CARLITO’S WAY, Brian De Palma’s Unsung Masterpiece, at 25

“Mi barrio… ya no existe…” – Carlito Brigante

Brian De Palma’s career was on life support in March of 1993, when he began production on his latest gangster fable, Carlito’s Way.

His last success was another gangster picture, albeit one in an entirely different tone than the one he was about to make. 1987’s The Untouchables was a crowd pleaser and a terrific callback to the serialized adventures of Eliot Ness and his team of lawmen, only with a more modern, brutal De Palma style.  It made $76.2 million, over three times its budget, and it got Sean Connery his elusive Oscar statue the following spring.

In 1989 De Palma made a serious war picture, Casualties of War, which made sense. The Untouchables had helped him shed the stigma of being, at least in the eyes of the stuffy cinematic opinion makers of the time, nothing more than a Hitchcock imitator with more blood and nudity. He was angling for the “serious filmmaker” label with Casualties of War, but the Michael J. Fox / Sean Penn Vietnam thriller – a true story about the sadistic rape and murder of a young female villager – proved too off putting and gruesome for audiences. It was a failure, but nothing on the level of his next film.

Tom Wolfe’s yuppie satire Bonfire of The Vanities was one of the most popular books of the 1980s, but De Palma’s film was such a disaster, from the troubled production to the spectacular box office failure, that it inspired its own book. Limping away from prestige and marketability, De Palma retreated to the thriller genre and directed Raising Cain, a salacious Psycho riff with a terrifically bonkers performance from John Lithgow that never connected with audiences – partly due to the oddball story, partly because that very story had been butchered and reorganized by the studio, thanks to some mixed focus group reactions.

Then he was offered Carlito’s Way, and wanted nothing to do with it. Based on the 1975 Edwin Torres novel, the story of a Latin gangster stoked De Palma’s memories of Scarface, and the director wasn’t eager to dive back into that extravagant world. Then he read the screenplay from David Koepp, who had just recently written the screen adaptation of Jurassic Park, and he knew this story was operating with an entirely different tone than Oliver Stone’s coke-addled exploits of an out-of-control Tony Montana.*

In many ways – the obvious roadblock of Montana’s spectacular execution at the end of Scarface notwithstanding – the story of Carlito Brigante could work as a Scarface sequel. Set free from prison five years into a thirty-year stint, thanks to prosecutor tampering and the shrewd eye of attorney David Kleinfeld, Carlito Brigante is ready to leave the kingpin days of his youth behind. He wants to go straight, to make enough money and move down to the Bahamas where he plans on renting cars to tourists and living out his days in peace and quiet. It is a reformed, mature version of Tony Montana who, despite all odds, survived his lifestyle and came out on the other side a changed man, a man who wants to do right, live right, and ride off into the sunset. The fact Al Pacino portrays the subject of both films also plays an undeniable hand in the connective tissue.

Of course, this being a gangster picture, all does not go as planned for Brigante. That’s clear in the film’s opening sequence where we see him, in a soft-focus, black-and-white prologue, get shot in the stomach and collapse to the ground. For years, this setup felt like it pulled the rug out from under the entire film, vanquishing all tension revolving around Brigante’s escape; in the Noah Baumbach De Palma documentary, however, the director discusses the plan to include this bookend scene. It was his goal to make the audience forget all about that opening sequence with the tension and the suspense of the story itself. In that way, he succeeds.

As problems arise, fester, and build on one another to a blood-soaked crescendo at Grand Central Station, De Palma’s set pieces are consistently dazzling. He has always been a master of the long take, and the set piece, and the pool-hall sequence at the end of the first act is on par with any set piece in the filmmakers oeuvre, as tense as the train-station sequence in The Untouchables or the prom scene in Carrie:

The tension that builds through Carlito’s Way relies on Carlito’s lack of power; it isn’t about how he is going to escape with Gail (Penelope Ann Miller) to the Caribbean, it’s how he is going to navigate each and every second he stays in New York as his mere presence grows increasingly dangerous. He is vulnerable, scared, and often powerless to the influences and the decisions of the characters who surround him, and powerless to his own code, a code that convinces him to stick with his lawyer, Kleinfeld, who is so clearly the biggest roadblock in Carlito’s exodus.

Sean Penn surprised everyone when he showed up on set with a perm shaved back to resemble severe male pattern baldness. His appearance smartly sets him apart from everyone in the picture. Davey Kleinfeld is the poisonous fruit Brigante cannot avoid, not one of the neighborhood guys, but a slick outsider; Carlito unknowingly helping Kleinfeld murder Tony Taglialucci in the East River outside Riker’s Island leads to the extended chase sequence finale, but ironically it is not the source Carlito’s ultimate demise.

The one time Carlito’s old instincts jump up to bite him is his conflict with Benny Blanco, From the Bronx (John Leguizamo). The bravado of Blanco may mirror a young Carlito, it may not, but one thing is certain: Blanco’s presence stoked a long-buried fire in Carlito’s youthful soul, the one he is working so fervently to leave behind. But his decision in this moment was enough to seal his fate in Grand Central:

Brian De Palma knew from the outset he needed to inject his signature style into as much of the film as he could in order for it to stand out from the scores of gangster films that had preceded it. Even The Untouchables has a feeling of familiarity in regards to the genre. Carlito’s Way is stylistically indulgent, with De Palma employing his psychosexual thriller aesthetics early and often. The split screens and the first-person POV work brilliantly to put the suspenseful building blocks in place, and the story lends itself more to a humanistic tale than what was present in De Palma’s previous gangster films.

Carlito’s Way opened second at the box office the weekend of November 10, 1993, with just over $9 million. Reviews were solid, but word of mouth was nil. Perhaps fatigue with the gangster genre had set in by the end of 1993; the success of Martin Scorsese’s Goodfellas had spawned Warren Beatty’s Bugsy, but it also generated ridiculous wannabes like Billy Bathgate, Hoffa, and the embarrassingly bad Christian Slater/Richard Grieco star vehicle Mobsters. Whatever the case, Carlito’s Way quietly drifted out of the picture, accruing a meager $36 million in ticket sales; enough to cover the $30 million budget, but nothing to write home about.

In his documentary, Brian De Palma says he didn’t think he could make a better movie than Carlito’s Way. He would return three years later to kick off the Mission: Impossible franchise, but it’s difficult to argue with De Palma’s assessment of his own work. Even though Carlito’s Way hasn’t seen the kind of reappraisal that Blow Up or Dressed to Kill has in recent years, and it doesn’t have the cultural currency of Carrie or Mission: Impossible, or the prestige of The Untouchables, it might very well be his best film. It is, at times, a beautiful film with true affection for its characters. It’s an endlessly engaging thriller, tactile and true, and its collection of incredible set pieces is held together by actors and actresses who hit the heightened notes of their characters with palpable passion.

And, no matter how many times you watch it, you always hold out hope that Carlito will make it to Gail in the end, as a smile breaks through his panicked sprint across the train platform. Even though you’ve known from the outset that happiness isn’t in the cards of a condemned man, you still hope. Because you are invested in Carlito’s salvation.

That’s how great filmmaking works.