First appearance: “22 Short Films About Springfield” (Season 7, Episode 21)
Voiced by: Hank Azaria
It's amazing that The Simpsons can create a character for the sole purpose of a single joke and have him become the standout part of one of the show’s best episodes. The Very Tall Man's introduced in “22 Short Films About Springfield” where he humiliates local bully Nelson Muntz, who previously “haw-hawed” about the Tall Man's immense size as he drove by in his shoebox car. His lumbering frame and baritone voice are perfect for this bit part, and though he's only appeared a handful of times since, he’ll always be remembered as a stellar addition to the show’s expansive background of characters.