Mayored to the Mob

"Mayored to the Mob" is the ninth episode of Season 10. It aired on December 20, 1998. The episode was written by Ron Hauge and directed by Swinton O. Scott III. The episode title is an obvious pun on the movie Married to the Mob.

Synopsis
When Homer rescues Mark Hamill and Mayor Quimby from a rowdy mob of sci-fi fanatics, he is appointed the mayor's new bodyguard. But after convincing Quimby that he needs to stop Fat Tony's mob from selling rat's milk to the town's schools, the mayor's life is placed in jeopardy. Also guest starring are Joe Mantegna as Fat Tony and Dick Tufeld as the Robot.

Plot
The family attends the Bi-Monthly Sci-fi Convention, featuring an appearance by Mark Hamill. Hamill tries to promote Sprint, but only causes a massive nerd riot. Homer fights through the mob of nerds and leads Mayor Quimby and Mark Hamill to safety. The mayor fires his bodyguards, who were too busy looking at clouds outside instead of protecting their boss, and appoints Homer his new bodyguard.

While enjoying the advantages of being a bodyguard Homer stumbles upon Fat Tony's black market of rat milking. Homer demands that the mayor put an end to the sting even though Mayor Quimby knows that Fat Tony will come after him. Homer tries to ease his troubles by taking him out to eat at the Springfield Dinner Theater, where Guys and Dolls is being performed. Fat Tony and his cronies also happen to be there. Homer fights them off but Fat Tony manages to beat Mayor Quimby anyway and send him to the hospital.

Reception
Empire magazine named Hamill's appearance in the episode as the tenth best film gag in the show, saying: "as a rule, celebrity cameos are rubbish, but good sport Hamill is hilarious when singing 'Luke, be a Jedi tonight' in a production of Guys and Dolls, and makes this list for urging bodyguard Homer to 'use the forks'". Eric Goldman, Dan Iverson and Brian Zoromski of IGN marked Hamill's guest appearance second on a list of Top 25 Simpsons Guest appearances.