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"You think you’re big time? You’re gonna fuckin’ die big time!"
"Favor gonna kill you faster than a bullet."
Carlito Brigante
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Carlito's Way is a 1993 Brian De Palma film in which Al Pacino plays a Puerto Rican gangster hoping to reconcile and start a new life after his five-year stint in jail. It's a far cry from being another Scarface, though Carlito's Way may be seen as its spiritual successor. Indeed, the two films are nearly inversions of each other; whereas Tony Montana rises from a nobody to a prominent drug lord, Carlito Brigante attempts to reform after a life of notoriety. Both films however, go their way to show that gangster life is not all it's cracked up to be.

In 1975, Carlito Brigante is released from prison with help from his lawyer and friend David Kleinfeld (Sean Penn), after discovering that the prosecutor's evidence has been gathered through questionable means. From this second chance at life, Carlito decides to reform himself for good, vowing to stay legitimate and out of crime's way. He manages to buy a stake in a successful nightclub and rekindle his relationship with Gail (Penelope Ann Miller), a beautiful dancer.

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Unfortunately, Carlito's criminal past catches up with him - his former associates, along with an up and coming gangster Benny Blanco from the Bronx, attempt to cajole him back into the gangster life. Further complicating things, the FBI wishes to see Carlito Brigante put back in jail. But the biggest obstacle is David Kleinfeld's dilemma with a mafioso boss 'Tony T.' who is locked up inside Rikers Island; Tony T. wants Kleinfield to spring him out, and Kleinfeld isn't sure of what other plans Tony T. has in mind for him afterwards..

The film was an adaptation of two novels by Edwin Torres: Carlito's Way (1975) and its sequel After Hours (1979). It left out several events of the first novel. Said events were eventually filmed for a prequel. Carlito's Way: Rise To Power was released straight to video in 2005. It covers the criminal activities of Carlito in the 1960s. The prequel was directed by Michael Bregman. The titular character was played by Jay Hernandez. The film remains relatively obscure, failing to gain much attention.

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This film has examples of:

  • Action Prologue: The delivery that Carlito accompanies his cousin on is this, given that it takes place a month before the main action of the film. It isn't specifically framed as a prologue, however, only being subtly disconnected from the main body of the film.
  • Adaptation-Induced Plot Hole: Carlito gets angry when anyone compares Benny Blanco to him in his younger years, which is implied to be Suspiciously Specific Denial. The 2005 prequel establishes young Carlito as just as ruthless, but a much better man than the cocky, sycophantic and misogynistic jerk Benny is.
  • Alliterative Name:
    • Benny Blanco from the Bronx.
    • And Tony T.
  • Amoral Attorney: Kleinfeld is probably the worst kind of crooked lawyer. He steals $1 million from his own mob boss client, Tony Tagliucci, then double crosses and murders him and his son. He also snitches on Carlito.
  • And This Is for...: Vinnie when he enters Kleinfeld's hospital room to assassinate him.
    Vinnie: There's a delivery for you, Mr. Kleinfeld.
    Kleinfeld: From who?
    Vinnie: [pulls out gun] From my father, and my brother!
  • Asshole Victim: Carlito decides to let his lawyer, Kleinfeld, get killed by Vinnie T. for killing Vinnie's father. Then there's also Pachanga, who was killed after betraying Carlito at the end.
  • Badass Beard: Carlito is a gangster who is a street legend, and he has a thick beard.
  • Badass Longcoat: Carlito's black leather coat.
  • Big Rotten Apple: The film is set in The Bronx, New York's most infamous crime-ridden district.
  • Bait-and-Switch: Just as Carlito makes it to the train and the police gun down Vinnie T, Benny Blanco shoots him three times, having been alerted by Pachanga to follow him.
  • Big Bad Friend: Kleinfeld has already sold out Carlito to the FBI with trying to frame him of cocaine dealing, even having offered to testify against him. Though interestingly, the FBI believe Carlito's attempt to go straight is genuine, and try to use him to instead bust Kleinfeld.
  • Bittersweet Ending: Though Carlito dies in the end, Gail makes it out to the Bahamas with their unborn child.
  • Bottomless Magazines: Averted. After firing a Colt .45 seven times, Carlito runs out of ammo and has to pretend to reload to scare some thugs.
  • Brooklyn Rage: Tony T., despite being Italian, is this flavor of threatening, being a stocky, brutish, meat-headed Guttural Growler with a Noo Yawk accent who promises Kleinfeld to "snap [his] neck like a breadstick".
  • Call-Forward: Several lines in the 2005 prequel:
    "You ain't X no more, <name>. You a Y now."
    "Hey, remember me? <Name> <Nickname> from <place>?"
  • Cassandra Truth: Carlito has the problem of not listening to warnings from anyone that isn't a gangster.
    • Gail constantly warns him about Kleinfeld. She was right, Kleinfeld tried to sell him out to Norwalk the minute he got cornered.
    • He also ignores Saso who informs him Pachanga is spying for Benny Blanco. This one costs Carlito his life.
  • Chekhov's Gun: Kleinfeld's .38 snub-nose
  • Chekhov's Gunman: Literally. At the end of the movie, after seemingly managing to avoid certain death, Carlito is gunned down by a young gangster he had several brief run ins with throughout the film.
    "Remember me? Benny Blanco from the Bronx?" * BLAM BLAM BLAM*
  • Chronic Villainy: Subverted. Carlito is unwittingly involved in several crimes, but he never directly perpetrates any himself. Unfortunately, the FBI and others suspect him of this.
    • Played straight with Kleinfeld however; the guy seems genuinely incapable of doing anything honestly. Norwalk informs Carlito of some of the crimes they suspect him of.
  • Cluster F-Bomb: Kleinfeld when he's high on cocaine, contrasting his nerdy outlook. Also Benny.
  • Damn, It Feels Good to Be a Gangster!: Deconstructed throughout the film. Everyone who believes in this trope is a young wannabe (or at best, an up and comer) that hasn't been in the game long enough to see how much it sucks. Older gangsters who've been in it awhile, such as Carlito, know the downside to the gangster life and have no illusions about it.
  • Diabolus ex Machina: See Hope Spot and Face–Heel Turn.
  • Determinator: Vinnie T takes at least two or three to the chest, drags himself covered in his own blood across Grand Central Station, and still keeps shooting.
  • Discriminate and Switch: Tony T to Kleinfeld.
    Tony T: I never liked you, Kleinfeld. Not because you're a Jew, huh. I know plenty of Jews. No, cause you're a lying piece of shit.
  • The Don: Tony T. is, if not a Don, a major mafia heavyweight, and he wants Kleinfeld to help him escape jail. He also openly states that he has very nasty things planned for Kleinfeld should Kleinfeld refuse.
  • Drugs Are Bad: Kleinfeld's cocaine habit culminates with him making big, stupid mistakes and then bigger and more stupid mistakes to try and cover up his earlier blunders.
  • Dutch Angle: Used pragmatically - whenever the camera tilts, it's levelling two or three faces which are at different heights. As it happens, this positioning occurs in especially tense moments.
  • Enemy Mine: Defied by Carlito. Norwalk offers Carlito complete immunity and asylum on the Bahamas with Gail if he testifies against Kleinfeld once he reveals the latter's betrayal. Carlito refuses because he places Honor Before Reason and gets his revenge on Kleinfeld by emptying his pistol, not cooperating with the police.
  • Exact Words: Benny told Carlito that if he didn’t kill him outside of the club that if he ever saw him again, he was going to kill him and boy he wasn’t lying.......
  • Face–Heel Turn: Carlito's best buddy Pachanga sells him out to a rival gangster, in the very end.
  • Fatal Flaw:
    • Either Carlito's past, his code of loyalty even to those who put him back In Harm's Way, or his determination to stay straight.
    • Kleinfeld's stemming inferiority complex, which leads to putting Carlito into deep trouble after he botches the Rikers Island breakout.
  • Fat Idiot: Saso (now Ron) who's vain, naïve and easily pushed around by tougher gangsters such as Carlito or Benny Blanco.
  • Foil: Contrast Carlito's determination to stay straight with Kleinfeld's efforts to dig himself into a hole of his own corruption and stupidity.
  • Foregone Conclusion: See How We Got Here.
  • Foreshadowing:
    • Pachanga is mentioned early on to be interested in selling Carlito out.
    • Kleinfeld's gun.
    'Kleinfeld: Would you fucking put that away? It's loaded! (Not anymore.)
  • Gambit Pileup: Carlito once his mistakes catch up to him. After Kleinfeld's death, Saso tries to steal his money and that costs him valuable time when he has to run for his life from Vinnie T. and company; after he narrowly escaped them, he's shot by Benny Blanco, whom Pachanga sold him out to.
  • Gang Bangers: Guajiro, Carlito's cousin who's still in high school but already an errand boy to the locak drug mob. He's really proud of it and hero-worships Carlito, but gets killed for it.
  • Genre Savvy: Carlito is experienced and perceptive enough to see when a situation is pointing south and survives many plots that would have put anyone else out of business. At the end, when betrayals pile up, it gets too much and even then he acknowledges he should have trusted his gut about a few things.
  • Good Cop/Bad Cop: Bill Norwalk as the bad cop, always being stern and menacing, and his Hispanic assistant Valentin whose role is to butter Carlito up to testify against Kleinfeld.
  • Friend Versus Lover: Gail doesn't like Kleinfeld at all and tells as much to Carlito, insisting that he cuts ties with him. Justified since Kleinfeld is acting erratically and possesively out of insecurity as well as anxiety because he is planning Tony T's murder and really does get Carlito in trouble.
  • The Hero Dies: Carlito was killed before he could escape on the train with Gail.
  • Hidden Wire: Norwalk's M. O. Carlito gets out of jail because Norwalk bungled one of these and taped him in an illegal fashion. He then sent Lalín, one of Carlito's past friends comes by for a visit, to have Carlito find Lalín, to get intel on who Carlito's selling drugs to (no one). Lalín claims he turned it off beforehand. Since later Norwalk only cites "word on the street" on the fact Carlito is clean and he has no reason to hide the fact he sent Lalín, he may have really turned it off. Later Norwalk reveals he used it again to tape Kleinfeld framing Carlito.
  • Honor Before Reason: Carlito in several instances, but it leads him into trouble. See Tragic Mistake.
  • Hope Spot: Carlito gets away from the Italian mobsters chasing him and it looks like he's going to make it to the train, but then Benny Blanco from the Bronx does Carlito in from petty revenge...
  • How We Got Here: The movie starts with Carlito on the gurney.
  • I Just Want to Be Badass:
    • Gaujiro, Carlito's wannabe Gang Banger cousin, looks up to him but gets killed for his efforts during a drug deal.
    You said they were your friends, but there ain't no friends in this shit business.
    • Kleinfeld when he pulls a gun on Benny Blanco. Carlito just tells him it's going to get him killed. Ironically, it might have saved him when an assassin came, but by then Carlito had caught wind of Kleinfeld's betrayal and secretly unloaded his revolver.
  • I Know You Know I Know:
    • Kleinfeld and Tony T. who's pretty sure he ripped him off for 1 million dollars. He was right.
    • Norwalk and Carlito about Carlito being with Kleinfeld on the boat when he murdered Tony and Frankie T.
  • It's All About Me: David Kleinfeld, who has the unfortunate character traits of a chronic inferiority complex and a massive ego.
  • It Works Better with Bullets: Carlito secretly unloads Kleinfeld's revolver so he's unable to defend himself against the mafia hitman waiting outside.
  • Jerkass Has a Point: Tony Taglilucci is quite rude and aggressive towards Dave Kleinfeld because he (correctly) suspects that Kleinfeld skimmed $1 million in bribery money.
  • Junior Counterpart: It's frequently said that Benny Blanco is a younger version of Carlito. Carlito thinks Benny is just a cheap punk, (and, it's implied, sees a lot of himself that he doesn't like in Benny) and does not take kindly to these comparisons.
  • Karma Houdini: Benny Blanco from the Bronx not only escapes his karma, but defies Carlito's as well.
  • Karmic Death: Kleinfeld and Pachanga at the end.
  • Kick the Dog: After all the trouble Carlito went through to help him, Kleinfeld has already betrayed him to the FBI anyway.
  • The Mafia: Tony T. and his family are gangsters of Italian origin, and at a time when the mafia still ruled the New York underworld.
  • The Millstone: Kleinfeld gets Carlito out of jail. After that, he only gets in the way of Carlito's goal to clean up his act.
  • The Mole: Carlito's friend Lalín is wearing a wire as part of the FBI's attempt to bust Carlito, but he's found out quickly. Also Kleinfeld and Pachanga.
  • My Girl Is a Slut: Carlito isn't incensed at all when he sees Gail dance at a strip club. On the contrary, he's captivated. Later he enjoys watching her moves when she dances with some Italian guy at a bar, not jealous in the slightest. The one who acts possessive then is Kleinfeld.
  • Narrator: Carlito narrates throughout the movie, stream-of-consciousness.
  • Neck Snap: Tony T. threatens Kleinfeld with that. "Like a breadstick".
  • Nervous Wreck: Kleinfeld. It's a result of his White Collar Crimes, paranoia, inferiority complex and the drugs. Selling his best friend out and planning Tony T's murder take a toll on him too. It's all in stark contrast to everyone else's Nerves of Steel.
  • Nice to the Waiter: Carlito treats the waiter, Rudy, with enough respect, unlike patrons like Benny Blanco or the club's previous owner, Saso, who constantly yells at him and orders him around.
  • No Good Deed Goes Unpunished: In an altercation with Benny Blanco, Carlito roughs up and humiliates Benny, but chooses to spare Benny's life, despite knowing that doing so is an enormous risk and may make people think he's gone soft, which could put a target on Carlito's back. Benny kills him in return.
  • No Honor Among Thieves: Carlito discovers this the hard way, getting betrayed three times by Lalìn, Kleinfeld and Pachanga.
  • Noodle Incident: Characters would often talk about incidents and people from the past that aren't in the movie. Example:
    Oh, Carlito! I heard of you, man. You used to run smack with Rolando.
  • Not-So-Harmless Villain: Benny Blanco at the end.
  • Off on a Technicality: Carlito got out of jail because of a prosecutor's mistake.
  • Pay Evil unto Evil: Kleinfeld uses Carlito to murder a prominent criminal because of his own egotism and gets Carlito a mark on his back from the Maffia. Carlito lets him have what is coming to him by arranging his death.
  • Pillow Pistol: Kleinfeld keeps one while he is recovering in the hospital. Carlito tells him to keep it in plain sight and unloads it. Cue Oh, Crap! from Kleinfeld before he is shot by Vinnie T..
  • Pretender Diss: Carlito does not like gangster wannabes. At all. The problem is the guy he directed the comment to, Benny Blanco, wasn't a gangster wannabe. He was a young modern version of Carlito himself. It's even pointed out in the film.
    "Maybe I don't give a shit! Maybe I don't remember the last time I blew my nose either.. Who the fuck are you? I should remember you? What, you think you like me? You ain't like me motherfucker, you a punk. I've been with made people, connected people. Who've you been with? Chain snatching, jive-ass, maricón motherfuckers. Why don't you get out of here and go snatch a purse."
  • P.O.V. Cam: Carlito on the gurney.
  • Prison Changes People: Carlito resolved to live lawfully after his experiences in prison.
  • "Psycho" Strings: When Kleinfeld visits Tony T. in prison. It serves to foreshadow Kleinfeld's villainous schemes.
  • Really Gets Around: Stephie sleeps with both Benny Blaco and Kleinfeld, then later bluntly asks Carlito why he never tried to sleep with her. This is true of a number of her friends too, as they start turning a party of Kleinfeld's into a semi-public orgy, much to Kleinfeld's chagrin.
  • Reformed Criminal: Carlito Brigante, or so it seems.
  • Retirony: Carlito is resolved to get out of gangster life, but it just keeps sucking him back in.
  • Rewarded as a Traitor Deserves: Benny Blanco is smart enough to dispose of Pachanga after his betrayal of Carlito.
  • Roaring Rampage of Revenge: Vinnie T., after his father Tony T. is killed in the botched Rikers Island breakout. Unfortunately, Carlito gets mixed up in it.
  • Shadow Archetype:
    • Benny Blanco is an unpleasant reminder of how nasty Carlito used to be.
    • In a meta-example, Carlito is this to Tony Montana from Scarface (1983).
  • Shout-Out: When he visits Gail at night, Carlito takes a peek into her apartment by putting his face into the half-closed white door.
  • Shouting Shooter: One of Vinnie T.' s hitmen yells his lungs out while chasing Carlito in the final scene.
    Sony Manzanero: MOTHAFUCKAAAAA! I'LL KILL YAAAAAAA! MOTHAFUCKAAAAA!
  • Shut Up, Kirk!: Kleinfeld at the end when he gets sick of Carlito berating him on his morals:
    Carlito: Never betray your friends, Dave.
    Kleinfeld: Fuck you and your fucking self-righteous "code of the goddamn street". Did it get you out of a 30-year stint in jail in 5 years? No, it didn't. I did. Did it get you acquitted four fucking times? No, I did. Your whole world is this big and there's only one rule - you save your own ass!
    Carlito: "Save your own ass!" leaves him to do exactly that, having just unloaded his gun
  • Sissy Villain: Somewhat justified (the sissy part) with Carlito's Evil Former Friend Lalìn, who rats him out to the FBI and is a whiny and broken shell of himself. Not so justified with Kleinfeld at the end.
  • Someone to Remember Him By: Carlito himself finds out that Gail had an unborn child before dying.
  • Spiritual Successor: As noted above, it's practically a complete inversion of Scarface (1983), including by way of a Shout-Out:
    • The protagonist is quickly involved in a scene where they're about to be unwittingly killed, but fight their way out of it.
    • In Scarface (1983), Tony Montana is utterly incensed by someone dancing with his sister, his... ''love'' interest. Here, he takes pleasure in watching his actual love interest dance with a man who's similarly skilled, and comments on appreciating the beauty of their movement. Of course it's Kleinfeld who takes offence to this...
  • Teeth-Clenched Teamwork: Tony T hates Kleinfeld for being a slippery lawyer but wants his help in breaking out of jail. He has a good reason since Kleinfld did rip him off, but Kleinfeld kills him first.
  • Time Skip: Lampshaded. After the murder of Carlito's cousin, Pachanga offers his condolences. Carlito is annoyed that he's only saying this now, when a month has passed. Other than Carlito having made a bit of money in the club, there are no obvious signs that any real time has passed besides this line.
  • Too Dumb to Live: Kleinfeld makes many mistakes in his constant paranoia and feelings of inferiority, leading to the majority of the trouble for Carlito after the breakout and his own Karmic Death in the end.
    • Most of his betrayals Carlito couldn't foresee, but not paying Pachanga and ignoring the rumors he hears about him spying for Benny Blanco is a case of this trope.
  • Tragedy: Carlito's Way is a tragedy of character in the backdrop of high-risk, stark gangster life.
  • A Tragedy of Impulsiveness: Carlito Brigate himself is pretty level-headed, but his lawyer friend David Kleinfeld dooms the entire cast by impulsively killing his mob boss client during a jailbreak. This might be a subversion, though, as Carlito suspects that Kleinfeld planned to kill the mob boss all along and played Carlito himself for a fool.
  • Tragic Mistake:
    • Carlito probably would have avoided all his troubles with Tony T. had he'd told his friend Kleinfeld to take a hike but his personal code prevents him from doing so.
    • Carlito's death at the hands of Benny Blanco from the Bronx would have been all avoided had he left Benny Blanco from the Bronx alone in the nightclub, killed him like Pachanga wanted to, or just gotten rid of Pachanga who everyone knows can't be trusted.
    • Simply not tipping his hand about leaving town, especially to Pachanga, would have made for a happy ending.
  • Toxic Friend Influence: All Carlito wants is to go clean, but Kleinfeld keeps involving him in his schemes. He makes him an accomplice in a mafia boss' murder, and also tries to sell him out to the FBI who only leave Carlito alone because they know he's clean and want to bust Kleinfeld instead.
  • Trapped in Villainy: Kleinfeld. Ripping one million dollars from Tony T makes him fear for his life since he knows the guy would figure it out and have him killed the moment he's free. Thus he needs to kill Tony first and requires Carlito's help. To gain immunity for the theft, he sells Carlito out to Norwalk, while taking care that Carlito doesn't learn about that when Norwalk sends another snitch to listen in on him. In the end the stress, the drugs and his insecurities make Kleinfeld a mess who can't keep track of his own villainy and he gets killed for it, dragging everyone else down with him.
  • Troll: Carlito pisses off the jury at his release trial, turning it into a farce with a speech that the judge thinks fits better at an awards ceremony. He also doesn't miss the chance to mockingly claim he's been "born again like the watergaters", which is an obvious jab at Norwalk for taping him illegally and thus creating the circumstances that allowed for Carlito's release.
  • Twerp Sweating: Norwalk, part of the job description. With Kleinfeld it takes little more than a glare to make false allegations against Carlito. With Carlito, it's a No-Sell.
  • Villainous Breakdown: Under the influence of drugs and planning Tony T's murder, Kleinfeld breaks down constantly, whether it's a threat from Tony T, a visit from Norwalk, or making plans with Carlito. At a dinner party with Carlito and Gail the night before Tony T's jailbreak and his murder he loses it and his behavior alarms everyone.
  • What an Idiot!: In-universe example. Carlito is pissed that Kleinfeld would be so stupid as to kill a mafia boss and his son. And this is the same boss who Kleinfeld had already ripped $1 million from. When he confirms the extent of Kleinfeld's villainous stupidity, Carlito delivers a very cutting remark as to just how in over his head he is.
    Carlito: You ain't a lawyer no more, Dave. You a gangster now. On the other side. A whole new ball game. You can't learn about it in school, and you can't have a late start.
  • White Collar Crime: Kleinfeld is being investigated for some of these. Namely, bribery, money laundering and theft of $1m.
  • Who's Laughing Now?: Kleinfeld loves to ask people who've threatened him before "How does it feel?" when the tables turn. He reveals to Carlito he feels that way about a lot of people.
  • You Have Out Lived Your Usefulness: Benny Blanco from the Bronx to Pachanga.
    "Naw, you stay here!" * BLAM*

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