22. Fat Tony from The Simpsons (1989-Presnt, FOX)
Played by: Joe Mantegna
Even in the small town of Springfield, organized crime is still seemingly everywhere, and one of the most prominent members of the only mafia family in town is Anthony “Fat Tony” D’Amico. Serving under Don Vittorio DiMaggio, Fat Tony usually leads a small group of soldiers in his never-ending quest to run his rat milk factory and his illegal gambling ring out of his “Legitimate Businessman’s Social Club.”
Always an ominous presence, Fat Tony has nearly killed every major character on the show, including Homer, Bart, Ned Flanders, Police Chief Wigum, and Mayor Quimby. Thanks to the on-point voice acting by Joe Mantegna, nearly every word out of Tony’s mouth is an absolute gem.