3. Frank Costello – The Departed

Jack Nicholson as Frank Costello in The Departed

The weirdest part about The Departed‘s Frank Costello is that he’s not just one real person, but two. In Martin Scorcese’s 2006 movie, Costello is played by Jack Nicholson. The film’s Costello is a prominent Irish mob boss in Boston. Unfortunately, that’s about as simple as this entry is going to get.

Frank Costello was also a real-life Italian-American crime boss and part of the real Luciano crime family in New York. However, despite sharing a name and occupation with the real-life Costello, The Departed‘s version is actually intended to represent another real-life mobster, Whitey Bulger. Bulger was also an organized crime boss in Boston and ran the infamous Winter Hill Gang.

It’s probably a much safer bet to base The Departed‘s villain on two separate crime bosses, so as to spread around any of the potential offense it could cause to criminal organizations. However, doing so seems somewhat confusing – though The Departed‘s antagonist shares a name with one real man, he’s actually directly based on another. Either way, Nicholson’s performance is both electrifying and gently terrifying, making the character of Frank Costello an unforgettable amalgamation of two notorious gangsters.