Carlito’s Way (1993)

Starring: Al Pacino, Sean Penn, Penelope Ann Miller, John Leguizamo, Luis Guzmán, Viggo Mortensen, and James Rebhorn, with a cameo from Vincent Pastore
Grade: A+

Being given the nickname of the “J.P. Morgan of the smack business” is pretty badass.


At the Grand Central Terminal right before he enters the train, former gangster Carlito Brigante (Pacino) is shot and drops to the ground. As he’s being taken away on a stretcher, he thinks to himself how calm he is because he’s been in this situation before. Following his rambling about how the hospital doesn’t save anyone, he stares at an advertisement with a silhouette of a woman and a few others on a beach. It states, “Escape to Paradise”.

We then move backwards to New York City in 1975. Carlito is in court and has just finished five years of a thirty-year prison sentence, and he’s excited, ranting to the courtroom about his life and mother. Reminding Carlito that there are still 56 cases on the court’s docket, the judge asks why they are hearing such nonsense. Carlito’s lawyer David Kleinfeld (Penn) speaks about how Carlito feels vindicated after years of incarceration, though the judge isn’t impressed because Kleinfeld only got him out because of illegal wire taps and tainted evidence, not because he was proven innocent or anything. Even so, Kleinfeld argues that Carlito should have the right to speak, so the judge relents. Carlito goes on, saying his time in prison was not in vain and promises to go straight. He wants nothing to do with the gangster lifestyle anymore, and he thanks District Attorney Bill Norwalk (Rebhorn) at the opposing table for making the illegal tapes that got him released. After thanking the Court of Appeals, the judge, and God himself, he also thanks his best friend Kleinfeld. Officially, the judge reluctantly discharges Carlito while calling him a “reputed assassin and convicted purveyor of narcotics” in front of the entire courtroom, though Carlito interrupts and says he was never convicted for dope. Upon being dismissed, he tells Kleinfeld he’s indebted to him and tells Norwalk there are no hard feelings, but Norwalk says he’ll be seeing him in the future.

Exiting the courthouse, Kleinfeld compliments Carlito on the bullshit he was spewing, but Carlito insists he was telling the truth. He’s done with that life. That night, the two party at a club with some women. While on the dance floor, Kleinfeld asks Carlito if he’s going to work with Rolando (Al Israel) again to get some money, but Carlito triples down on his promise to not go back to the street. Through narration, Carlito says he’s known Kleinfeld back when he first got out of law school. He was working as a clerk for a big mafia lawyer, he kept a tire iron under the seat of his car, and he tried his best not to look scared by all his wise guy clients. Now, Kleinfeld has experience enough to where he’s not scared anymore. As the two sit down at a table, Carlito gives him props at being a big shot now, and Kleinfeld gives it right back to him, admitting he wouldn’t be where he’s at without Carlito because all of his first clients came from him. Changing the subject, Kleinfeld tells him that Saso (Jorge Porcel) bought the lease on this bankrupt disco, and he got some investors together to back him. He has $50,000 personally invested. The problem is Saso himself. He’s been shaking the till and paying off his gambling debts. If he doesn’t get another $25,000, Saso is going to lose the lease. Kleinfeld likes the place, but he wants someone to run the place straight and clean, suggesting Carlito take over for him. Carlito isn’t sure at first, but he agrees because he owes Kleinfeld for getting him out of prison. As the night gets closer to ending, and the two women leave them because they won’t stop drunkenly thanking each other, Kleinfeld asks what Carlito’s big plan is.

Carlito mentions Clyde Bassie, a guy who got out of prison a couple of years ago. He went to the Bahamas, Paradise Island, and he opened a car rental place. It’s doing really well. A couple of months ago, he wrote Carlito and said he can buy in at any time once he gets $75,000 together. Kleinfeld laughs this off, but he’s serious about it.

It’s now August, and Carlito walks the street with Pachanga (Guzmán), who talks about how the newcomers on the scene have no respect for human life. Additionally, former colleague Victor was shot in front of a local high school, and Lalin Miasso (Mortensen) is doing thirty years in Attica. Walberto (Ángel Salazar) interrupts the two to tell Carlito that Rolando wants to talk to him, so Pachanga checks out, though he does offer his services of any kind in case Carlito needs anything. Carlito tells his cousin Guajiro (John Ortiz) to wait back for him, and Carlito goes and follows Walberto. He sits down with Rolando, who thanks Carlito for never giving up his name despite spending five years in prison. While he was there, Rolando got rich though, so he’s wondering if Carlito thinks he owes him, though he assures him this isn’t the case because he’s retired. Later, he drives with Guajiro, and Guajiro tells him how he’s still in school, but he also has a job making deliveries for Senor Pablo Cabrales. He shows Carlito the $30,000 in his pocket that he has to deliver, but he’s not too impressed. As Guajiro drives, he asks Carlito if he can accompany him on a pickup he has to make because it’ll scare the people there, though he insists they’re all friends. Carlito does not want to be involved but relents and gives him ten minutes because he promised Guajiro’s mother they would be there for dinner. They walk into a barbershop that’s a front, and Carlito is very aware that they’re going to be walking out with $30,000 worth of drugs that is more than enough to put him right back into prison.

They walk into the back, and everyone is playing pool and hanging out. The main guy doesn’t know Carlito but realizes he does after Guajiro mentions how he used to work with Rolando. As they talk, Carlito notices the bathroom door in the back, and it’s opened slightly. Carlito is becoming a bit suspicious as to what is happening. The guy takes Guajiro over to count the money on the side of the room while Carlito watches the guys play pool. Carlito walks a bit and asks if the bathroom is open, but the guy gets in front of him and says it doesn’t work. As he says this, Carlito sees the door of the bathroom close. Something is up and he’s now on high alert. To distract the two guys about to play a game of eightball, he interrupts to show them a trick shot. At the same time, his eyes constantly glance over at the other end of the room in search of potential danger. As he sets up the shot, the main guy has Guajiro reach into the cooler for a beer. Using the reflection of one of the pool player’s sunglasses, Carlito sees a man exit the bathroom with a knife just as the guy tells Guajiro that his boss is dead and so is he. Carlito shoots a ball directly at one guy and springs into action. He hits the other guy with his pool cue and takes his gun, prompting a shootout. Unfortunately, the guy with the knife kills Guajiro. Carlito is also shot in the process but recovers and runs into the bathroom for cover. He shuts off the lights and challenges anyone remaining to come at him, but they’re all either dead or dying. So, he comes out and sees the aftermath. Hearing police sirens, he says goodbye to his deceased cousin, takes the money, and escapes.

Following this, Carlito meets with Kleinfeld in his office. He saw Saso’s place and agrees that it could do big business with the right owner. Kleinfeld offers to advance him $25,000 to take over the lease, but he decides to use his own money. He says it’s money Rolando owed him, but we know it’s the money from the Guajiro incident. Before Carlito leaves, Kleinfeld asks him for a favor. He says it’s not a big deal or anything, but he needs a temporary bodyguard because of a “misunderstanding”, so Carlito says he’ll get Pachanga for him. They both discuss their positive feelings about the potential of the club, but Carlito once again tells him that he’s leaving once he makes his $75,000. That night, he goes to the club to see Saso, though he tells Carlito that everyone calls him “Ron” now. They sit down and talk business. He knows Saso owes money for his gambling, so he asks how much. When Saso says it’s around $50,000 to $60,000, Carlito knows he’s lying and it’s actually around a $100,000. Additionally, he owes it to a group of people, but Saso says $25,000 will quiet them down and he wants Carlito to cover a quarter of his end. Carlito tells him he’ll give him $25,000 cash tomorrow and he’s going to come in for half his end instead. Saso laughs this off, but Carlito gets real with him. He’s saving his ass because he assumes Saso either owes money to Fat Anthony or Scooze, and he’s going to end up dead in a trunk somewhere. Realizing what could happen, Saso agrees to the deal. Now, Carlito is in charge, and he brings in Pachanga as his backup at the club. Pachanga thinks Carlito is going to make him rich, so there’s an extra incentive to protect Carlito because he thinks Carlito might die before he scores big. After arguing with Pachanga once he pronounces Kleinfield’s name wrong, a waiter interrupts and points out a customer to Carlito who said he doesn’t have to pay.

This is unacceptable.

Carlito walks over to the customer, Benny Blanco from the Bronx (Leguizamo). Carlito confronts him about the check. Blanco initially ignores Carlito until he looks up and realizes who he is. He apologizes but explains that Saso owes him money and is slow to pay, so he’s just working it off for him. Though he understands, he explains to Blanco that the place is under new ownership. Saso may owe Blanco, but Carlito does not. So, he has to pay. Blanco agrees and squares everything away. Before Carlito can leave, he gives Carlito major props in front of the people he’s with and asks for Carlito to sit down with him. He talks about how he’s starting out small and building up his own organization and how he just wants two minutes of his time to talk about potential work stuff, but Carlito turns him down and leaves. As the club is getting closer to closing time, a worker named Steffie (Ingrid Rogers) comes by and they discuss Benny Blanco and how Carlito doesn’t have a woman because he’s a workaholic. As they talk, he glances over at a woman on the dance floor. She looks a lot like his ex-girlfriend Gail (Miller). Carlito met her a year before he went to prison. She was this dancer who studied ballet and had dreams of being a Broadway star. He misses her deeply and is still sad over breaking her heart all those years back. One night, he tracks her down but can’t seem to approach her before she goes into a building for her ballet practice. Even so, he watches her from a building across the street. Once it concludes, he approaches her and they go to a cafe to reconnect.

Gail updates him on some shows she’s acted in, but she’s only doing club dates right now. She asks about prison, but he downplays it. This spirals into the both of them talking about how Carlito broke up with her for her own good because he didn’t want her waiting for him when he was facing a thirty-year prison sentence because not only would it not be fair to her, but it would have drove him crazy because he would just be wondering what she’s doing all the time.

Honestly, that’s a fair point.

He tells her about the club and how he just plans on making a certain amount of money and seems calmer than usual, which she notes. She can see something has changed in him, and he admits he’s never felt like this before. She has to go though, so he asks if he can call her. Gail tells him that she’ll call him instead. After they embrace, he apologizes for breaking her heart and she heads out the door. Carlito has some making up to do, but his intentions are real. He is a changed man. However, the streets will do their hardest to try and pull him back in. Additionally, his loyalty to Kleinfeld will not help matters much either. In fact, it will cost him dearly.

My Thoughts:

Don’t call this a retread. Don’t minimize the greatness of Carlito’s Way. Yes, this is another Spanish-speaking gangster film with a lot of violence that leads to a tragic end. Yes, this is director Brian De Palma teaming up with star Al Pacino again ten years after the first time they collaborated. Yes, Pacino’s character is in love with another white girl, and yes, oddly enough, there are a lot of club scenes. Despite this overwhelming evidence, don’t disrespect this cool crime thriller by calling it a Scarface copy. Carlito’s Way is one of the most underrated gangster films of all time and deserves to be in the conversation much more often than it’s brought up. Filmmaker Brian De Palma brings 1975 New York to life and fills the backdrop with the melting pot of different cultures and people in the area and how it became infiltrated by criminal activity, corruption on both sides of the law, the mafia and the glory coming with the gangster lifestyle, and the rising influence of cocaine and how much it changed the world our star Carlito Brigante once knew. It’s all about the potential for quick money, the power that comes with it, and the notoriety, whether it be good or bad. With a magnificent combination of unforgettable characters, action that is not only exciting but reminds you how precious life is, memorable and stylish costuming, a great score that not only encapsulates the time period but mixes in well with the emotion of the story, and some seriously wonderful set pieces, this is one of Brian De Palma’s best works and should be talked about a lot more when in comparison to other great films of the 1990s, especially the others in its genre.

Once again, Al Pacino is an invigorating and enigmatic presence that carries this awesome and unforgettable crime epic. It’s hard to narrow down the list because of such an unbelievably successful career, but this is one of my favorite Pacino roles, though it’s not necessarily because his choices were flawless. For instance, there’s not a single soul who would wear a black leather trench coat that often in the late summer in New York. Also, his Puerto Rican accent sounds much more like Pacino himself attempting an impression of Dusty Rhodes. Despite this, he still has the “movie star” aura around him any time he’s onscreen. It’s undeniable. He commands the room and carries himself like the respected gangster he plays. He is very much the famed “Carlito Brigante” in every way. Even the characters who don’t necessarily know him can tell there’s a quality about him that cannot be denied. Any time he’s in a scene, you can’t take your eyes off him because not only is he telling us things through the character’s narration (which is arguably an unnecessary addition depending on who you talk to), but he also tells us so much through his reactions to the blocking of the scene and everyone else who occupies it. The greatest example of this is in the phenomenal pool hall scene. Again, despite his odd accent, this is how good later Pacino still was. Right from entering the room, along with a serious mood change highlighted by Brian De Palma’s direction, the audience can sense something different as soon as the two characters walk in. The heavy lifting of the intensity is straight from the nuances of Carlito’s body language. With Pacino, it’s a master of his craft at work.

From his unsure greetings to the people Guajiro is meeting up with to noticing the bathroom door slightly open, he owns the scene with just his eyes. It’s the widening of them, the glossy look, and the way in which he looks at certain objects and people that draw us into the anxiousness of the moment, despite the happier music being played. We become numb to it, only focusing on his actions and wondering who and what will strike first because we know things are about to turn up in any given moment. In so many different Pacino-led films and my subsequent reviews of them, a regular occurrence is me complimenting his expressive face and how well he uses his eyes for emotional appeal in so many different ways. Whether it was in Dog Day Afternoon, Scarface, or whatever else, Pacino can always say so much by just scanning the room and looking ever so slightly in certain directions. Here, it continues as he distracts the others with his trick shot and through this build up, with De Palma’s switching back and forth between this and the setup to kill Guajiro, your heart starts to pump like you wouldn’t believe. With this scene alone, the movie makes a statement. Death is creeping around every corner in Carlito’s world. Despite his honest plea of not wanting to be involved again, the circumstances of his previous life continue to grab onto his ankles and pull him slightly closer to a tragic end. As he takes a few steps forward to his dream of living in the Bahama, there’s something that continuously forces him to take a few steps back into his old life in spite of his best efforts. With this, it gets him closer to the impending doom he’s trying hard to avoid. This first shootout is made well enough to keep us on high alert for the rest of the film.

Carlito’s Way is not filled with the violence or action of a Scarface, but that’s okay. The story is done well enough that it never needs it. Sure, there are some sequences sprinkled in here and there, but it’s handled in a much different way that spotlights why this is a much different gangster film in comparison. It differentiates itself from so many other gangster films because of how it treats the preciousness of human life. It’s never glorified. Any time there is a murder or a beat down, you think, “Oh shit. This could be bad”. It’s treated with care. Obviously, there are still action sequences and shootouts, but a lot of gangster movies have instances where certain killings are thrown at you for entertainment purposes. In the grand scheme of things, that’s okay, but this is why I enjoyed Brian De Palma’s third turn at the gangster genre. With every death or violent action, the audience becomes increasingly worried for our main character trying his best to stay straight and get out before hellfire and brimstone comes towards him and doesn’t let him leave. He knows he’s getting closer to leaving, but he also becomes very aware of the trouble looming on him if he stays just a minute past the due date. Again, Carlito is a main character who appreciates his new lease on life. He realizes how lucky he is to receive this second chance few are afforded, and he knows he can’t screw up, which is why he is so set on his goal. Everyone is surprised, which only reminds us how bad the enviornment he lives in actually is and how few of these people he can actually trust.

Remember kids, the environment that you surround yourself with and the company you keep are very important in regard to your mentality, especially if you aren’t strong-willed to begin with.

Thankfully, Carlito is strong-willed, which is why the viewer wants him to succeed. With a committed Pacino, we are fully invested in his plight even though we know because of the opening scene that it may not end well. Unfortunately, he’s not strong willed enough to completely remove himself from the people he associates with. It’s almost impossible, but he thinks it’s okay because he knows it’s temporary. Once he gets his $75,000, he’s out. Unfortunately, this is just another theme of the film: time. There is never enough time. No matter what you do or intend to do, there will never be enough time for you to do everything you want. Along with this, a few bad decisions can make life move at such at a rapid pace and you will miss out on even more time. Remember, we’re only on this Earth for so many years. Then, it’s over. You never realize how precious every minute is until you’re reminded when death flashes its gun before your very eyes. Just when Carlito is understanding this concept and how he wants to redirect the course of his life to appreciate the years he has left, those few small decisions and his fateful attribute of undying loyalty become the decisions that move his life at a pace similar to a speeding bullet headed directly into the ground. This is a gangster who has repented and wants to save his own life. Not only do we like Carlito, but we understand him. He just wants his girl and to live somewhere by the beach, is that too hard to ask?

Evidently yes, as time tells us.

Because Carlito is so adamant about moving on, certain lines are spoken with such emotion that you can’t help but get goosebumps. It’s like after the boat scene where Carlito comes to the realization of what has happened with, “You killed us, Dave. You killed us”. In a true tragedy, characters will eventually reach the point of no return, where there is no coming back from what you did. Carlito says Kleinfeld has gotten there because of what he did, as he has now become a marked man of the Italian mafia. He has crossed the line into pure villainy to where Carlito can’t even save him. What our star doesn’t realize is that with him being there, Carlito has also reached the point of no return simply because of participation in the matter. The audience still believes in him, but the world in which the movie resides in sees it as stepping over the line completely into “Dead man walking” territory. Everyone knows how close he is with Kleinfeld and how he’s defended and backed him up on so many occasions. Early on, he tells Pachanga that Kleinfeld is his “brother”. Even Gail knows Carlito’s loyalty to the man, despite the obvious red flags of his best friend. Though Carlito isn’t blind to Kleinfeld’s issues throughout, he still stands by his side because it’s like he said in that courtroom, he’s indebted to him. This is why what follows is so powerful. Immediately after the fateful boat scene, he gets in Kleinfeld’s face and demands he say they’re even. This is when you know he’s serious. Everyone knows he should’ve dropped the self-destructing lawyer a while ago, but he stuck with him at every turn. When he finally gets in his face and demands Kleinfeld say they’re even, it’s clear that he can’t defend him anymore. This is the point of no return that he wants no part of. Unfortunately, it’s too late. Too much time has passed and too much is known about their friendship. They will forever be linked, and Carlito gave up too much time trying to help him.

When Carlito was younger, it’s heavily implied that he was involved in more violent situations, which is why he shies away from the conversation, a true mark of a man who has seen and done it all. Based off his instincts and suspicions in scenes like in the pool hall or how he interacts with “made men” and other gangsters, it’s obvious he’s experienced and learned a lot. However, this is why he’s done with that life. He’s tired of trying to keep his “killer” reputation and watching his back at every turn. The gangster life is always about trying to stay at the top and to maintain your clout, so you are respected and not messed with. You have to do things here and there to keep the up-and-comers at bay too. Otherwise, they’ll try and test you. It’s a tale as old as time, but Carlito is too old for that. It’s like how the counselor said to him in prison about how life eventually slows down. Now, he wants to start preparing for it. Can he still strike fear into anyone when tested? Without a doubt, but the responsibility and stress of always being on the ball doesn’t seem necessary anymore. He knows how precious life is, and he’s already missed five years of it in prison. He’s not stupid. He knows how lucky he is to miss out on that other twenty-five years because of the technicalities of the American justice system, which is why he’s taking his promise of steering clear of his previous lifestyle seriously. Again, despite some obvious similarities, Carlito’s Way is entirely different from Scarface. The feared and respected Carlito Brigante is not the loose cannon who wanted it all in Tony Montana. Sometimes, he can’t help but find himself in these situations because of the people he knows, but he wants no part of it. For the first time in a while, we have a gangster that promises to be done with the lifestyle but actually makes us believe it. How many times have we seen the often-used trope of, “I’m done with this life…after one last job”. We go along for the ride more often than not, but mainstream audiences have seen this so often, it has become increasingly hard to fully believe it nowadays. With Carlito’s Way though, the character of Carlito Brigante’s promise to stay clean, though muddied because of the company he keeps, is earnest.

With his concerned expressions about those around him and an honest demeanor that brings in the viewer to his authentic plight, we can’t help but feel for Carlito and want him to succeed in getting out. The only thing holding him back is his adherence to the street code he’s lived his life by. Basically, it boils down to the Chappelle’s Show skit, “When Keeping it Real Goes Wrong”. Even if Carlito wants to avoid criminal activity at all costs, loyalty is ingrained in him. It’s his biggest attribute. Though it’s a strength for most, it’s his biggest weakness. Carlito can’t seem to give up on this internalized trait of his even if it takes him in directions he clearly doesn’t want to go. From the opening scene, we know Carlito will be fatally shot at some point in the film. This isn’t a spoiler. If anything, it’s crucial in understanding the flaws of our main character and in knowing how deep his feelings of loyalty go and why it could lead to his own undoing. It’s a great setup for the rest of the story to make sure we don’t get too comfortable. Of course, this all leads us to David Kleinfeld. Played by Sean Penn at his most despicable, Kleinfeld is the definition of a scumbag lawyer. With an unforgettable look resembling Larry Fine if he was on cocaine and an attorney, the almost unrecognizable Penn embodies the role of a lawyer that cannot be trusted. When every bad thing that happens in the movie can be rooted back to your character, you know you did a great job. Dealing with serious criminals, heavy hitters, and wise guys since he came out of law school, Kleinfeld is in deep with some of the worst people in New York and has turned into an untrustworthy, slimy, sleazeball of a person because of it. Eventually, Norfolk reveals to Carlito that during his time in prison, Kleinfeld turned into a bigger criminal than what he was at his worst.

Maybe it was out of survival, as Carlito states in narration that Kleinfeld had to initially act like he wasn’t scared when dealing with so many unsavory characters, going to extra lengths to try and protect himself. However, now that Carlito is out, lying piece of shit Kleinfeld is a hotshot lawyer who isn’t scared of anyone. He’s fucking women in clubs, threatening gangsters at gunpoint, and going as far as he possibly can without a care in the world. With the exception of his involvement to Tony T, wealthy cokehead Kleinfeld is starting to think he’s untouchable. He’s living life to the fullest and has found himself deep into in criminal activity because of the company he surrounds himself with. When springing Tony T from Rikers Island is brought up, Carlito can’t believe it asking, “Dave, you’re a lawyer man. What the fuck is happening to you?”. This shouldn’t be a possibility, but this is how deep Kleinfeld has gotten into all of this. He doesn’t see it because he’s blinded by the drug use and his own ego, but it gets to the point where even his best friend Carlito tells him straight up once Kleinfeld admits to ripping off a mob boss for a million dollars, “You ain’t a lawyer no more, Dave. You’re a gangster”. As Carlito states though, this isn’t a lifestyle that you can join later in life. Essentially, this is something you have to train for, something you have to be born into because of your learned environment or whatever else. If you don’t have the experience and respect of a Carlito, you will get too comfortable and you will make mistakes, which is why Kleinfeld’s recklessness becomes a death sentence. He forgets that there’s always a bigger fish, and that bigger fish will always be the Italian mafia. Honestly, it’s some of Penn’s best work and easily his most underrated.

Along with a highly memorable one-off scene involving wheelchair bound Viggo Mortensen, rounding out the rest of the supporting cast is John Leguizamo as up-and-coming gangster, who was described by Saso as Carlito “20 years ago”, Benny Blanco from the Bronx. In a smaller role, Leguizamo makes every line count while maintaining a swagger and an attitude of someone who could snap in an instant. On paper, Leguizamo coming face to face with Pacino would be a little hard to believe as far as acting heavyweights go, but they play up the tension so well between them that the audience buys in without question. One of the best scenes of the film is when Carlito finally has enough of Blanco causing a ruckus in his club because Blanco wants club whore Steffi to leave Kleinfeld and join him. This prompts a scuffle to happen where Kleinfeld points a gun to Blanco’s face. They take Blanco to the back, and Carlito tells Blanco that he could have him killed just like that if he ever showed his face again. There’s this unforgettable closeup of Carlito’s serious expression right after he says it. Then, it switches to the dry-eyed and confident Blanco closeup, where he brandishes a crooked smile and doesn’t even wince, promising the same for Carlito. It’s a moment of foreshadowing that cannot be ignored, with even Carlito admitting he screwed himself by not taking it a step further. Heightened by the red lights of the club in the background, the intensity of this momentary silence between the two speaks volumes and becomes an omen of what is to come. It’s magnificent. Though it may be forgotten about in the grand scheme of things, it was one of the most eloquently filmed scenes of the entire film.

The only thing that never grabbed me was Penelope Ann Miller as Gail. Maybe it’s because she looks 30 years younger than Pacino, and it’s noticeable, but I wasn’t feeling the chemistry between the two. It makes sense for Carlito to want Gail back and make up for what happened years ago between them. As I stated in the summary, his reasoning for breaking up with her before he went to prison was actually hard to argue with. With this being said, something wasn’t clicking with Miller and Pacino. Maybe it’s because he didn’t have to fight too much for her, and she was just too willing to come back to him after not seeing him for five years, but I find it hard to believe that she had no one else in her life for a five-year span despite being a dancer who frequents clubs. At the very least, some emotional scarring she has to overcome first would make a great deal of sense. How does she feel about his gangster lifestyle? How did they even meet? The only conversation they had where it was a little bit introspective was when she asked if he killed anybody, but she immediately apologizes. Then, it just leads to Carlito talking a bit about his backstory as a kid in New York and how he grew up to become the person he did. We really never learn much about Gail or her life, hopes, or dreams. Besides her wanting to be an actress, this is pretty much all we learn about her. Plus, she gives up on the one dream she had to follow Carlito to the Bahamas. Does she have a plan following this, or is she just going because there is literally nothing else to look forward to? You don’t care enough to find out either because her characterization, along with Miller’s performance, is so bland.

It’s just one of those inclusions that never gets going. Even the small discussion they have after Carlito finds out she’s a stripper is exactly what you’d expect. The discourse between them seems like it came word for word from a comment thread found under someone promoting their OnlyFans on Twitter. Even so, the Carlito/Gail angle doesn’t ruin Carlito’s Way because a love story was a logical element to help a gangster become a better person. It gives him more of an incentive to work harder at his goal. Unfortunately, there’s never enough included in this part of the story for us to really care about Gail. That’s what hurts it. Also, Miller was overly melodramatic in the role, especially in the earlier scenes when he’s trying to win her back. It becomes even more groan-inducing when they argue. Sure, it gave us the cool moment where Carlito cuts his hand bashing the mirror, but everything she’s arguing just comes off as whiny. Carlito is right. She is not listening to him or his points. Even if she was right about Kleinfeld, Carlito isn’t stupid. He knows his best friend is getting too far into the deep end, but if she actually understood who Carlito was as a person, she should know why he has to go through with this. Otherwise, it would bother him for the rest of his life. Then again, it could be chalked up as a dialogue issue. The intention of the scene was necessary, but the actual lines were poorly constructed. It just felt wrong for Gail to actually believe she was right in telling Carlito that he hasn’t changed a bit.

Really? I don’t even know him personally, and it’s still obvious he’s changed for the better. The man is just loyal to a fault. Sometimes, reactionary commentary like that just bothers me to my core.

With every rewatch, I go back and forth about the narration. In one viewing, it felt like Pacino was saying the most random shit possible to practice his accent and most of it seemed to be ramble on about nothing. If you agree with this side of it, chances are you won’t like the ending as I was initially in that camp. With a second viewing though, it started to feel right considering the circumstances and the final thoughts of someone who was ever so close to fixing his life. In another viewing, you start to appreciate the little insights of Carlito’s thought process as he wanders through the landscape narrowly avoiding death. On the other hand, you may also find it unnecessary at times. Obviously, it’s up to you, but it really depends on your mood if you feel like the narration is a useful tool that adds to the final product or a distracting element that doesn’t add any real value to the character. It’s hard to say, and it depends on the day.

Carlito’s Way should never be forgotten when discussing the great gangster films of the 1990s. When discussing films like Goodfellas, Casino, Bugsy, King of New York, or Donnie Brasco, Brian De Palma’s beautiful return to the genre should be spoken of in the same breath. With Al Pacino adding another legendary character to his resume, a frenetic third act that is worth every bit of the buildup, and a litany of sequences, moments, and supporting stars that piece this fantastic crime drama together, I will always recommend this borderline classic.

Fun Fact: Producer Elliot Kastner claimed that when they thought about doing this film in the 1980s, Marlon Brando was going to play David Kleinfeld.

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