A rewatch that I have been aiming to fit into my schedule for weeks now, Carlito's Way is, to many, just another gangster film from a director who has done more than his fair share. That's how I thought about it, and that is why I didn't rush to rewatch it when the opportunity first arose. It's actually a more interesting film than that though, and generally looks at the struggles someone can have as they try to shed their past, as well as the reputation they once had, while also having undeniable benefits to being exactly who they are.
Al Pacino is the titular Carlito, giving a performance that veers between ridiculously over the top and surprisingly restrained. Released from prison after serving five years of a sentence, all thanks to a mishandled investigation, Carlito wants to go straight. And that's what he does. But a lot of people would rather get him back into his old line of work, including his own greedy and reckless lawyer, Kleinfeld (Sean Penn).
Considering the iconic gangster movies that Brian De Palma gave audiences in the 1980s, two very different approaches to different eras being portrayed onscreen, it must have been a hell of a risk for him to take on this project, although perhaps the appeal was just how this would allow him to take another unique approach and show a slightly different era. Adapting material by Edwin Torres, writer David Koepp crafts a screenplay that allows Carlito to keep his moral compass pointing the right way, even as many others do their best to turn him around. This isn't a film interested in crime, not really. It's a character study, but the character is, for better or worse, surrounded by people and locations tied to different criminal factions.
Although not doing so well with his voiceover narration, Pacino has a number of expected great moments here, made all the better by the fact that his character is always trying to resist the easiest option. Penn is loud and ridiculous, and keeps everything lively as his descent into uncontrollable carelessness starts to create problems and obstacles for our lead. Penelope Ann Miller does well as Gail, a potential love interest, and there's a scene set in a strip club that plays out like a fascinating inversion of the way a certain Tony Montana would have reacted to what is revealed. Luis Guzmán is as dependable as ever, John Leguizamo steals one or two scenes as the up-and-coming Benny Blanco, James Rebhorn is the lawyer wanting to make up for messing up and allowing Carlito to be released back onto the streets, and there are a number of familiar faces in other small roles, including the likes of Viggo Mortensen, Ingrid Rogers, John Ortiz, and Rick Aviles.
Making use of numerous gangster movie tropes without letting the main character stay rooted in the archetypal persona that he clearly had in his past, this also has some typical moments of De Palma brilliance when it comes to the shot choice and composition (not to dismiss the cinematography of Stephen H. Burum). It's a shame that some of the editing and structuring doesn't work, I am one of the people who don't agree with the idea that the scenes shown at the start of this add to the tension or impact of the finale, but those are very minor criticisms for a film that almost keeps you riveted for the entire 144-minute runtime. Almost.
9/10
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