20 Facts About Carlito’s Way You Didn’t Paci-know

Perhaps you’ve heard of Carlito’s Way, a film too often cast as the awkward younger brother of the legendary Scarface. But this film, released in 1993, is a lot more than just a pale imitation of Brian De Palma’s most famous project.

The story of a man struggling to escape his criminal past, the movie was even lauded as the best film of the 90s by the French magazine Cahiers du Cinéma. Just as Carlito Brigante struggles to leave his past behind, we bet you’ll find it difficult to wrest yourself from the grasp of these intriguing behind-the-scenes secrets!

20. The title was changed to avoid confusion with a Martin Scorsese film

Carlito’s Way is in fact based on two novels: Carlito’s Way and After Hours, by Edwin Torres, with the screenplay for the film drawing more from the latter.

After Hours is set later in Carlito Brigante’s life, and was chosen as the main source for the film adaptation due to the character then being closer in age to Al Pacino.

Unfortunately for the filmmakers, there was already another movie called After Hours: a 1985 Martin Scorsese black comedy.

That film follows a man whose attempted sexual encounter turns into a wild goose chase involving suicide and the Mafia; the next morning, he straightens his jacket and goes into work.

De Palma naturally wanted to avoid confusion, especially since his film also features crime. As a result, he named his film for Torres’ first novel, despite it more closely resembling the second.

Incidentally, ‘After Hours’ was used in 2019 as the title of R&B musician The Weeknd’s latest album, though we suspect he wasn’t surreptitiously nodding to Carlito’s Way.

19. Al Pacino was sued for $6 million over the project

Three years before Carlito’s Way went into pre-production, Al Pacino was sued by Carlito’s Way producer Elliott Kastner for breach of contract. How? Well, like all litigation, it’s complicated.

Kastner was not, in fact, the producer of the Carlito’s Way as we know it, but of a project that was also looking to adapt Edwin Torres’ work for screen, having previously produced classic neo-noir films like The Long Goodbye.

In 1989, Kastner sued Pacino for $6 million, claiming that the actor had agreed to star in his version of Carlito’s Way, set to star Marlon Brando as lawyer David Kleinfeld in what was hoped to be a Godfather reunion.

After a four-year hiatus, Pacino had just released Sea of Love, a neo-noir thriller that put the actor’s name straight back on the Hollywood A-list.

Ultimately, the lawsuit was dropped and Kastner project scrapped, paving the way for Brian De Palma’s 1993 cult classic.

18. Worried about making “another Scarface”, Brian De Palma initially turned the film down

You might have thought that Brian De Palma would have jumped at the chance to work with Al Pacino again.  After all, Scarface remains one of the shiniest jewels in the De Palma crown, alongside Carrie and The Untouchables.

But you should sentence your expectations to 30 years in prison: in reality, De Palma was reluctant to make what he viewed as another Scarface.

The two films are superficially alike, featuring as they do Spanish-speaking criminals and a plot that focuses on narcotics, but they differ wildly in tone.

After all, Scarface is the story of how a man with nothing rises to become an almost imperviously powerful mob boss; Carlito’s Way is all about escaping that system, rather than glamorising it.

De Palma’s fears didn’t stop him including a significant reference to Scarface, however: Carlito’s nightclub is called El Paraíso, the same name used for Tony Montana’s food stand.

17. John Leguizamo turned the film down four times

Another figure who seemed hesitant to join the film was John Leguizamo, who turned it down an astonishing four times.

Leguizamo is a notoriously prolific actor, having starred in over 100 films. While this might seem unremarkable for a seasoned actor, it’s worth remembering that Leguizamo is only 55 at the time of writing, and was only active from the early 90s.

Caption: MiamiFilmFestival via Wikimedia Commons

What convinced Leguizamo to join the cast was Brian De Palma’s offer to let him improvise much of his character, and so Benny Blanco from the Bronx was born.

What’s less clear is why Leguizamo was so reluctant to take the part in the first place. We have two theories: one is that the actor was also starring as Luigi in Super Mario Bros, which would have taken up much of his time.

Secondly, having played several bit-parts as Latin thugs, it’s possible that Leguizamo was seeking more authenticity from his characters, rather than caricatures, hence why he insisted on adding a personal edge through improvisation.

16. Al Pacino turned up on the first day on crutches

If you know anything about filmmaking, you’ll know that time is the enemy. Basically, film schedules need to be planned precisely to avoid wasting time and incurring costs.

Now imagine the nightmare of your lead actor, the film’s most bankable draw, turning up to set the first day on crutches.

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And now imagine that what you had planned to shoot first was an elaborate action sequence, one that involves your lead jumping from trains and sprinting around Grand Central Terminal. That’s exactly what happened to Brian De Palma.

It’s not entirely certain what was the reason for Pacino’s injury (Pacino’s main hobby is apparently reading, rather than mixed martial arts), but we know that De Palma had to instead film the pool hall scene first.

Ultimately, Pacino’s lessened ability to move that day worked out well for the scene, which is tense, claustrophobic, and full of what in retrospect seems like real pain from the lead actor.

15. De Palma tricked the studio into thinking he’d shortened the film

Credit: Gordon Correll via Wikimedia Commons

For a film about an ex-con pulled back into the seedy underworld of Harlem, there isn’t actually that much action in Carlito’s Way, which made the pool hall scene even more important. As a result, it’s quite long.

Not only is the sequence itself quite a drawn out affair – with Carlito accompanying Guajiro to a drug deal that turns sour – but De Palma also spent a significant amount of time shooting it.

Credit: Gorup de Besanez via Wikimedia Commons

On viewing an early cut, the studio complained that the scene was too lengthy. Instead of cutting it down, however, De Palma added even more.

With the help of editor Bill Pankow, De Palma significantly upped the tension in the scene, making it a nail-biting encounter. Nervously, De Palma sent this lengthened version off to the studio.

The director received only a brief note in response: the producers were thrilled, claiming that the scene was “much better shorter.”

14. Sean Penn lost it when De Palma wouldn’t let him film more than 30 takes for one scene

Sean Penn plays the shady mafia lawyer David Kleinfeld; in addition to his deliberately eccentric appearance, Penn’s notoriously mercurial personality brings vigour to the character.

Unfortunately, said personality once led to an altercation with Brian De Palma, with Penn’s bad behaviour on full display.

Penn supposedly demanded upwards of 30 takes of the scene in which Kleinfeld ropes Carlito into securing Tony Tagliucci’s escape. De Palma, a filmmaker on a timetable, didn’t see the need.

Penn then became enraged, and wouldn’t stop yelling at De Palma even on the ride back to New York City, and after they parted ways called the director to yell at him some more.

Credit: Seher Sikandar via Wikimedia Commons

According to De Palma, that was the only argument he ever had with Penn during filming. The actor likely didn’t have the energy for any more!

13. Al Pacino and Penelope Ann Miller became a couple in real life during shooting

Al Pacino and Penelope Ann Miller, who plays Gail and is 24 years younger than her Carlito’s Way co-star, embarked on a real-life romantic relationship during the film’s shoot.

“It’s not a secret and I’m not ashamed of it,” Miller told People Magazine in 1993. The only issue, of course, was that Pacino was then in a two-year-long relationship with director Lyndall Hobbs.

“Al is a very passionate person, and he brought out a certain womanliness … in me,” she continues, adding that they had to keep the relationship discreet “for the sake of the movie.”

For Pacino’s part, these rumours went unaddressed, though Miller did produce a photograph of the two of them visiting her aunt and uncle as proof. Plus, Pacino had specifically asked for Miller to be cast in the first place, a sign of evident chemistry.

Pacino ended up bringing Lyndall Hobbs to the premiere, and avoided Miller completely the entire night. Pacino’s relationship with Hobbs didn’t survive much longer.

12. The Grand Central Station shootout was intended for the World Trade Centre

There’s a reason why Cahiers du Cinéma named this film the best of the 90s: the Grand Central Station scene, at the climax of the film, must be one of the best action sequences of the decade. Amazingly, this scene originally was supposed to take place in the World Trade Center.

“I had elaborate storyboards of this whole shootout on the escalators that were in the World Trade Center,” De Palma told Rolling Stone. “I spent weeks and weeks photographing it … and a couple of days before we were about to shoot, they blew it up.”

De Palma here is referring to the February 1993 World Trade Center bombing, which involved a truck filled with explosives being driven beneath the North Tower.

The intended effect was to collapse the North Tower into the South Tower, killing thousands, in a manner reminiscent of the eventual 2001 tragedy.

Thankfully, both towers remained standing, but thousands were injured. De Palma was forced to move his shootout to Grand Central Station instead.

11. Alan Dershowitz threatened to sue the film for defamation because he thought Kleinfeld was based on him

Credit: Sage Ross via Wikimedia Commons

Sean Penn’s perm was a deliberate choice, and one he says was based on a “picture in Life magazine of a law student from around the right time period,” but that explanation didn’t fly with pugnacious lawyer Alan Dershowitz.

Dershowitz was already a famous lawyer at the time, having become the youngest law professor in history in 1967 – he was only 28 – and taken on controversial clients like adult film actor Harry Reems. Two years after Carlito’s Way, Dershowitz would represent OJ Simpson.

After reviewers claimed that Penn had “borrowed Alan Dershowitz’s hair,” he clearly smelled blood, and threatened to sue Epic Productions for defamation.

Naturally, Dershowitz was keen to avoid comparisons to a lawyer who had, in the words of Carlito Brigante, become “a gangster now.”

Ultimately, the threats amounted to nothing, likely because Penn had an airtight alibi: Torres had got Penn a meeting with Albert Krieger, the lawyer for infamous mob boss John Gotti, and who served as David Kleinfeld’s primary inspiration.

10. The film nearly starred Alison Doody as Gail

Alison Doody’s feature film debut was as one of May Day’s bodyguards in A View to a Kill, aged just 19. Four years later, she would be catapulted to fame as Elsa Schneider in Indiana Jones and the Last Crusade.

Four years after that film, Doody might have continued her fame by starring in Carlito’s Way as Gail, a part that she was offered but turned down.

Instead, Doody went on to star in Major League II, a film that rates a limp 5% on Rotten Tomatoes. Still, there was a good reason for her choice.

Doody was reportedly uncomfortable with the topless dancing scenes she’d have to perform in Carlito, and it’s fair to say that Brian De Palma was both upfront and creepy about the requirements of the role.

According to Penelope Ann Miller, the eventual Gail, De Palma insisted she be auditioned in a bikini.

9. A direct-to-video prequel was released in 2005

After a lukewarm critical and commercial reception upon its release, Carlito’s Way has become a cult classic. It makes sense, then, that canny filmmakers would aim to capitalise on the resurgence of its reputation with a prequel, which is just what happened in 2005.

Carlito’s Way: Rise to Power is based on Edwin Torres’ first novel, Carlito’s Way – with, as we’ve mentioned, Carlito’s Way the film being based on After Hours.

Jay Hernandez steps into the large, loud boots of Al Pacino, with the film detailing the rise of Carlito Brigante’s criminal empire prior to his three-decade incarceration.

Rise to Power was written and directed by Michael Bregman, who had produced De Palma’s 1993 effort, as well as having been responsible for Sea of Love.

While the film was critically panned, it nonetheless earned the admiration of Edwin Torres, who described it as an accurate adaptation of his novel.

8. Pacino heard about the film while working out for Serpico

There’s no question that Al Pacino’s big break came in the form of The Godfather, with the first film in the series being released in 1972. But the following year, Pacino was sensational in Serpico, a film about the corrupt New York Police Department, in which Pacino played a real-life police officer.

Ever the consummate method actor, Pacino bulked up for the film, working out at a local YMCA. One day, he happened to find a gym buddy, none other than Edwin Torres, who at the time was working on a novel about a man called Carlito Brigante.

Once the novel and its sequel were completed, Pacino read them and resolved to play Carlito on the silver screen, however long it took to make it happen.

It would be two decades after this initial encounter that Pacino would finally star as Carlito Brigante; in the meantime, Torres had become a judge on the New York State Supreme Court.

For his efforts in Serpico, the future Carlito was nominated for a Best Actor Oscar, having been nominated the year before for Best Supporting Actor in The Godfather. Back in the 70s, it was all coming up Pacino.

7. The hospital scene was rewritten up to 30 times

With Pacino so heavily invested in the character of Carlito Brigante, and Brian De Palma being a contentious director, it’s no surprise that there were issues during production. The most severe was the filming of the hospital scene, which had to be rewritten 25-30 times before both parties would deem it satisfactory.

Screenwriter David Koepp had initially planned for the hospital scenes to feature voiceover, but De Palma suggested that voiceover be used on the train station platform instead, leaving a gap in the script.

Pacino, ever the spanner in the works, wasn’t convinced the scene should be filmed at all, wondering if Carlito Brigante would even go to the hospital in the first place.

Ultimately, Koepp had to rewrite the scene dozens of times. De Palma even requested the writer’s presence on set to produce new material on the fly.

While you might think Koepp would be furious at his, he apparently has nothing but respect for De Palma. “The whole idea of something being truly romantic is that it’s about loss,” he said. “And that’s what so many of Brian’s movies are about.”

6. Abel Ferrara nearly directed

Before Brian De Palma, there was another man in the director’s chair, one perhaps even more controversial: Abel Ferrara.

Ferrara began his career directing (and even starring in) adult films. As per a Guardian interview in 2010, “It’s bad enough paying a guy $200 to f**k your girlfriend, then he can’t get it up.”

On breaking through to less explicit cinema, Ferrara honed his craft in ultra-violent slasher films; later, he would direct films like King of New York and Bad Lieutenant, both neo-noir crime films.

It’s likely that these later films were what attracted producer Michael Bregman to Ferrara. What we know less about is why Ferrara left the Carlito’s Way project.

It’s fair to say that, given his track record, Ferrara might have made more of a Scarface than a Carlito’s Way. It’s possible that producers, and Pacino himself, were more interested in the dramatic aspects of the film than the hyper-violence of Tony Montana.

5. The courtroom featured in the film was author Edwin Torres’ real workplace

It takes all kinds to make a Hollywood success story, and there have been no shortage of authors from unlikely backgrounds – Harper Lee, of To Kill a Mockingbird fame, worked as an air hostess before becoming an author. As for Edwin Torres, he was a state Supreme Court judge.

It’s perhaps not as unlikely as you’d expect: Torres based the characters in his novels on his own hardscrabble background and on the defendants who appeared in his court.

And it’s no coincidence that, when De Palma needed to shoot inside a courtroom, they didn’t need to splash out on a set: they were able to use Torres’ workplace.

Torres presided over several high-profile murder cases during his time on the bench, and became notorious for handing out harsh sentences.

On once sentencing a man to 50-100 years in prison for sexual assault, Torres was unapologetic, saying that “a society that loses its sense of outrage is doomed to extinction.”

4. The river scene was actually filmed in a shipyard

Tony Tagliucci’s escape from Rikers Island is one of the most thrilling sequences of the film, combining Carlito’s angst about being dragged back into the criminal world with a strong action set piece. But De Palma initially thought shooting it would be impossible.

As the shoot took place at night, in the middle of the river, it was thought too difficult to choreograph lighting and camerawork. But to make sure this pivotal scene took place, producers devised an ingenious solution.

Filming was moved to a shipyard in Brooklyn, and Kleinfeld’s boat was floated in a lock full of water, simulating a river instead.

To mask the industrial look of the rest of the shipyard, smoke machines were installed, and space lights were used to imitate the lighting.

If you look closely, you might be able to spot these imperfections; but, with being so caught up in the moment, we doubt you even noticed.

3. The film’s depiction of Grand Central Station makes no sense

When you’re shooting one of the greatest action scenes of the decades, and one of the greatest steadicam scenes of all time, you have to take a few liberties with geography and logistics.

What this meant in practice was that De Palma had to lobby Penn Central, the owners of Grand Central Station, to accommodate the demands of his scene, which even affected train schedules for the duration of the shoot.

As you might recall, the Grand Central scene features a chase from Harlem-125th Street Station all the way to Grand Central Station and, memorably, up its escalators.

Trains had to be re-routed and specifically timed so Pacino could quickly move between trains (unsurprisingly, the train system does not run on the schedule of an Al Pacino crime film).

Incidentally, the escalator chase features one of the longest moving staircases in cinema history; Bill Pankow, the editor, struggled to piece together all of the footage in a way that distracted from the escalator’s inordinate and illusory length.

2. The film includes an oblique reference to Death Becomes Her

If you were to guess which movies Carlito’s Way might make reference to, you probably wouldn’t even consider a black comedy about glamorous, undead women. Yet this Pacino crime flick has a beautifully subtle reference to 1992’s Death Becomes Her.

The question is: why? Well, it turns out that the screenwriters behind Carlito’s Way and Death Becomes Her are one and the same in David Koepp.

Koepp, who is otherwise best known for penning Jurassic Park and Mission: Impossible, had one heck of a 90s, having written some of the decade’s highest-grossing flicks.

As for the Easter egg in Carlito’s Way: Gail, an aspiring actor, at one point mentions that she had a role in a fictional musical called Songbird, based on the Tennessee Williams play Sweet Bird of Youth.

This is the same Songbird in which Madeline Ashton – Meryl Streep’s character in Death Becomes Her – is the lead. That’s certainly one way of leaving your signature as a screenwriter!

1. Pacino was forced to wear a thick coat in summer

As one of the most complex sequences in the film, Carlito’s Way’s foot chase scenes took several months to film. Back in 1993, seasons still existed, and this caused issues for Pacino on set.

According to Brian De Palma, the shoot for the chase began in winter and finished in the middle of summer. As we’ve mentioned, De Palma had originally planned to shoot at Grand Central Station first, but had to change schedule due to a Pacino injury.

You might think this is unimportant, but there’s one factor you might not have considered: Al Pacino’s swish black coat that Carlito Brigante permanently wears.

This meant that Pacino was “sweating to death,” says De Palma, as he jumped from carriage to carriage in sweltering heat, take after moistening take.

“At one point he said he’d had enough and he actually took the train home,” De Palma continues. If only all workplaces were so lenient!