An Offer You Can Do Whatever You Want With #21: Carlito’s Way (dir by Brian De Palma)

It’s been a week so I guess it’s time for me to get back to reviewing mob movies, right? Usually, I do my best not to take such a long break in-between reviewing films — especially when it’s a themed-series of reviews — but I just got busy this week. It happens. Luckily, even when we get busy, the movie’s remain ready to be watched and reviewed.

Last week, I reviewed Scarface and The Untouchables, two gangster films from Brian De Palma. It only seems right to return to my look at the gangster genre by considering another Brian De Palma film. Released in 1993, Carlito’s Way reunites De Palma with Scarface’s Al Pacino. In Scarface, Pacino played a Cuban named Tony who was determined to get into the drug trade. In Carlito’s Way, Pacino plays a Puerto Rican named Carlito who is desperate to escape the drug trade.

Carlito’s Way opens with Carlito getting released from prison in 1975. He’s spent the past five years serving time on a drug conviction. Originally, Carlito was sentenced to 30 years but his friend and attorney, David Kleinfeld (Sean Penn), managed to get the conviction thrown out on a technicality. Now a free man, Carlito finds himself torn between two options. He can either get involved, once again, in the drug trade or he can go straight. Returning to his life of crime will mean once again doing something that he’s good at but it will also require him to deal with people who he can’t stand, like the sleazy Benny Blanco (John Leguizamo). Going straight will mean escaping from New York with his girlfriend, a dancer named Gail (Penelope Ann Miller). The problem is that it takes money to start a new life and there are people in New York who have no intention of allowing Carlito to leave.

Of the three De Palma-directed gangster films that I’ve recently watched, Carlito’s Way is probably the weakest. De Palma has always been a frustratingly uneven director and Carlito’s Way contains some of his worst work and some of his best. For instance, there’s a brilliant sequence where Carlito goes to a hospital to get revenge on someone who betrayed him and it is perhaps one of DePalma’s best set pieces. But then there’s other scenes where DePalma’s trademark style feels rather empty and counterproductive. Just when you’re starting to sympathize with Carlito’s predicament, DePalma will suddenly toss in a fancy camera trick and remind you that you’re just watching a film and that Carlito Brigante is just a character in that film. That technique worked well in the satiric Scarface and the mythological Untouchables but it often feels unnecessary in Carlito’s Way.

Al Pacino plays Carlito and, like DePalma’s direction, the end result is a bit uneven. On the one hand, Pacino and Penelope Ann Miller have a likable chemistry, even if Carlito and Gail don’t really make sense as a couple. On the other hand, this is one of those films where Pacino does a lot of yelling. Sometimes it works and sometimes, it’s just too theatrical to be effective. It’s hard not to compare Pacino’s performance here with his slyly humorous work in Scarface. Tony Montana yelled because he genuinely enjoyed getting on people’s nerves. The way that Tony expressed himself told us everything that we needed to know about the character. Carlito yells because that was Al Pacino’s trademark at the time the film was made.

The best thing about the film is Sean Penn’s performance as David Kleinfeld. Kleinfeld is one of the sleaziest character to ever appear in a movie and Penn seems to be having a good time playing him. (Watching the film, I found myself wishing that Penn was willing to have that much fun with all of his roles.) Penn doesn’t make Kleinfeld into a straight-out villain. Instead, he portrays Kleinfeld as being a somewhat nerdy guy who thought it would be fun to pretend to be a gangster and who has snorted too much cocaine to understand the amount of trouble that he’s brought upon himself. Just check out Penn in the scene where he’s dancing at a disco. There’s a joy to Penn’s performance in Carlito’s Way that you typically don’t see from him as an actor. He’s actually fun to watch in Carlito’s Way.

It’s a flawed film but fortunately, the movie’s good moments are strong enough to help carry the audience over the weaker moments. The movie often threatens to collapse under the weight of its own style but it seems like whenever you’re on the verge of giving up on the film, De Palma’s kinetic camerawork will calm down enough to allow you to get at least mildly invested in Carlito’s predicament or Sean Penn’s amoral dorkiness will create an amusing moment and you’ll think to yourself, “Okay, let’s keep giving this a chance.” Carlito’s Way may not be an offer that you can’t refuse but it’s still fairly diverting.