“When I went to Berlin and I was watching it in Berlin after it opened and did okay in the United States, I remember watching in Berlin and said, ‘I can’t make – I can’t make a better picture than this.’” – Brian De Palma
He said these words with a heavy heart while recounting a story of seeing Carlito’s Way (1993) at the Berlin Film Festival, realizing he had poured his heart and soul into a film that received mixed reviews from critics and did well but not great at the box office. The start of the 1990s had not been good to Brian De Palma with the high-profile and costly failure that was The Bonfire of the Vanities (1990). It shook his filmmaking mojo so much that he second-guessed the narrative structure of Raising Cain (1992), a return to more familiar territory with the psychological thriller, which took a personal toll on the man.
He was in need of a hit to appease the studios and moved on to what he hoped would be a commercial hit by reteaming with Al Pacino in an effort to recreate the magic of Scarface (1983). If fans were expecting the same over-the-top bombast with Carlito’s Way they would be sorely disappointed as it took a more melancholic, introspective approach while still featuring De Palma’s virtuoso camerawork and masterful action set pieces, crafting a tragedy about how a criminal tries to go straight but is ultimately doomed from the get-go.
Carlito’s Way features one of the oldest chestnuts in the world. Narrating his story during the last moments of his life, Carlito Brigante (Pacino), a veteran criminal, has recently been released from prison, intent on leading a normal, law-abiding life. Of course it isn’t going to be that easy – when he returns to his old neighborhood, his reputation precedes him. Local gangster Benny Blanco from the Bronx (John Leguizamo), a cocky, up-and-comer, sets his sights on Carlito after being shamed by him in public. Carlito, however, barely notices him as he’s torn between reuniting with an old flame and a struggling Broadway dancer, Gail (Penelope Ann Miller), and keeping his lawyer and friend, David Kleinfeld (Sean Penn), out of trouble.
As a personal favor to David, Carlito runs a nightclub for the latter to raise enough money to move to the Bahamas and start his own business renting cars in a tropical paradise with Gail. However, Carlito’s loyalty to David will be his undoing – his friend has become so corrupt during the time that Carlito was in prison that he’s not only wanted by law enforcement but the mafia as well.
Carlito’s Way begins at the end (even though we don’t know it yet) with Carlito being shot and rushed to the hospital. While lying on the stretcher going through the train station, he flashes back to how he got there. De Palma lets it all play out over the opening credits, in dreamy slow motion, with somber classical music playing over it all. The entire sequence is shot in black and white save for a billboard that says, “Escape to Paradise,” with inviting tropical imagery symbolizing Carlito’s desire to escape a life of crime for a better one.
It is 1975 and Carlito has been released from prison after a five-year stint, reinvigorated and reborn. At his hearing he sticks it to the judge (a cameo by Paul Mazursky no less!) and the District Attorney (James Rebhorn) in classic Pacino style, delivering a speech like he’s accepting an Academy Award. It’s as close to Scarface as Pacino gets and, in a bit of irony, Carlito is actually sincere about going straight. Unlike Tony Montana, he doesn’t want to rise to the top of the criminal underworld – he wants to get out. He even tells both the local crime boss and David that he’s retired but they don’t believe him. An ex-con career criminal going straight? No way.
Sure enough, he gets roped into an “errand” with his young cousin (John Ortiz) that turns into a bloody shoot-out. As always, De Palma injects the film with his trademark bravura action sequences. One look at the set-up and, like Carlito, we know that something is not right. Pacino shows how his character survived for so long as he expertly sizes up the situation and takes stock of the room: how many guys and where they are in relation to each other and him. Carlito is calm, unruffled, while his eyes convey a readiness for anything.
De Palma thrives at orchestrating these kinds of set pieces, masterfully using editing to build anticipation and suspense as we wait for the inevitable explosion of violence, gradually building the tension as we feel Carlito’s apprehension. Despite his desire to go legit, he gets drawn back into a life of crime; he can’t escape.
Carlito is a role tailor-made for Al Pacino, allowing him to essay another larger-than-life character. Carlito is a smart guy who cannot escape what he is no matter how hard he tries and the actor conveys the melancholy that lurks behind the bravado of his character. For all of his street smarts, Carlito makes the fatal mistake of underestimating local small-time tough guy Benny Blanco (a perfectly cast motor-mouthed Leguizamo) who keeps trying to get an audience with the veteran crook only to be rebuffed every time.
Carlito also pines for Gail and goes up to the top of a neighboring building in the rain to watch her in a dance class. He is still in love with her and envisions being reunited with her as part of his dream of escaping a life of crime. Like James Caan’s safecracker in Thief (1981), Carlito is making up for lost time and wants to start his new life right now, but his old one won’t let him go.
The real scene-stealer, however, is Sean Penn’s sleazy, coked-up lawyer. The actor reportedly did the film to help finance his directorial debut, The Crossing Guard (1995). For a paycheck role, Penn does a great job immersing himself in the part, complete with a frizzy Afro and receding hairline. It’s as though Pacino’s presence inspired Penn to step up his game, making Penn’s memorable turn so much fun to watch. Even though David dresses in expensive clothes and smokes fancy cigarettes, he’s a cokehead that runs with a dangerous crowd who thinks he’s untouchable. His hubris is his undoing.
The rest of the cast is filled out by solid character actors like John Leguizamo, who plays Benny as a pushy little runt not to be underestimated, and the always-reliable Luis Guzman as Carlito’s right-hand man. There’s also Viggo Mortensen in a small role as a former contemporary of Carlito who has been let out of prison to get the dirt on his friend. Wheelchair-bound and wearing cheap, stained clothes, the actor isn’t afraid to portray a pathetic snitch, a shadow of his former self. He plays a sad figure that really gets under Carlito’s skin. It also shows how far the D.A. is willing to go to send him back to prison.
The only miscasting is Penelope Ann Miller as Pacino’s love interest. She looks out of place and just doesn’t have the acting chops to hold her own against Pacino. She does have a good scene with Pacino when, much to Carlito’s surprise, he discovers that Gail moonlights as a stripper to make ends meet. It is a continuation of his disillusionment in the sense that despite all of her talk of trying to make it as an actress, Gail gets naked for other men. Like Carlito, there is her dream and there is her reality. They have an interesting conversation as he awkwardly disapproves of her dancing for men, to which she unashamedly counters, “You ever kill anybody, Charlie?” Carlito realizes that he has no right to judge her as he’s done far worse for money.
Loyalty is both Carlito’s greatest attribute and vice. It is his loyalty to David that gets him in trouble with Benny Blanco and the Italian mobsters that go after in him in the film’s exciting climax. He has a personal code that he adheres to no matter what happens. However, it is the internal conflict that rages within him that ultimately clouds his judgment. It is his natural instinct to be the ruthless criminal he was versus the legit businessman he wants to be, which results in the sparing of Benny’s life when the smart play was to kill him, as he’ll be a problem later on.
Carlito knows that David is out of control and taking unnecessary risks, like ripping off a wiseguy for $1 million, but helps him break said crook out of Riker’s Prison out of friendship, a debt he feels he owes him. Ultimately, he can’t change who he is. The two men finally have it out and Carlito realizes what a true friend David is as the lawyer lays it out for him, tells him that he looks out for himself, while Carlito lives by an antiquated code. That’s all Carlito needs to hear and ends their friendship, leaving him at the mercy of a mob assassin.
New York State Supreme Court judge Edwin Torres wrote Carlito’s Way in 1975 and its sequel After Hours in 1979, both chronicling the rise and fall of Puerto Rico drug kingpin Carlito Brigante. Al Pacino came to producer Martin Bregman with these two novels and said that they could be made into a film. Screenwriter David Koepp was already working for Bregman when he was given the two novels and told to adapt them into a screenplay. He liked them but taking 800 pages and making them into a film was a daunting task. Koepp was also unfamiliar with Spanish Harlem in the 1970s. When it came to adapting the novels, he ended up using more of After Hours as it featured an older Carlito that Pacino could play.
Bregman felt that Brian De Palma was the best person to direct but he wasn’t interested in making another gangster film. At the time of making Carlito’s Way, De Palma’s personal life was in turmoil. He said, “In the space of two years, I got married; I had a child; and I got divorced!” He elaborated further: “I wasn’t able to reconcile my private life and my professional life.” Like Carlito loses Gail, De Palma lost his second wife, movie producer Gale Ann Hurd. To this end, De Palma was drawn to Koepp’s script as he recognized his own crisis in Carlito’s:
“A guy who just got 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.”
When De Palma called Sean Penn about Carlito’s Way he hadn’t acted in four years and needed money as his wife at the time, Robin Wright, was pregnant again. The actor said, “I certainly was interested in working with Al Pacino. And I’d had a very good relationship with Brian on Casualties of War.” When he initially talked to the director, Penn got the impression that the film was going to be very raw and his research uncovered a very gritty setting. When he arrived on the night club set during filming to find a very expensive-looking set with many extras and complex moving shots that took a long time to set up, which did not allow for multiple takes. Penn felt “a little duped. And that created tension.”
Torres gave Pacino and Penn a personal tour of the criminal justice system and Puerto Rican New York, taking them to the South Bronx, the barrio and to various clubs and bars. To prepare for the role he took Pacino to salsa clubs in Spanish Harlem. The actor said, “It was the Disney tour of the barrio: ‘So-and-so got shot here. So-and-so got shot right over there.’” According to De Palma, Pacino patterned his character’s cadences and speech patterns after Torres. The judge also arranged for Penn to watch Bruce Cutler sum up the Thomas Gambino racketeering case. The actor also talked to Albert J. Krieger who defended John Gotti. Penn looked through period articles on lawyers and came across a still photograph in Life magazine of a young law student that he based the look of David on.
There are several colorful anecdotes about the filming of Carlito’s Way. De Palma and Penn clashed over the scene in which David asks Carlito to break a mobster out of Riker’s. Penn had done ten takes with the director – happy with take three – but the actor wanted to do another 15 takes until he was happy with his performance. Incredulous, De Palma wanted to do Pacino’s side of the scene. After 25 takes, he insisted on shooting Pacino and Penn got upset as a result. Afterwards, Penn disrespectfully chewed out De Palma over the course of the rest of the day.
De Palma started filming the final chase sequence in the winter – and finished it in the middle of summer. They shot the train-to-train scene over and over again (in the blistering New York heat) with Pacino running up and down the train in a long, black leather coat and De Palma in another running parallel filming it. It was a complicated shot that took many hours. An exhausted Pacino finally had enough and took the train home at four in the morning without telling De Palma. The director recalls, his assistant director telling him, “Al took the train home. And he thinks you’re crazy. He doesn’t know what you’re doing.” When the studio first saw the pool scene they felt it was too long. De Palma interpreted that to mean it wasn’t long enough! He added more footage, setting up the action and building more suspense. Bizarrely, the studio saw the new version – and congratulated him on making it shorter.
Carlito’s Way received decidedly mixed reviews from critics. In her review for The New York Times, Janet Maslin wrote, “Carlito’s Way is best watched as lively, colorful posturing and as a fine demonstration of this director’s bravura visual style.” Rolling Stone magazine’s Peter Travers gave it four stars and wrote, “The drug wars have raised brutality and betrayal to levels we see reflected on Pacino’s eloquently ravaged face. It’s that face that holds us even when Pacino’s ‘Rican’ accent slips into his Southern drawl from Scent of a Woman. It’s that face that cuts through De Palma’s erratic pacing and derivative shootouts.”
There were critics who wrote decidedly negative words about the film. Entertainment Weekly’s Owen Gleiberman gave it a “B” rating and wrote, “Watching Carlito’s Way, I never really believed that a heroin dealer and coolly pragmatic killer could be such a simple, romantic guy.” In his review for the Washington Post, Hal Hinson wrote, “De Palma’s direction is alert but dispirited, and certainly for us there is a sense of drudgery in having to observe this gifted filmmaker run through his tired bag of tricks.” Finally, the Los Angeles Times’ Kenneth Turan criticized Miller’s character: “Miller works hard to make the part believable, but finally the role fits too snugly into the traditional ‘exotic dancer with a heart of gold’ category to allow for much genuine impact.”
Despite the clichéd premise, Carlito’s Way works well because of the caliber of actors, David Koepp’s screenplay with memorable dialogue (“You think you’re big time?! You’re gonna fucking die big time!”), and De Palma’s stylish direction. The last 20 minutes plays out in an exciting chase as the director pulls out all the stops, like the impressively choreographed tracking shot, as Carlito tries to evade mobsters and make it in time to meet Gail at the train station; he is literally racing for his life. What makes the film’s ending so heartbreaking is that Carlito got so close to realizing his dream only for it to be cruelly ripped away at the last minute by someone he could’ve dealt with earlier on but chose not to, and therefore pays for this lapse in judgment dearly.
While De Palma did not originate this project, he certainly made it his own. He found something in Koepp’s script that he connected with on a personal level and transformed what could have easily been a paycheck gig into an artistic expression for what he was going through in his own life. This might explain why he seems crestfallen in the De Palma documentary when recounting watching Carlito’s Way at the Berlin Film Festival years ago. The film was a personal expression and its mixed critical reaction and decent but unremarkable box office was likely a bitter pill for De Palma to swallow at the time. His desire to stay in the game and enjoy the resources that a major studio could provide, coupled with his hunger for a commercial hit, drove him to team-up with Tom Cruise and direct the first movie in the Mission: Impossible franchise, which allowed him to fulfill this goal.
Roger Ebert gave the film three-and-a-half out of four stars and wrote, “Carlito’s Way, like Scarface, is first and last a character study, a portrait of a man who wants to be better than he is.” Much like Carlito, De Palma was also struggling to become a better man in his own life, not wanting to look back. Unlike, his cinematic alter ego, the director overcame his personal demons and triumphed in the end, thereby proving that he was able become a better filmmaker than he had been before, delivering a powerful, personal film that stands as one of the strongest efforts in his filmography.
De Palma. Dir. Noah Baumbach and Jake Paltrow. Empire Ward Pictures. 2015.
Feeney, Sheila Anne. “So New York…Yet So Hollywood.” Los Angeles Times. November 4, 1993.
Grimes, William. “His Honor Himself is Counselor to Pacino.” The New York Times. July 27, 1993.
Keesey, Douglas. Brian De Palma’s Split-Screen: A Life in Film. University Press of Mississippi. 2015.
Kelly, Richard T. Sean Penn: His Life and Times. Canongate U.S. 2004.
“The Making of Carlito’s Way.” Carlito’s Way Blu-Ray. Universal Pictures. 2010.