The Departed

2006: Martin Scorsese, director; starring Leonardo DiCaprio, Matt Damon, Jack Nicholson. DiCaprio and Damon play conflicted informants, one burrowing into the Boston Mob and one into law enforcement, in a plotline reflecting the real-life compromising of the New England FBI by Southie mobster Whitey Bulger in the 1970s to 1990s. Nicholson plays Mob boss Frank Costello – a hat-tip but no other relation to the real-life Frank Costello, who was the “prime minister” of the national Syndicate and leader of Lucky Luciano’s crime family from the 1930s into the 1950s.