Category Archives: Simon Woosterfield

The Woosterfield Family

Hi folks and welcome to another Simpsons Sunday. Before I get into this weeks post, I want to tie up a loose end from last week. If you have the album Contractual Obligation there is a bit called String, which is track 4 on the CD and the digital download. The bit has two characters: Adrian Wap-Caplit voiced by John Cleese. He is a rather aggressive cellar and will stop at nothing to promote and cell this string. Mr. Simpson voiced by Eric Idle, is a rather mild mannered man who has come to see Mr. Wap-Caplit to help him cell a bunch of string, which he inherited. Unfortunately, the string is only in 3 inch lengths. This is where Mr. Wap-Caplit goes crazy with trying to cell the string and we don’t know what happened in the end, because the bit doesn’t go far enough to reach the conclusion.

Is it any wonder that Eric Idle was asked to voice a character on The Simpsons in 2003? After all, he was a Simpson before The Simpsons. Right?

This week’s post is all about Simon Woosterfield. Okay, in case you don’t know who I am talking about, he appears in the Season 20 episode Double Double Boy In Trouble, when Bart and Simon decide to switch lives. Simon is in a rich family and Bart enjoys it, until he learns that Simon’s siblings are planning to kill him, during a skiing trip. Also, Simon has to put up with Homer’s talking with food in his mouth and his treatment of Bart. Of course, this all comes about as the two boys look exactly alike, but with different dialects.

Watching the episode got me to thinking if Simon became a regular character, the Simpson family would have a rich and possible powerfull ally, if things get out of hand, which always happens. Maybe the Woosterfield’s could invite the Simpson family to their living quarters, similar to how Mr. Burns asked the family to house sit his mansion in the episode The Mantion Family. All though, there could be differences in this potential plot point, in that they would have to travel outside Springfield and Homer would probably take advantage of the cook, similarly to Oh Brother, Where Are Thou? when he constently asks for pork chops.

I don’t know if this will ever come to fruition but I’m sure the writers have idea’s, whether or not to bring Simon and the rest of the Woosterfields family back. It would be nice to see more one time characters being used again, so that Wikipedia article of the list can be shortened.

Well that’s about it for this weeks post. Check out Chris Ladesma’s blog. He is the Music Editor for The Simpsons and has been since day 1.
Also, check out Yeardley Smith’s blog at
Don’t forget about Marchez Vous, which is her women’s shoe designer company, which she started earlier in the decade. You can check out their website at
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You can follow Simpsons Executive Producer Al Jean on Twitter and his Twitter handle is @AlJean.
He has ran the show since Season 13 and has ran it during Seasons 3 and 4.
Anyway, that is it for this weeks post. Talk to you again next Sunday