Carlito's Way (1993) * * * 1/2

Directed by:  Brian De Palma

Starring:  Al Pacino, Sean Penn, Penelope Ann Miller, John Leguizamo

During a recent read through of my blog, I came across a review of Scarface, a Brian De Palma film with Al Pacino as a criminal.  It's a great film and I mentioned near the end how Carlito's Way could be seen as a companion piece to Scarface.   If Tony Montana lived long enough, he might've turned out like Carlito Brigante.   Either way, a life of crime is a case of high risk and temporary reward filled with regret, loss, and paranoia of losing it all.

Carlito's Way opens in a New York courtroom circa 1975.  Carlito, a crime lord serving a thirty-year prison sentence, is being freed after five years on a technicality.    Carlito delivers an ecstatic speech about how he is a changed man and will walk the straight and narrow.    No one believes him, especially the district attorney who thinks he will be sent back to prison very soon.     However, Carlito makes it clear that he is through with a life and crime.   He wants to buy a share of a rental car company in the Bahamas and pick up the pieces with the ex-girlfriend Gail (Miller) left behind when he went to prison.    Unfortunately, Carlito's past haunts him at every turn, as does his loyalty to his attorney David Kleinfeld (Penn) who got him out of prison early.    It is this loyalty that gets him trouble with the mob later.  

Pacino as Carlito is streetwise, insightful, and knows all too well how hard it will be to walk away.   Gail also knows this and is hesitant to come along with him in his new life.    She has been down the road too many times with him.    Kleinfeld, played as an oily hustler by Penn, knows Carlito's loyalty and uses it to his advantage; having Carlito partake in schemes both know will end badly.   However, like all tragedies, we see this unfolding and can only shake our heads.     Carlito believes he can escape his old world and start fresh in a new one, but as it has been said, he is through with the past, but the past isn't through with him. 

Looking over De Palma's resume, it is amazing that he is so underrated.    Breaking into the business along with Scorsese, Spielberg, and Coppola, he has been overlooked, but look as the titles to his credit:  Carrie, Dressed To Kill, Blow Out, Scarface, Wise Guys, The Untouchables, Casualties Of War, Carlito's Way, and even Bonfire Of The Vanities, which I found to be pretty good even if others didn't.    De Palma is a master filmmaker who aims big.   His milieu isn't small, personal projects, but big films that swing for the fences.   He has mostly succeeded too.   

I've seen Carlito's Way a few times now and it's funny how the final shootout at the train station works on me.    As Carlito eludes the men sent to kill him, I know how it turns out but I keep hoping that somehow it doesn't work out like fate seems to have planned it.   His tragic flaws came back to haunt him.    What a shame.