100 Greatest Gangster Films: Carlito’s Way, #20

Al Pacino, Penelope Ann Miller and Sean Penn in Carlito’s Way (1993-R)
© Universal Pictures

Brian De Palma was worried about doing another Hispanic drug kingpin movie after Scarface. But the story and the acting in Carlito’s Way go in such a different direction that there ended up being few similarities between the two films. This is a personal look at one man’s attempt at redemption. Scarface, on the other hand, is a saga about one man’s one-way trip to hell.

Carlito’s Way and Scarface do share a couple of important things. They both succeed at what they are trying to do and have Al Pacino as the primary reason to thank for it.

While Carlito’s Way was not a box office smash, Pacino’s portrayal of the title character, Carlito “Charlie” Brigante, is in many ways stronger, and certainly more simpatico, than his portrayal of Scarface’s Tony Montana a decade earlier.

Critics were not overwhelmed by this De Palma/Pacino effort, with one suggesting the story would have played better and leaner as a Miami Vice episode. That’s harsh. Pacino, as he does on occasion, chews some of the scenery (see: Scent of a Woman, Dog Day Afternoon and And Justice for All for other examples). But if you like Pacino—and what gangster film fan doesn’t?—then his spurts of overacting can easily be ignored. Or even savored.

Using voice-overs throughout and told in flashback after Carlito is shot on a train platform, Carlito’s Way offers an interior view of the drug underworld. Carlito provides cynical commentary about the greed, corruption and treachery that simply come with the territory.

It is territory that Carlito hopes to leave behind after having his conviction and 30-year prison sentence for drug dealing overturned. His dream is to go to the Bahamas, where a friend has opened a car rental business and has promised him a piece of the action.

“I’ll tell you something, car rental guys don’t get killed that much,” he says in explaining his desire for the seemingly inexplicable career makeover.

But like another Pacino character that we’re all familiar with, Carlito can’t seem to find his way. Just when he thinks he’s out, forces keep pulling him back in.

Those forces include a wannabe kingpin who starts out idolizing Carlito but ends up gunning for him and a coked-up lawyer/best friend who once helped spring Carlito from jail on a legal technicality. The friend now needs Carlito to help him deal with a mob boss who is less than pleased with the legal service he has been receiving.

Sean Penn gives a pulsating performance as attorney David Kleinfeld, who spends more time snorting coke and chasing broads than filing legal briefs. With a frizzed-out, red mop of hair and tight-fitting, three-piece suits that scream shyster, Kleinfeld looks more at home in Carlito’s nightclub than he does in a courtroom.

John Leguizamo’s Benny Blanco (“Benny from the Bronx”) gives Charlie a chance to see what he used to be, even if he doesn’t want to accept or admit it. And that vision reinforces his desire to put that life behind him and leave New York.

When they first meet, Blanco calls Carlito the “J.P. Morgan of the smack business.” Benny thinks he’s paying a compliment. But Carlito doesn’t like the reminder.

But there are flashes of the old Carlito. A second meeting with Blanco ends with a confrontation. Carlito and his bodyguards throw the young drug dealer down a flight of steps.

“Dumb move, man, dumb move,” Carlito says in a voice-over as Blanco tumbles down the concrete stairway at the back of the nightclub. “But it’s like them old reflexes comin’ back.”

When his bodyguards want to finish the job in the alley behind the club, Carlito calls them off and tells them to let Blanco live. That, from an underworld perspective, turns out to be an even dumber move.

Honor and loyalty (or the lack thereof) and betrayal drive the rest of the movie.

“Fuck you and your self-righteous code of the street,” Kleinfeld says in an early argument that hints at what is to come.

“Favor gonna kill you faster than a bullet,” Carlito muses at another point, letting us know that he knows that he has lost his edge.

Viggo Mortensen makes a brief appearance as Lalin, an old drug-dealing friend now confined to a wheelchair as the result of a gangland shooting. His conversation leads Carlito to quickly surmise that he’s wearing a wire for the cops. When Charlie confronts him and rips the wire from his chest, Lalin is reduced to tears and says he’d be better off dead than confined to the chair wearing diapers.

While trying to maneuver through his old world and legitimately build up a stash that can finance a move to the Bahamas, Charlie rekindles his romance with Gail (Penelope Ann Miller). In the novels on which the movie is based, Gail was a teacher. De Palma, reaching into a bag of urban movie clichés, makes her a struggling dancer who moonlights at a strip joint.

Reluctant at first to get involved again with Carlito, Gail buys into his dream, but then realizes it is going to play out like a nightmare.

“I know how this dream ends,” she says while urging him not to help Kleinfeld deal with the mob boss.

But Carlito’s sense of honor trumps his common sense.

“Dave is my friend,” he says. “I owe him. That’s who I am. That’s what I am. Right or wrong, I can’t change that.”

Gail turns out to be the only person close to Carlito who doesn’t betray him. His final wish is for her to get out of New York.

“No room in this city for big hearts like hers,” he says.

In an attempt to recapture this film’s magic, Michael Bregman, one of the producers here, directed a 2005 prequel called Carlito’s Way: Rise to Power. It was a bust. Or as Carlito might have said, “No mas.”

HIT: The running gun battle/chase scene through the subway and train station that takes up nearly 10 minutes at the end of the film is a cinematic classic that echoes some of the great film noir finales from the past. Taut and nerve-racking, it perfectly sets up the climax.

MISS: Pacino doesn’t quite nail his character’s Puerto Rican accent. At times it seems he’s back in Scent of a Woman and at other times he sounds like Michael Corleone doing Tony Montana.

DON’T FAIL TO NOTICE: The exterior of the hospital where Carlito goes to visit Kleinfeld after he is stabbed by the mobsters is the same hospital exterior used in The Godfather. In that movie, as we all know, Pacino’s character, Michael, goes to visit his father, Don Corleone, after he was shot. And it’s in front of that hospital that Michael Corleone has the confrontation with police that eventually leads to his exile in Sicily. The ramifications of the hospital visit here are just as interesting.

BEST LINE: “I don’t invite this shit, it just comes to me,” Carlito says after he tries to help his cousin and, instead, gets caught in a drug deal gone bad in a Harlem pool hall. The scene, early in the movie, sets the stage for all that follows.

WHAT THEY WROTE AT THE TIME: “Carlito’s Way harks back to the gangster flicks of yore, where the molls were window-dressing and all the real action belonged to the hombres. De Palma’s vibrant, visceral crime drama is hombre hoo-ha—and a whole lot of fun.”—Steven Rea, the Philadelphia Inquirer

CASTING CALL: In an earlier attempt to make the movie, there was talk of Marlon Brando playing Kleinfeld, a move that would have teamed the two principals from The Godfather in a decidedly different on-screen relationship.

GOOF: At the end of the movie, Carlito and Gail plan to flee New York on a train to Miami. They meet at Grand Central Station in Manhattan. The only trains out of New York to Miami depart from Penn Station.

BET YOU DIDN’T KNOW: The movie is based on two novels by Judge Edwin Torres, Carlito’s Way and After Hours. Pacino met the judge while filming Serpico. He later read and liked the novels. Torres, who cowrote the screenplay, took Pacino around Spanish Harlem to get a sense of the place and his character before filming began.

BODY COUNT: Twelve.

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[Reprinted from The Ultimate Book of Gangster Movies by George Anastasia and Glen Macnow. Available from Running Press, a member of The Perseus Books Group. Copyright © 2011.]

George Anastasia, Glen Macnow

George Anastasia is a crime reporter for the “Philadelphia Inquirer” and author of several books, including “Blood and Honor” which Jimmy Breslin called “the best gangster book ever written.”

Glen Macnow was a writer for the “Philadelphia Inquirer” and “Detroit Free Press.” He is currently a talk-radio host on 610-WIP in Philadelphia.

George and Glen have co-authored “The Ultimate Book of Gangster Movies.”