Any movie about an ex-con who tries to go straight but comes up against all sorts of obstacles, really has to be good to overcome the natural scepticism of audiences who will justifiably feel that they've seen it all before. Fortunately, there's enough about "Carlito's Way" that's original, interesting and enjoyable to prevent it from being seen as too hackneyed, too predictable or too run-of-the-mill and a great deal of the credit for this must be down to the fact that it's based on two books called "Carlito's Way" and "After Hours" which were both written by Judge Edwin Torres who, no doubt, drew extensively on his experience as a New York State supreme court judge to inject his story with its impressively high level of authenticity.
In a New York City courtroom in 1975, Carlito Brigante (Al Pacino), a Puerto Rican drug dealer and alleged assassin, becomes a free man again after having served only 5 years of his 30-year prison sentence. The legal loophole that was exploited to secure his release was spotted by his shady lawyer and best friend David Kleinfeld (Sean Penn). Now feeling older and wiser after having had plenty of time to reflect on his life, Carlito announces to the court that he has been totally rehabilitated and is determined to leave his old criminal life behind and finally go straight.
Carlito makes his first mistake when he returns to his old neighbourhood and is persuaded by his young cousin Guajiro (John Ortiz) to accompany him on a routine delivery of some drugs to a local dealer. Their meeting descends into chaos when Guajiro is double-crossed and murdered and after the ensuing shoot-out, Carlito finds himself back on the street but $30,000 richer, after having pocketed some money which had been left unattended after all the shooting had stopped.
Carlito promptly uses his newly acquired windfall to buy a partnership in a nightclub with the intention of earning the $75,000 he'd need to fulfil his long-held ambition of taking up an offer he'd had from an old friend to buy a share in his car rental business in the Bahamas. Soon, he starts to make good progress in achieving his goal and things then get even better when he meets up with his ex-girlfriend Gail (Penelope Ann Miller) and they rekindle the relationship which they'd been forced to end when Carlito was imprisoned.
An unwelcome development then follows when Kleinfeld is cornered into assisting an Italian mob boss to escape from the Riker's Island prison barge where he's been incarcerated and Carlito feels that he can't refuse when his friend asks for his help. When the escape plan is put into action, the seriously unstable and coked-up Kleinfeld kills both the mob boss and his son and this leads Carlito to decide that if he's ever going to fulfil his dream of going to the Bahamas with Gail and their unborn child, he'll need to do so rapidly because the mob boss' son and his men will inevitably be coming after him with revenge on their minds.
Told in flashback with Carlito providing the narration, this gangster movie is consistently tense, violent and very fatalistic but it's also surprisingly romantic. The relationship between Carlito and Gail is beautifully portrayed throughout and a hug that they share soon after reconciling provides an especially warm and powerful expression of their feelings for each other. Similarly, there's another particularly romantic moment at the end of the movie when Carlito, accompanied by the sound of Joe Cocker's "You Are So Beautiful", stares wistfully at an illuminated advertisement which features a picture of a Caribbean Island and the slogan "Escape to Paradise".
Brian De Palma's use of slow motion, black and white and revolving camera-work at various points is both stylish and effective and the extended chase sequence that brings the movie to its climax is brilliantly executed. Commendably, there's also a consistent vibrancy that runs through the whole movie that makes its duration seem significantly shorter than its actual 144 minutes.
Al Pacino is marvellous as the ageing gangster whose downfall is ironically sealed by two of his more noble actions when he, through loyalty, agrees to help Kleinfeld and also unwisely shows mercy to another character who doesn't deserve it. Sean Penn is terrific as the corrupt, duplicitous and cocaine-fuelled lawyer who long ago lost sight of the line between what's legal and what isn't and the remaining cast members are also excellent with stand out contributions from Penelope Ann Miller, Luis Guzman and John Leguizamo (as the unforgettable "Benny Blanco from the Bronx").