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  1. Nate Winchester
  2. Caption This
  3. Sunday, 10 July 2022
  4.  Subscribe via email
Welcome back you beautiful people! Time once again for "Caption This!", the game where the images are real, but the dialog is made up. In our previous contest it looks like everyone had as much fun with special guest star Linda Blair as I hoped they would. Quite a few "coffee or pea soup?" jokes were tossed out there, but the "evil coffee" joke several people also submitted I feel was just funnier. I went with Jill's exact phrasing (and pop culture pun), but consider yourself a co-winner, Pam.

This week, I decided to spoil myself and go to an episode with one of my favorite guest stars, Anna. I was able to find a great shot with Ruby in it too, from the classic episode 4.10 "Heaven and Hell."
https://thewinchesterfamilybusiness.com/wp-content/CaptionThis/2022/SPN_04x10.jpg

Don't forget that on our front page, down past the articles, are "CAPTION THIS WINNERS!" - Random CT winners on display every time you visit!

And here is our vast gallery of past winners.
#1-50
#51-100
#101-150
#151-200
#201-250
#251-300
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Marion
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Anna "What time do you call this. We've got an Apocalypse on our hands and you chose now to act out like overgrown teen-agers?"
  1. more than a month ago
  2. Caption This
  3. # 1
Esther
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"Dad said it's OUR turn with the homoerotic subtext!"
  1. more than a month ago
  2. Caption This
  3. # 2
cheryl42
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Anna: It's true Ruby's pregnant.

Ruby: Wait...what?
  1. more than a month ago
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  3. # 3
Hani
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Anna: "Don't objectify us!"
  1. more than a month ago
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  3. # 4
Marion
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Ruby "Oh great, it's the Hardy Boys, we're saved"
  1. more than a month ago
  2. Caption This
  3. # 5
Marion
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Anna "Which one of you put the cookies out of reach?"
Dean "Don't look at me, I'm the vertically challenged one"
Ruby "Look who got smart after his Airbnb stay downstairs"
Sam "Ignore her Dean, she's hangry"
  1. more than a month ago
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  3. # 6
Laura
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You know, we wanted to go to the concert too.
  1. more than a month ago
  2. Caption This
  3. # 7
AlyCat22
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Anna: "Hey Dean. You know that opening for an Angel and Demon in your pornographic dream?"

Dean: "What opening?"

Anna: "Exactly."
  1. more than a month ago
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  3. # 8
curlybean
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Anna: Sam, would you please tell your brother that we won’t sit on your shoulders? That’s an Angel and a Devil that does that, not an angel and a demon.
  1. more than a month ago
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  3. # 9
AlyCat22
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Anna: "You do realize it's past both your curfews?"
  1. more than a month ago
  2. Caption This
  3. # 10
AlyCat22
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Anna: "You don't write. You don't call..."
  1. more than a month ago
  2. Caption This
  3. # 11
AlyCat22
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Anna: "You don't write. You don't call. You don't pray..."

Cas: "But he does! To me.
A lot."

Dean: "Ixnay on the relationship-ay."

Cas: "Mostly at night."

Dean: "Oh my God, Cas!"

Cas: "See?"
  1. more than a month ago
  2. Caption This
  3. # 12
AlyCat22
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Dean: "One night stand in the backseat of the Impala. Not a proposal of matrimony! These religious types, I swear."
  1. more than a month ago
  2. Caption This
  3. # 13
AlyCat22
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Anna: "But we cleaved unto!"

Ruby: "I tried to warn you."

Dean: "I'm more the cleaved and then leaved type. Don't smite me."
  1. more than a month ago
  2. Caption This
  3. # 14
Cali
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Ruby: whats a girl gotta do to get some fries around here?

Anna: Me..??
  1. more than a month ago
  2. Caption This
  3. # 15
AlyCat22
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Anna: “Ruby locked me in the panic room.”

Ruby: “Tattletale.”

Dean: “Okay, let’s all just calm down now.”

Anna: “And then she ate all the pie!”

Dean: “You bitch!”
  1. more than a month ago
  2. Caption This
  3. # 16
AlyCat22
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Anna: “I made a pie especially for you and Ruby ate it!”

Dean: “Exorcism now!”

Sam: “Let’s all just calm down.”

Ruby: “Sam had some too!”

Sam: “You really are evil!”
  1. more than a month ago
  2. Caption This
  3. # 17
AlyCat22
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Anna: “I made a pie with your name baked in the crust and Ruby ate it!”

Ruby: “What? I thought it read Demon!”
  1. more than a month ago
  2. Caption This
  3. # 18
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