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The Departed (2006)
151 min
To take down South Boston's Irish Mafia, the police send in one of their own to infiltrate the underworld, not realizing the syndicate has done likewise. While an undercover cop curries favor with the mob kingpin, a career criminal rises through the police ranks. But both sides soon discover there's a mole among them.
Synopsis via TMDB

GoodFellas (1990)
145 min
The true story of Henry Hill, a half-Irish, half-Sicilian Brooklyn kid who is adopted by neighbourhood gangsters at an early age and climbs the ranks of a Mafia family under the guidance of Jimmy Conway.
Synopsis via TMDB

The Aviator (2004)
170 min
A biopic depicting the life of filmmaker and aviation pioneer Howard Hughes from 1927 to 1947, during which time he became a successful film producer and an aviation magnate, while simultaneously growing more unstable due to severe obsessive-compulsive disorder.
Synopsis via TMDB