The Departed

The Departed is a 2006 film directed by Martin Scorsese, an American remake of the 2002 Hong Kong film Infernal Affairs relocated to Boston's Irish-American organized crime scene, following an undercover police officer, played by Leonardo DiCaprio, who infiltrates a crime boss's gang while an informant for that same boss, played by Matt Damon, rises within the police department, and the parallel efforts of each man to expose the other before he is discovered himself. Its tense double-mole structure and Jack Nicholson's performance as the crime boss helped make it Scorsese's biggest commercial hit to that point. It won the Academy Award for Best Picture and Best Director at the 79th Academy Awards, Scorsese's first competitive directing Oscar after several prior nominations.