Directed by: Brian De Palma
Written by: David Koepp
Starring: Al Pacino, Sean Penn, Penelope Ann Miller, John Leguizamo, Luis Guzmán
One would hope anyone coming from prison has learned their lesson and uses this release as a second chance at life and to no longer commit the crimes that got them there to begin with. Some fall right back into the trap while others like the protagonist in Carlito’s Way simply cannot avoid having his past drag him into a world he wants to leave. This constant dragging turns his fantasy into what could be a tragedy.
After having his lawyer get him out of his 30-year sentence in 5 years, Carlito Brigante (Al Pacino) has decided to leave the criminal game behind. He rekindles his relationship with longtime girlfriend, Gail (Penelope Ann Miller), but gets dragged into criminal activities. He hopes to get through all of this new nonsense and eventually get out of the city and begin a new life with Gail.
The tragedy of Carlito’s Way is one of attempted reform and how some cannot escape the life they lived before. No matter how many times he attempts to leave everything behind, he just gets dragged back into a world he no longer sees as a viable future. Even with this reluctance to return to his previous profession, we get the pleasure of seeing what made Carlito a household name in his neighborhood. His smooth-talking and sharpshooting characteristics come flying through showing us why this world will never let him retire in peace.
Relationships drive much of what Carlito wants and needs to accomplish when he steps out of prison. Driving Carlito through this journey is his girlfriend, Gail, who makes him want to leave this life and start anew with her. Through all of the hardships he faces, the dream of ending up on a Caribbean island with her pushes him to persevere. On the other hand, there’s also David Kleinfeld (Sean Penn), who got Carlito out of prison but also becomes the reason why his dream cannot be accomplished in the timeline he expected. The respect and gratitude our protagonist has for David cause him to be dragged back into his old life. If you’ve seen any film with a plot point of “One last …,” you know things will not go as planned.
David and Carlito’s relationship in the film goes through quite the roller coaster, as the latter must deal with the former’s issues of possessiveness and avarice. Carlito provides a type of cover David needs to unload whatever goals he wants to achieve, which brings their entire relationship into question. David drags everything down into the pits and his obsession with getting to the top of the food chain complicates everything for everyone, especially for Carlito.
The world-building done in these New York City streets come together very well with the introduction of a host of characters, who have a stake in several businesses and people we should be wary of as Carlito tries to get his happy ending. It comes with good Latinx actors like John Leguizamo and Luis Guzmán having the ability to display their acting skills alongside Al Pacino. Every street corner presents a threat and alliances may be broken at any moment, which adds to the stress of watching this film. With a goal set, any instance where Carlito gets into a dicey situation, I could not help but get nervous knowing our lead character wants nothing to do with the nonsense. Building that momentum of stress comes from creating a character worth rooting for and establishing a world where one could lose their life at any instant.
I know saying this must be groundbreaking but Al Pacino knows how to act. The fact this man has only one Oscar should be considered an insult because when he’s in the mood he can outact anyone across from him. In Carlito’s Way, he channels this completely fatigued look for the entirety of the runtime. His character has had enough of this world, and all of the little games he used to enjoy to mess with people just get on his nerves now. It makes for some unintentionally comedic moments, but it comes through Pacino’s performance. It looks similar to a parent trying to listen to the same excuses from their kids about not doing their chores. Pacino also brings forth this volatility in this character, where at any moment he could snap from the frustration.
This film pairs well with Pacino and director Brian De Palma’s other major contribution, Scarface. While the coked-up 80s film follows a man of crime, it feels revved up to 100 mph for the amount of heat happening. Conversely, Carlito’s Way shows a different sort of struggle and a story filled with more melodrama rather than unleashing all of Pacino’s explosiveness. De Palma uses more restraint with this film, which pretty much solidifies why this feature may be his best. It utilizes the style of the famed director but applies some control other films of his seem to lack.
With its groovy soundtrack and a dangerous look at New York, Carlito’s Way creates a ticking time bomb where our protagonist must fix his loose ends in order to enter paradise. Bumps are on the way, but he must persevere through the madness of his friend, David Kleinfeld, and the rest of the streets refusing to leave this line of work for good. The story feels epic and fulfilling, as it completes the saga of Carlito on the streets of New York. Whether he gets the happy ending he seeks can be found when you watch the film.