- "Poor Tony. He didn't deserve this. He was just a solider in a war he started."
- ―Homer Simpson
"Donnie Fatso" is the ninth episode of Season 22.
Homer spends time in the Springfield Penitentiary after getting caught bribing an official. An FBI agent (guest voice Hamm) offers to reduce his jail time if Homer agrees to go undercover as an informant to investigate Fat Tony (guest voice Mantegna). When Homer forges a special bond with Fat Tony and his family, he becomes conflicted between his obligation to the government and his loyalty to his new family. After an unexpected turn of events, Fat Tony’s cousin Fit Tony (Mantegna) seeks to settle a score with Homer, but winds up teaching him an important lesson.
On New Year's Day, Homer recycles his bottles and paper together, which is now a $50 fine. He then accidentally breaks lots of other laws until he hits $1000. After going to Moe's, Moe tells Homer that he should go to window 9 at the court and leave a $100 bribe there to get all his crimes removed. He is caught and ends up in Springfield Penitentiary prison.
Homer is then offered an alternative by a FBI agent who plans to get Homer into Fat Tony's gang. He gives him a wig with a camera and microphone in and changes Homer's name to Nicky Bluepants Altosaxophony. Homer takes out the agent in prison, as he is dressed as a guard, to gain Louie's trust. Fat Tony finds out about this and Homer's apparent beating and breaks him out as the prison was built by the mafia.
After showing that he feels, Fat Tony believes that Nicky is like him. He then asks Homer to burn down Moe's, which Moe does anyway. Homer is then welcomed into the mafia.
They then go to a dock to collect guns from Belgium. However, the FBI are still listening in and Homer tells Fat Tony to leave. Before he does, he realises that Homer is a spy and has a heart attack as a result, and dies. Homer is upset after this.
Homer is later kidnapped by Fit Tony, Fat Tony's cousin. After realising that Fat Tony's memories lived on in Homer, he doesn't kill him and lets him go. Fit Tony then takes over the Springfield Mafia and becomes fat and eventually known as Fat Tony.
Jon Hamm guest starred. Hamm said appearing on the show was "an incredible experience, I got to work on The Simpsons, which I watched for 20 years and the show is still fresh and still funny and the characters still resonate. It’s one of the best shows on television. It was an honor to be asked to be a part of it." Joe Mantegna returned to the show to voice Fat Tony, who dies in this episode.
The episode earned mixed reviews from critics. Many said the storyline felt as if it had already been done as well as a lack of comedy.
Darren Franich called Fat Tony's death the 9th "Best TV Character Death of 2010" writing that "give the writers some credit for doing something different: In the middle of an otherwise straightforward mob-themed episode, they actually went ahead and killed off Fat Tony, a character who was first introduced almost twenty years ago." However, he later went on to criticize the addition of Fit Tony.
For this episode, Dan Castellaneta was nominated for an Emmy Award for "Outstanding Voice-Over Performance" The episode is nominated for a 2012 WGA Award.
Fat Tony and Homer, disguised as Nicky Bluepants Altosaxophony