Ten years after teaming up on 1983's Scarface, Al Pacino and director Brian De Palma reunited for Carlito's Way (1993), a tale about Carlito Brigante, a Puerto Rican ex-con who gets drawn back into illegal activities soon after getting out of prison, despite genuinely wanting to keep his nose clean. Penelope Ann Miller (playing Carlito's girlfriend, Gail) and Sean Penn (the lawyer David Kleinfeld) co-starred in the film, delivering performances that earned them both Golden Globe nominations.
1. NEW YORK STATE SUPREME COURT JUDGE EDWIN TORRES MADE A LOT OF MONEY SELLING THE MOVIE RIGHTS TO HIS BOOK REPEATEDLY.
He sold the movie rights to his Carlito books 10 times before it was finally optioned. “When the producer told me they were going to finally make it, I told him I’m losing money here!” Torres said. “I just as soon kept selling the options.”
2. AL PACINO WAS ONE OF THE FIRST PEOPLE TO READ TORRES'S BOOKS.
”I showed him the books in galleys. It was just predestined (that Pacino would play Carlito)," Torres told Entertainment Weekly. The two used to work out together at the YMCA. Carlito's Way, Torres's first book to feature the titular character, came out in 1975, the year Pacino's Dog Day Afternoon was released.
3. ONLY TORRES KNOWS WHO CARLITO IS PATTERNED AFTER.
Carlito Brigante is based on three people that Torres knew, but he could never reveal who they were because of their criminal histories. Torres also said that Kleinfeld was based on actual attorneys he had encountered over the years. "Three lawyers I knew personally have been murdered in situations not dissimilar to Kleinfeld’s."
4. BRIAN DE PALMA WASN'T SURE HE WANTED TO MAKE ANOTHER GANGSTER MOVIE.
De Palma read the screenplay by David Koepp (Jurassic Park with Michael Crichton), even though he didn't think he wanted to go back to a familiar genre. "I didn't even want to read it. I didn't want to return to this terrain again," he said.
5. MARTIN SCORSESE PREVENTED IT FROM BEING CALLED AFTER HOURS.
Torres's two Carlito Brigante books are titled Carlito's Way and After Hours (1979). Despite the titles, the movie Carlito's Way is actually based on After Hours. However, Scorsese came out with a black comedy titled After Hours in 1985, and De Palma wanted to avoid repeating the title. The prequel Carlito's Way 2: Rise to Power (2005) was based on Torres's first book.
6. JOHN LEGUIZAMO TURNED DE PALMA DOWN FOUR TIMES.
Leguizamo played the memorable (to most) Bronx native Benny Blanco only after De Palma let him create his own character. He told The A.V. Club that he turned the director down four times because he "just felt that it wasn't enough of a part. Luckily, [Brian] De Palma and I had worked together on Casualties Of War (1989), so he let me improvise my ass off. I totally went off. I created this character, you know, all the bizarre back story, that he's a go-getter who can't wait to meet Pacino. I think that was the first time I really felt like I had found myself in movies. That was a great time... I'll always love De Palma, because Carlito's Way was where I found myself in film."
7. PACINO AND PENELOPE ANN MILLER GOT VERY CLOSE.
When asked about the alleged romantic relationship she had with her co-star, Miller (Adventures in Babysitting , Kindergarten Cop ) shrugged and answered, "It's not a secret and I'm not ashamed of it." Miller added that the two tried to keep the relationship discreet "for the sake of the movie."
8. SEAN PENN SAID "YES" TO CARLITO'S WAY SO THAT HE COULD DIRECT THE CROSSING GUARD.
Penn had written The Crossing Guard (1995) but had trouble getting studios to finance it. Then De Palma, his director on 1989's Casualties of War, called him late one night. "I needed a chunk of change—because I had a kid now and bills to pay—and the part Brian was offering me in Carlito's Way was a good one, plus it was with Al [Pacino], whom I love, so I did that. And then eventually I was able to set up The Crossing Guard."
9. PENN AND DE PALMA DID NOT ALWAYS GET ALONG.
"He's an operatic moviemaker, so the reality level is somewhere off in De Palma-ville, and to get hold of it is impossible," Penn claimed in 1996. "How to serve him is hard to get a grasp on, so it can become confrontational. And it did, to a degree, on Carlito's Way." He also said that working with Pacino was something he loved. "Working with him balanced that whole experience out."
"I remember when I was shooting Carlito's Way," De Palma said, after he was asked if any of his actors took things too far. "There's this scene where Sean is all coked up, and he's trying to get [Al Pacino] to go on the boat trip with him. Because of where the sun was, I was shooting Sean over Al's back for the beginning. I shot ten, fifteen takes, and I thought it looked pretty good. But Sean said, 'No, no, no, no, no.' I said 'What?!' He said, 'We don't have it.' I said, 'I think we do.' He said, 'I need a few more takes.' He said, 'Twenty.' I said, 'Twenty?? Ok…' I shot ten more, I think, and then I said, 'Sean, I have to shoot this two-shot, then I gotta go over and shoot Al. He's been playing to you all morning.' But Sean was never happy with the scene. And I came around, and shot a two-shoot, and an over-the-shoulder."
10. PENN DID NOT INTEND FOR HIS CHARACTER TO LOOK LIKE ALAN DERSHOWITZ.
Sean Penn's perm in the film was inspired, the actor claimed, by a picture in Life magazine of a law student from the Carlito's Way time period. "I tucked it into my script and went from there."
Viewers, and some movie reviewers, noted that he resembled Dershowitz, who supposedly threatened litigation. In reality, Torres brought in John Gotti's lawyer, Albert Krieger, to the set to talk to Penn about his earlier years on Gotti's team.
11. A PLANNED WORLD TRADE CENTER SHOOTOUT HAD TO BE CHANGED AT THE LAST MINUTE.
"I had elaborate storyboards of this whole shootout on the escalators that were in the World Trade Center," De Palma said. "I spent weeks and weeks photographing it … and a couple of days before we were about to shoot, they blew it up." The epic shootout took place in Grand Central Station instead.
12. THE STUDIO WANTED TO MAKE IT SHORTER.
Universal Pictures asked De Palma if the movie could be cut down from its two hours, 25 minutes length, since a shorter time would ensure more showings in theaters. But De Palma knew a release date was already in place. De Palma told Universal, "Hey, guys, do you want me to have the movie open November 8th, or do you want me to figure out how to make twenty minutes out of it?" The release date obviously won out.
13. BENNY BLANCO MADE AN UNEXPECTED IMPACT.
After the movie opened, bags of heroin called "Benny Blanco" were dealt in New York City.