The narrative opens on Carlito Brigante, known cocaine distributor and Puerto Rican mob assassin who, thanks to some shady dealings from the prosecutor and some deft legal maneuvering from his own attorney, David Kleinfeld (an unrecognizable Sean Penn), is being set free after five years behind bars instead of serving his entire thirty year sentence. Carlito is ecstatic beyond words, and once he is out he and Kleinfeld celebrate by a night out at a disco. Carlito has some plans to go over with Dave.
But Carlito’s plans don’t involve getting back into the drug world. Instead, he plans on investing in a local disco club so he can save up enough money and move to the Bahamas and rent cars to tourists. “Car rental guys don’t get shot.” And Carlito sheepishly seeks out his former flame, Gail, watching her first from a rooftop in a touching scene. Gail is apprehensive to “Charlie’s” plan; she thinks it’s all a pipe dream, and she may very well be right. Right not because Carlito is apt to fall back into his own ways, but right because of the so many wicked people and extenuating circumstances that were and always will be a part of Carlito’s world.
Carlito’s plan hits its first rough patch when he agrees to go along on a drug exchange with his young cousin. See, Carlito is a legend, he was big time before he went behind bars, and him showing up with his cousin will impress everyone. But once they get there, it isn’t long before Carlito senses trouble. He devises a plan, but it is too late when he springs into action; his cousin is dead, along with everyone else in the bar after a fast and furious gunfight in close range that leaves Carlito stranded in a bathroom with an empty gun and only the threats of more to come to those who might be still alive. This scene is DePalma at his very best, a sequence of unreal tension that tightens with each passing step, each dart of Carlito’s eyes. And the gunfight is staged in a brilliant way, in close quarters with the camera spinning and rotating between two men. Top-notch direction.
Carlito endures his own Book of Job, tested at every corner by the wickedness of his past life. There is a young up-and-comer in the neighborhood, Benny Blanco from the Bronx (John Leguizamo), a kid not unlike a young Carlito but a kid who Carlito has no time for. There is Lalin (Viggo Mortensen), a former partner of Carlitos that is trying to beat his time behind bars by luring Carlito back into drug trafficking while wearing a wire. And there is Kleinfeld, his attorney, who became a heavy hitter in the mob, or so he thinks, while Carlito was incarcerated.
Sean Penn plays Kleinfeld, and he disappears beneath a curly red wig and beady-eyed sliminess. Carlito owes his life to Davey, and no matter the situation he backs Davey. But Kleinfeld has become a cokehead and is in the pockets of too many gangsters. He pleads with Carlito to help him break a mafia boss from prison via boat one night, even though the mafia boss has plans to kill Kleinfeld for stealing money once he gets out. Carlito reluctantly agrees to help, and the night of the prison break things, as you could imagine, go south, possibly spelling doom for both men.
Carlito’s Way is a series of fantastic and powerfully tense moments tied together by a compelling character played by Al Pacino. Carlito continuously struggles to steer clear of those intent on ruining him, but it is his loyalty to Kleinfeld that ultimately becomes his biggest problem, culminating in a thrilling chase sequence that is the final act of the picture. The chase begins on the streets, then hits the subway, then Grand Central Station, and again DePalma shows his uncanny knack for using the camera, actor staging, and deft editing to create some brilliant moments of nerve-racking tension.
The relationship between Carlito and Gail, a talented dancer who has to strip to make the rent, is the second of the central relationships in the picture, the other being Carlito and Kleinfeld. The two clearly are in love, were in love, and Gail wants to believe Charlie. She wants to run away with him to the Bahamas, to grow old with him, but she fears the worst. Penelope Ann Miller is excellent here.
As great as Carlito’s Way is, it has one major, major flaw. That is the opening and closing sequences of the film, bookends to the narrative that truly spoil the story before it has even started. I cannot, for the life of me, understand why DePalma decided to show these bookend moments rather than keep the audience guessing, wishing. DePalma has the ability to be a top-tier director, despite his countless missteps, and Carltio’s Way is one of his finest achievements. And let us all collective erase the straight-to-DVD prequel Carlito's Way: Rise to Power from our mind. In three, two, one...