Looking back at Carlito’s Way

With sterling performances from Al Pacino and Sean Penn, Carlito's Way is a classic 90s thriller. Ryan takes a look back...

Cracked Magazine once published a little series of cartoons where various characters’ activities were accompanied by unexpected comic book sound effects. A defecating bull was accompanied by the word “Buussshhh” – referring to George Bush Senior, the US president at the time of publication. Another panel showed a wild-eyed maniac firing a gun over and over again – the blasts dramatised with the words, “De Palma! De Palma! De Palma!”

This odd, throwaway cartoon summed up the prevailing critical attitude to Brian De Palma’s films throughout the 80s. Often met with criticism for their violence and misogyny, censors often demanded cuts. Protestors railed against the treatment of women in Dressed To Kill. De Palma received death threats for the portrayal of migrant Cubans in Scarface.

Yet by the start of the 90s, there were signs that De Palma’s confrontational approach to filmmaking was already starting to change. The Bonfire Of The Vanities (1990) and Raising Cain (1992) contained all the stylistic flourishes De Palma excelled in, but were notable for their lack of controversy.

It’s worth comparing 1993’s Carlito’s Way with Scarface, made a decade earlier. The seethingly violent Scarface – not just in terms of physical brutality, but also in terms of its cinematography and hectoring music by Georgio Moroder – enlivened by Al Pacino’s raging turn as migrant drug capitalist Tony Montana, was a highlight for both actor and director, even though some critics were horrified by its excess.

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Carlito’s Way saw De Palma and Pacino join forces again for another crime drama. But where Scarface dealt with the brutal rise and fall of a grasping career criminal, Carlito’s Way is quieter and more introspective. Theoretically, this second collaboration could have been a mistake, since producing another movie in the same genre as Scarface might have drawn unfavourable comparisons with that gaudy 80s masterpiece, which had already acquired cult status by 1993.

In fact, when De Palma was given the Carlito’s Way script (based on the book After Hours by  criminal judge Edwin Torres), he initially had misgivings about making it. “I didn’t even want to read it. I didn’t want to return to this terrain again,” De Palma remembered in The Making Of Carlito’s Way. But Carlito’s Way finds both director and actor in a very different frame of mind, and the resulting film is, thanks in part to its more subtle approach, perhaps even greater than Scarface.

Pacino plays Carlito Brigante, a convicted criminal who, thanks to the assistance of his weasel-faced lawyer Dave Kleinfeld (Sean Penn), has had his 30-year prison sentence overturned on a technicality. But as Carlito emerges back onto the streets of 1975 New York, he realises that five years in jail is still an awfully long time for a once respected and feared gangster. Fashions have changed. Music has changed. There’s a new generation of criminal on the streets, which is as arrogant and aggressive as Carlito was in his prime. 

Determined not to squander his unexpected freedom, Carlito resolves to go straight, but fate conspires against him. His cousin is killed in a drug deal gone wrong, and his opportunistic swiping of a considerable chunk of cash allows him to acquire a local nightclub, but also puts him back on the radar of the local lowlifes. Meanwhile, Carlito’s warped sense of loyalty leaves him feeling indebted to Kleinfeld, who’s become drawn ever deeper into a world of coke and corruption during Carlito’s spell in prison. An attempt to bust an Italian mobster out of prison goes awry, and just as Carlito plans to retreat to the Caribbean with his lover Gail (Penelope Ann Miller), New York’s criminal element begins to close in.

One of Pacino’s great characters – certainly among his finest of the 90s – Carlito cuts a lonely, rueful figure. Through a series of voice-overs, we hear his private regrets, his observations, and his suspicions that a net is gradually tightening around him. We can sense the toughness of this once streetwise character, but also his intelligence and his humility. He’s learned from his past mistakes, but doesn’t have the opportunities or the knowhow to distance himself from them. It’s said that screenwriter David Koepp (who scored an extraordinary hit with his adaptation of Michael Crichton’s Jurassic Park that same year) worked for a long time to get the tone of Carlito’s voice-over just right, and the effort was worthwhile; far from a narrative crutch, Pacino’s monologues add an extra layer of poignance.

De Palma’s performance behind the camera is no less layered. Shorn of the aggression of his late-70s and 80s work, his direction here is still full of unforgettable set-pieces – perhaps some of his very best. The opening sequence, shot in black-and-white, where De Palma’s camera floats and rotates like a disembodied spirit to Patrick Doyle’s swooning score, is little short of beautiful. There are many sequences in De Palma’s films which have been singled out for praise; the Hitchcock-referencing gallery scene in Dressed To Kill, for example, or the pram descending the steps in The Untouchables. The opening scene in Carlito’s Way, although mentioned less often, is arguably on a par with those. 

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The action sequences, while few, are also brilliantly staged. One oft-celebrated scene, where a stand-off between Carlito and a pool room full of bad guys gradually builds to boiling point, all to the music of Ray Barretto’s El Watusi, is a masterful exercise in rising tension: everything, from the choice of music, to the camera positioning, to the crimson colour of the walls, adds to the unease.

Carlito’s Way begins and ends at Grand Central Station, with another shoot-out along the lines of The Untouchables’ six years earlier. In spite of how familiar this location is, De Palma manages to use the fixed environment to create a compelling game of cat and mouse, as Carlito’s futile attempts to evade a group of somewhat inept mafia guys eventually gives way to a tense, abrupt shoot-out.

The real fireworks, however, come from the actors themselves, and De Palma appears to know this. Sean Penn is absolutely perfect as Kleinfeld, and this may well be the performance of his career – remarkable, considering he reportedly took on the role in order to finance his film, The Crossing Guard. Nevertheless, Penn put an obsessive level of effort into his performance, demanding take after take from De Palma for one particular scene. Conniving, passive-aggressive, with an absurd afro hairdo which nevertheless perfectly suits his cocky, arrogant personality, he’s both the film’s true antagonist and its engine, providing Carlito with his route out of jail, and also playing a part in his downfall. 

Penn and Pacino spark off one another spectacularly in every scene they share, from their initial friendship to the last act, where Carlito realises the depth of Kleinfeld’s criminality (“You a gangster now,” Carlito says in one key scene. “You can’t learn it at school. And you can’t have a late start”). It’s their pairing, rather than Carlito and Gail, which drives the film along, even though Penelope Ann Miller puts in a fine performance. In fact, the cast is uniformly great, from John Leguizamo’s spiteful Benny Blanco from the Bronx, to James Rebhorn’s District Attorney Norwalk. (Look out for Viggo Mortensen, too, in a bit part as a wheedling snitch.)

Sadly, the film’s qualities weren’t widely recognised at the time of release. Although a bigger critical and financial success than the misfiring Bonfire Of The Vanities, it wasn’t a particularly major hit, either. Predictably, reviews complained about its similarities to Scarface, even though its approach was wildly different.

Certainly, you could pick fault with the film’s attention to period detail – a quick skim through the facts pages on IMDb reveals that several of the disco-era songs weren’t actually released in 1975, the year the film’s set. But really, none of this matters. More so even than Scarface, Carlito’s Way is a character study, a portrait of regret. Scarface was a splashy, angry comment on boom-and-bust capitalism, and Carlito’s Way is its quieter companion piece.

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A director once criticised for his lack of empathy, De Palma brought genuine pathos and romance to Carlito’s Way – something David Koepp once summed up perfectly:

“One common misperception people have with the word romantic, is that it ends with two people walking away on a beach together,” Koepp said. “The whole idea of something being truly romantic is that it’s about loss. And that’s what so many of Brian’s movies are about: loss of innocence, loss of love, loss of life. What’s truly romantic is to find something that’s truly ideal for you; that which seemed unobtainable in life, and then to find out that it is.”

In turning away from the violent excess that had commonly followed his name in the previous decade, Brian De Palma made one of the finest crime dramas of the 1990s. 

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