6. Captain Horatio McCallister
Created by Conan O'Brien during his stint writing for the show, the Sea Captain, as he is more commonly known is another Hank Azaria performance, referencing Horatio Hornblower (though in name alone) as well as Popeye (in his squint - he has two glass eyes somewhat confusingly.) McCallister is another in the long line of inept professionals on the show: he is first presented as a restaurant owner at the gimmicky all-you-can-eat style The Frying Dutchman, who Homer sues for not allowing to eat all he can, and whose restaurant is a perpetual failure, leading to a number of comical business opportunities, including his "small academy for lobsters." McCallister is a caricature in the oldest tradition, playing on the accepted, grotesque image of the sailor - with his hints as situational homosexuality, and general saltiness - and the pathos that touches his character is the chief foundation for his appeal. As a bonus, the Sea Captain also occasionally comes with a sidekick to match his appeal, in the shape of Handsome Pete, the Krusty the Clown-alike dancing midget who works for nickles.
Selected Quote: "Yarr, I don't know what I'm doing."