List of the greatest fictional mobsters of TV, film, and comics. These rankings incorporate each of the best fictional gangster of all time. If you are curious to see if your favorite mob boss or sidekick from film and television has made it to cream of the crop status, peruse this list of the toughest and/or funniest gangsters ever invented by the writer who invented them and the actor who portrayed them.Some of the most popular media-made gangsters from onscreen history come from the ultimate mob movie, "The Godfather." Individuals will also notice that many of these make believe mafia members come from the godfather of all mafia shows, "The Soprano." While many of these television series and motion pictures feature characters who seem to be similar to real-life people from crime history, they are truly unique in their own ways. While Frank Costello is supposedly inspired by Boston's Whitey Bulger, Jack Nicholson's character in "The Departed" is so distinct that he's one of our favorite fictional (and thank goodness) gangsters.