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That Moment In Carlito’s Way (1993): A Fateful Choice

Carlito’s Way is a crime drama about an ex-con who return from prison only to be pulled back to the life he wanted most to leave behind. A powerfully acted story, it earned high praise and was a box office success.

Have you ever mucked something up so spectacularly bad that you wish you could do it again? And no, not like that time you went to work wearing that ridiculous red scarf the blonde hottie behind the sales counter said you looked “fabulous” in because she knew that you’d risk a lower credit score just to stand there a few minutes more and stare into her dreamy eyes. I mean something really bad. Take Carlito Brigante (Al Pacino) for example. Here’s a guy with a long list of seedy crimes who is now free from jail after his equally seedy lawyer got him out on some judicial technicality. (Actually, the D.A. was using illegal wiretapping, so thanks, justice system.) Carlito is getting a second chance and he’s not going to let it go to waste. He says he’s legit. No more crime. Five years in prison showed him the path of righteousness. Or at least the sidewalk of laudable. He tells the court all about it.

Back on the streets of Spanish Harlem, the ol’ crowd is happy to see him but he’s left the life of crime behind. He wants to rent cars and get enough cash to retire in the Caribbean. He tells this to his best friend and lawyer, Dave Kleinfeld (Sean Penn), who isn’t entirely convinced. Nor should he be. Carlito ain’t exactly got himself a solid plan. And its really only a matter of time before he falls back in with old ways. That happens almost immediately. While accompanying his younger cousin on a drug deal in a local tavern, things go just a little sour. A little. A few guys get smashed with pool cues, there’s some throat slicing, a lot of gunfire, and bloody bodies are strewn about the room like there were in a Brian De Palma film. Oh wait. They are in a Brain De Palma film. That explains it. But Carlito survives it and just like that, he’s back in the game. Goodbye rental car plan.

Universal Pictures
Universal Pictures

As he’s just relieved some baddies of their mortal coils, and his poor cousin has met his untimely doom, he decides the heaps of cash lying around the bloodied place are in need of a new home. Hey, even dollars needs a fresh start once in a while. That new home is his pocket and now that they are deep, he buys into a gangster-owned nightclub because there’s no way anything bad happens in gangster-owned nightclubs. They’re safe as opening a cupcake bakery. It’s there where he meets Benny Blanco from the Bronx (John Leguizamo), who right away wants to partner up for some shady business. Carlito also gets that deep down longing feeling for the lost love of Gail (Penelope Ann Miller), his ex from before prison. He finds her working days as a ballet dancer and nights on a stripper pole. No shame in that. Ballet dancers are perfectly respectable people.

Carlito's Way
Penelope Ann Miller (Carlito’s Way, 1993)

Meanwhile, Kleinfeld has got himself into some very hot water. Seems he mismanaged a cool million dollars from his currently incarcerated mob boss client, and when I say mismanaged I mean outright stole. The boss threatens to dump his sleazy body into the East River, and the only way he won’t is if Kleinfeld help’s him escape. All he has to do is show up with the boat and pick him up. Everything else is set. Kleinfeld has no choice and begs Carlito for help. See, Kleinfeld’s pretty darned sure once he rescues the boss, he’s a dead man, and he thinks if Carlito is on the boat, he’ll be safe because nothing bad has ever happened with Carlito around.

The problem is that Kleinfeld is too coked up and strung out to see that. He’s too coked up and strung out to see just about anything and is a constant paranoid wreck. He hates everyone, trusts only Carlito and is about as fun to be around as well, a paranoid coked up lawyer too strung out to see what he’s doing. At the nightclub one evening he goes too far. After insulting some Italian patrons, he spills the beans to Gail that Carlito and he are taking a boat ride. This raises her suspicions and back at her place, she and Carlito argue, with him eventually walking out, Mr. Pouty Head.

Out on the boat, in the middle of the night, Kleinfeld, Carlito, and the boss’s son arrive at the designated spot, and there they find the old mobster clinging to a buoy in the choppy water, just as planned. But that plan is about to get Kleinfeld-ed. (Let’s see if that word catches on!) Instead of picking up the mob boss, he does off with the son and then beats the old guy to death with a crowbar, tossing him into the East River just as he had been threatened with if he didn’t comply. Sweet, sweet irony. This does not go over well with Carlito, who had only come along because of the debt he felt he owes to his friend. Now he’s got a mob boss murder on his hands and he’s thinking this might not go over well with those hoping the boss would make it our of prison alive. He’s right. For a guy trying to live it clean, he’s got just about every part of himself up in the stink.

Carlito's Way
Sen Penn (Carlito’s Way, 1993)

Directed by Brian De Palma, Carlito’s Way is an often taunt and highly suspenseful thriller that is full of classic De Palma-isms, including some wonky dialogue and odd moments, like when two fans of Gail approach her after her strip show telling her over and over that she’s “Wonderful. Just wonderful, really really wonderful.” Awkward much? Or when the District Attorney shows up at Kleinfeld’s office and just says, “Your problems aren’t just going to go away, David.” And that’s it. End scene. It has this build up with Kleinfeld snorting a line before the D.A. walks in and feels like something turbulent is about to happen, but then just stops. Phfffft. Wonky. But then there’s great moments, like when Gail entices Carlito into her chain locked apartment, which almost became this post’s chosen moment. I won’t spoil it (too much), but a line like, “If you can’t get in, you don’t get in” is tingle-inducing. This is pretty much standard for De Palma who shifts between nerve-crackling set pieces to huh? shots throughout, but ultimately, Carlito’s Way is very satisfying, mostly because of Pacino and Penn, who are utterly absorbing. The worst offender though, and the main reason the film suffers, is the intolerable narration. This is so unnecessary and feels just as tacked on as Rick Deckard explaining everything we see in the original Blade Runner. Another case where studios think audiences need their hands held in order to follow anything remotely off the well beaten path. Shameful. That said, like every movie, it has one great moment.

A Fateful Choice

Carlito, despite a rough start with his cousin getting killed at the drug deal gone amuck, has been doing well for himself, setting up shop in the night club and regaining his old position of power. While the place is partly owned by the mob, he’s been doing his part legit, packing gobs of money in an office safe, intent on getting out of the city and retiring to the Bahamas. A local dime bagger trying to make a bigger name for himself has made the club his landmark, surrounding himself with heavies and taking one of the leggy waitstaff girls as his own. Carlito isn’t impressed with Benny Blanco from the Bronx, refusing to take him up on his offers for a partnership. Meanwhile, Kleinfeld decides that Steffie, the waitress, is just the kind of girl he’s been missing and lures her into the club men’s room for a little cocaine fused poke in the stall. Things come to a head when Bennie tries one more time to give Carlito respect but demands some for himself.

Carlito and his thug Pachanga (Luis Guzmánare sitting at a table in the club with a view of the dance floor. Kleinfeld and Steffie (Ingrid Rogers) join them, having just, ahem, banged one out in the toitty. Across the way, Benny sends a bottle of champagne to the table, still trying to get in with Carlito, but Carlito isn’t having anything to do with it. He recognizes that Benny is weak, that he is nothing but a punk, thinking he is bigger and better than he has a right to believe. Carlito came up with made people, ones who came up just as hard, earning their way to the top. Benny is small time and thinks he’s not, trying to flash his way up instead of living it the way a made man does. He is small time and will always be small time. Benny, hoping to keep face with his goons behind him, brushes the insults off and settles for taking Steffie back, demanding she follow. But Carlito isn’t done. “Steffie belongs here” he barks. “That’s where she belongs.” Well Benny finally snaps and lunges at his girl, which springs Kleinfeld into action. He draws a snub-nosed revolver and points it at Benny’s face.

Universal Pictures

From there, chaos breaks out and a struggle ensues, with goons drawing weapons. Carlito stays calm and orders Kleinfeld to put his away. He does and soon all of Carlito’s boys have all of Benny’s boys separated and strong-armed. Benny gets dragged up to the office while the henchmen are tossed. Two thugs, including Carlito’s right hand man Pachanga have a hold on Benny. They’ve got him teetering on the edge of a nasty looking stairwell leading to the back ally. Carlito warns him straight. If he shows his face again, he’s dead. Benny, recognizing he’s probably gonna draw his last breath anyway, gets in Carlito’s face. A quick tip here for if you find yourself facing down three mobsters while at the top of a stairwell: don’t mention death. Compliment their shoes. Casually remark on the weather. Maybe suggest a spot of tea. Avoid potentially threatening words like, I don’t know, I’ll kill you.

Benny goes with, “I’ll kill you.” Carlito flips and whacks Benny from the Bronx on the head, sending him reeling head over heels down the stairs. Ouch. Then they carry his crumpled body out to the alleyway and we expect Carlito is gonna have his boys advance the young man’s expiry date. That’s certainly what the goons want, especially Pachanga. But Carlito shows mercy and tells his thugs to let Benny go.

The moment is crucial. From this, three divergent stories are born and reveal exactly how Carlito will meet his fate. 1) By walking away, letting Benny go, and showing mercy when he should–by the rules of the street–have brutally murdered him, Carlito weakens his position. Too proud and too sure of his status, he is blind to the repercussions. And the repercussions are great. 2) Benny survives and doesn’t see mercy as a gift. He sees it as opportunity. Even though he doesn’t show up again until the end, we suspect that he has a further role to play. And he does. 3) Pachanga turns. Feeling frustrated and letdown by Carlito’s continued efforts to go straight, Pachanga has had enough. He’s looking to go bigger, to be stronger, and be made, he finds all of that in the form of Benny Blanco from the Bronx.

None of this is understood until the last scene of the film. That’s how well-crafted this moment is, and De Palma does a masterful job of framing the ally scene (pictured above) to reveal much about what will happen. Carlito walks away while Benny and the two goons stand over him. First, Carlito walks away, toward us, his face moving in and out of the light, just as his thoughts and ambitions are doing in real life. He moves off to one side, making a choice. A shallow stream of dirty water separates Carlito from the others, signifying his departure and transition to the other side. Pachanga watches and lifts his arms in frustration, the first sign that he is unhappy, and a clue that his actions from now on will remain behind Carlito’s back. Benny is out of view, slumped and hidden behind a toppled trash can, which itself represents the bronx mobster. He is trash, meant to be forgotten. We do, and so does Carlito.

The main story is about Kleifeld and Carlito, or so we are meant to believe. It’s about the brutal and vengeful hand of the mob. Indeed, it is that story that propels things forward, but for Carlito, it is the forgotten story, the punk, the dime bagger who thought himself something more than who he was that should be remembered. It is he who proves the most dangerous.

Carlito's Way (1993)

Film Credits

Director: Brian De Palma
Writers: Edwin Torres (novels), David Koepp (screenplay)
Stars: Al Pacino, Sean Penn, Penelope Ann Miller, Luis Guzmán, John Leguizamo