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Empire Magazine Greatest Movies List - #278: Carlito's Way

Throughout his career Al Pacino has played many criminals, but as he aged so did the gangsters. In 1983 he played the demented Tony Montana in Brian de Palma’s Scarface, setting the bar for ambitious drug lords the world over. Ten years later Pacino and De Palma reunited for Carlito’s Way, which asked the question: what if Montana got caught, sent to prison, released back into society, and then tried to be a good boy? Well as Pacino said in The Godfather Part III:  “Just when I thought I was out, they pull me back in.”

The movie came out in 1993 when I was seven years old so of course this is not a movie I saw on the big screen. Too bad, because it is filled with De Palma’s visual flair, specifically in a climactic shootout at a train station. Fortunately I eventually caught up with it about 15 years later when it was playing on the Movie Network, which is always a great help if you want to catch up on classics during a long weekend. Chronologically it worked out great since I had already seen The Godfather trilogy and Scarface. Carlito’s Way is the natural progression for these characters.

The movie opens in 1975 as criminal Carlito Brigante (Pacino) is bragging to a New York City court how he has been rehabilitated and is now a changed man. The judge assumes Carlito is simply spitting in the court’s face because one way or another he is walking out of a 30-year prison sentence after his lawyer David Kleinfeld (Sean Penn) has exploited a legal technicality. Yet to the surprise of his criminal friends, Carlito really does try to leave his life of crime behind him. He does end up taking part in a drug deal that goes bad as a favour to his cousin, however he uses the money from the deal to buy a nightclub and become a legitimate businessman.

Next on his list is rekindling the romance with his girlfriend Gail (Penelope Ann Miller), a ballet dancer. Much to his surprise, Gail also makes money on the side by dancing at a strip club. How is he supposed to react when two excited patrons come to her table and congratulate her on her dancing when he is sitting right next to her? The old Carlito would probably have beaten them senseless in an alley in a fit of jealousy, yet here again he shows he has changed by demonstrating restraint. No matter their past or present life career choices, Carlito’s dream is to make money the hard way and run away with Gail down south.

Unfortunately Carlito may have changed but the world hasn’t. The district attorney (James Rebhorn) is looking for any excuse to throw him back in prison while at the club young gangster and big fan Benny Blanco (John Leguizamo) keeps harassing him for a business deal. The threat he never expected comes from his lawyer Kleinfeld who has been busy while Carlito was in prison. Not content with just being paid to be a mob lawyer, Kleinfeld thought it would a good idea to steal money from one of his mob-boss client. When the mob finds out, instead of being killed he must break the client out of prison and for this he begs for Carlito for help. Even though he is disgusted by Kleinfeld’s life choices Carlito accepts out of a sense of loyalty to his old friend. You know what they say about good deeds going unpunished.

If anybody can stand toe-to-toe with Al Pacino playing a gangster, it has to be Sean Penn playing his lawyer. In fact, Penn just about steals the show as the high-strung Kleinfeld. With his glasses, receding hairline and curly hairdo, he is nearly unrecognizable. While Carlito is trying to make his way out of the criminal underworld, Kleinfeld just keeps sinking in deeper and deeper while getting high on the products his clients sell. When criminals can’t rely on their lawyers to keep it together it is time to leave town.


Although not as successful as Scarface, this second collaboration between Pacino and De Palma is just as engrossing. The character of Carlito is much more sympathetic than Tony Montana even though he most likely deserved to be in prison for another 25 years. But as you watch him rekindle his love with Gail and try to walk the line you end up rooting for him and hoping he actually makes it to the tropics. He may not have inspired rappers and gangsters, but Carlito is another shining addition on Pacino’s long list of memorable characters.

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