YMMV / The Simpsons S18E20 "Stop! Or My Dog Will Shoot"

• Unintentional Period Piece: Rudy Giuliani is portrayed in a relatively neutral manner (save for some weirdness, but that is the Simpsons standard) and is played by the man himself. When the episode came out, he was still riding his reputation as "America's Mayor" but by the 2020's, he would be better known for a number of controversies during and after the Trump presidency, including being implicated in the January 6th riots. Chances are that modern Simpsons would not be as kind to him nor be willing to ask him to voice a character.