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  1. Nate Winchester
  2. Caption This
  3. Sunday, 12 July 2020
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At last! We're back everyone, having wrested control of the site back from that dastardly Ash. Hope you all had fun these last two weeks (and happy birthday, America). Even though he hijacked us, I was hoping the previous contest would be easier to judge with 2 extra entries. Of course I was wrong as you all just had way too much fun. I asked Ash what his opinions were and he apparently decided that for picture a) curlybean was the winner. Then for picture b) Phoebe Devereaux.

This week, things are back to normal and we look at episode 3.4 "Sin City." This episode has another short-lived ally of the Winchesters. (hmm... a new possible theme?) So have fun with Ritchie here, he won't be around long.
https://thewinchesterfamilybusiness.com/wp-content/CaptionThis/SPN_03x04.jpg

The first 50 winning entries are here. Winning entries numbered 51-100 are here. The winners of 101-150 are here. And 151-200 are now here.
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AlyCat22
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Sam: "How you doin?"

Ritchie: "No, its "How yu doin?"

Dean: "Hey."

*Leaves with the hot bartender*

Ritchie/Sam: "Everytime!?!"
  1. more than a month ago
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  3. # 1
AlyCat22
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Ritchie: "Designer threads. Slays the ladies! Watch this-"

*Dean leaves with hot bartender*

Sam: "Winchester Musk slays Oriental Silkworms."
  1. more than a month ago
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  3. # 2
AlyCat22
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Ritchie: "She has toys."

Dean: "Mmmmm.... "

Sam: "I'm partial to board games myself."

Dean: "Just how longs that dry spell been?!"
  1. more than a month ago
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  3. # 3
AlyCat22
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Dean: "Could fit that ass on a nickel!"

Ritchie: "A dime!"

Sam: "No change but I got a dollar?"

Dean: "Dry spell."

Ritchie: "Extra shirt?"

Sam: "Fuggedaboutit!"
  1. more than a month ago
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  3. # 4
@SPNNeverSaid
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Dean: Hunters now come in fun size.
  1. more than a month ago
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  3. # 5
Marion
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Richie "I'm gonna need a box to stand on to compete with you Winchesters"
Dean " Don't worry Richie, with that shirt you'll stand out from the crowd"
  1. more than a month ago
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  3. # 6
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"It's less of a crime than Ritchie's shirt."
  1. more than a month ago
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  3. # 7
@superunditchabl
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Dean: "No, we're not antiquers!"
  1. more than a month ago
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  3. # 8
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