Photo: Universal Pictures/Corbis via Getty Images

As the ’80s turned into the ’90s, Brian De Palma thought he was done with gangsters. He’d had tremendous success with The Untouchables in 1987, pitting Kevin Costner’s squeaky-clean Eliot Ness and Sean Connery’s pragmatic Irish cop against a Chicago underworld led by Robert De Niro’s Al Capone. And that was his third visit to gangland in four years, arriving on the heels of the instantly forgotten dark comedy Wise Guys, starring Danny DeVito and Joe Piscopo, and the very-much-not-forgotten Scarface, a bloody, Oliver Stone–scripted remake of a Howard Hawks classic starring Al Pacino as a Cuban refugee who embarks on a bloody ascent to the top of the Florida drug trade. Scarface had been controversial in 1983, thanks to some notoriously violent sequences and Everest-like mounds of cocaine, and it had never really faded from the conversation, becoming a home-video favorite and the go-to reference point for a particular strand of hip-hop. So, as proud as he was of Scarface and as much as he enjoyed working with Pacino, when a chance arose to make another film about a Latino gangster with Pacino in the lead, De Palma figured he’d pass, that he could say nothing more by returning to this world. Then he read the script, and changed his mind, quickly realizing that this was a different sort of movie.

Twenty-five years ago, Carlito’s Way might have looked like a virtual sequel to Scarface, thanks to a poster that screamed “PACINO” above a shadowy image of the star toting a gun. But its relationship to its predecessor is much more complicated. Where De Palma’s Scarface reveled in operatic scenes of violence and its bloody consequences, ending at the moment when Tony Montana runs out of rope, Carlito’s Way is the rare crime film to consider what happens after a life of crime. Is reform possible? Can a gangster with a changed heart find a way out? Can anyone escape the sins of the past? The film would play just as well in a world in which Scarface never existed, but it works even better as the somber bookend to that earlier film. Where Scarface is a film of manic highs leading to a sudden stop, Carlito’s Way is a movie of regretful mornings after. To argue one is better than the other is to miss the point: They belong together.

Any association didn’t help much at the time, however. Carlito’s Way arrived to mostly middling reviews and a restrained reception at the box office. Maybe it was the shouting. Pacino had won the Best Actor Academy Award just a few months before the film’s November 1993 release for his work in Scent of a Woman, a performance that found him working the upper range of his vocal register in most scenes. He begins Carlito’s Way as if picking up where he left off. The film opens with Pacino’s Carlito Brigante in court, about to walk away after serving 5 years of a 30-year sentence thanks to his lawyer David Kleinfeld (Sean Penn), who’s discovered that the DA used some shady practices to put him away. Brigante crows in triumph and behaves as if, as the judge notes, he’s accepting an award. Then he settles down, as the reality of his new situation sets in, and the film settles down with him.

Brigante emerges in the New York of 1975, but it might as well be another century. The fashions have changed, the music has new rhythms, and he recognizes few of the faces around his old haunts. He returns to his old neighborhood, but it’s not really his anymore. And though his courtroom theatrics sound like bullshit to everyone in shouting distance, he really means what he says: He’s going straight and getting out, packing up for the Bahamas and joining a buddy’s rental-car business, just as soon as he can scrape the money together.

Trouble is, nobody around him believes him or particularly wants to help him. Not even Kleinfeld, who sets him up managing a nautical-themed nightclub — a meticulously realized set that De Palma’s camera glides through and explores from every angle — and then waits for him to succumb to temptation. Then, when Kleinfeld gets in over his head with some Italian gangsters, he grows tired of waiting and tries to drag Brigante down with him. They call each other brothers, but by film’s end, Brigante will realize that he understands the term much differently.

Penn plays Kleinfeld as a man who snorts his breakfast through a straw, less for pleasure than to summon up the bravado he needs to convince himself that he can navigate a world of gangsters and bad men. This may have worked prior to Brigante’s release — it’s certainly worked well enough for him to accumulate trappings of wealth that would make Tony Montana nod in appreciation — but it doesn’t work long after, and Kleinfeld spends the film trying to employ every trick he knows to survive. Behind owl-like glasses and beneath a shaved hairline and a mop of curls, Penn captures a man who ultimately knows only how to look after himself — and is in the process of scrambling his brain, so even that basic instinct doesn’t work anymore.

His betrayal feels foreordained, and an air of inevitability hangs over the whole film, which opens with Brigante’s apparent death then spends nearly two-and-a-half hours circling back to that fatal moment. Within that frame, Pacino plays Brigante as a man who doesn’t quite realize that he’s already a ghost. Reluctantly accompanying a younger relative on a drug run, he finds himself in a room full of dealers who only vaguely remember his name. He reconnects with Gail (Penelope Ann Miller) an old flame whose dreams of dancing on Broadway have met the realities of road companies and strip clubs. They bond over their shared past and the possibility of a better future, both having grown disenchanted with a present that keeps presenting new dangers. Brigante does his best to lay low and bide his time, but the old ways come back to him when he roughs up a pushy new arrival on the scene named Benny Blanco (John Leguizamo) who’s from, he’s always quick to point out, the Bronx. “This guy is you 20 years ago,” someone else tells Brigante in confusion. That doesn’t make it any easier; Brigante has come to hate who he was then.

De Palma and screenwriter David Koepp fill the film with period detail, perfectly chosen songs, and rich local color, no doubt helped by source material written by someone who was there. The film is adapted from a pair of novels by Edwin Torres — Carlito’s Way and After Hours, with most of the plot coming from the latter — the son of Puerto Rican immigrants who grew up in Spanish Harlem and served as an assistant DA and defense attorney before being appointed to the New York Supreme Court. Torres wrote crime fiction on the side, drawing from the world in which he grew up and using its tougher characters for inspiration. (Based on Torres’s appearance on the making-of doc included on the film’s home-video releases, he also seems to be the primary influence for Pacino’s vocal inflections in the film. Whether or not Pacino’s casting as a Puerto Rican would fly in 2018 is, of course, another matter entirely.) The prevailing sensibility is that of someone who’s seen how hard it is to escape a life of crime. No matter how deep the commitment, one obstacle or another keeps getting in the way.

For all of the film’s fatalistic qualities, however, Carlito’s Way is also a thrilling piece of filmmaking. Brigante’s early encounter with a new generation of gangsters in a bar’s creepy backroom is among the most tightly constructed suspense sequences of De Palma’s career, and the film ends with a set piece to rival The Untouchables’s Union Station climax or the heist at the heart of Mission: Impossible in scale and ambition: a long chase from a club to the subway to Grand Central Station to a train that’s waiting to whisk Brigante and Gail away to a new life in a better place if he can just slip away from his enemies and make it before it pulls out of the station. The filmmaking’s so breathtaking that it becomes easy to forget that you already know how this ends — that there was always only one way it could end.

Tony Montana’s story is the tale of a coke-fueled Icarus; Brigante’s is more complex, and sadder — even if neither of them makes it out of their films alive. Carlito’s Way is the moodier, more mature film, a tragedy of misplaced loyalty and a story of how our surroundings can short-circuit even our loftiest instincts. It was never destined to inspire Funko POP! figures and ridiculously expensive leather jackets. Even with its can’t-miss “crime doesn’t pay” moral, Scarface is a power fantasy. Carlito’s Way understands that power doesn’t last. Tellingly, its most sampled bit of dialogue — Brigante shouting, “Okay, I’m reloaded!” — isn’t a brag but a bluff. He’s out of ammo, faking it, just trying to get out, to live another day. The world, he now understands, is not his and never was. He may not even have a place in it much longer.