Caption This! – 20th Anniversary Edition
Welcome to Caption This, 20th Anniversary Edition! We are continuing our celebration of Supernatural turning 20 years old with a special edition of Caption This! There’s no better episode to choose from than the one that premiered 20 years ago on September 13, 2005, The Pilot.
I went through all the episode screen caps to find a few nice brotherly shots that we haven’t shared on this site before. I found three that I thought were especially caption worthy. So, which did I pick? You know me, I couldn’t decide, so I chose to use them all. After all, I should make this challenging!
Caption #1
Caption #2
Caption #3
Got any ideas? I mean look at them, they’re pups! I’m sure there’s inspiration out there to come up with something magical. Or just enough to get myself and Nate to laugh.
Given the special nature of this game, I’m not announcing a winner for Caption This #437 until next week. We will run that game one more week. So next week, you’ll get the results of two games.
Instructions on How to Enter
Scroll all the way down to Disqus below:
Click on one of the icons to log in with an existing social media account (Discord, Facebook, X, Google, etc) or click the “Name” box that is next to all the icons. It will bring up the following screen:
There you can create a Disqus account, or you can check “I’d rather post as a guest” (that small check box after the 5 terms and conditions) and provide a screen name (that will be posted with your caption) and your email address (which will NOT be posted. It just keeps out all the spam responses). Enter your Caption in the “Join the Discussion” text box then hit the arrow to submit.
Here are the past winners:
Okay, you know what’s next…time to Caption This! Good luck and Happy Anniversary Supernatural!

Alice Jester is the founder, editor-in-chief, head writer, programmer, web designer, site administrator, marketer, and moderator for The Winchester Family Business. She is a 30 year IT applications and database expert with a penchant for creative and freelance writing in her spare (ha!!) time. That’s on top of being a wife, mother of two active kids, and four loving (aka needy) pets.
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