Carlito's Way (1993)

That finale. I've watched a lot of films in my life, a genuinely embarrassing number, and I will go to my grave arguing that Carlito's Way contains the greatest finale in cinema history. It's tense, it's heartbreaking, it's masterfully constructed, and it pays off everything that came before it with an almost cruel precision. If that sequence doesn't get your pulse racing and your stomach dropping in equal measure, I'm not sure what to tell you.

Brian De Palma is a director I love deeply. I've got enormous affection for Carrie (1976) and The Untouchables, and both are brilliant films. But Carlito's Way is his best. I'll stand on that. It's a film that somehow gets overlooked whenever people talk about the great American crime pictures of its era, and that's a genuine injustice. Criminally underrated doesn't even cover it.

Al Pacino is the heart of the whole thing, playing a man trying to escape the world that made him. And look, Pacino being brilliant is hardly a news bulletin. I've seen him magnetic in Scent of a Woman, ferocious in Scarface, and somewhere between the two in plenty of other films. But there's something about this performance that I find particularly special. It's controlled. It's layered. He plays a man who genuinely believes he's changed, who wants the quiet life, and you believe it right alongside him. That hope is exactly what makes the tragedy land so hard.

Then there's Sean Penn. I don't think he gets nearly enough credit for what he does here. His lawyer, Dave Kleinfeld, is a sweaty, twitchy, morally disintegrated wreck of a human being, and Penn commits to it so completely that he's almost unrecognisable. I've always thought this character is the direct inspiration for Rosenberg in GTA Vice City, and once you see it, you can't unsee it. It's a performance of real bravery. Penn isn't trying to be liked. He's trying to be real, and real people can be deeply unpleasant.

It was also, as it happens, the first film I saw Viggo Mortensen in after Lord of the Rings. Coming off Aragorn and then watching him here was quite the experience. He's playing something completely different, something grittier and more street-level, and he handles it brilliantly. That's the mark of a proper actor, being able to do that without carrying the weight of a previous role into the room with you.

One thing I want to specifically defend is the film's handling of the love story. Gail, the woman Carlito is desperate to escape with, could so easily have been a passive figure, just a reason for the plot to matter. But she isn't. There's a genuine sincerity to how her relationship with Carlito is written and performed. You feel the weight of what they're reaching for together. The romance earns its place in the film rather than just decorating it, and that matters enormously because the whole story depends on you believing Carlito has something real to lose.

The pacing, too, is gorgeous. De Palma lets the film breathe without ever letting it drag. There's a rhythm to it, a steady building of dread, almost like a piece of music building towards a crescendo you already know is coming but can't look away from. The film tells you early on that things won't end well. It tells you right at the start. And yet you watch the whole two-plus hours still hoping, somehow, that it might work out differently this time.

Five stars. No hesitation, no qualification. Everyone should see this film.

Rating: ★★★★★  | Year: 1993  | Watched: 2025-04-07

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Related on Movies With Macca

More from Brian De Palma: The Untouchables (1987) · Carrie (1976) · Scarface (1983)
More with Al Pacino: Scent of a Woman (1992) · Cruising (1980) · Insomnia (2002) · Scarecrow (1973)
More from the 1990s: Lessons of Darkness (1992) · Shinjuku Boys (1995) · Blue (1993) · Cemetery Man (1994)
More crime: A Better Tomorrow (1986) · Angst (1983) · Stolen Face (1952) · Cairo Station (1958)
More drama: Viy (1967) · Wonder (2017) · A Better Tomorrow (1986) · Beautiful Boy (2018)