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#9 Contest #9 Entries
I couldn't quite pick out a really bad episode in season 5, so I went with "Swap Meat" hoping to get some fun interactions with the boys and some people outside their usual sphere.
The winner was a Guest entry:

Honorable Mention:
Not!Sam: So ... plaid shirt, jeans, jacket ...AND
Dean: Right. That should do it for most monsters!
Dean: "What the FUDGE is going on with Sam? He likes my music, my food. Did he do something to Baby? Hmm..."My thought? young Actor: And that's all you do all day? - Jensen: I know, right? Best. Job. Ever!
Not!Sam: So, these aliens abducted a guy last night and...
Dean: Woah, WOAH, woah! That subject is off limits, Sammy! Not!
Sam: ... "Boy, he is weird..."