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  1. Nate Winchester
  2. Caption This
  3. Sunday, 12 January 2020
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I have not had to do this in awhile.

We just had so many good entries in the previous contest and no clear vote winner I just couldn't pick which one should win. So I test entries on the image itself to see which words fit best. I was down to 3 by Alycat22, @SPNNeverSaid, and the one who actually won, Jennifer. Good job all.

Now let's see...

Poor S3 is still light on entries, so now let's pull an image from its finale! Wow, this was a dark show back then. Both for images and just subject matter. Not a lot of possible comedy clips... oh! How about Ruby (or Lilith) and Sam here? From episode 3x16 "No Rest for the Wicked."
https://thewinchesterfamilybusiness.com/images/CaptionThis/SPN_03x16.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 coming soon.
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Anne Hall
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Sam: what the heck, why does she keep looking at Dean? Dean, Dean, Dean. Sometimes I wish I was Marsha.
  1. one week ago
  2. Caption This
  3. # 1
cheryl42
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Ruby: Sam Winchester is available in 3 varieties...human, Demon possessed and Angel possessed
  1. one week ago
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  3. # 2
Marion
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Ruby "Hey Sam, I can't save your brother, but look I have this really neat trick where you can dislocate your head....."
  1. one week ago
  2. Caption This
  3. # 3
Marion
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Ruby " I wonder if I can grab a Winchester to go, I'm tired of fries ..."
  1. one week ago
  2. Caption This
  3. # 4
Marion
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Sam " Maybe Becky wasn't so bad after all.."
  1. one week ago
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  3. # 5
Marion
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Sam " wish I'd stocked up on goofer dust today"
  1. one week ago
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  3. # 6
Laura
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Heck no I’m cutting his hair, I don’t have a death wish. That’s next season.
  1. one week ago
  2. Caption This
  3. # 7
Sammyscougar
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Ruby: Well Dean, pity you won’t be around while I screw up your brother
  1. 3 days ago
  2. Caption This
  3. # 8
Demented_Becky
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RUBY: Of course I'm standing on a box. What of it? It's a standard practice for managing height discrepancies in our industry.
  1. 2 days ago
  2. Caption This
  3. # 9
Demented_Becky
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RUBY: So you jerks out there in TV land think I'm not believable playing a demon because I'm blond haired, blue-eyed and have a Southern California suntan, eh? And you're wondering, "where's her surfboard". Well, that's just peachy!
  1. 2 days ago
  2. Caption This
  3. # 10
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