There was a lot of anticipation when Carlito’s Way was released in 1993. Director Brian De Palma had just come off a lukewarm reception for yet another Alfred Hitchcock homage, Raising Cain (1992) and was in need of a hit to appease the studios. And so, a re-teaming with Al Pacino in an effort to recreate the magic of Scarface (1983) made commercial sense. Carlito’s Way was much more somber in tone than the cinematic shotgun blast that is Scarface. It is a tragedy about how a criminal tries to go straight but is ultimately doomed from the get-go.
Carlito’s Way features one of the oldest chestnuts in the world. Narrating his story during the last moments of his life, Carlito Brigante (Pacino) is a veteran criminal recently released from prison and intent on leading a normal, law-abiding life. Of course, it isn’t going to be that easy and when he returns to his old neighborhood, his reputation precedes him. Local gangster Benny Blanco from the Bronx (John Leguizamo) is a cocky, up and comer who sets his sights on Carlito after he is shamed by him in public. Carlito, however, barely notices him as he’s torn between reuniting with an old flame, Gail (Penelope Ann Miller), a struggling Broadway dancer, and keeping his lawyer friend, David Kleinfeld (Sean Penn) out of trouble.
As a personal favor to David, Carlito runs a nightclub so that he can raise enough money to start his own business renting cars in a tropical paradise with Gail. However, Carlito’s loyalty to David will be his undoing because his friend has become so corrupt during the time that Carlito was in prison.
As always, De Palma injects the film with his trademark bravura action sequences, including one early on when Carlito accompanies his cousin on a routine drug deal that turns into a violent blood bath. One look at the set-up and, like Carlito, we know that something is not right. De Palma prolongs the violent confrontation for as long as possible, gradually building the tension as we feel Carlito’s apprehension. The director orchestrates the entire scene like a pro, knowing just how long to build things up before the inevitable eruption of violence.
Carlito is a role tailor-made for Al Pacino, allowing him to essay another larger-than-life character. Carlito is a smart guy who cannot escape what he is no matter how hard he tries and Pacino conveys the melancholy that lurks behind the bravado of his character. The real scene stealer, however, is Sean Penn’s sleazy, coked-up lawyer. The actor reportedly did the film to help finance his second directorial effort, The Crossing Guard (1995). For a paycheck role, Penn does a great job as he disappears into the character, complete with a frizzy afro and cheap suits. It’s almost as if Pacino’s presence inspired Penn to step up his game. And this makes Penn’s memorable turn so much fun to watch.
The rest of the cast is filled out by solid character actors like John Leguizamo, who plays Benny as a pushy little runt with a motor-mouth, and the always reliable Luis Guzman as Carlito’s right-hand man. The only miscasting is Penelope Ann Miller as Pacino’s love interest. She looks out of place and just doesn’t have the chops to hold her own against Pacino.
Despite the cliched premise, Carlito’s Way works so well because of the caliber of actors, David Koepp’s screenplay with memorable dialogue (“You think you’re big time?! You’re gonna fucking die big time!”), and De Palma’s stylish direction. This film is proof that given the right material, De Palma can still make a hell of an entertaining movie.