Brian De Palma’s 1993 crime drama Carlito’s Way, based on the 1975-set novel of the same name and its companion piece After Hours, written by Edwin Torres, a former New York State Supreme Judge, and the first person of Puerto Rican background to hold such a position, is about a man trying to escape the myth of the past, for a phantasmic future with the woman he loves. Al Pacino plays the titular Puerto Rican brigand Carlito Brigante, a former legendary heroin dealer in the NY underworld. Just when he thought he was out, to paraphrase Pacino’s Michael Corleone from 1990’s The Godfather Pt III, Carlito’s slimy lawyer Dave Kleinfeld (Sean Penn), a wannabe player, drags him back in to get the Italian mob off his coked-up ass. Carlito sees himself as a man adrift after five years inside, released thanks to Kleinfeld on a technicality. The story begins in media res, or more strictly speaking, after the action – we know ego-pricked humiliated player Benny Blanco “from the Bronx” (John Leguizamo) shoots Carlito just as he is about to board the night train to Florida with reconnected dancer girlfriend Gail (Penelope Ann Miller) at NY Grand Central Station. De Palma and the scriptwriter David Koepp use this to create a “whydunnit”, and so begins a ruminative, fatalistic present tense narration from Carlito (that will continue to elide through the film’s run-time on his poor choices and awareness of the shifting sands beneath his feet), as a woozy black-and-white floating shot shows him being rushed to medical aid. He is, as he wryly puts it to himself later, the “Last of the Mo-Ricans”, a (literally) dying breed. There’s always somebody who wants to take out the King. “Benny’s gotta go down. And if I don’t do it, they’re gonna say: ‘Carlito, he’s flaky, man. Slacked-out. A used-to-be bad guy. Joint got to Carlito.’ The street is watchin’. She is watchin’ all the time.” 

If that sounds pessimistic, Carlito dies knowing he did his best to go straight, did his best to do right by Gail, the woman he had cut off in five years of jail time to survive unencumbered (he passes her the thick wad of notes he retrieved from his in-debt club partner who ripped him off) and helps her at least embody their future together in spirit (she’s pregnant with their child, off to their dream of a life in the tropics). “The dream don't come no closer by itself. We gotta run after it now.” The film is a romance as much as a drama, that line the Mo-Rican’s equivalent of Daniel Day-Lewis’ “Stay alive! No matter what happens. I will find you,” from Michael Mann’s The Last of the Mohicans.

Carlito’s Way is also oft-compared to a previous De Palma/Pacino collaboration, Scarface, the two films sharing other overlapping actors, though obviously not characters. We get some idea of how successful a criminal Carlito was, but not how ruthless. He doesn’t seem like the animal Tony Montana was, consumed by his own appetites. Carlito tells Gail, from growing up in a rapidly segregated city, “Guys went down, yeah, but it ain’t like, you know, you just decide one day and that’s it. No. You just do what you gotta do to survive. Somehow, you know, you just end up where you are.” Carlito is more reflective than Montana, but that’s with several years on a hard road behind him. The Godfather Pt III was stymied by the slow pace and mannered style of its classier forebears and its 1970’s setting seems barely noticeable. By contrast, Carlito’s Way, apart from the tension of a once venerated relic being squeezed by tough choices and misjudged loyalties, pops and crackles off the screen, the 1970s brought to vibrant life, from the poor but colorfulneighborhood barbershops and groceries and pool halls, to the chic, debauched country house and club disco party scenes (even if some of the classic songs weren’t released in 1975, the vibe is real). All shot with De Palma’s trademark swirling and zooming freeform camera. “Dick (Richard Sylbert) is a great art director,” says Brian De Palma. “If you have a great art director, you give him your ideas, and he gives you back ideas that are better. I wanted a two-level club, and I conceived the ground-floor space to accommodate these long, sinuous tracking shots so you could use a Louma crane to go up and down and follow them around. I showed the drawing to Dick, and he designed the club along the lines I had created. When we looked at the exterior, he said to me, 'This building looks like a boat. We should make the inside of the club look like a boat that they're trying to sail away in and can't.' I said it was a great idea, and that's exactly what he did.”

The action sequences are naturally suspenseful, and equally lovingly mapped-out. Early in the film Carlito reluctantly accompanies his star-struck young cousin on a money drop-off. Carlito’s eye is drawn to the suspicious crack of light behind the door of the “out of order” restroom in a backroom pool hall. Carlito sets up a trick shot, the camera and his eye catching little details, marking out the players, where a weapon is, who to hit first, and so on, all underscored by the diegetic music of Ray Barretto’sEl Watusi. The painted red brick walls and Carlito’s silhouette framed in the darkened restroom suggest a descent into hell. As he enters to a now deserted room, his young cousin’s throat sliced open, he takes the money, voice-over reflecting sadly, “Oh, Jesus. Jesus Christ, look at you. You said they were friends, Guajiro. But there ain’t no friends in this shit business.”

Lesser remarked upon than his other railway station shoot-out in The Untouchables is the cat and mouse back and forth, first through Carlito’s club, then the subway, and along the concourse and elevators of Grand Central Station, the set-piece a ticking clock maneuvering to evade vengeful mob members who want Carlito for unwillingly abetting Kleinfeld’s offing of their Riker’s escaping boss, and the framing tragedy of Carlito’s demise. De Palma uses train platforms, pillars, escalators, even a floating bunch of balloons to drag out the tension of who sees whom when. Almost unnoticed by the viewer is a rushing figure past Carlito down the platform, Bennie in disguise.

Sylbert told Biskind, “Brian is a movement director, like Bertolucci. Writing with the camera. It's very good for this movie because of all these big spaces. Grand Central and Times Square. He really appreciates this set, dreams about it. He walked in the first day, looked at me, said, 'I'm gonna shoot every inch of this fucking thing.'”

David Koepp said “one common misperception people have with the word romantic, is that it ends with two people walking away on a beach together. The whole idea of something being truly romantic is that it’s about loss. And that’s what so many of Brian’s movies are about: loss of innocence, loss of love, loss of life. What’s truly romantic is to find something that’s truly ideal for you; that which seemed unobtainable in life, and then to find out that it is.” On one level Carlito might seem to be undone by his need to get even with Dave, visiting him in the hospital, giving the mob and Benny time to catch him at the train station whilst Gail frets. Although he doesn’t kill Dave, he leaves with a warning (“You ain’t a lawyer no more, Dave. You’re a gangster now. You’re on the other side. Whole new ball game. You can’t learn about it at school, and you can’t have a late start.”) and in a brilliant kiss-off, when the disguised hood comes in to kill him, Dave finds his revolver is empty – cut to Carlito tumbling the bullets in slow-motion into a trash-can. Similarly, Robert De Niro’s Neil McAuley in Michael Mann’s Heat seems to be clear away with Eady (Amy Brenneman) but can’t resist stopping to get even with Kevin Gage’s Waingro.

The film ends with Carlito’s eyes closing on the holiday poster high above him, “Island Paradise” with the silhouette of a dancing woman, a tourist, and young islanders coming to life, a boy among them, gaily dancing with abandon, as if Gail has made it. All to the reprise of Joe Cocker’s You Are So Beautiful, first heard as an entranced Carlito spies from across the street on Gail at her dance class, lost in the moment. The “Way” of the title not so much Carlito’s moral code, or reputation, but as Matt Zoller Seitz eloquently put it, a passing on through a state of grace: “Carlito has been magically transformed just as that billboard was transformed, and that his essence was passed on. Against all odds, De Palma gives us a happy ending. But not out of nowhere: the entire film is borne aloft by hope, a sense that nothing is fixed, that anything is possible in life. As Carlito details his past mistakes and delusions, the film is suffused with a warmth that comes from knowing that despite the pain of existence, it’s better to be alive than dead. Cocker’s song speaks simultaneously in two directions: it expresses the movie’s love for its transformed hero, and Carlito’s love for life itself.”

Screenwriter must-read: David Koepp’s screenplay for Carlito's Way [PDF.(NOTE: For educational and research purposes only). The DVD/Blu-ray of the film is available at Amazon and other online retailers. Absolutely our highest recommendation.

Carlito's Way screenplay by David Koepp

Brian De Palma interview on CARLITO'S WAY

How Working On "Carlito’s Way" Forever Changed John Leguizamo

Penelope Ann Miller "Carlito's Way" 11/6/93 - Bobbie Wygant Archive

Brian De Palma "Carlito's Way" 11/6/93- Bobbie Wygant Archive

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Brian de Palma with Jimmy Carter "Carlitos Way"

Tim Pelan was born in 1968, the year of ‘2001: A Space Odyssey’ (possibly his favorite film), ‘Planet of the Apes,’ ‘The Night of the Living Dead’ and ‘Barbarella.’ That also made him the perfect age for when ‘Star Wars’ came out. Some would say this explains a lot.