Al Pacino has played the ultimate badass countless times in his career. From The Godfather to Scarface and even Dog Day Afternoon, Pacino has found himself in roles that really let him flex his acting chops and muscles. There's an intensity that surrounds many of his roles, and 1993's Carlito's Way is no different.
Directed by Brian DePalma, Carlito's Way was something of a sleeper hit that didn't really grab the attention of audiences until it hit home video (it was also followed by a DTV prequel). Though the title was obviously different, Carlito's Way was actually an adaptation of the book After Hours by Edwin Torres. The film starred Al Pacino as Carlito Brigante, Sean Penn as David Kleinfeld, Penelope Ann Miller as Gail, and John Leguizamo as Benny Blanco.
The film begins with Carlito being shot in a subway and reminiscing about his life on the streets. We're soon given a flashback to the thing that set this event in motion, and that was sadly his decision to turn his life around. You see, Carlito was a legend when he was on the streets. He was a successful assassin and narcotics dealer who really carved a name out for himself. He was a connected man and feared for all the right reasons, but then he was caught and sent to jail. It was only due to a snafu during the investigation that his lawyer, David Kleinfeld, was able to get him off.
Now that he's a free man Carlito feels he's born again for a new life. He takes great strides to make it known that he's gone clean and wants nothing to do with the seedy underbelly of the underworld. Eventually he partners up with David to co-manage a nightclub in an effort to make enough money to move to the Bahamas. Things seem to be going good for a while, especially since he rekindles an old flame with Gail and the club is rather successful. That's when his buddy David decides to mess things up by getting involved with things he shouldn’t be. Thus the dominoes of Carlito's fall eventually start lining up.