Adapted by Peter Steinfeld from the Elmore Leonard novel, Be Cool finds one-time wise guy Chili Palmer (John Travolta) restless after having sullied his critical and commercial success as producer of the hit movie Get Leo by surrendering to studio seduction to produce an unsuccessful and widely disparaged sequel. For reasons that are very un-Hollywood-like and therefore unconvincing, Chili doesn't have another project to promote. So he takes a meeting with Tommy Athens (James Woods), another former mobster who has enjoyed modest success as a record producer. Tommy wants Chili to produce a movie about Tommy's life, a notion that doesn't interest Chili.
Chili does get interested, however, in a young African-American singer named Linda Moon (Christina Milian), who possesses a tiny waist and big voice. Chili thinks Linda has the pipes and presence to be the next huge recording superstar. So he enlists Tommy's not-so-bereaved wife, Edie (Uma Thurman), to help him produce a CD that will launch Linda's career. Here the storytelling is sloppy once again. Chili should have amassed plenty enough money from his movie work to produce this record, so the various shenanigans he and Edie go through to fund the production don't make any sense.
Chili's management of Linda's career is extensively complicated by the fact that she's under contract to still another former mobster, Nickie Carr (Harvey Keitel), and handled by Carr's partner Roger "Raji" Lowenthal (Vince Vaughn). Much of the bare-knuckled comedy in Be Cool is generated by Raji, a white dude who speaks in the patois of a black hip-hopper, and his "enforcer," a gay, wannabe singer and actor named Elliot Wilhelm (The Rock). Vaughn's Raji plays the role that Joe Pesci's Leo Getz character did in the Lethal Weapon movies. Raji is conniving, relentless and irrepressible but a nonetheless predictable screw-up. Former professional wrestler and aspiring action star The Rock really stretches out as Elliot, and a lot of the laughs he generates arise because of his counter-to-type casting. There's an effectively humorous sequence involving Chili giving Elliot tips on how to advance his entertainment aspirations: When asked to prepare a monologue for an audition, try to avoid scenes with two speaking parts; when selecting music material, concentrate on songs written for men rather than women.
The plot in Be Cool is wildly complicated, utterly implausible, ultimately inconsequential and perfectly serviceable. Tommy owed $300,000 to black record mogul Sin LaSalle (Cedric the Entertainer), who is obviously modeled on a lineup of gangsta-rap producers. Sin wants Edie to honor the debt and gets crosswise of Chili when Chili tries to protect her. The Russians want to kill Chili because he witnessed Tommy's murder. Nickie and Raji want to kill Chili because he's trying to take Linda from them. And this provides Chili sundry opportunities to fix a series of bad guys with his knowing stare, and say, "Look at me." The notion that Chili is so cool that he's intimidating worked in Get Shorty because he employed the tactic, for the most part, on people who didn't negotiate with threats of violence. Here Chili is constantly saying, "Look at me," to unsmiling guys pointing shiny pistols at him. The notion is preposterous, and the filmmakers don't do anything to flip it around on itself. There's plenty of hyper-textual winking in this movie, but some is needed in these scenes, and we don't get it.
The middle of the movie involves an attempt to get Linda a guest gig at an Aerosmith concert. Turns out Edie used to be a roadie and has an Aerosmith logo tattooed on her derriere. So she shakes her fanny in Steven Tyler's face at a Lakers game to get an interview where Chili does some sycophantic analysis on Tyler's lyrics vaguely reminiscent of the conversation about Madonna's "Like a Virgin" in Reservoir Dogs. The whole passage seems forced, but it is executed with an expected and palliating charm. Actually, the previous sentence pretty much applies to the entire movie.