Frank Costello from ‘The Departed’

The Character: In Martin Scorsese's Academy Award-winning film 'The Departed,' Jack Nicholson plays the role of hard-nosed (and cocaine-nosed) mob boss Frank Costello, a guy who plants an informant named Colin Sullivan (Matt Damon) in the Massachusetts State Police, while at the same time, the cops have planted an undercover cop (Leonardo DiCaprio) within Frank's crime syndicate. Eventually Frank is killed during a drug raid by Sullivan right after revealing that he himself is an FBI informant.

The Inspiration: Costello was loosely based on real-life criminal Whitey Bulger, an organized crime boss from Boston who ran a racket focused on protecting his neighborhood from drug kingpins and illegal gambling operations. When Bulger became and FBI informant, the bureau ignored his organized crime activities in exchange for information. In 1994, Bulger received a tip from an informant about a pending federal indictment charge, so he fled and went into hiding for sixteen years until he was apprehended outside an apartment in Santa Monica in 2011.