16. Lyle Lanley
First appearance: “Marge vs. the Monorail” (Season 4, Episode 12)
Voiced by: Phil Hartman
Conan O’Brien made a name for himself in Hollywood as a writer on The Simpsons in the early ‘90s. His credits include “New Kid on the Block” and “Homer Goes to College” (one of our favorites), but he's best known for “Marge vs. the Monorail.” In this gem, a nod to The Music Man, Springfield is swindled out of $3 million by a shifty businessman named Lyle Lanley, who builds a shoddy monorail for the town that Homer is hired to conduct.
Voiced by the legendary Phil Hartman, Lanley is nothing more than a lowly carnival barker in a candy cane striped suit with the uncanny ability to break into spontaneous song and dance. The combination of Hartman’s voice and Conan’s writing is the perfect blend of absurdity and cynicism, and it helped turn Lanley into one of our favorite, if not overlooked, characters.