drives away, he notices a billboard showcasing Elliott as a co-star alongside Nicole Kidman, indicating that the journey is just beginning for them all.
