Carlito “Charlie” Brigante (Al Pacino) is a one-time Puerto Rican heroin kingpin whose shady lawyer, Dave Kleinfeld (Sean Penn) has just gained him early release from a long prison sentence on a legal technicality. Rather than returning to his old life, Carlito decides to try and play it straight: he buys an upscale nightclub, hooks up with old flame Gail (Penelope Ann Miller), and makes plans to earn enough money for the two of them to escape the mean streets of New York for a new life in the Bahamas. His old ways, and old associations, come back to haunt him, though: the sleazy dealings of his friend and attorney put him in the cross-hairs of both the law and the Italian mob; his old associate, Lalin (Viggo Mortensen) is sent in to try and set him up for a fall; and an up-and-coming young drug lord named Benny Blanco “from the Bronx” (John Leguizamo) is out to make his bones at Carlito’s expense.