Carlito Brigante (Al Pacino) has a dream and he has a problem. The dream is as simple as it is big: to escape the streets and thereby his violent criminal past, and to head to paradise in the Bahamas with the love of his life. Simple. The problem? Those same streets won’t let him be. And ultimately, although he doesn’t realise or admit it, neither will Carlito himself.
Carlito’s Way (1993) is a classic gangster film and yet in a lot of ways, it is a sheep in wolf’s clothing. In this article, I will demonstrate how Brian De Palma used the film to reflect his own personal issues of the time, and how Carlito Brigante is a classic tragic figure, unable to completely leave his past behind and achieve redemption, struck by his own mortality as he notices the world around him changing.
Brian De Palma did not want to make another gangster film. He particularly did not want to make another gangster film starring Al Pacino as a Latino gangster. Scarface cast a long shadow, and De Palma was well aware of his reputation as a purveyor of violence. Critical reaction to his attempts at more ‘serious’ works—Casualties of War (1989), Bonfire of the Vanities (1990), Raising Cain (1992)—were mixed, with the upshot being that people struggled to see him as anything other than a dabbler in blood. For a strand of critics, this was anything but favourable. Unhappy to go back to his roots, but condemned for trying to progress, his subsequent adaption of Carlito from novel to screen could lead one to believe that Carlito was a stand-in for De Palma himself.
If De Palma’s professional life was in a state of flux, his personal life offered little respite: ‘At the time I began the film I was going through a personal crisis. In the space of two years, I got married; I had a child, and I got divorced!… I wasn’t able to reconcile my personal life, whereas the majority of my friends have done so’. 
The script for Carlito’s Way came through at a time of obvious flux for De Palma and he saw something of his personal situation within the pages. ‘I was asking myself some questions about my life. It was your classic midlife crisis. In a sense, it was this aspect of the Carlito’s Way script that attracted me. Because, basically, what is this film about? A guy who just assassinated and who thinks, ‘Shit, I’m dead! How did I end up here?’ And he reviews his life to understand the chain of events and to accept what has happened to him. That was my situation at the time. To make this film that conveyed what I was feeling, I had to lay myself bare.’ 
Carlito, like De Palma, is a man in flux. But it is not so much a midlife crisis he experiences. Carlito knows exactly what he wants: to leave behind the brutality and vicious pecking order of the streets and to get to his ideal vision of paradise, the Bahamas, with his ideal vision of a woman, dancer Gail (Penelope Ann Miller). For $75,000 he can buy a stake in a prison acquaintance’s car rental place. It’s a mundane job, but for the benefit of living in paradise with his angel, plus removing the constant threat of assassination that hangs over his head, it’s a very small price to pay.
Before this, Carlito had been a key player in the drug trade, the ‘J.P. Morgan of the smack business’. He is venerated as a God, a myth. As he is told by his nephew when he opines that his nephew’s friends won’t have heard him, ‘You? You’re a fucking legend!’ Then came his arrest on a drug bust and a 30-year prison sentence. 30 years is an awfully sobering length of time, enough to give rise to a bout of serious self-examination. The eventual 5 years he did serve, freed on a technicality, does not appear to have lightened Carlito’s load.
What happened in prison exactly to make him so rethink his course? It’s never explicitly stated, and it appears there’s a form of sarcasm at play when Carlito announces in court with a flourish, ‘my time in the sterling correctional facilities of Green Haven and Sing Sing has not been in vain. I’ve been cured! Born again, like the Watergaters’.
Later, Carlito reveals a little more to Gail in a moment of vulnerability: ‘Never felt like this before. It’s a funny thing. This guy, this counselor at Lewisburg, Mr. Seawald, once said to me: ‘Charlie, you run out of steam. You can’t sprint all the way. You gotta stop sometime. You can’t buck it forever. It catches up to you. It gets you. You don’t get reformed, you just run out of wind’. Maybe it was the very real loss of the prime of his life to the penal system, but it seems somebody was able to get through to him.
If it seems funny to Carlito himself, his friends are baffled. His solicitor Dave Kleinfeld (Sean Penn) openly laughs at him when he talks about the car rental business, and his close associate and stooge Pachanga (Luis Guzmán) cannot understand why Carlito lets Benny Blanco (John Leguizamo) live when it appears Blanco has disrespected him. The idea of getting out of the streets is either laughable or unfathomable to those who cannot see a bigger picture.
And yet, how much bigger is Carlito’s vision really? Look at the language he ascribes to his counselor; it catches up to you; it gets you. Not even a smack kingpin can outrun a bullet. Here is a fear of a life lost, figuratively or literally; either prison or the funeral parlour. But there is no question of morality involved. At no point does Carlito show any remorse for the victims of his actions. There are no tears shed for the people addicted to the heroin he was peddling or for the ways in which they might have had to degrade themselves to buy said heroin. No flowers are laid at the graves of those who died at his order or at his own hand. It is this lack of remorse, the instinctive street mentality, which is to lead to his downfall.
See, only five years have passed but the times they are a-changing and Carlito suddenly feels his age. He sees the new young hustlers on the block, full of hunger, anger, and swagger, and he is not impressed. Does he rue them following the same bloody path as him? Club owner Saso (Jorge Porcel) touches nearer the truth. Referring to Benny Blanco (from the Bronx) he says, ‘What happened to you? What are you acting like this for? It doesn’t make sense you should hate this guy. This guy is you 20 years ago’.
Carlito can’t recognise the familiarity because he can only see the generation gap, and with any generation gap there comes a difference of values. Carlito has a romantic view of how the streets ran when he was a player. He defines his generation’s values by discussing the younger generation in opposing, negative terms: ‘All right, what happened? Ain’t no more rackets out here, just a bunch of cowboys ripping each other off’. Pachanga takes it one step further: ‘these new kids nowadays, man, they got no respect for human life. They shotgun you, just to see you fly up in the air. ‘Chacho, you’re better off in jail’.
Although never explicitly stated, we can deduce that the difference Carlito sees between the generations is one of honour. The old-time crowd would only kill when it was necessary; the new generation shoots each other in the same way you might play cards – for kicks, to pass the time. Where is the professionalism, the understanding at least of the value of life?
It was, of course, a mirage at best. There never is any honour among gangsters. When all that stands between you and either prison or the grave is another person, friend or foe, you best believe there’s a bulls-eye painted between their eyes.
Carlito himself suggests he only half-believes his ideals when he loses his temper and throws Benny Blanco (from the Bronx) out of his club. Benny’s been pushing his reputation into everybody’s face and (quite understandably) is upset when he finds his girlfriend Steffie (Ingrid Rogers) entwined with Dave Kleinfeld.
Not only does Carlito not recognise Benny’s upset over Steffie (claiming she ‘belongs’ to Dave now, as if she is club property), he decides without being asked to deflate Benny’s ego: ‘Who the fuck are you, I should remember you? What, you think you’re like me? You ain’t like me, motherfucker. You’re a punk. I’ve been with made people, connected people. Who you been with? Chain-snatchin’, jive-ass, maricón motherfuckers. Why don’t you get lost? Go ahead, snatch a purse. Take a fuckin’ walk’. While Benny is obnoxious, this attack does seem provocative for someone who is trying to adhere to the straight and narrow.
Carlito takes things further and threatens Benny, and when Benny responds in kind Carlito resorts to violence, knocking him down the fire escape. Only Carlito’s intervention prevents Pachanga from taking things to their natural murderous conclusion: ‘Let him go. Get him outta here. Any other time, that punk would die, but I can’t do that shit no more. Don’t want to burn nobody, even when I know I should. That ain’t me now. All I want is to get my $75,000 and get out’. The fact that Carlito would kill a man he has met at this point twice, over some minuscule bragging rights and not much more, is something you would expect from Benny, not Carlito.
In fact, Benny has paid his respects to Carlito more than once, acknowledging his status and place in the pecking order and even paying his bill when Carlito asks when he would not pay it to Saso. Carlito sees Benny as a punk so he treats him as a punk, plain and simple. He indicates he would kill Benny any other time, as he knows he should, and refers to his ‘old reflexes kicking in.’ It suggests that this isn’t the first time Carlito has acted so aggressively over something minor.
Not only that, he can’t seem to stay away from trouble. But at who’s fault? ‘I don’t invite this shit’, says Carlito, ‘it just comes to me. I run, it runs after me. Gotta be somewhere to hide’. It seems to me, though, that Carlito has been looking in all the wrong places, and the code of honour has struck again.
When he first gets out of prison, his nephew convinces Carlito to accompany him to a drug deal. Carlito is hesitant but a few minor mentions of ‘the legend’ flatters his ego and persuades him. If he was really dead set on keeping his nose clean, he would have stood steadfast in his refusal to go. Yet this would have gone against his code of honour. His nephew asked him to help, blood is thicker than water, and he knows only too well what could and does lie in wait at the drug deal. How can he say no to family?
The same applies when he is asked by his solicitor Dave Kleinfeld to help break Tony Taglialucci (Frank Minucci) out of prison. Kleinfeld’s been a naughty boy and stolen a million dollars of Taglialucci’s money and has been ‘persuaded’ that breaking Tony out of prison would be in the best interests of his health. Carlito knows it’s a setup—Kleinfeld is a dead man whether he carries out the break–out or not. Kleinfeld has also been acting erratically, high on copious amounts of coke and on ideas of being a Carlito–like gangster figure himself. Not a safe bet for a ticket to paradise, then.
Gail can’t understand why Carlito is putting himself at such risk, but to him it’s simple. Kleinfeld is his friend, but more than that he’s the man who got him out of jail. He feels indebted. ‘Dave is my friend. I owe him. That’s who I am. That’s what I am, right or wrong. I can’t change that!’ To which Gail responds with perhaps the only true wisdom in the entire film: ‘You don’t owe him shit! You think you do. That’s the problem. That’s why nobody like you gets out’.
In the end, Carlito’s code of honour spits right back in his face. Kleinfeld kills Tony Taglialucci and his son, forcing Carlito to help dispose of the bodies. Taglualucci’s other son is furious for vengeance and is gunning for the pair. Kleinfeld does not seem to feel particularly guilty for putting his friend in such a position, a friend he knows is trying to leave that life behind. In fact, he seems to think himself bigger than Carlito, and as to what he thinks of his code of honour, well…
‘Fuck you and your self-righteous code of the goddamned street. Did it pull you out of a thirty-year stint in five years? Did it? No, I did. Did it get you acquitted four fucking times? No, it didn’t. I did. So fuck you, fuck the street. Your whole goddamn world’s this big and there’s only one rule: you save your own ass’. Kleinfeld sounds more like one of the new generation Carlito looks down upon rather than one of his contemporaries.
He is also, along with Gail, able to sum up Carlito’s problem: Carlito dreams big but his thinking is still small, still of the street. And it is ultimately this street mindset, this romantic dedication to honour among gangsters, contradicted by his disdain for modern hustlers, that kills him before he can even get one foot on the train to paradise. If he had said no to Kleinfeld, he wouldn’t have been forced unknowingly into aiding the murder of Tony Taglialucci, which would mean Tony’s son would not have chased Carlito down to Grand Central Station, where Carlito is forced into one more murderous burst of violence. But the biggest mistake, the one he didn’t see coming, was to trust indiscriminately—not one of the new generation either but one of his compadres from the street.
Carlito’s disdain of the new generation comes back to bite him when Benny, poor jilted Benny, abused without substantial provocation, steps to Carlito at the train door and plugs him with shots to the chest. And with paradise so close! But Benny wouldn’t have known Carlito’s whereabouts without a tip-off from someone deep in Carlito’s circle. As Carlito lies there ebbing away, the traitor steps into view: Pachanga. ‘No hard feelings’, he says by way of explanation, ‘but I got to think about my future, too. You know, it is that way sometimes, papi’. Pachanga acts in his own self–interest, suggesting that not too much is different between the two generations after all.
If only Carlito had treated Benny with a little more respect, or at least not verbally and physically assaulted him, he would still be alive and able to take the train to paradise. Paradoxically, and rather ironically, if instead of letting Benny go he had shot him in the alley, like the new generation Carlito disdains, he would also still be alive. And yet the code of honour, through Pachanga, has betrayed him yet again (Pachanga will also be betrayed in turn by a bullet from Benny). Carlito tragically learns, much too late to change, that there ‘are no friends in this shit business’. There is no honour among gangsters. Therein lies the tragedy of Carlito.
Thankfully for Brian De Palma, the aftermath of the film did not resolve in a tragedy of its own. Cautious praise from the critics and two Golden Globe nominations, one for Sean Penn and one for Penelope Ann Miller, made De Palma attractive to the industry. On the recommendation of Tom Cruise, who had loved Carlito’s Way, De Palma found himself in the director’s seat for one of the big summer blockbusters of 1996, Mission: Impossible. After the struggles of the past, here, at last, was a film that was a mass success, critically and commercially (it was the third highest-grossing film of the year). For De Palma, vindication never felt sweeter. He had even got married again (although sadly this was not to last). Paradise? Maybe not quite, but for once things were looking up.
And as for Carlito’s Way? Eventually, it has been recognised for the great film that it is. The prestigious Cahiers Du Cinéma film journal even named it as one of the best films of the 1990s. Honour indeed upheld.
 Keesey, Douglas. Brian De Palma’s Split Screen: A Life In Film. United States of America:: Univ Press Of Mississippi, 2017.