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300 Supernatural "Caption This" games! It's amazing that Nate and The WFBFamily have been teaming together for seven years to imagine what could have, should have, or forever will be the perfect commentary on Supernatural's unsuspecting moments! Nate's first "Caption This" challenge appeared on The WFB in July of 2015. Before him, Karen, Alice and a former team writer Ardeospina sparked our love for adding humor and irony to Supernatural scenes. With all that practice, you have gotten really good at this!

It was incredibly hard to narrow down all the amazing winners to just a few finalists, but if we're going to award prizes (yes, real, tangible Supernatural grand prizes are coming!), we had to find a way to choose the best of the best.  To evaluate the 100 winners most fairly, Nate, Alice and I each reviewed the 100 captions independently. That way, each entry was judged by three different senses of humor and perspectives on the show. Nate kicked off our celebration by announcing his Editor Choice Awards. I was happy to see his favorites included Young Dean daring Young Sammy (#268) and Sam looking for a Moose Crossing (#297), as those were both semi-finalists for me, too.

In total, 30 winners out of the last 100 made it to my semi-final list! I wish I could acknowledge all of them. After several passes and lots of laughs, though, the following 15 captions rose to the top as my favorites. They are the ones that make me smile, touch my heart and express my sentiments about the show the best. They are presented in categories that best showcase why I think the caption is a perfect match with the picture.

Thank you for sharing your inspiring creativity with us. 

Best Dean Voice

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Winning Captioneer: AlyCat22

Even if he didn't say it aloud, you know Dean was thinking it!

Best Sam Voice

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Winning Captioneer: Stephen Burns

Poor Sam! I laugh every time I see this caption. One of the bravest men in the universe who has stared down God, Death and the devil is terrified of clowns! 

Best Castiel Voice

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Winning Captioneer: Melissa Wyatt

Freeze frame on a moment when Castiel learns about human children in tutus. Perfect! 

Best Jack Voice

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Winning Captioneer: Marion

This is one of the moments that should have/could have been the future for TFW2.0. Overachieving dads and the most powerful entity in the universe dealing with the omnipresent curse of school science projects!

Best Crowley Voice - Tie

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Hokey Pokey Winner: Joan  ;   French Fries Winner: CrowleyLives

I love them both so much, I couldn't choose between them. Crowley always was one step ahead of our boys, teaching them the ways of the world! 

Best Bobby Voice

Winning Captioneer: Alycat22

You can hear Bobby saying this with his deadpan, disarming honesty. Love it. 


Best Supporting Character

Winning Captioneer: @superunditchabl

Donna's "What the cuss?!" reaction to hearing about vampires is one of my favorite comedic lines in Supernatural. Put that together with Jody's blunt practicality, add the chemistry between these two ladies, and you have genius.

Best Meta 

Winning Captioneer: Alycat22

From two years ago, the clever tie-in of Walker and Supernatural was too good to pass up. Jared would be proud.

Best Plot Callback

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Winning Captioneer: Wendy

Jared's puppy dog eyes and brilliant delivery made a throwaway line in season 3 ("Bad Day at Black Rock") a beloved classic of Supernatural.  Many years later, Wendy gave us this character-perfect reminder that Dean will never stop teasing Sammy, Sam will never stop being exasperated with his brother's pranks, and we will never stop loving their moments as brothers. 

Wittiest Caption

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Winning Captioneer: Tara

The "wait for it" boomerang connection between Dorothy, Charlie, Oz and the bunker is so smart. I wish I had thought of it. 

Most Unexpected 

Winning Captioneer: Alycat22

This is another one-liner that makes me laugh every time I see it. Balthazar could easily have slipped this question into a conversation with Castiel, amid a rapid fire stream of consciousness about his latest exploits, fleeing his deadly enemies and catching up with his old friend. It SO fits his personality. 

Honorable Mention to the Most Heartwarming Caption that I want in a Poster...
if we Completely, Entirely, Utterly Ignore Season 15

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Winning Captioneer: Claire Brandenburg

The old Chuck - the Chuck that was Castiel's hero, the Chuck that played the guitar in BG's Canteen, and hoarded toilet paper, and lovingly explained to Dean that his issues with his father couldn't be blamed on God - that Chuck advising a na├»ve, altruistic, hopeful, faithful, gullible angel that the road is hard but always keep fighting is the inspiration I need every day on the wall of my home. I absolutely love it. 

3rd Place

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Winning Captioneer: Carly

Too funny! A completely random scenario that fits the picture perfectly and could absolutely have happened in Supernatural

2nd Place

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Winning Captioneer: The Green Cooler

The dialog is so perfectly in character, I can hear the boys arguing about their inanimate, constant companions taking on personalities of their own. I'm sure it was a scene that was written, directed and printed but ended up on the cutting room floor. Considering the captioneer, I'm sure this really happened. 

**1st Place**

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Winning Captioneer: Curlybean

Absolutely the one thing I would say to Dean given the chance. Change the ending, Dean. Don't die. Live a long and happy life. 

This caption expresses in one picture the very deep emotions about Supernatural that are so hard to put into words, and it does it by reprising what Dean tried to tell his mom when he thought he had a chance to save her. It perfectly says what I didn't know I needed to say. Brilliance.  

Next up: Alice shares her Editor Choice Awards for "Caption This" #201-300 Winners! There may even be a surprise announcement involving prizes... 

Drop into our #CaptionThis contest page any time! You can enter your captions, get a laugh from all the creative entries and vote on your favorites each week! 
Enjoy all of Nightsky's musings on Supernatural!  Check out her Reviews, Top 10's, Books, Interviews and more, all on her Writer's Page!