First appearance: “The Way We Was” (Season 2, Episode 12)
Notable appearance: “Duffless” (Season 4, Episode 16)
Voiced by: Hank Azaria
The Simpsons is notorious for featuring similar-looking background characters in multiple jobs and roles during its 20+ year run, and the most memorable of all of these is what fans have dubbed the Wiseguy. He appears in dozens of episodes, yet all we get from him is a sarcastic remark or two delivered with impeccable comic time. It’s not until you've been watching the series for years that you notice that this odd character is a constant presence in the Simpson's lives, most notably as the limo driver at Homer’s prom in “The Way We Was,” the exterminator who fumigates the Van Houten house in “Bart Sells His Soul,” and as the pet store clerk who sells Lisa a hamster in “Duffless.”
He may be lowly and unimportant in the grand scheme of the show, but his nasty disposition and penchant for mockery typifies what the show is all about. And with Hank Azaria doing his best Charles Bronson impression for the voice, the Wiseguy should take his rightful place among the more memorable characters in Springfield.