This How You Beat Your 30 Years: The Legacy of Carlito’s Way

Brian De Palma’s masterful crime saga Carlito’s Way was released 30 years ago this month. That number—30 years—hangs over the entire film. It’s the amount of years in prison Carlito Brigante (Al Pacino) is serving before his best friend/lawyer Dave Kleinfeld (Sean Penn, nearly unrecognizable behind glasses and a receding hairline of fizzy locks) springs him on a technicality after only five. It’s also the amount of time another friend and former criminal compatriot is looking at before he betrays Carlito by attempting to entrap him for the DA. 

In the criminal milieu of 1972 New York City, 30 years is, more often than not, a high life expectancy. The pull of the underworld—figuratively and, as staged by De Palma in the film’s elegiac prologue and bravura climactic shootout, both set in and around the subway tunnels of New York’s Grand Central Terminal, literally—is simply too strong. Once you’re in, there’s no way out save prison or death.

On paper, the story of Carlito’s Way—a Puerto Rican drug runner and assassin attempts to give up his life of crime, only to doom himself when he agrees to do one last job—reads like a derivative version of any number of gangster stories, not least of all De Palma and Pacino’s magnum opus of exactly 10 years prior, Scarface. But in execution, the film has less in common with that genre than it does classic film noirs, specifically fatalistic morality tales like Kiss of Death and Force of Evil, in which morally-stricken criminals attempt to go straight, only to find the institutions, both legal and criminal, that surround them won’t let them go.

De Palma explicitly approached the material as a noir, as he’d initially been uninterested in making another gangster story—especially a Spanish-speaking gangster story—with Pacino after Scarface. Although it stands as one of the most beloved and iconic of all American gangster films (behind only the first two Godfathers and Goodfellas) today, at the time of its release it didn’t exactly light the world on fire. It did okay at the box office, but it wasn’t quite a hit, and the reviews and controversy surrounding it—particularly its mostly non-Cuban cast’s depiction of Cubans—caused stress for the filmmakers. In this light, De Palma’s initial reticence towards Carlito’s Way is entirely understandable, although once he read David Keopp’s script and saw the story for what it was, he was keen to come aboard. 

The end result is amongst the director’s most visually stunning works, which is saying a whole hell of a lot. From his signature steadicam long shots and swooping camera moves to the bold but moody color palette (Scarface’s sunbaked menace and eye-popping pastels are swapped out for nocturnal blues, blacks and reds) courtesy of cinematographer Stephen H. Burum and production designer Richard Sylbert, he really pulled out all the stops for this one. As he himself says in Noah Baumbach and Jake Paltrow’s 2015 doc De Palma, “I can’t make a better picture than this.”

Even though many, including the man himself, would hold Carlito’s Way up as De Palma’s best, it really was Pacino’s baby. He first discovered the story in the early 70’s while prepping for Serpico. That’s when he met Judge Edwin Torres, a Puerto Rican-American from New York who served on the state’s Supreme Court and would use real-life stories as inspiration for the novels Carlito’s Way (1975) and After Hours (1979). (Between them, he penned the 1977 book Q&A, adapted into a 1990 bruiser by Sidney Lumet.) Upon reading the novels, Pacino spent years trying to bring them to screen. (Although both books are credited as source material for the movie, it’s mostly an adaptation of the latter, taking the first novel’s title to avoid confusion with Martin Scorsese’s After Hours of eight years earlier.) De Palma was actually the third choice for director, after attempts to make the film with John Mackenzie and Abel Ferrara fell through. (Per Ferrara during a recent post-Bad Lieutenant screening: “I was supposed to direct Carlito’s Way until they fucking fired me.”)

And for as stunning a work of visual cinema as the film is, it is just as much an actor’s showcase, with Pacino turning in one his most measured and soulful performances, even as he does go big when the occasion calls for it. (If there is one criticism that can be levied against Pacino’s performance, it’s that his Spanish accent, which is never that convincing to begin with, often slips into the weird Southern drawl he used in the previous year’s Scent of a Woman.) But it’s Penn who steals the show, completely disappearing into a character whose nebbish looks and mannerisms can’t quite mask the deep well of anger, violence and self-hatred boiling up inside of him. He’s one of the most repulsive, unnerving, and yet oddly sympathetic characters in all of crime cinema, and Penn should have received his first Oscar for the role. 

Penelope Ann Miller is very good as Gail, Carlito’s wounded soulmate and moral conscience, and if she’s not given as much to work with as, say, Michelle Pfieffer in Scarface, she also never devolves into the cliché of stripper with a heart of gold that a lesser movie would have made her into. The cast is rounded out by a murderer’s row of New York faces and character actors, particularly Latino actors who would go on to successful careers, including John Leguizamo, Louis Guzman, John Ortiz, and, in a non-speaking role, John Seda. (Viggo Mortensen also has an early memorable role, and while he’s very good in his one scene, he’s even less convincing as Puerto Rican than Pacino.)

Even as everything clicked into place to create a great film, De Palma set his expectations low for the reception. His instinct proved right: Carlito’s Way wasn’t a bomb by any means, but neither was it a financial hit. The reviews were mostly middling, with the majority of critics charging it as being by-the-numbers, although a few, such as Roger Ebert, recognized the mastery at work and gave it raves.  

Interestingly, unlike the controversy that erupted within Cuban-American groups upon Scarface’s release, Carlito’s Way seems not to have brooked much, if any, public backlash from the Puerto Rican community, although Leguizamo has since gone on record to express some lingering unease about the casting. This likely owes to the much more muted reception the film received as a whole, as well as the fact that it’s not nearly as garish or violent a spectacle as its predecessor. (Also, it’s just a fact of American life that Cuban-American political groups are much more fervent than other Latino coalitions.) Regardless, the film stands as one of the finest examples of (the much more complicated than many would have you believe) cinematic whitewashing and brownface.

Carlito’s Way remains the very definition of an underrated classic, which isn’t to say it hasn’t received its flowers. It was always too good not to be rediscovered and reconsidered. As with horror movies, any gangster movie of quality, no matter how underseen initially, will find its audience, and while Carlito’s Way doesn’t enjoy the cultural ubiquity of Scarface—a good thing, given how reductive and shallow that tends to be—it proved popular enough to spawn a 2005 prequel (albeit, direct-to-video), Carlito’s Way: Rise to Power (an adaptation of Torres’s first novel) and, like Scarface, references to it continually pop up in music, video games, and other pieces of pop culture.

But regardless of whatever footprint Carlito’s Way has left behind, it will continue to be discovered by new viewers simply because it’s the work of a master operating at his highest level. That was true 30 years ago, it’s true today, and it will be true 30 years hence.

“Carlito’s Way” is available for digital rental or purchase, and is out in a new 4K UHD set from Arrow Video.

Zach Vasquez lives and writes in Los Angeles. His critical work focuses on film and literature. He writes fiction as well.

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