“Times have changed. What happened to the miniskirts? Where’s all that marijuana? Now everything is platforms, cocaine, and dances I don’t dance.”

Ten years after making the superbly extravagant crime opus Scarface, Brian De Palma and Al Pacino reunited for Carlito’s Way, a rich and rangy character study of a reformed con looking to go straight, that also doubles as a plaintive tribute to the gangster film genre. Though both films unfold in similar milieus—flashy clubs, disco music, violent crime, drug trafficking—they are distinguished by their central figures. Tony Montana and Carlito Brigante are both trying to attain the American Dream by clawing their way to the top of the drug game, but only the latter is canny enough to realize that such a life is ultimately doomed.

In contrast to the increasingly debauched Tony, Carlito presents himself as a pragmatic, enlightened fellow. Released from a 30-year prison sentence after just five years on a technicality discovered by his sleazy cokehead lawyer (Sean Penn), he’s only looking to scrounge up $75,000 so that he can retire to the Bahamas and open up a car rental business. “I’ll tell you something, car rental guys don’t get killed that much,” he says. He hopes to enact his new plan with his former lover (Penelope Ann Miller), if he can convince her that he’s truly changed his ways.

Don’t take me to no hospital, please. Fuckin’ emergency rooms don’t save nobody. Son of a bitches always pop you at midnight, when all they got is a Chinese intern with a dull spoon.

But like James Caan’s safecracker in Thief—indeed, like virtually all reformed gangsters looking to turn over a new leaf in the movies—Carlito seems to naturally and mutually attract conflict. He wants to believe his drugging, thieving, and murdering days are behind him, but his connections and mythic notoriety ensure the worst is yet to come. Chief among his problems is the unpredictable, hubristic lawyer who’s in over his head ripping off a mob boss, but to whom Carlito feels he owes a debt. Other role players who factor into the story include John Leguizamo, Luis Guzmán, James Rebhorn, Joseph Siravo, John Ortiz, and Viggo Mortensen, plus about a dozen others. In the film’s brutal climax, which features among its assets a flashy long take in a subway station, the looming tragedy predicted in the black-and-white opening sequence comes to fruition just when you think Carlito might escape to a new life, with all his unattainable dreams symbolically materializing in tantalizing fashion on a billboard which advertises a Caribbean vacation.

Less showy than most of De Palma’s high profile films (though still plenty astonishing with its style and energy—an early scene in which Carlito stages an elaborate pool trick in order to keep tabs on a drug deal as it goes bad is masterfully done), Carlito’s Way uses its sympathetic antihero to explore a seldom-seen poetic and pensive dimension to the director’s work, achieving a haunting quality that renders the film extremely poignant in addition to its evident gangland appeal.