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  1. Nate Winchester
  2. Caption This
  3. Sunday, 03 November 2019
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Happy short hiatus everyone.

Some fun and creative entries were had in the previous contest with veteran captioneer AlyCat22 winning with a short, but painful, pun.

For our brief vacation, I decided to go back and fix my earlier mistake before the premiere and pick a screenshot original to episode 5x22, Swan Song. Funny, heartfelt, or sweet, any style of caption you wish for this one.

https://thewinchesterfamilybusiness.com/images/CaptionThis/SPN_05x22b.jpg
(heh, it does look like the boys are read this post)

The first 50 winning entries are here. Winning entries numbered 51-100 are here. 101-150 coming soon.
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AlyCat22
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Sam: “I’m wishing upon a shooting star Dean.”

Dean: “That’s a falling angel Jiminy.”
  1. more than a month ago
  2. Caption This
  3. # 1
AlyCat22
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Dean: "Its a good thing Baby doesnt have a hood ornament..."
  1. more than a month ago
  2. Caption This
  3. # 2
AlyCat22
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Sam: "When you wish upon a star-"

Dean: "-like a bolt out of the blue, fate steps in and squashes you..."
  1. more than a month ago
  2. Caption This
  3. # 3
AlyCat22
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Sam: “Fireworks are a lot more enjoyable when you aren’t dodging them in a field...”
  1. more than a month ago
  2. Caption This
  3. # 4
AlyCat22
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Dean: “Love going to the Drive-In!”

Sam: “Me too but did we have to park right up against the screen?”
  1. more than a month ago
  2. Caption This
  3. # 5
Gina Virgilio
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Sam: "What is that? Looks like.. sky-writing?"
Dean: "Uh.. it says Will You Marry Me, Dean? What the hell?"
Sam: "Wait.. it says, Love Gina at the end.."
Dean: "Son of a bitch!"
  1. more than a month ago
  2. Caption This
  3. # 6
Pat Hutchison
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Dean: "Nice night."
Sam: "Yeah..... Funny I didn't think it would be like this."
Dean: "What?" (he glances at Sam)
Sam: "Dunno, so well calm....ya know peace."
Dean: "Screw that Sam there ain't nothing calm about any of this."
Sam: "Yeah. It's just........"
Dean: "What Sammy, what?" (Sam frowns at Dean)
Sam: "Never mind." (Sam watches Dean gesture with his hand and Sam can't help but chuckle.
Dean: "Dude No chick flick moments, like ever. You know the rules Sammy. No chick flick moments and No controling the tunes. I drive I control the tunes. What now?" (as Sam laughs, shaking his head)
Sam: "The Rules? Seriously, are you gonna go there? Seriously." (Now Dean laughs.)
Dean: "You do know how you get. But go on what were you gonna say."
Sam: "I was gonna say its Kansas, winter and too damn cold out here. I'm going back in the bunker where it's warm and where the beer is."
Dean: "Crap the beer." (hops off the car and throws Sam the keys)
Dean: "In the garage, in her spot and no detours. Last time I left you alone with Baby you put like what a hundred miles on her. I will be checking the odometer."
Sam: "Whatever Dude!" (Sam catches the keys and opens the driver door. Dean points at Sam as he gets behind the wheel)
Dean: "Sammy I am serious here. Just a beer run."
Sam: "Hey Dean." (as he starts the impala) (Dean who was headed to the door of the bunker turns to see the passenger window open and Sam leaning over the seat)
Dean: "Yeah."
Sam: "It is a nice night.........for a drive.....thanks Dude. Oh and I won't forget the beer." (Sam drives off laughing as he hears Dean)
Dean: "Asshat! Sammy! Sammy! Son of a Bitch! Baby better be in one piece and no hundred mile drive either. Sam! Sam! Sammy!"
  1. more than a month ago
  2. Caption This
  3. # 7
Marion
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Dean " Hey Sam, maybe tonight we could get a pizza , have a few beers and see if we can make sense of the Game of Thrones ending?"
  1. more than a month ago
  2. Caption This
  3. # 8
Marion
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Sam " Do you.remember when I was little you told me once Mom had her very own star? "
  1. more than a month ago
  2. Caption This
  3. # 9
AlyCat22
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Dean: "Sammy, consider yourself the yummy chewy center in the Tootsie Roll Pop that is me."
  1. more than a month ago
  2. Caption This
  3. # 10
AlyCat22
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Dean: "I'm the hard outside of the Tootsie Roll Pop protecting the soft chewy center that is you."

Sam: "How many licks does it take to get to the center of a Tootsie Roll Pop anyway?"

Dean: "Now you just made it weird..."
  1. more than a month ago
  2. Caption This
  3. # 11
AlyCat22
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Dean: “Every time I stare up at the stars I wonder-“

Sam: “About the immensity of it all?

Dean: “-where that sonnuvabitch is that stole Dads leather jacket!”
  1. more than a month ago
  2. Caption This
  3. # 12
SuperTimeMag
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Dean: “Starlight Star bright..yada yada...I wish I may, I wish I might.....Hey Sammy, should I wish for pecan or apple?”
  1. more than a month ago
  2. Caption This
  3. # 13
White_Bat
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Sam: Do you think Cass can see us down here?

Dean: Nope, but I know for certain he can smell us! Lay off the burritos, Sam!
  1. more than a month ago
  2. Caption This
  3. # 14
AlyCat22
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Dean: "I wonder..."

Sam: "Bout?"

Dean: "Whether or not the Caption Contest qualifies as an instrument of torture.. "
  1. more than a month ago
  2. Caption This
  3. # 15
@boredannika
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Dean: Do you think they have beer in the universe that's only has squirrels?
Sam: And what color do you think beer is in the universe that doesn't have yellow?
Both: *huh*
  1. more than a month ago
  2. Caption This
  3. # 16
Demented_Becky
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Fortunately, upskirting laws don't apply when the 50-foot woman positions herself directly above you.
  1. more than a month ago
  2. Caption This
  3. # 17
@SPNNeverSaid
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Sully:
Still watching over my kids. Sometimes they're scared, but that just means the thing they're facing, it's super important, and nobody else is gonna go for it because nobody else has got the balls.
  1. more than a month ago
  2. Caption This
  3. # 18
Cori Dean
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Sam: " Hey Dean, did you know that stars are big balls of gas?"

Dean: " Sam, with you, everything is a big ball of gas".
  1. more than a month ago
  2. Caption This
  3. # 19
Laura
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“What a peaceful night Sammy”

“How? The AC/DC concert is right behind us”

“Yep”
  1. more than a month ago
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  3. # 20
Curlybean
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Dean: I don’t know, Sammy.... I’m pretty sure I can leap over that building in a single bound...

Sam: Dean, you’re Batman, not Superman.....
  1. more than a month ago
  2. Caption This
  3. # 21
@superunditchabl
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Dean: "Watching the stars for hours is SO not a chick-flick moment."
  1. more than a month ago
  2. Caption This
  3. # 22
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