Keith Phipps, Vulture
Carlito’s Way, Scarface, and Brian De Palma’s Fantasies of Power

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.

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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.

The tension that builds through Carlito’s Way relies on Carlito’s lack of power; it isn’t about how he is going to escape with Gail (Penelope Ann Miller) to the Caribbean, it’s how he is going to navigate each and every second he stays in New York as his mere presence grows increasingly dangerous. He is vulnerable, scared, and often powerless to the influences and the decisions of the characters who surround him, and powerless to his own code, a code that convinces him to stick with his lawyer, Kleinfeld, who is so clearly the biggest roadblock in Carlito’s exodus.

Sean Penn surprised everyone when he showed up on set with a perm shaved back to resemble severe male pattern baldness. His appearance smartly sets him apart from everyone in the picture. Davey Kleinfeld is the poisonous fruit Brigante cannot avoid, not one of the neighborhood guys, but a slick outsider; Carlito unknowingly helping Kleinfeld murder Tony Taglialucci in the East River outside Riker’s Island leads to the extended chase sequence finale, but ironically it is not the source Carlito’s ultimate demise.

The one time Carlito’s old instincts jump up to bite him is his conflict with Benny Blanco, From the Bronx (John Leguizamo). The bravado of Blanco may mirror a young Carlito, it may not, but one thing is certain: Blanco’s presence stoked a long-buried fire in Carlito’s youthful soul, the one he is working so fervently to leave behind. But his decision in this moment was enough to seal his fate in Grand Central.

Brian De Palma knew from the outset he needed to inject his signature style into as much of the film as he could in order for it to stand out from the scores of gangster films that had preceded it. Even The Untouchables has a feeling of familiarity in regards to the genre. Carlito’s Way is stylistically indulgent, with De Palma employing his psychosexual thriller aesthetics early and often. The split screens and the first-person POV work brilliantly to put the suspenseful building blocks in place, and the story lends itself more to a humanistic tale than what was present in De Palma’s previous gangster films.

Carlito’s Way opened second at the box office the weekend of November 10, 1993, with just over $9 million. Reviews were solid, but word of mouth was nil. Perhaps fatigue with the gangster genre had set in by the end of 1993; the success of Martin Scorsese’s Goodfellas had spawned Warren Beatty’s Bugsy, but it also generated ridiculous wannabes like Billy Bathgate, Hoffa, and the embarrassingly bad Christian Slater/Richard Grieco star vehicle Mobsters. Whatever the case, Carlito’s Way quietly drifted out of the picture, accruing a meager $36 million in ticket sales; enough to cover the $30 million budget, but nothing to write home about.

In his documentary, Brian De Palma says he didn’t think he could make a better movie than Carlito’s Way. He would return three years later to kick off the Mission: Impossible franchise, but it’s difficult to argue with De Palma’s assessment of his own work. Even though Carlito’s Way hasn’t seen the kind of reappraisal that Blow Out or Dressed to Kill has in recent years, and it doesn’t have the cultural currency of Carrie or Mission: Impossible, or the prestige of The Untouchables, it might very well be his best film. It is, at times, a beautiful film with true affection for its characters. It’s an endlessly engaging thriller, tactile and true, and its collection of incredible set pieces is held together by actors and actresses who hit the heightened notes of their characters with palpable passion.

And, no matter how many times you watch it, you always hold out hope that Carlito will make it to Gail in the end, as a smile breaks through his panicked sprint across the train platform. Even though you’ve known from the outset that happiness isn’t in the cards of a condemned man, you still hope. Because you are invested in Carlito’s salvation.

That’s how great filmmaking works.