You’re in Trouble, Baby: Carlito’s Way and the Rise of Benny Blanco

Carlito's Way poster

VHS Revival takes to the streets with Brian De Palma’s slick, retrospective crime thriller

It’s rare to see Al Pacino upstaged in any movie, and his performance as a Puerto Rican ex-con attempting to go straight is typically inspired, a controlled blend of both the fiery and understated sides of one of Hollywood’s most consistently brilliant performers. Then you have Sean Penn in perhaps his greatest ever role, almost unrecognisable beneath a shock of red curls as he sneers and struts his way from arrogant big city lawyer to crime world player, and all under the nose of one of New York City’s most legendary gangsters. Not only does Davey Kleinfeld manage to fool his supposed friend, Carlito Brigante, he even manages to string him along while he’s still of use, feeding off his client’s skills and reputation while secretly setting him up for the fall. In the end, Kleinfeld is a criminal of an entirely different breed.

Carlito’s Way is a movie of great style and energy, one that delights in the heady decadence of the disco scene while mired in the scum of the barrio, a place described as being ‘like them old cowboy movies, only instead of tumbleweed and cow dung we got stripped car wrecks and dog shit.’ Since Carlito went away, things have changed, and though some of those old faces remain, they look at him differently, and those who came up while he was gone have no respect for what went before. Respect for ones peers is a thing of the past it seems, and perhaps never existed. The moral code to which Carlito clings appears to be illusory.

Carlito's Way Carlito

Whether that was always the case we will never know. Carlito is a new man having beaten a thirty year rap on a Kleinfeld-spun technicality, and when his old partner Rolando scoffs at the very notion, you can only imagine what Carlito had been like before his sentence took him out of the game. The only window we have into that part of our protagonist’s life is through the people who fill it. The movie features a wonderfully colourful cast, both lead and supporting, characters who are laced with slick and sleaze, the bold and brightly coloured becoming dulled by greed and desperation.

Carlito Brigante: 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.

Perhaps the most blatant hint at the person Carlito is trying to escape is young hothead Benny Blanco. Benny is a brash up-and-comer with a devil moustache and sinister glare, the kind of full-throttle delinquent who will either crash and burn or rampage his way to the very top. Benny is reminiscent of another De Palma character — Tony Montana from Scarface — and you can imagine this movie as kind of a quasi-sequel. Benny is played by a blossoming John Leguizamo in one of his finest performances to date; a godsend following his role as Luigi in video game adaption and monumental flop Super Mario Bros. In a 2016 interview with Birth. Movies. Death., the actor would say of his most iconic turn, “In Carlito’s Way, I found myself as an actor. With my entrance as Benny Blanco, [De Palma] let me do between twenty and thirty takes. And we’re talking about doing this on film, not digital. This was the era when you usually got three takes and had to beg for more. Not with Brian. Brian would let you play, because he was digging what I was doing; all my flamboyance and improv.

Benny Blanco

Benny seems smarter than your average thug, with the sense and ambition to offer Carlito some restraint as he sets about picking his brains. Of course, Carlito isn’t interested. He simply wants to take enough out of a club investment and escape the streets that stalk him at every turn. He sees himself in Benny and resents him for it, and eventually his ego takes hold as the new kid in town flaunts his growing power on his premises. Carlito is who Montana could have been had he not careened over the proverbial canyon. All of this comes to a head in a hyper tense confrontation between the two characters following a conflict in Carlito’s club, one beautifully orchestrated by a director who is infamous for stirring emotions between cast members and having them translate to the screen. “[De Palma] loves to tell one actor one thing and another actor another thing and then just watch them go at it,” Leguizamo would explain, “It’s all about conflict with Brian. He just wants to get everyone riled up. He gets off on tension and watching actors cross the line. I’m so glad you brought him up because he’s really one of the geniuses of our time.”

In spite of these parallels, Carlito’s Way is very much a different animal. Unlike Pacino and De Palma’s previous foray into the world of crime, the movie is free of political leanings, extricated from the vengeful scribe of screenwriter Oliver Stone, who would cite Scarface as a revenge piece against cocaine after struggling with addiction, but that doesn’t mean the screenplay is any less quotable. Adapted from a novel of the same name, the film is saturated in Elmore Leonard-style prose, punchy and lyrical with the kind of pulp poignancy which adds a peculiar depth to a world spray tagged with grandiose caricatures. Hypnotised by our protagonist’s narration, we are led wandering through a cinematic dreamworld, so dazzled by the poetic deceit and colourful language that we are unable to see the path in front of us, and by the time we arrive at our hero’s fated destination we fail to see it coming.

Carlito Gayle

A man drowning in the clarity of change, Carlito is swamped by the surreptitious and the sinister, and the angles are there, he just can’t see them — or at the very least doesn’t want to. When Lalin —a former friend purportedly doing thirty years in Attica — turns up out of the blue in a wheelchair, he is wearing a wire. When Sasso suggests that his bodyguard is spying for the enemy, Carlito waves the former club owner away, clinging to the fact that Pachanga is his brother. When Carlito takes Bennie out back for disrespecting the club, he knows he should kill him but lets him go. It is this restraint, known to the streets as weakness, that will ultimately cost him everything. The game, it seems, has passed the old dog by.

Carlito Brigante: Dumb move, man. Dumb move. But it’s like them old reflexes comin’ back. I know what’s supposed to happen now. 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.

The only face that still looks at Carlito the same way it always did is that of Gayle (Penelope Ann Miller), a former love whose heart he broke when at last the streets caught up with him. Gayle is a once idealistic soul whose dreams of becoming a Broadway dancer have succumbed to the same social ills prevalent in her beau ‘Charlie’s’ world, reducing her to pole dancing duties in order to survive the unforgiving city. Once again the two are drawn to one another as Gayle champions Carlito’s plans to go straight and move to paradise as an unscheduled pregnancy only adds to their pressures, but people are the products of their environment, and for a man like Carlito, once you’re in you’re in. You can’t just disappear when it suits you. You have to keep running, and it’s only a matter of time before you run out of steam.

Carlito's Way Kleinfeld

Ultimately, the movie is about decisions and what leads us to make them. Throughout the picture, Carlito clings to a moral code that the rest of society seems to have outgrown, and because of this his decisions prove progressively harmful. Carlito owes Klieinfeld for getting him out of the joint, and it quickly becomes apparent that the increasingly out of control lawyer plans to use that favour. You might even argue that Carlito’s debt to him was the reason he helped his client in the first place. Engulfing every last frame, Kleinfeld drips with insincerity, burrowing his way into the pockets of the city’s most treacherous like a beady-eyed mole dipped in cocaine. Gayle can sense this, and warns her conflicted love from the very beginning, but Carlito has to stay true to his code. It is the only element of control he can maintain as his plans begin to unravel, and when Kleinfeld manipulates his so-called friend into an ill-fated boat ride, the two of them cross a line from which there is no coming back.

The boat ride in question is one of several set-pieces that rank up there with De Palma’s very finest. It’s no secret that the director borrows rather heavily from the Hitchcock book of suspense, sometimes brazenly so, and though Carlito’s Way is something of a sleeper in the filmmaker’s extraordinary catalogue, the movie often shows him at his most masterful. The film’s finale, in particular, showcases De Palma’s unbridled abilities. Beginning with a gilt-edged show of deception with a suspicious mafioso crew, the director puts us in Carlito’s slippery shoes as he pulls every last trick in the book to evade the pursuing rabble, De Palma plunging us into one tense situation after another with an ostentatious show of skill that thrills and deceives and ultimately devastates. Pacino may forge Carlito’s carefully muted flamboyance, but it is De Palma who shows us exactly the kind of man we’re dealing with.

Carlito Brigante (voiceover): There is a line you cross, you don’t never come back from. Point of no return. Dave crossed it. I’m here with him. That means I’m going along for the ride. The whole ride. All the way to the end of the line, wherever that is.

Carlito’s Way may lack the rebellious tone of Scarface or the rampaging performance of Tony Montana, but what it lacks in political power it more than makes up for in panache. This is a more experienced director at work and for such a pitch-perfect movie it seems almost effortless, featuring a cast of characters and performances that are sure to stay long in the memory, despite the movie’s relative anonymity. The redemptive goals of Carlito inhibit that urge to explode in the kind of violent frenzy that fans of gangster flicks typically crave, but when push comes to shove Carlito shows there is still some fight left in the old dog, and during the kind of dizzying climax that only De Palma can deliver, we get a glimpse of the legendary skills and resourcefulness that kept Carlito alive all those years, the kind befitting of a director at the very top of his game.

But in the end, a person can only protect oneself from the enemies that are apparent, and in Carlito’s world the definitions that separate enemies and friends are precarious, the lines blurred, and when you can’t see the angles no more, you’re in trouble, baby. You’re in trouble.

Carlito's Way Logo

Written by Edison Smith Editor-in-Chief

Science Fiction Writer, Horror Enthusiast, Scourge of Plutocracy, Creator of


  1. This is one of my favorite Pacino movies. I feel he was at his best in this film which came before another flick that I like Donnie Brasco. Yes, he won the Oscar for Scent of a Woman but in Carlito’s Way, Al was harkening back to the days before he was a self parody, the Dog Day Afternoon and Serpico years. His acting is quiet and understated which made him extremely convincing as a man who just wants to live a normal life. Sean Penn was flamboyant and totally unrecognizable in his role as the smarmy lawyer. Carlito’s Way also brought out his best acting as well. All around terrific movie!


  2. It speaks volumes about the validity of the Oscars that Pacino won an Oscar for Scent of a Woman, a movie of saccharine sentimentality which as you say smacked of self-parody.

    I shouldn’t be surprised. Not only are the Oscars quick to distance themselves from movies of political value, they have become little more than a promotional event in which marketable young actors are chosen as a platform for a financially fruitful series of movies, or legendary performers are given honorary awards with a view towards one last money-spinning hurrah.

    Actually, it’s not such a new phenomenon. The Oscars were established as a way to outmode silent movies as the talkies came to prominence. The original event was an ostentatious foray designed to enforce obsolescence, and as a promotional tool it just grew from there. Personally, I don’t pay much attention to it.

    You’re right, Carlito’s Way was a return to classic Pacino after almost a decade of shouting. It’s amazing to think that it went on for so long, but I suppose that was the Pacino everyone wanted. It is testament to the cultural impact of his role as Tony Montana in Scarface.


  3. Yeah, I think that similar to Pacino’s Tony Montana character, his Carlito has a value system (a complex mix of new & old) which is out of place in the world he inhabits and runs counter to both his success & survival. I had more sympathy for Carlito than Tony Montana, so in that respect the story for this film affected me more on an emotional level. Do I prefer understated Pacino over shouting Pacino? Probably, but I can get onboard with shouting Pacino too, especially in “…And Justice For All”. I’m not much into the Oscars either, and the reasons stated in the comment section about says it all (I’d like to add that I don’t put much stock in people winning things which rely on subjective points of view & forces out of their control. I guess no one can really truly “win” an Oscar, just be given one.


    1. I can get behind shouty Pacino too. When he’s not phoning it in a loud Pacino can be just as engrossing, and in some cases even more so. He gives us both sides in Michael Mann’s Heat, another superb movie. He is utterly compelling in that one.


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