Streetwise mobster-turned-movie producer Chili Palmer is back, but this time Chili has abandoned the fickle movie industry and veered into the music business, tangling with Russian mobsters and gangsta rappers and taking a talented, feisty young singer named Linda Moon under his wing. From the recording studio to an Aerosmith concert to the MTV Music Awards, he manipulates events to watch them play out the Chili way, using his signature blend of wiseguy skills and negotiation tactics. It’s a dangerous business, and everyone’s looking for their next big hit.
After being imprisoned for six years on a grand theft auto charge, Rudy Duncan (Ben Affleck) and his cellmate Nick (James Frain) are finally going to be paroled. After hearing endless stories during his incarceration of Nick’s romantic correspondence to a woman named Ashley he has never met (Charlize Theron), Rudy is looking forward to returning to his family and having a fresh cup of hot chocolate. When Nick is killed during a prison riot, Rudy decides to assume Nick’s identity upon release from prison and meet up with the unknown woman. Burdened with a base knowledge of Nick’s Indian casino employment past, Rudy finds himself in too deep with Ashley’s brother Gabriel (Gary Sinise) and is violently forced to cooperate with a casino robbery that Gabriel and his gang have been planning with Nick in mind.
