Both Al Pacino and Brian De Palma team up once again in perhaps the spiritual sequel to Scarface. And while I like Carlito's Way for what it is trying to do, I don't like it as much as Scarface.
Let me first by saying that the performances of the pivotal characters are top-notch. Pacino is as great as he can be, but I would say that Sean Penn basically steals the scenes whenever he is present. Arguably because his character is far more complex than Carlito. Klein (Penn) obviously is a pretty shady lawyer. I mean, anyone with a haircut like he has, is not entirely right in the mind. Apparently, he finds his life too boring and wants to become a gangster himself. Carlito mentions that Klein used to be afraid of his clients, but not any more. This could be the consequence of not having Carlito around and that he had to man up. Who knows? But the way he carries himself is infinitely more compelling than Carlito's arc.
I get that Carlito has seen the light and wants to retire from the criminal life. But what does he do to get out from there? He keeps hanging with former members of his crew. He even has a monologue stating that bad things come to him, and it's not him going to them. Sorry to say Carlito, but that is not true. He had opportunities to opt out from them. Like for example the pool scene. He goes along with his cousin for a pickup. Granted, he is not too fond of the idea, but he caves. Bad things ensue. Klein does the same thing, Carlito protests but eventually caves. Now, I do know what that is like. I will usually do my best to help people out, but if it is something shady and there are too many things that are beyond my control, I will opt out. Carlito could have done this. Perhaps he was fooling himself, he would still need some of the old life to enable the new one. But was it really that impossible for him to make money outside the life? If he was at the top of the food chain, couldn't he have ensured some money in case he would get locked up or something? He is supposedly to be intelligent and not someone to mess with yet the people don't see him that way.
The whole romance angle makes sense in relation to Brigante wanting to start a new life. But there was zero chemistry between Pacino and Penelope Ann Miller. If you remove this romance, it wouldn't have changed a thing. So why even bother? Especially if that has impact on the duration and pacing. Yes, Carlito's Way is too long and boring. It's too predictable and never goes deep enough exploring the struggle that Carlito has. I was expecting more, so much more, but instead it's a slow brooding narrative that never leads to anything interesting.
Overall, an underwhelming film with some good moments. Contrary to general opinion, I don't think this is underrated. In fact, I would say it's quite the opposite.
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