Carlito's Way (1993)

Carlito Brigante tells everyone in New York he’s retired, and nobody, including you, believes him for a second. That’s the hook and the problem: Carlito’s Way plays the old last-job tune so faithfully you can hum along before the band does. Al Pacino is quieter here than usual, a tired man in a leather coat talking himself into being good, and it works better than his accent. The scene stealer is Sean Penn as Dave Kleinfeld, a lawyer slowly coming apart under frizzy curls and tiny glasses, so jittery you want to hide the furniture. John Leguizamo’s Benny Blanco is pure cocky trouble. Penelope Ann Miller does her best with Gail, who’s written mostly as a reason to leave. Brian De Palma’s Grand Central chase is as good as anything he ever shot. It made $63.8 million worldwide on a reported $30M. A 7.8 because the ending is a knockout and the road there is familiar. $991.15 says you delete a game off your phone this week, swear you’re done for good, and reinstall it before bed.

What works: Sean Penn is electric as a lawyer falling apart, and the Grand Central chase is a masterclass in suspense.

What doesn’t: The story follows the one-last-job formula beat for beat, and Gail is written as a reason for Carlito to quit rather than a person.

Who it’s for: Crime drama fans who like their gangsters tired, their lawyers sweaty and their finales built like a ticking clock.