Carlito's Way | 1993
In Brian De Palma's gutsy thriller, Al Pacino is ex-con Carlito Brigante trying to go straight, until scuzzy lawyer David Kleinfeld (Sean Penn) involves him in a crazy plot to spring a client from the notorious Riker's Island Prison Barge.
The island, in the East River north of Astoria, Queens, is reached by the Riker's Island Bridge from Hazen Street in Steinway just west of La Guardia Airport. Sean Connery is released from Riker’s Island at the beginning of Sidney Lumet’s The Anderson Tapes, and the facility later stood in for ‘Sing Sing’ prison in Analyze That.
The nightclub, where the coked-up Kleinfeld lets slip about the prison break, was the, now-closed, Copacabana, 10 East 60th Street at Madison Avenue on the east Side – site of the famous tracking shot in Martin Scorsese’s Goodfellas.
Brigante, released from prison, watches old flame Gail (Penelope Ann Miller) from a rainswept roof. The dance class is at the Joffrey Ballet School on the corner of Sixth Avenue and 10th Street in Greenwich Village. Nearby, the turreted Gothic building past which Brigante follows Gail is the old New York Public Library on Sixth Avenue.
It’s in Le Figaro Cafe, 168 Bleecker Street at MacDougal Street, that the pair talk over old times.
Gail's apartment is 17 Gay Street, also in the village, and it's at the end of Gay Street, at the junction with Waverly Place, that Brigante is arrested.
Dodging the bad guys, Brigante jumps onto the South Ferry subway train at 125th Street Station on Park Avenue in Harlem.
The final bravura confrontation takes place all over Grand Central Station, 42nd Street at Park Avenue, with a shoot-out on the Park Avenue elevator.