10. Fat Tony - The Simpsons
Marion Anthony "Fat Tony" D'Amico is such an on-point satire of the gangster genre that I'd be remiss not including him. Running all of the organized crime in Springfield seems like a pretty good gig as the police force are incompetent and the city officials have a weakness for bribes. This corruption was most evident in the absolute classic 'Mayored to the Mob' in which Fat Tony is shown to be paying off Mayor Quimby so as to supply the local schools with rats' milk. Everything Fat Tony or any of his cronies says is lifted straight from the gangster genre and twisted into something hilarious. Lines like 'Play some ominous music, so that our trip to the body dumpery might be more cinematic' show that they know their source material well, and the loving way with which they lampoon it makes the Springfield mob some of the most entertaining characters on the show. It's perhaps worth noting that the original Fat Tony has been killed off by the writers of the show and replaced with his cousin Fit Tony. In reality it turned out to be the largest cop-out in recent times as the stress gets to the new boss and he turned to food, thus becoming Fat Tony again. It's exactly the same character, is what I'm saying. Aside from the comedy, Fat Tony is a serious mobster and not to be crossed. He frequently puts hits out on people and isn't averse to physically intimidating people himself. Dangerous, cunning and rightly feared in the community, Fat Tony is a worthy addition to any list of television gangsters.