- “It's chowder, say it right!”
- ―Freddy Quimby
Freddy was first featured in the episode “The Boy Who Knew Too Much”, in which he was charged with beating up a French waiter. (In actuality, the French waiter almost killed himself due to his clumsiness, with Freddy Quimby having absolutely nothing to do with it, and even his incriminating words, "All right, you asked for it! I'm gonna enjoy this!", were actually in reference to a champagne bottle that he chose to drink rather than use for battery). The court ruled in favor of Freddy because Bart Simpson testified with an eyewitness account.
Freddy was also seen in a nonspeaking role in “Trash of the Titans” when Homer barges ahead of him in line in order to file papers to run for office, but then realizes that Freddy is among those in line who have to register as sex offenders. Freddy also once owned a Fish Stick Factory before Mayor Quimby fired his own nephew and took over the production himself. He is seen appearing briefly in “See Homer Run” with an altered appearance and improved look, and with a different voice. (Apparently, he started becoming somewhat of a law-abiding citizen, as he is like his press secretary, and as evidenced in the town hall meeting that started the recall elections, he seemed willing to even call out his uncle for the crimes that he and his administration caused.)
Like most characters surrounding Joe Quimby, Freddy Quimby is intended to be a satire of the famous Kennedy family political dynasty. The character's name is in homage to Fred Quimby, the producer of many 1940s and early 1950s shorts of Tom and Jerry.
- Episode – "The Boy Who Knew Too Much"
- Episode – "Trash of the Titans"
- Episode – "See Homer Run"
- Episode – "The Old Blue Mayor She Ain't What She Used To Be"
- Video game – The Simpsons: Tapped Out