9. Captain Horatio McCallister (a.k.a. The Sea Captain)
First appearance: “New Kid on the Block” (Season 4, Episode 8)
Notable appearance: “The Mansion Family” (Season 11, Episode 12)
Voiced by: Hank Azaria
We have absolutely no idea where Springfield is located. Sometimes it’s next to a desert, sometimes it’s near a snow-capped mountain range, and sometimes it’s a coastal town by the ocean. It's that last location that leads to the Sea Captain. Unlike other characters on the show, the Sea Captain hasn’t had his personality fleshed out over the years with entire episodes dedicated to him. Still, we love watching him wreck ocean liners full of hot pants, or try to sell a 90-track CD he recorded of famous sea shanties on public-access television.
Ironically enough, the Sea Captain’s only notable contribution to the town can be found on land in his very own restaurant, The Frying Dutchman. The Captain’s most famous appearance on the show comes in “New Kid on the Block,” where he offers his customers an all-you-can-eat seafood deal that Homer attempts to take advantage of before being thrown out for eating the Captain into the red. This leads the Captain to respond, “Tis no man. 'Tis a remorseless eatin' machine.”