2. Phil Hartman (1948-1998)
"Hi, this is the-late Phil Hartman. You might remember him as the voice of such
Simpsons' characters as Troy McClure, and Lionel Hutz!" The distinctive voice of Philip Edward Hartman brought such life to every character he portrayed on
The Simpsons, it was only right that all of his characters be forever retired following his untimely death at the hands of his wife in 1998. Not just his two main characters in crooked lawyer Lionel Hutz and former C-list actor Troy McClure, but every character he was asked to voice: including one-off characters like Bart's "big-brother" Tom; "Undersecretary for International Protocol: Brat and Punk Division" Evan Conover; and traveling musical monorail salesman Lyle Lanley. In the last years of his life, Hartman felt he could make a live-action movie about Troy McClure, and looking at what McClure did in the world of
The Simpsons, it certainly would have been fun. McClure hosted "The Simpsons' 138th Episode Spectacular", a half-fictional look at the previous six seasons; he also hosted Season 8's "The Simpsons' Spin-Off Showcase"; and was briefly married to Marge's sister, Selma. But his role of laywer (and shoe-repairer) Lionel Hutz is considered his best by many, and it's hard to argue. Lionel Hutz represented The Simpsons many times in court: suing Mr. Burns when he hit Bart with his car; defending Marge against charges of shop-lifting; (unsuccessfully) fighting for custody of Bart (losing to Mr. Burns); and eventually (and in Hutz's final appearance) taking a second job as a realtor, employing Marge at Red Blazer Realty. Without McClure, other celebrities like Gary Busey and Robert Wagner took brief cameo roles introducing short, educational films. Without Hutz, both the Blue-Haired Lawyer and Gil Gunderson found more time arguing in Springfield Municipal Court. But without Phil Hartman,
The Simpsons lost their go-to special guest for any character the writers could come up with, and it's arguable if they've come close to replacing him.