June 2024

Carlito’s Way (1993)

DIRECTOR: Brian De Palma

CAST: Al Pacino, Sean Penn, Penelope Ann Miller, John Leguizamo, Luis Guzman, James Rebhorn, Viggo Mortensen, Adrian Pasdar, Rick Aviles, John Ortiz


Carlito’s Way, an adaptation of the same-named novel and its sequel After Hours (combining material from both) is director Brian De Palma returning to the gangster trough he previously explored with Scarface and The Untouchables (reuniting with Al Pacino from the former). To that end, Carlito’s Way lacks the depth and epic scope of The Godfather, but is less cartoonish than Scarface, and provides a colorful and engaging two and a half hours for fans of the genre.

In 1975 New York City, Puerto Rican gangster Carlito Brigante (Al Pacino) is set free five years into a thirty-year sentence with the help of legal technicalities exploited by his sketchy lawyer David Kleinfeld (Sean Penn), but determines to go straight, concerned only with raising $75,000—obtained legitimately through co-ownership of a swinging nightclub—so he can split for the Bahamas, where he intends to join an old friend’s car rental business and live the rest of his life in peaceful paradise, along the way hopefully winning back his ex-girlfriend, dancer Gail (Penelope Ann Miller). But like Michael Corleone, “just when I thought I was out, they pull me back in”, and events conspire to pull Carlito back into a world of trouble. When he went into the slammer, Carlito was a bigshot, but now he’s walking unfamiliar streets with faces he doesn’t recognize, including up-and-coming cocky punks like Benny Blanco (John Leguizamo), whom he makes an enemy of when he throws him out of his club one night. The District Attorney (James Rebhorn) doesn’t like Carlito being back on the streets, and is waiting and watching for a chance to put him right back where he came from. And not least among Carlito’s problems is his misplaced loyalty to Kleinfeld, a reckless cokehead who’s gotten himself in way over his head with some very angry mobsters and draws Carlito in with him.

Al Pacino, hot off his Oscar-winning role in Scent of a Woman and taking his second turn playing a Hispanic gangster for Brian De Palma (and again showing his dubious accent skills), does a little of his customary scenery-chewing, but Carlito is less cartoonish than Tony Montana, and a more conflicted and more sympathetic figure, someone who is a little older, a little wiser, a little less ruthless, and wants to go straight but can’t fully escape his own nature. As his vaguely noir-ish narration intones, Carlito likes to think he knows all the angles, but he still has blind spots, the most glaring of which is his friendship with Kleinfeld. Speaking of, the real points for playing against type go to Sean Penn (who came out of acting retirement and sole focus on his directing career for his role here), who all but buries himself behind flashy suits, glasses, and a head of balding, frizzy curls as the weaselly, cocaine-addled Kleinfeld, whom everyone knows is bad news except for Carlito himself. The movie draws a little parallel between criminal and client; as Carlito tries to straighten himself out, Kleinfeld gets increasingly lost in a haze of drugs and greed, but as Kleinfeld circles the toilet bowl, he threatens to drag Carlito down with him. Penelope Ann Miller is a little bland apart from some vivacious dancing (and no inhibitions about stripping), and the age difference between grizzled Pacino and girlish Miller doesn’t help (actually, the whole romance subplot with Gail feels a little shoehorned in to make Carlito more sympathetic). An assortment of colorful gangster movie types populate the supporting cast, including John Leguizamo as the flamboyant punk Benny Blanco, Luis Guzman as Carlito’s bodyguard, James Rebhorn as the stern District Attorney, and a bit part from Viggo Mortensen (wheelchair-bound and sporting a Latino accent).

Brian De Palma isn’t known for things like subtlety and restraint (Scarface and The Untouchables are virtually cartoons come to life), and he brings equal stylization here. The nightclub looks borrowed from Saturday Night Fever, the ghetto looks like a leftover set from West Side Story, and he uses Grand Central Station for a climactic cat-and-mouse chase and shootout that recalls the one in Chicago’s Union Station in The Untouchables, some of which is even filmed similarly (except the grand staircase has been replaced with escalators). There’s equal slow burn tension in an earlier scene, in which Carlito, determining to stay clean, grudgingly lets himself get dragged along to what’s supposedly a routine transaction and turns into an ambush and shootout. At essence, though, it’s a character study, a Greek tragedy of a man trying to be better than he is and drawn back in by everyone and everything he knows, and his own misplaced loyalties. There are moments of hope (mostly Carlito’s romantic interludes with Gail), but a sense of inevitability hangs over the proceedings. These kinds of gangster flicks (especially ones where the gangster is the lead role) aren’t known for happily ever after endings, and Carlito’s Way is not an exception.

Carlito’s Way lacks the operatic grandeur of The Godfather (arguably the definitive “gangster movie”), but it lands somewhere in between the grittiness of Scorsese and the comic book cartoonishness of Scarface and spins an involving gangland tale bolstered by solid performances from Al Pacino and Sean Penn and De Palma’s customary sense of style. It’s not quite a gangster classic, but it’s a respectable entry.

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