Chief Clancy Wiggum is a fictional character from the animated television series The Simpsons, voiced by Hank Azaria. In the Italian version of the show his name was changed to Clancy Winchester, and he speaks with a thick Southern Italian accent.

Clancy Wiggum, more commonly known as 'Chief Wiggum', grew up in Springfield, but is originally from Ireland and was among the same class and age group as Homer Simpson, Lenny Leonard, Carl Carlson, Barney Gumble, and Marge Simpson (née Bouvier). At an early age Wiggum played cops and robbers with Homer and other kids his age and he showed a clear ambition to become a police officer. At the age of 16, he was a hall monitor at high school, and possibly had a part-time security guard job at Springfield State University. Wiggum was present at the University's germ research labs (Prof. C. Montgomery Burns was chairman at the time) when Mona Simpson and the hippie activist group she was part of sabotaged the germ experiments. Wiggum, who had suffered from asthma prior to that, was cured by antibiotics that the group released to kill the germs, and helped Mona Simpson escape the police when she was on the run twenty-five years later for curing his asthma and making the police force. In the episode "The Bob Next Door", his age is given as 43.

Henry Albert "Hank" Azaria ( /əˈzɛəriə/ ə-ZAIR-ee-ə; born April 25, 1964) is an American film, television and stage actor, director, voice actor, and comedian. He is noted for being one of the principal voice actors on the animated television series The Simpsons (1989–present), on which he performs the voices of Moe Szyslak, Apu Nahasapeemapetilon, Chief Wiggum, Comic Book Guy, Carl Carlson and numerous others. Azaria, who attended Tufts University, joined the show with little voice acting experience, but became a regular in its second season. Many of his performances on the show are based on famous actors and characters; Moe's voice, for example, is based on actor Al Pacino.

Alongside his continued voice acting on The Simpsons, Azaria became more widely known through his live-action appearances in films such as The Birdcage (1996) and Godzilla (1998). He has continued to star in numerous films including Mystery Men (1999), America's Sweethearts (2001), Shattered Glass (2003), Along Came Polly (2004), Run Fatboy Run (2007), Night at the Museum: Battle of the Smithsonian (2009) and The Smurfs (2011). He also had recurring roles on the television series Mad About You and Friends, and starred in the drama Huff (2004–2006), playing the titular character, as well as appearing in the popular stage musical Spamalot. Originally primarily a comic actor, in recent years Azaria has taken on more dramatic roles including the TV films Tuesdays With Morrie (1999) and Uprising (2001). He has won four Emmys and a Screen Actors Guild Award. Azaria was married to actress Helen Hunt from 1999 to 2000.

Marion Anthony "Fat Tony" D'Amico is a recurring character in the animated sitcom The Simpsons. He is voiced by Joe Mantegna and first appeared in the third season episode "Bart the Murderer". Fat Tony is a gangster and the underboss of the Springfield Mafia and his henchmen include Legs, Louie and Johnny Tightlips, and he answers to Don Vittorio DiMaggio.

In the season 22 episode "Donnie Fatso", Fat Tony dies of a heart attack and is subsequently replaced by his identical cousin Fit Tony, who soon gains weight and is rechristened "Fat Tony".

"Fat Tony" D'Amico was behind several of Springfield's criminal enterprises. His rackets included illegal gambling, cigarette smuggling, and bootlegging. In "The Twisted World of Marge Simpson", Homer contracts with the mafia to drive out Marge's rival snack food distributors. Fat Tony took out a hit on mayor Joe Quimby in "Mayored to the Mob" in retaliation for a raid on their rat milk facility, which Quimby opposed, as they had promised him "dog or higher". Fat Tony puts out a contract on Homer after his private security business interferes with the mob's interests in "Poppa's Got a Brand New Badge". Homer would have been executed gangland-style if not for Maggie coming to the rescue with her rifle. Fat Tony's son Michael is first mentioned by Fat Tony as he is talking to Marge in "The Seven-Beer Snitch", saying she drove him home from school sometimes. He is then properly introduced in the episode "The Mook, the Chef, the Wife and Her Homer". The episode also reveals that Fat Tony's wife "was whacked by 'natural causes'." Fat Tony and his associates meet in what is known as the "Legitimate Businessman's Social Club". Fat Tony played the violin in "Insane Clown Poppy".