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  1. Nate Winchester
  2. Caption This
  3. Saturday, 30 January 2021
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Hello, everyone! In the interest of some updates, we have decided to shift some of the scheduling around here on WFB so caption this! will now drop on Saturday nights. I was actually surprised we did not get as many Walker, Texas ranger jokes in the previous contest but Brittney Cole won the day with... well let's be honest, I'm still 9 at heart.

For our next effort, we go to #26 on our top 100 list: episode 2.14 "Born Under a Bad Sign." And... how about Jo & Sam this time? We don't get to see them together very often.
https://thewinchesterfamilybusiness.com/images/SeasonTwo/BornUnderABadSign/JoandSam.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. Winners #201-250 will be coming soon.
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AlyCat22
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Sam: "Ooh nice. Cashmere?"
  1. more than a month ago
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  3. # 1
AlyCat22
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Sam: "Look. I just want a pickled egg and I'll go!"
  1. more than a month ago
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  3. # 2
AlyCat22
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Jo: "I suppose you think REO sings it from the hair too huh?"

Sam: "I'm more of a Vince Vicente fan myself."
  1. more than a month ago
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  3. # 3
AlyCat22
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I lost my Hat trick to a fart caption.

You're a cruel, cruel taskmaster Nate...

AC22
  1. more than a month ago
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  3. # 4
Nate Winchester
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Hey, yours were pretty good, AC22, but you have to admit the fart joke is just a bit funnier. :p
  1. more than a month ago
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  3. # 5
AlyCat22
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Unlike you Nate. I am not a connoisseur of fart jokes. I only occasionally allow myself to cross over to the dark side of potty joke humor. :)
  1. more than a month ago
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  3. # 6
Laura
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Jo, I said I wanted a whiskey sour, not a shot of whiskey
  1. more than a month ago
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  3. # 7
Jamie Pkay
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Jo: So... tell the truth Sam, how do you get your hair to be so wavy and shiny?

Sam: Lorèal Paris. Because your worth it.
  1. more than a month ago
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  3. # 8
Curlybean
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Jo: Sam, there was some girl named Rhonda in here earlier and she kept talking about Dean and a pair of pink, satiny panties. What’s that about?!

Sam: I have no idea what you’re talking about, Jo. And I definitely wouldn’t ask Dean about it.
  1. more than a month ago
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  3. # 9
AlyCat22
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Jo: "This is my "I want you to take me seriously even tho I'm a spoiled brat pose."

Sam: "Actually it looks more like a "this is why Dean will never consider me as anything more than a baby sister" pose."
  1. more than a month ago
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  3. # 10
Marion
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Jo " Sorry Sam, but it's obvious my hair is best"
Sam " I think we should let Dean be the judge of that"
Dean " Guys, guys, leave me out of it, just be glad you got hair"
  1. more than a month ago
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  3. # 11
Marion
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Sam "My hair's the best"
Jo " is not"
Sam " is too"
Dean " I hear you two squabbling one more time, I'm getting my clippers"
  1. more than a month ago
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  3. # 12
AlyCat22
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Sam: "What do you mean no Purple Nurples!?"
  1. more than a month ago
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  3. # 13
Nate Winchester
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Entry from facebook.

I don’t know Sam. I’ve got laundry and I have to wash my hair. -Rusti Grandinetti
  1. more than a month ago
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  3. # 14
AlyCat22
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Sam: "Look. I know you have my purple greyhound T -shirt!"
  1. more than a month ago
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  3. # 15
AlyCat22
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Jo: "Its not me, it's you."

Sam: "No. No, it's definitely you."
  1. more than a month ago
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  3. # 16
AlyCat22
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Sam: "He thinks of you as a school girl-"

Jo: "Sam, do demons lie?"

Sam: "Yeah."

Jo: "I knew it! So Dean's in love with me AND hes a demon!"
  1. more than a month ago
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  3. # 17
Marion
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Jo " No Sam, how ever much you beg, I'm not stocking Kale Smoothies"
  1. more than a month ago
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  3. # 18
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