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For those who may not know, I'm a bit of the site's jokester. As part of that I run the weekly "Caption This" contest (see here for all 100 contests so far).
The rules are pretty simple.  Each week, I pick a frame from a Supernatural episode, and then everybody is welcome to invent words to go with them. The captions can be related to the scene or completely from left field. Each contest runs for a week in WFB's Discussion Pages. Supernatural fans enter their captions as "replies" to the picture, then people vote for their favorites. There is no limit to how many captions fans may enter for each scene nor how many different captions a person can vote for. Serious or silly, the only two real rules are that the winning caption has to be able to fit onto the picture, and each voter only votes once for each entry (i.e. no stuffing the ballot box!).  It's fun for everyone - the creative fans among us get to put words into Sam and Dean's mouths, and the rest of us get to laugh at the hillarious things people see in each scene!
Having finally reached #100, it seemed time to take a moment, look back and pick out some of my favorites over the past two years. As with Alice's Editor's Choice Awards, theses categories are random and totally made up by me!


First up, I generally don't participate myself but every once in awhile I will do one.  Of all the ones I've done, my favorite is this moment from episode 2.22 (contest #97).
 097addtext com MjEwNjQxNjQyMjU


We don't get as much crude humor as you might expect, but sometimes the right moment in the car leaves little else to the imagination... Such as this moment from 11.01 (contest #13). Caption Winner: Leah
013addtext com MTgxNzA0MTMwOTk0


I'm a "live and let live" kind of guy when it comes to shipping, but even I had to wonder about this pairing from episode 9.02 (contest #88).  Plus now you have that song stuck in your head. Caption Winner: Leah
088addtext com MDk0NzMwMTkzNDU4


This contest isn't just funny, it's also sometimes educational as I learned about an Italian play from this entry from episode 11.15 (contest #32). Caption Winner: Elif
032addtext com MTg1MzA5MTM2OTg3


Referencing a story told at a con of Jared's adventure in a foreign land, this entry from episode 1.14 (contest #94) was a runaway favorite. Caption Winners: Cheryl42, Sue Nash (and others with similar ideas)
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 Hit "Next" for five more creative winning captions!