"Penny-Wiseguys" is the fifth episode of season 24. The episode takes its title from 'Penny Wise', which was a pseudonym used by writer Jon Vitti to avoid getting credit for clip shows. It featured Steve Carell as Dan Gillick - Fat Tony's accountant, who is also Homer's bowling buddy.
Otto's replacement on the Pin Pals is Fat Tony's accountant, who ends up being named Fat Tony's temporary replacement while he is on jury duty, and asks Homer to stop him from killing mob members; when Lisa's fainting spell during a concert is diagnosed as iron deficiency, she starts eating insects, but her attempts to grow a supply of them end up working a little too well.
Homer is shocked to discover that his neighbor and bowling teammate Dan Gillick is an accountant for Fat Tony and his mob. When the government finally catches up with Fat Tony and he is forced to serve time on a jury, he names Dan as his temporary replacement. Dan eventually becomes power-hungry from the position, which frightens him. Things take a tipping point when Fat Tony orders him to make a hit, to which Dan tries to get Homer to stop him. Despite Homer's efforts, the ploy fails when Dan escapes and goes after the people he was assigned to kill. Homer eventually catches up with him and convinces him to stop. When Fat Tony is relieved of his jury duty, he regains control of the mob, while Dan goes on to run an ear-piercing stand at the Springfield Mall,
commenting that he loves the job because he gets to use an ear-piercing gun.
Meanwhile, Lisa decides to add insects to her vegetarian diet after passing out during a saxophone solo from iron deficiency. She enjoys the solution, but when the bugs haunt her in her dreams, she immediately quits eating insects. Out of guilt, she decides to breed a swarm of grasshoppers, but it turns disastrous after they escape from their container and contribute to Dan's escape. They eventually retreat to the outside world and feed off of a corn maze.
In the game The Simpsons: Tapped Out, there was a promotion called as the chapter in which you may get to Fat Tony to level 5, after the promotional ended, Fat Tony was rereleased, and one can get him when one is at level 28.