Brian De Palma was not in a good place prior to the release of 1993's Carlito's Way. He was coming off three disappointments in a row, 1990 Tom Wolfe adaptation The Bonfire of the Vanities above all. The film was so disastrous it made journalist Julie Salamon's making-of book, The Devil's Candy, a must-read for the way she aptly demonstrates how a few bad decisions, most made by individuals other than the director, can snowball into dozens.
De Palma needed a hit. He started by acquiring the rights to criminal judge Edward Torres's novels, Carlito's Way and After Hours, about Puerto Rican kingpin Carlito Brigante (Al Pacino, who had starred as gangster Tony Montana in De Palma's pulp-operatic Scarface remake). Instead of tracing his rise to power, screenwriter David Koepp, a hot property after Jurassic Park, picks up the story in 1975, just after Carlito has served time and returned to New York to rebrand as a legit businessman.
Carlito's biggest strength--and weakness--is his loyalty, and he believes he owes defense attorney David Kleinfeld (Sean Penn, who had appeared to menacing effect in De Palma's Casualties of War) for helping to whittle his 30-year sentence down to five.
If Pacino, with his beard and black leather, looks much as he did in Sidney Lumet's Serpico--but 20 years older--Penn is virtually unrecognizable in tiny spectacles and thinning, tightly-coiled hair. After representing hardened criminals for years, the cocaine-powered shark has turned into one himself, though his client doesn't realize the depths of his buddy's depravity while they're hanging out in the nightclub Carlito manages, at Dave's baroque office, or at his extravagant King's Point mansion.
If Dave fills his coffers by any means necessary, Carlito is saving up to relocate to the Bahamas--after buying into a car rental business--with Gail (Penelope Ann Miller, quite good in a stock role), the dancer with whom he has rekindled a romance. Just as Carlito aims to break free from hood life, Gail welcomes a fresh start after turning to stripping when her Broadway dreams died.
Though dedicated to his plan, Carlito's association with Dave, in addition to hoods like Guajiro (John Ortiz in his film debut) and Benny Blanco from the Bronx (an electrifying John Leguizamo), a strutting up-and-comer who reminds him of his younger self, leads him down some dark and dangerous paths, and inspiring De Palma to orchestrate some of his most ingenious chase-and-shootout set pieces in a pool hall, a series of subway cars, and most impressively, Grand Central Station.
The film, as a whole proved that the director hadn't lost his touch, despite controversy that he had cast an Italian-American--and not for the first time--as a Latino character. Unsteady accent aside, Pacino's heartfelt performance helped to win over many skeptics, along with the plethora of real-deal Latino actors in the cast, including Luis Guzmán, Jaime Sánchez (who co-starred with Pacino in Serpico), and even Viggo Mortensen, whose fair-haired looks belie his Argentinian heritage.
This two-disc Arrow release comes stacked with three commentary tracks, among numerous extras from previous editions, including interviews with both author and director. It's a career highlight for Brian De Palma and Al Pacino alike.
What film collection does this belong in?
Carlito's Way belongs in academic and public libraries with drama and crime collections.
What kind of film series would this movie fit in?
Carlito's Way would fit with film series on crime classics of the 1990s, stories set in the disco-fueled New York of the 1970s, and the extensive filmographies of Brian De Palma, Al Pacino, and Sean Penn, including the actors' directorial efforts.
What type of library programming could use this title?
Library programming on Latino/Puerto Rican culture and 20th-century literary adaptations could use Carlito's Way as part of the lineup, in addition to De Palma's Oliver Stone-penned, Cuban-American version of Scarface with Al Pacino.