The Best Movie You Never Saw: Carlito’s Way

Last Updated on July 30, 2021

Welcome to The Best Movie You NEVER Saw, a column dedicated to examining films that have flown under the radar or gained traction throughout the years, earning them a place as a cult classic or underrated gem that was either before it’s time and/or has aged like a fine wine.

This week we’ll be looking at CARLITO’S WAY!

THE STORY: Carlito Brigante (Al Pacino) is a former New York City drug kingpin who’s freed from prison on a technicality by his unscrupulous lawyer, Dave Kleinfeld (Sean Penn). Upon his release, he surprises his old underworld cronies by vowing to go straight, aiming to save up enough money to set himself up in a legit business in Florida, and win back the love of his former girlfriend, Gail (Penelope Ann Miller). To that end, he buys into a mobbed-up nightclub, only to find the path to redemption is a dangerous one.

THE PLAYERS: Starring: Al Pacino, Penelope Ann Miller, Sean Penn, John Leguizamo, Viggo Mortensen & Luis Guzman. Written by David Koepp. Based on the novels Carlito's Way and After Hours by Edwin Torres. Directed by Brian De Palma.

And "Carlito’s Way" was again, treated like another Al Pacino gangster movie kind of business. But it was really a great script, based on two novels written by Edwin Torres. Again, at the time it came out, not much attention was paid to it, though I thought it was a very skillfully made movie from a very good script.” Brian De Palma interview w/ Matt Zoller Seitz

THE HISTORY: By 1993, SCARFACE was already infamous. A modest hit upon its initial release, it soon became a staple of video stores all over the world, and had already begun to get heavily referenced in hip hop culture. This is most evocatively portrayed in the film NEW JACK CITY, where Wesley Snipes’s gangster, Nino Brown, parties with it playing on a massive screen. Thus, when it was announced that the director/star/producers (Brian De Palma/ Al Pacino/ Martin Bregman) were re-teaming in another gangster epic, CARLITO’S WAY, everyone expected SCARFACE 2.

Instead, audiences were treated to a contemplative tale of redemption, one that sought to suck the glamor out of the gangster lifestyle that SCARFACE arguably promoted. Audiences and critics were mostly left cold, and the big-budget epic only grossed $36 million domestically. All involved were surprised by how harsh the notices were, with De Palma guessing much of it had to do with the lingering resentment felt towards him for THE BONFIRE OF THE VANITIES debacle, while Pacino was coming off a controversial Oscar win over Denzel Washington for MALCOLM X (and the screenwriter, David Koepp, had just written JURASSIC PARK). Years later, many critics would retract their overly harsh views, while Cahiers du Cinéma named it the best film of the 1990’s – many years after its initial release.

In Carlito's Way, I play Pachanga, which was Pacino's main sidekick. That for me was such a great movie because it captured that quote-unquote "criminal element" of someone just trying to make it [who] gets sucked right back into it, and you can't trust nobody. Johnny Leguizamo was in there too, and it was a great story about a guy from the neighborhood who just couldn't get out of it. – Luiz Guzman- Random Roles Interview

WHY IT’S GREAT: Of all the films I’ve profiled in this column, I’m going to guess this one is the most seen. However, I still think too many people view it as a kind of side note to SCARFACE, and I’d be surprised if our younger, post-millennial demo knows this film all that well. It’s never had the same kind of cultural currency as SCARFACE or other Pacino classics like THE GODFATHER or HEAT. That said- CARLITO’S WAY just might be better than any of them.

I really think this film is a masterpiece, and while thoroughly different than SCARFACE, it’s nonetheless a richer experience if you know that well as it does play somewhat like a sequel. Imagine if Tony Montana hadn’t been killed. Imagine that instead he went to prison and had years to contemplate on his actions and came out genuinely wanting to make amends for his past deeds and to live a good life. That’s kinda what CARLITO’S WAY is. Granted, Carlito is nowhere near the loon Tony was (even though Tony had a line he wouldn’t cross – like when he refused to execute children in an assassination gone wrong). He’s a killer, but a thoughtful, remorseful one full of empathy and restraint. If he doesn’t have to kill he won’t. Heck, even times when he should kill he won’t, an element of his character that inevitably leads to his downfall.

If modern audiences are used to the gloriously over-the-top Pacino they’ve seen in many latter-day films, they’ll be surprised at how restrained and quiet he is here. Looking ultra-cool with his beard and leather duster, he’s among the coolest tragic heroes the genre has ever seen, comparable to a guy like Chow Yun-Fat in his “heroic bloodshed” classics. He’s badass, but he has a heart, as shown by his low-key romance with Penelope Ann Miller’s Gail, who’s desperate for him to go straight and leave his gangster cronies behind.

Said cronies are a memorable bunch, none more so than John Leguizamo as the iconic “Benny Blanco from The Bronx”. Watch the way Leguizamo tries to dominate Pacino in their scenes together and note the authentic look of loathing on Pacino’s face. They’re only together in a handful of scenes, but as a pair they’re electric. Hollywood lore suggests Pacino hated Leguizamo’s scene-stealing when they were shooting, but no doubt realized later how good he had been and sure enough, the two worked together again. Luis Guzman is similarly good as Carlito’s muscle, Pachanga, a hard-core thug looking out for himself and no one else, a lesson Carlito learns the hard way.

Of course, the movie is all but stolen by Sean Penn in an atypical role as a coked-up, frizzy-haired lawyer, Kleinfeld, who’s in deep trouble with the mob. You know right off the bat that he’s trouble, but you also get Carlito’s devotion to him, as he saved him from a life sentence in jail and arguably gave him the chance to turn his life around. And let’s not forget Viggo Mortensen, in a single-scene role as a former, embittered friend of Carlito’s that’s pathetically trying to turn on him.

It’s all topped off by Brian De Palma’s directing, which is him at the top of his game. He sprinkles the film with some absolutely masterful set pieces, including a dynamic shootout in Grand Central station (which I prefer to the one in THE UNTOUCHABLES), while the soundtrack is peppered with non-stop disco classics that evoke the era beautifully (and oddly enough, sparked a fascination of mine with disco culture of the era).

BEST SCENE: While I love the Grand Central Station shootout, the absolute best scene in CARLITO’S WAY is the stone-cold classic pool hall shootout. Here, Carlito’s nephew (a young John Ortiz!) has lured him into a drug deal; one which Carlito’s immediately recognizes is a set-up. Watch the way De Palma plays with long shots, reflections, camera movement and music here. This is top-shelf filmmaking.

SEE IT: CARLITO’S WAY can be easily found on many streaming platforms, as well as DVD/ Blu-ray and even HD-DVD (a format I actually watched this on pretty recently).

PARTING SHOT: When people ask me what my favorite movies of all time are, CARLITO’S WAY usually falls on the list somewhere. I’ve seen it countless times, but I can almost watch it on a loop. It’s the perfect gangster tale and stands with GOODFELLAS and THE GODFATHER as the genre at its absolute peak.