Production History (Carlito's Way) Carlito's Way

Edwin Torres sold the film rights ten times before the movie got made

Judge Edwin Torres wrote two novels about Carlito Brigante: Carlito's Way (1975), a coming-of-age crime narrative, and After Hours (1979), the sequel about Carlito's doomed attempt to go straight. British producer Barry Hanson first optioned the rights in 1981. Torres later joked about the parade of buyers who came and went before the project finally reached production: he sold the rights ten times. Abel Ferrara was attached to direct at one point and later expressed frustration about being replaced before production began. (wikipedia, mentalfloss)

Al Pacino first heard about Carlito Brigante at a YMCA gym in 1973

Pacino encountered Torres while training for Serpico and read the first novel in galley form. The character stayed with him for twenty years. When Pacino eventually approached producer Martin Bregman, who had also produced Scarface and Serpico, Bregman initially rejected an early draft but recognized that Carlito suited Pacino's range. Bregman then brought in screenwriter David Koepp, who had just finished Bregman's forthcoming The Shadow, and the two spent two years developing the shooting script. (wikipedia, mentalfloss)

David Koepp adapted After Hours but wrestled with the voice-over through dozens of rewrites

The screenplay draws primarily from Torres's second novel, After Hours. The title was changed to avoid confusion with Martin Scorsese's 1985 film of the same name. Koepp chose the sequel because Carlito's age in that story was closer to Pacino's, and because the reformation narrative offered more dramatic tension than the rise-to-power story. The voice-over proved the script's hardest structural problem. Initially it was placed in the hospital; De Palma suggested relocating it to the train station platform. The hospital scenes were rewritten twenty-five to thirty times, partly because Pacino believed Carlito would not even visit Kleinfeld in the hospital. With one final rewrite, Koepp found a version that satisfied everyone. (wikipedia, mentalfloss)

In Koepp's first draft, Pachanga spoke in very heavy slang. Following feedback from Latino cast and crew members, Koepp toned this down. (mentalfloss)

De Palma took the job after hesitating about directing another gangster film

Brian De Palma became attached in August 1992. He had directed Scarface a decade earlier and was reluctant to revisit the genre, but Koepp's script changed his mind. De Palma conceived the project as film noir rather than a Scarface reprise, emphasizing Carlito's fatalism and the circular narrative structure. He later described his personal connection to the material in the documentary De Palma (2015):

"I can't make a better picture than this." — Brian De Palma, De Palma (2015)

De Palma saw parallels between Carlito's trapped situation and his own midlife reckoning with marriage, divorce, and critical rejection. (crookedmarquee, filmobsessive)

Sean Penn came out of early retirement and shaved his forehead to play Kleinfeld

Penn had stepped away from acting and was lured back by two incentives: the challenge of disappearing into Kleinfeld and the money to finance his directorial project The Crossing Guard (1995). He shaved the hair on the front of his forehead to create a receding hairline and permed the rest, inspired by a Life magazine photograph of a 1970s law student. Attorney Alan Dershowitz allegedly threatened a defamation action, believing Penn was mimicking him. Penn's transformation was so complete that he is barely recognizable beneath the tinted glasses, nasal voice, and nervous energy. (wikipedia, mentalfloss)

Penn was notoriously demanding on set. De Palma recounted one scene where Penn, playing Kleinfeld coked up and trying to persuade Carlito to join the boat scheme, refused to move on after fifteen takes:

"I shot ten, fifteen takes, and I thought it looked pretty good. But Sean said, 'No, no, no, no, no.'" — Brian De Palma, SlashFilm (2023)

Penn insisted they did not have it and requested twenty more. De Palma usually deferred to Penn's instincts but the sun was going down. Penn later acknowledged the friction:

"De Palma is an operatic moviemaker. His reality level is somewhere off in De Palma-ville. Serving him can become confrontational. And it did, to a degree, on Carlito's Way." — Sean Penn, Mental Floss (1996)

Penn tempered the criticism by adding that working with Pacino balanced the whole experience out. (slashfilm, mentalfloss)

Pacino visited East Harlem with Torres and abandoned a ponytail after local feedback

Pacino conceived Carlito's beard and black leather coat himself but originally envisioned a ponytail. Torres brought Pacino to East Harlem to absorb the atmosphere, where a local gangster remarked that Pacino would be wearing ballerina slippers next. The ponytail was dropped. Pacino pitched his voice lower and softer than in Scarface, delivering what many consider his most restrained 1990s performance. (wikipedia, crimereads)

John Leguizamo turned down Benny Blanco four times before De Palma let him improvise

Leguizamo refused the role repeatedly until De Palma agreed to let him create the character through improvisation rather than strictly following the script. The result was the strutting, chest-out Benny Blanco whose four-beat arc across the film (introduced, confronted, spared, returned to kill) drives the tragedy's final act. Leguizamo later expressed lingering unease about the film's predominantly non-Puerto Rican cast portraying Puerto Rican characters. (mentalfloss, variety)

The film was shot almost entirely on location in New York City

Filming began on March 22, 1993, and wrapped on July 20, 1993, with a $30 million budget from Universal Pictures. The first scheduled shoot was the Grand Central Terminal climax, but that had to be postponed when Pacino arrived on crutches. Production designer Richard Sylbert and cinematographer Stephen H. Burum created the film's nocturnal palette of blues, blacks, and reds. Key locations included:

• New York County Courthouse at 60 Centre Street for the courtroom sequences
• Kaufman Astoria Studios in Long Island City for the Paradise nightclub set, designed as a multi-level 1970s art deco discotheque
• Tenements on 115th Street for the barrio homecoming
• A Brooklyn shipyard for the Rikers prison barge escape, using an empty lock with pumped river water
• Grand Central Terminal and the Harlem-125th Street station for the climactic chase

Apart from a poster sequence shot in Florida, the entire film was made in New York. De Palma roamed Manhattan searching for locations that would anchor the 1975 setting in recognizable geography. (wikipedia)

The Grand Central escalator sequence was relocated from the World Trade Center days before filming

An elaborate escalator shootout was originally planned for the World Trade Center. Days before filming, the location was changed to Grand Central Terminal. The substitution produced one of De Palma's most celebrated sequences: a sustained moving-camera shot around the escalator that editor Bill Pankow had to structure so audiences would be too absorbed in the action to notice how long the escalator actually runs. De Palma re-routed trains and timed them precisely for Pacino and the pursuers to dart between cars. (mentalfloss, wikipedia)

Patrick Doyle composed the score after receiving a single directive from De Palma

Doyle was only seven films into his career when he scored Carlito's Way. De Palma gave him one note and never gave another:

"Don't tell my story, don't foretell my story, don't rush my story, and watch my film even closer than you're doing." — Brian De Palma, Pop Disciple (2019)

Doyle later said that of all his film scores, Carlito's Way is the one he still listens to. Musical supervisor Jellybean Benitez supplemented the score with period salsa, merengue, and authentic Latin styles, plus tracks including Labelle's "Lady Marmalade," Santana's "Oye Como Va," and Billy Preston's "You Are So Beautiful." (popdisciple, wikipedia)

The film opened to $9 million and earned $64 million worldwide against its $30 million budget

Carlito's Way was released on November 12, 1993. It earned $37 million domestically and $27 million internationally, enough to turn a modest profit but far short of the breakout success Universal had hoped for. The film was not a flop, but it landed in a crowded fall season and was overshadowed by comparisons to Scarface. (wikipedia)