It’s always tricky to know what counts as under- or overrated, but my strong sense is that Carlito’s Way is one of the more underrated – or at least overlooked – movies that came out during the 1990s.
In fact, I revisited it recently and it’s downright magnificent. So much so that I’m willing to proclaim it as a Mount Rushmore New York City movie.
Carlito’s Way: so what’s the story?
Carlito Brigante (Al Pacino, in a grounded and wonderful performance) gets out of jail in 1975 to a world that has changed, but he’s fundamentally changed too. He’s done with “the game,” and all he wants is to scrape together enough money to head to the Caribbean and buy into a car rental business.
However, fate – and some seriously bad dudes, including his attorney Dave Kleinfeld (Sean Penn) – have a way of intervening.
Carlito’s Way is Brian De Palma’s best film
Some people will consider this sacrilege, so be it.
Brian De Palma has directed some widely hailed classics such as Scarface (also starring Pacino), The Untouchables, and Carrie, but he’s at his very best here. The pacing, the atmosphere, the tension, and the music all pulse and breathe in a way that makes the story feel both compulsive and inevitable.
Putting on my film professor’s sport coat for a moment, this is De Palma’s purest expression of operatic pulp.*
* Note: I am not a film professor, but like to fantasize about the notion now and again.
And then there’s the New York City of it all
While slightly stylized, Carlito’s Way is a dazzling immersion into a mid-1970s NYC replete with wild fashion, drugs, dancing – and an ever present and lurking sense of danger.
You can smell the anxiety, you can taste the cheap champagne, and you feel the doomed ambition.
It’s the final half hour of the movie – a riveting, heart-pounding sequence in which Carlito races to grab his cash, meet Gail, and hop on a train to get out of Dodge while there’s still time – that elevates Carlito’s Way to Mount Rushmore status.
It’s one of the best action set pieces involving the subway ever filmed, and also makes gorgeous use of the iconic Grand Central Station while it’s at it.
It also includes an all-time performance by Sean Penn
This is important. Penn is off-the-charts great in everything, but the singular performance as the nerdy, jittery, sleazy, and ultimately repugnant Kleinfeld is worth watching alone if you care about movies.
The cast is ridiculously stacked top to bottom
Pacino and Penn would be one thing, and plenty at that. But then you get Penelope Ann Miller as Carlito’s girlfriend, Gail, and a murderer’s row of character actors such as Luis Guzman, John Leguizamo, James Rebhorn (Dickie Greenleaf’s dad from The Talented Mr. Ripley!), and Viggo Mortensen.
We’ve even got future Sopranos legend Vincent Pastore as Copa Wiseguy #1.
It’s one of the low-key best gangster flicks ever made
Another incredible scene early on is Carlito stumbling into a routine money transfer gone very bad. Carlos Santana’s version of “Oye Como Va” is used to perfection here, and we also get Carlito’s iconic line as he prepares to storm out a bathroom (with zero bullets left in his now-empty gun): You think you’re big time? You gonna fuckin’ die… big time!
What other NYC Mount Rushmore movies qualify?
This is a much larger conversation obviously, but I’ll nominate the following as an elite group to consider: Rear Window, The Apartment, West Side Story, The French Connection, Annie Hall (setting aside the real life Woody), The Godfather (more Pacino!), Taxi Driver and Goodfellas in the Scorsese category, Ghostbusters, Wall Street, Coming to America, When Harry Met Sally, Do the Right Thing, Birdman, Vanilla Sky…
There’s a lot, okay!
In conclusion: should you check out the prequel, Carlito’s Way: Rise to Power?
Let me be clear: no. Do not check out Carlito’s Way: Rise to Power.
Just don’t.
Rewatch Carlito’s Way instead.