Carlito Brigante (Al Pacino) is released from a thirty-year prison sentence after five years when his lawyer David Kleinfeld (Sean Penn) takes advantage of a legal loophole. Carlito is glad to be out and is set up by his connections as the owner of a nightclub; but life has changed since he's been inside, and although he reunites with Gail (Penelope Ann Miller), an old flame, things start to go badly wrong...
This conventional, occasionally inspired, gangster movie was scripted by David Koepp from two novels by real-life judge Edwin Torres. We see Carlito getting shot while boarding a train at the beginning of the story, so the rest of the action is devoted to detailing his downfall in flashback. Since we know how he ends up, Carlito's Way is more about the journey than the destination.
The trouble is, it is made clear early on that Carlito is a man whose code of honour is out of step with the times, in this case the mid-seventies. He apparently comes from an era where gangsters had nothing but respect for each other and the young punks rising up to take his place are nothing but thugs, living by a code of violence and arrogance, fueled by drugs and alcohol. Pacino supplies us with an introspective voiceover in case we haven't picked up on this theme, which is pretty much reiterated throughout the film, making for a one-note experience.
While Brian De Palma has been accused of misogyny in the past, here he goes too far the other way with the character of Gail. She represents all that Carlito wants to aspire to: settling down with a good, honest woman, having a family and giving up on the criminal life. This means that Gail is put up on a pedestal from which she never descends; although the romance is sweet and shows us an admirable side of Carlito, it's too saccharine for a thriller like this.
Pacino stylishly imbues his hero with a mixture of grace and steel, but it's Sean Penn who impresses the most. Kleinfeld is a crooked lawyer, sick of being pushed around by the crooks who are his bread and butter, but growing too coke-addled to make sensible decisions. So he becomes foolhardy, which leads to an act of spectacular stupidity during a jailbreak he has reluctantly taken part in. Penn's slimy perfomance manages to paper over the cracks of his role's less believable excesses.
As the whole thing is fairly predictable, you can just sit back and enjoy De Palma's talent with the camera and his way with a setpiece. The climactic chase is superbly handled, with Carlito pursued by hoodlums through the subway as he tries to reach the station. Incidentally, this film must hold the record for the frequency that people say the main character's name - even though Gail calls him "Charlie" for a variation, "Carlito" must be spoken over fifty times. Music by Patrick Doyle.
He's not aversed to directing blockbusters such as Scarface, The Untouchables and Mission Impossible, but Bonfire of the Vanities was a famous flop and The Black Dahlia fared little better. Even in his poorest films, his way with the camera is undeniably impressive. Was once married to Nancy Allen.