Carlito's Way

Carlito's Way is a 1993 American crime drama film directed by Brian De Palma and written by David Koepp, based on the novels Carlito's Way (1975) and After Hours (1979) by Judge Edwin Torres. It stars Al Pacino, Sean Penn, Penelope Ann Miller, Luis Guzman, John Leguizamo, Jorge Porcel, Joseph Siravo, and Viggo Mortensen.

Pacino plays Carlito Brigante, a Nuyorican criminal who vows to go straight and to retire in paradise. However, his criminal past proves difficult to escape, and he unwittingly ends up being dragged into the same activities that got him imprisoned in the first place. The film is based mainly on After Hours, but used the title of the first novel to avoid it being confused with Martin Scorsese's 1985 film of the same name. This is the second film collaboration between Pacino and De Palma, after Scarface (1983).

Carlito's Way was released on November 12, 1993, by Universal Pictures. It initially received mixed reviews from critics and lukewarm results at the box office, though general reception to the film has improved in the subsequent years since its release. The film gained a strong cult following, and it is generally considered one of De Palma’s most enduring films. Both Penn and Miller received Golden Globe nominations for their performances. A prequel titled Carlito's Way: Rise to Power, based on the first novel, was released direct-to-video in 2005.

Plot
In 1975 New York, after having served five years of a thirty-year prison sentence, career criminal Carlito Brigante is freed on a legal technicality exploited by his close friend and lawyer, Dave Kleinfeld. Carlito vows to end his unlawful activities but is persuaded to accompany his young cousin Guajiro to a drug deal at an illegal speakeasy. Guajiro's suppliers betray and kill him, forcing Carlito to shoot his way out. Later, Carlito takes Guajiro's $30,000 from the botched deal and uses it to buy a stake in a nightclub owned by a gambling addict named Saso, intending to save $75,000 to retire to the Caribbean.

Carlito declines several offers for a business partnership with a hot-headed young gangster from the Bronx named Benny Blanco. Carlito also rekindles his romance with his former girlfriend Gail, a ballet dancer moonlighting as a stripper. Dave develops a love interest with Benny's girlfriend, Steffie, a waitress at the club. Benny's frustration with Carlito's rejections boils over and he confronts Carlito at his table. Carlito publicly humiliates Benny, who reacts by manhandling Steffie. Fueled by his now-extensive use of alcohol and cocaine, Dave brazenly pulls out a gun and threatens to kill Benny, but Carlito intervenes. Despite being personally threatened by Benny himself, Carlito lets him go unharmed, a decision that alienates him from his friend and bodyguard Pachanga.

Dave, who stole $1 million in payoff money from his client, Mafia boss Anthony "Tony T" Taglialucci, is coerced into providing his yacht to help Taglialucci break out of the Rikers Island prison barge. Dave begs for Carlito's assistance in the prison break, and Carlito reluctantly agrees. That night, Carlito, Dave and Taglialucci's son Frankie sail to a floating buoy outside of the barge where Taglialucci is waiting. As they pull Taglialucci aboard, Dave impulsively kills him and Frankie and dumps their bodies in the East River, claiming that they would have killed him anyway. Knowing mob retaliation is imminent, Carlito immediately severs his ties with Dave and decides to leave town with Gail. The next day, Dave is hospitalized after a mob hitman stabs him several times.

The police apprehend Carlito and take him to the office of District Attorney Norwalk, where he learns that Dave has already agreed to perjure himself should Carlito be tried again. Despite being threatened with charges of being an accomplice to the Taglialucci murders, Carlito refuses to betray Dave. In the hospital, Carlito visits Dave, who confesses to selling him out. Having noticed a suspicious man dressed in a police uniform waiting in the lobby, Carlito secretly unloads Dave's revolver and leaves. The man is Taglialucci's other son, Vinnie, seeking vengeance for his brother and father. After sending the officer already guarding Dave away, Vinnie enters Dave's room and shoots him dead.

Carlito buys train tickets to Miami for himself and Gail, now pregnant. When he stops by his club to get the stashed money, he is met by a group of East Harlem Italian gangsters led by Vinnie. The Italians plan to kill Carlito, but he manages to slip out through a secret exit. The Italians pursue him throughout the city's subway system and into Grand Central Terminal, where they engage in a gunfight. Carlito kills all of his pursuers except Vinnie, whom the police shoot and kill. As Carlito runs to catch the train where Gail and Pachanga are waiting for him, Benny ambushes him and fatally shoots him several times with a silenced gun. Pachanga admits to Carlito that he is now working for Benny, but Benny then shoots him dead as well. Carlito hands a tearful Gail the money and tells her to escape with their unborn child and start a new life. As he dies, Carlito stares at a billboard with a Caribbean beach and a picture of a woman. The billboard then comes to life in his mind, and the woman, now Gail, starts dancing.

Cast

 * Al Pacino as Carlito Brigante (called "Charlie" by Gail). Pacino came to Carlito's Way directly from his Oscar-winning role in Scent of a Woman. To get into the character, he accompanied Torres through East Harlem to absorb the sights and atmosphere. Pacino first envisioned Carlito with a ponytail, but, after visiting Harlem, he quickly realized such a hairstyle was uncommon among the local men. The beard was Pacino's idea. The black leather coat fit into the period setting.
 * Sean Penn as Dave Kleinfeld. For the pivotal role of Carlito's sleazy lawyer and best friend, Penn was lured back from early retirement by the challenge of playing the corrupt lawyer. Taking the role meant that he could finance his movie The Crossing Guard and work with Pacino. De Palma and Penn discussed what 1970s mob lawyers looked like. Penn shaved the hair on the front of his forehead to give the appearance of a receding hairline. He permed the rest. Alan Dershowitz, believing that Penn was attempting to look like him, threatened the filmmakers with a defamation lawsuit.
 * Penelope Ann Miller as Gail. Casting for Gail proved difficult because of the character's striptease scenes. The character needed someone who was both a talented dancer and actor.
 * John Leguizamo as "Benny Blanco from the Bronx", an up-and-coming gangster who is determined to exceed Carlito's reputation but lacks any sense of ethics.
 * Luis Guzmán as Pachanga. In Koepp's first draft of the screenplay, Pachanga spoke in a very heavy slang style. Following rumbles from the Latino cast and crew, Koepp toned this down.
 * Ángel Salazar as Walberto
 * Jorge Porcel as Reinaldo "Ron" Saso
 * Al Israel as Rolando Ruiz
 * Ingrid Rogers as Steffie
 * James Rebhorn as District Attorney Bill Norwalk
 * John Finn as Detective Duncan
 * Michael P. Moran as Party Guest
 * Joseph Siravo as Vincent Taglialucci
 * Frank Minucci as Tony "Tony T" Taglialucci
 * Rocco Sisto as Panama Hatman
 * Adrian Pasdar as Frankie Taglialucci
 * Richard Foronjy as Pete Amadesso
 * Vincent Pastore as Copa Wiseguy
 * Viggo Mortensen as Lalin Miasso
 * John Augstin Ortiz as Guajiro
 * Jaime Sánchez as Rudy

Production
Pacino first heard about the character Carlito Brigante in a YMCA gym in New York City in 1973. Pacino was working out for his movie Serpico when he met New York state supreme court Judge Edwin Torres (the author who was writing the novels Carlito's Way and After Hours). When the novels were completed Pacino read them and liked them, especially the character of Carlito. Inspiration for the novels came from Torres' background: the East Harlem barrio where he was born and its atmosphere of gangs, drugs and poverty. In 1989, Pacino faced a $6 million lawsuit from producer Elliott Kastner. Kastner claimed Pacino had gone back on an agreement to star in his version of a Carlito movie with Marlon Brando as criminal lawyer David Kleinfeld. The suit was dropped and the project was abandoned.

Pacino went to producer Martin Bregman with the intention of getting a Carlito Brigante film made and showed him an early draft of a screenplay, which Bregman rejected. Both Bregman and Pacino agreed that the character of Brigante would provide a suitable showcase for Pacino's talents. Bregman approached screenwriter David Koepp, who had just finished writing the script for Bregman's forthcoming The Shadow, and asked him to write the script for Carlito's Way. The decision came that the screenplay would be based on the second novel After Hours. Carlito at this stage would match closer with Pacino's age. Although based primarily on the second novel, the title Carlito's Way remained, mainly because of the existence of Martin Scorsese's movie After Hours. Bregman worked closely with Koepp for two years to develop the shooting script for Carlito's Way.

Koepp wrestled with the voice-over throughout the writing process. Initially the voice-over was to take place in the hospital, but De Palma suggested the train station platform. The hospital scenes were written 25 to 30 times because the actors had trouble with the sequence, with Pacino even thinking that Carlito would not go to the hospital. With one final re-write Koepp managed to make the scene work to Pacino's satisfaction. In the novels Kleinfeld does not die, but De Palma has a huge sense of justice and retribution. He could not have Carlito killed off and have Kleinfeld live.

At one point, The Long Good Friday director, John Mackenzie, was linked with the film. When Carlito's Way and its sequel After Hours were optioned, Martin Bregman had Abel Ferrara in mind. However, when Bregman and Ferrara parted ways, De Palma was brought in. Bregman explained that this decision was not about "getting the old team back together", rather than making use of the best talent available. De Palma, reluctantly, read the script and as soon as Spanish-speaking characters cropped up he feared it would be Scarface all over again. He said he did not want to make another Spanish-speaking gangster movie. When De Palma finally did read it all the way through, he realized it was not what he thought it was. De Palma liked the script and envisioned it as a noir movie. Bregman supervised casting throughout the various stages of pre-production, and carefully selected the creative team who would make the film a reality. This included production designer Richard Sylbert, editor Bill Pankow, costume designer Aude Bronson-Howard and director of photography Stephen Burum.

Initially, filming began on March 22, 1993, though the first scheduled shoot, the Grand Central Station climax, had to be changed when Pacino showed up on crutches. Instead, the tension-building pool hall sequence, where Carlito accompanies his young cousin Guajiro on an ill-fated drug deal, started the production. Because the film was heavily character based and featured little action, the early pool sequence had to be elaborate and set up right. A huge amount of time was spent setting it up and filming it. After the film studio had viewed a cut of the pool hall sequence, a note was passed onto the crew stating that they felt the scene was too long. De Palma spent more time adding to the sequence and with the help of editor Bill Pankow made it work. The producers came back saying "much better shorter."

Apart from the poster sequence, which was shot in Florida, the entire movie was filmed on location in New York. De Palma roamed Manhattan searching for suitable visual locations. A tenement on 115th Street became the site of Carlito's homecoming: the barrio scene. The courtroom, in which Carlito thanks the prosecutor, was shot in Judge Torres's workplace, the State Supreme Court Building at 60 Centre Street. The Club Paradise was initially in a West Side brownstone as the model for the book's postprandial premises. But this was considered too cramped for filming. A multi-level bistro club designed by De Palma took shape at the Kaufman-Astoria Studios in Long Island City, in a style of 1970s art deco disco.

Tony Taglialucci's escape from Rikers Island, a night shoot mid-river, was considered impossible. Instead, the production used a Brooklyn shipyard where Kleinfeld's boat was lowered into an empty "lock" into which river water was pumped. Smoke machines and towers of space lights were installed.

For a climactic finale, De Palma staged a chase from the platform of the Harlem-125th Street (Metro-North) Station to the escalators of Grand Central Terminal. For the shoot, trains were re-routed and timed so that Pacino and his pursuers could dart from car to hurtling car. The length of the escalator scene during the climactic shoot out at Grand Central Station caused a headache for editor Pankow. He had to piece together the sequences so that the audience would be so tied up in the action that they would not be thinking about how long the escalator was running.

Reception
Carlito's Way wrapped on July 20, 1993, and was released on November 3, 1993. Critical response to the theatrical release was somewhat lukewarm. The film was criticized for re-treading old ground, mainly De Palma's own Scarface and The Untouchables. Roger Ebert stated in his review that the film is one of De Palma's finest with some of the best set-pieces he has done. Patrick Doyle was praised on his scoring of the film soundtrack, which was described as "elegiac" and "hauntingly beautiful," which "displays Doyle as one of the major talents of modern film scoring." Peter Travers (of Rolling Stone) criticized the film for Pacino's "Rican" accent slipping into his "Southern drawl from Scent of a Woman", "De Palma's erratic pacing and derivative shootouts" and "what might have been if Carlito's Way had forged new ground and not gone down smokin' in the shadow of Scarface."

On the Siskel & Ebert show, Ebert gave the film a thumbs up while Gene Siskel gave it a thumbs down. Owen Gleiberman (from Entertainment Weekly) described the film as "a competent and solidly unsurprising urban-underworld thriller" and is "okay entertainment," but went on to say that the plot would have worked better "as a lean and mean Miami Vice episode." The film has an approval rating of 84% on Rotten Tomatoes based on 50 reviews, with a weighted average of 7.20/10. The site's consensus states: "Carlito's Way reunites De Palma and Pacino for a more wistful take on the crime epic, delivering a stylish thriller with a beating heart beneath its pyrotechnic performances and set pieces."

Bregman was surprised about some of the negative reviews, but stated that some of the same reviewers have since "retracted" their views upon further discussions of the film. A few weeks before the film's premiere, De Palma told the crew not to get their hopes up about the film's reception. He correctly predicted that Pacino, having just won an Oscar, would be criticized; Koepp, having just done Jurassic Park, would "suck"; Penn would be "brilliant" because he had not done anything for a while; and he himself, having not been forgiven for The Bonfire of the Vanities, would not quite be embraced.

Carlito's Way premiered with an opening weekend box office taking of over $9 million. At the end of its theatrical run, the film had grossed over $37 million in the United States and Canada, and $27 million overseas, for a $64 million total. Sean Penn and Penelope Ann Miller both received Golden Globe nominations for their respective roles as Kleinfeld and Gail. The later appreciation of the film was highlighted when the French publication Cahiers du cinéma named it as one of the three best films of the 1990s, along with The Bridges of Madison County and Goodbye South, Goodbye.

Music
Patrick Doyle composed the original score, while Musical supervisor Jellybean Benitez supplemented the soundtrack with elements of salsa, merengue and other authentic styles.

Releases
The film was released on VHS, and on LaserDisc in standard and widescreen versions. It was later released on DVD in 2004, with an Ultimate Edition following in 2005. The Ultimate Edition DVD includes deleted scenes, an interview with De Palma, a making-of documentary, and more. In 2007, an HD DVD version was released, which features the same bonus material as the Ultimate Edition. The film was released on Blu-ray on May 18, 2010.

Prequel
A prequel based on Edwin Torres' first novel was released direct-to-video in 2005, with the title Carlito's Way: Rise to Power. Critically panned, the film nevertheless received Torres's blessing as an accurate adaptation of the first novel.

In popular culture
Samples from this film have been used by many bands including Slipknot and Overkill. Carlito's threatening monologue was sampled for the intro in "Brooklyn's Finest" by Jay-Z featuring The Notorious B.I.G. The line "here comes the pain" was sampled in the introduction to the Slipknot song "(sic)" from their 1999 debut album. The Manic Street Preachers song "Black Dog on My Shoulder" (from the 1998 album This Is My Truth Tell Me Yours) contains the lyric "like Carlito's Way, there are no exit signs..." American singer Lana Del Rey compared herself to the titular character in the line "when I'm violent, it's Carlito's Way" from her 2023 song "Taco Truck x VB".