12. Phil Hartman (Lionel Hutz & Troy McClure)
Additional Voices: Lyle Langley
You might remember Phil Hartman from such films as Jingle All The Way and Small Soldiers, although his best known work is probably The Simpsons or Saturday Night Live. He was a huge part of the show’s earliest success, and it always felt a bit empty without him.
Though monorail shyster Lyle Langley is a contender for one of the all time best one-off characters, it’s his recurring characters Troy McClure and Lionel Hutz that made the biggest mark. Blue Haired Lawyer is decent, but he can’t hold a candle to Hutz.
Ultimately though, the show probably made the right decision to retire the characters after Hartman’s untimely death. In 1998, Hartman was killed by his wife Brynn, who accidentally shot him in the chest while drunk and high on cocaine.
The show just quietly moved the characters on, which seems better than simply recasting them and asking someone to replace Hartman.