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
23 Most Wanted Movie Gangsters
Flip through mugshots of feared crime-flick kingpins, from Johnny Depp's John Dillinger in ''Public Enemies'' to Tony Montana to Vito Corleone
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