Carlito's Way

 Number 412 on the top 1000 films of all time is Brian De Palma's 1993 crime drama 'Carlito's Way.'

Former crime kingpin Carlito (Al Pacino) is released from prison back into his New York neighbourhood. Determined not to go back, he resolves to go straight, but when his best friend/lawyer Dave Kleinfeld (Sean Penn) rips off the Italian mob, he find going straight will be harder than he thought. Luis Guzman, Penelope Ann Miller and Viggo Mortenson all co-star.

I love a good redemption story. Take a bad man, a ,man who knows he's made mistakes and have him repent? I'm all for that. Plus it's a great source of conflict. It's no secret that America has an awfully high recidivism rate with 2/3 released prisoners  going onto reoffended. Once released, convicts find it difficult to leave their old lives. The transition is no easier for Carlito.

Upon release, all he wants is to earn enough money to retire to the Bahamas but it isn't that simple. His cousin Guajiro takes him to a drug deal with his supplier, butt he deal is a set-up and Carlito only escapes with his life. Later on, he refuses multiple offers to go into business with the young, hotshot gangster Benny Blanco from the Bronx. When Benny later crosses a line, Carlito has a chance to kill him, but instead sets him free. To see Carlito wrestling with his true nature made for delightful viewing and pushed the narrative along.

Loyalty is a key theme of the film and is Carlito's fatal flaw. His best friend is the unstable, coke-addicted Kleinfeld. Kleinfeld is very much the foil for Carlito's character; always causing problems and upsetting his plans to go straight. And nowhere is this more obvious when Kleinfeld steals a million from the mob. The mob promises to forgive the debt if Kleinfeld breaks mob boss Tony Taglialucci out of Riker's Island prison. And who does he ask for help, but Carlito who reluctantly agrees. But, of course, things go wrong. The whole breakout plan is a setup for Kleinfeld to kill Taglialucci and his son. Realising the truth, Carlito severs ties with his former friend. But the loyalty he shows Kleinfeld is not reciprocated. The feds later pick up Carlito and explain that Kleinfeld is prepared to testify against him. Considering how much of a slimy worm he is, this shouldn't come as a surprise to anybody but Carlito who has been blinded by loyalty.

I also want to give a quick shoutout to Viggo Mortenson who is always great. Although he only appears in one scene, it is one of the film's best. He plays a former associate of Carlito, Lalin Miasso, who is rendered wheelchair-bound after he was shot in the back. But it is revealed that he is wearing a wire. Breaking down in tears, he confesses that since he was shot, he has no life. He can't walk or have sex. he has to wear nappies. It was a powerful and surprising way of humanising a morally bad character. While Carlito should kill him for his betrayal, he lets him live, showing how much he wants to change. Any other crime boss would not suffer a rat to live.

Although there is one big plot hole that I would like to address. When the feds tell Carlito that Kleinfeld has betrayed him, they also tell him that his bodyguard Pachanga (Luis Guzman) has betrayed him and is now working for Benny Blanco from the Bronx. Despite knowing this, he still entrusts the safety of his girlfriend Gail (Penelope Ann Miller) to Pachanga. Lo and behold, right at the end, just as it looks like Carlito has won, Benny Blanco shoots him dead - thanks to Pachanga's devious ways. There was no way Carlito was ever going to walk off into the sunset, but his death was unrealistic. He is far more sentimental and trusting than any gangster has any right to be, but you think he would be more careful when it came to Gail. Especially when he knows that Pachanga has betrayed him.

But that notwithstanding, I did enjoy this film. It was the perfect telling of a redemption arc and it has a surprise standout performance from Viggo Mortenson.