Carlito's Way (1993)

Released in 1993 and running at a generous 144 minutes, Carlito's Way is a crime thriller from Universal Pictures that follows Carlito Brigante, a New York drug lord who walks free after a prison sentence and sets his sights on a clean life, only to find the city has other ideas for him. The film sits comfortably in a tradition of American crime pictures that treat the underworld less as glamour and more as a trap, the kind of story where a man's past is less a chapter he can close and more a room he never quite leaves. It arrived at a curious moment for the genre, when Hollywood crime films were beginning to shift in tone and style, and Carlito's Way occupies a space that is polished but unmistakably personal in its concerns.

Behind the camera is Brian De Palma, a director whose relationship with crime cinema had already produced some of the most discussed American films of the preceding decade, including Scarface and The Untouchables. By the time Carlito's Way came along, De Palma had built a reputation for kinetic set pieces, a very deliberate visual style, and a willingness to let films breathe at their own pace rather than cut to satisfy the impatient. The screenplay was adapted from two novels by Edwin Torres, a New York judge who had written about the city's criminal world from a position of some authority, which gives the material a certain grounded credibility beneath all the genre machinery. The production was handled by Universal Pictures alongside Epic Productions and Bregman/Baer Productions, the latter having previously collaborated with De Palma on Scarface.

The cast assembled here is, by any measure, a strong one. Al Pacino, who by this point had earned an Academy Award for Scent of a Woman the year prior, takes the lead as Carlito, bringing a weight to the character that the role genuinely requires. Sean Penn, barely recognisable beneath a frizzy wig and oversized glasses, plays Kleinfeld, Carlito's lawyer and closest associate. Penelope Ann Miller plays Gail, the love interest at the centre of the film's quieter emotional story, while John Leguizamo and Ingrid Rogers round out a supporting cast that keeps the New York milieu feeling populated and lived-in. Viggo Mortensen also appears in an early role that will mean something to anyone who came to him later through bigger productions.

The greatest finale in cinema history. Carlito's way is Brian De Palma's best film. It's a criminally underrated movie. Sean Penn had the performance of his career as the lawyer here which is 100% the inspiration for Rosenberg in GTA Vice City. Al Pacino is as usual... absolutely flawless. This is the first Viggo Mortensen movie I saw after LOTR too so it was amazing seeing him play a different character. The pacing of the movie is beautiful and the love interest Gail is handled with such sincerity. Everyone should see this film.

What strikes me on reflection is how rare it is for a film of this scale to hold its nerve so completely from the opening frame to the last. The street-level texture, the performances, the way De Palma builds and releases tension without ever feeling mechanical, it all adds up to something that deserves far more conversation than it tends to get. If you have somehow let this one pass you by, do yourself a favour and sort that out. Some films you watch once and appreciate. Some you carry around with you a bit longer. This is one of the latter.

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

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Trailer

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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)