FRANCIS COSTELLO (Jack Nicholson)
The Departed (2006)
This old-school crime boss had a very new-school plan: Embed one of his own boys (Matt Damon) in the police department, and work the Crew in Blue from the inside. Sure, it didn't work out exactly as planned these things never do but that kind of street-level insight is what kept Frank at the top of Boston's heap.
Image Credit: Andrew Cooper
Flip through mugshots of feared crime-flick kingpins, from Johnny Depp's John Dillinger in ''Public Enemies'' to Tony Montana to Vito Corleone