5. Charles Napier (1936-2011)
In Season 12's "Pokey Mom," Marge decided to volunteer at Springfield Penitentiary, teaching an art class to many inmates, including the talented Jack Crowley, voiced by that episode's special guest, Michael Keaton. But also in that episode, voicing The Warden for the first time, was American film tough-guy actor Charles Napier. Napier played the Warden so well, he was invited back three more times to reprise the roll, and later also brought-to-life professional hunter Grant Connor in Season 15's "The Fat and the Furriest" and a completely different prison guard, Officer Krackney, in Season 16's "The Seven-Beer Snitch." With the number of Springfielders who have spent time in jail- and that's the majority of the town- The Warden could have seen as much screen time as Fat Tony or Sideshow Bob. As it is, The Warden was last seen attempting to execute Snake in the electric chair in Season 20's "Gone Maggie Gone," which may have been Napier's last role of any kind (his last film was also released in 2009,
The Goods starring Jeremy Piven.) Napier passed away at the age of 75; the exact cause have death has never been released.