It’s rare to see Al Pacino upstaged in any movie, and his performance as a Puerto Rican ex-con attempting to go straight is typically inspired, a controlled blend of both the fiery and understated sides of one of Hollywood’s most consistently brilliant performers. Then you have Sean Penn in perhaps his greatest ever role, almost unrecognisable beneath a shock of red curls as he sneers and struts his way from arrogant big city lawyer to crime world player, and all under the nose of one of New York City’s most legendary gangsters. Not only does Davey Kleinfeld manage to fool his supposed friend, Carlito Brigante, he strings him along while he’s still of use, feeding off his skills and reputation while secretly setting him up for the fall. Kleinfeld is the personification of a society gone rotten, the kind that has no time for Brigante’s misguided moral code.

via You’re in Trouble, Baby: Carlito’s Way and the Rise of Benny Blanco — VHS Revival