The Simpsons: 10 Worst Guest Stars Ever

8. Martin Sheen

Episode: Season 9, "The Principal and the Pauper" Martin Sheen is a fantastic actor with a distinct voice who is good in just about anything. Apocalypse Now. The West Wing. The Dead Zone. Catch-22. JFK. Spawn. The Departed. And then there's his turn as "the real Seymour Skinner" on The Simpsons, in one of the most disliked episodes of all time, "The Principal and the Pauper." To be fair to Sheen, this really isn't his fault. He took his guest starring role, and delivered his lines as written. Sadly, the writers came up with such an awful storyline that there was really no saving the episode (in our opinion, though it has its defenders), and what could have been a classic guest star up there with Dustin Hoffman was wasted on a horrible plot twist that was almost completely ignored in later years.
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Contributor

Primarily covering the sport of MMA from Ontario, Canada, Jay Anderson has been writing for various publications covering sports, technology, and pop culture since 2001. Jay holds an Honours Bachelor of Arts degree in English from the University of Guelph, and a Certificate in Leadership Skills from Humber College.