5. “The Departed” (2006)
The twisted tale of rats on both the side of the mob and the police never fails to surprise. Scorsese manages to weave the dangerous cat and mouse game from a variety of angles. Even as we deal with cops versus gangsters, its never clear who’s right and who’s wrong. Colin Sullivan (Matt Damon) is a dutiful mobster who has grown accustomed to the perks of his high position in the Boston police department as a cover. Likewise, undercover cop Billy Costigan (Leonardo DiCaprio) can barely find which way is up as he becomes so deeply engrained in the mob world. At the center of this is Frank Costello (Jack Nicholson), the wiley mob boss everyone is after but no one can pin down. Keeping all these storylines not only cohesive, but always sharp and engrossing, is Scorsese’s greatest trick.